Career Q&A with Heather Hatlo Porter, Chief Communications Officer at Chegg (#13)

The next Career Q&A is with Heather Hatlo Porter. Heather offers exceptional advice on how mentors can help us get unstuck, how failure can be a career accelerator, and how to find the courage to seize opportunities that may initially intimidate us.

Heather is Chegg’s Chief Communications Officer, leading all internal and external communications efforts for the company. Previously, as VP of Marketing, she was responsible for building Chegg’s brand narrative, creating innovative campaigns with major influencers, and spearheading cause-marketing efforts. Her passion for the mission inspired her to help launch the Chegg Foundation in 2013, later transitioning it in 2019 to, the new social impact, grant-giving and advocacy arm of the company that elevates the student voice through policy efforts such as the “Unlocking The American Dream” student debt policy report.

When she is not focused on putting students first at Chegg, Heather is focused on her own students, her two sons, and can be found cheering at the ice rink for her kids as a devoted hockey mom or volunteering with local organizations as a passionate community member.

Was there an experience you had before age 21 that shaped who you are? What was it?

My very first job, in high school, was a courtesy clerk for Nob Hill Foods. And, it wasn’t so much the work or the role that had a profound impact on me, but it was the lessons I learned from the leadership team there.

Back then, I was going through some challenging times in my personal life, and I will never forget how caring and supportive the management team was. On the days when I couldn’t make it to work, because of one reason or another, or on the days I showed up late, they met me with such compassion and understanding.

When so many employers would have seen a flighty 17-year-old girl who wasn’t fulfilling her obligations to the job – which certainly should have led to getting fired – they took the time to ask what was going on and inquire as to why my schedule seemed so unpredictable. They got to know me and, through that, were able to show a level of compassion I never expected from “the big bosses”. In fact, during a particularly rough spot in my life, one of them even offered to let me stay with their family temporarily. Thankfully, that wasn’t necessary but just the thought that someone who I worked for would do that for me had a deep impact on how I think about my own employees today.

I have learned to really prioritize getting to know what is going on in people’s lives outside of the four (virtual) walls at Chegg. By understanding where they are coming from, what they are experiencing, what challenges they might be facing, I can do a better job of supporting them in their work. Quite frankly, I treat them like they are family because I think that’s the best way to bring out the best in people. I always start team meetings by asking how they and their families are doing so I know how to support them in any way they may need.

Giving your employees grace, encouragement, and understanding creates a culture where they know they can trust you to lead them to grow and succeed. When a person feels cared for and supported, they are much more likely to be fully invested in their work and deliver superior work at that.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

I have failed many times; I am not sure where to start! Some of the marketing campaigns that I thought would be phenomenal over the years ended up falling flat. I learned afterwards that these campaigns failed not because the idea and execution were lacking, but because the audience’s appetite for it simply wasn’t there. The biggest takeaway from all these failed campaigns is to always research before executing an idea and to find out what the audience actually wants. Assumptions are great, but data is better.

At Chegg, we have an entire research team dedicated to surveying students’ needs and wants, and we deep dive into the survey results to create products and services that benefit them the most. Along those same lines, I really value our interns’ feedback every summer because they are much closer to our target demographic than I am, and some of my ideas have been shot down by them for being irrelevant or outdated (and let me tell you, sometimes that makes me feel so old!). What this has really ingrained in me as I have progressed throughout my career is to do my homework, identify what it is I am trying to accomplish, understand if it is big enough to matter, and then make sure I know how we would define success for whatever it is we are working on.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

My advice for students is to go easy on yourself. Like most other college students, I used to experience a lot of self-doubt and anxiety about my future. I felt rushed to land the perfect job and enter a relationship, putting way too much pressure on myself about every decision I made in my early twenties.

Looking back now, I realize that my career path looked nothing like I expected but, each step along the way, I learned invaluable lessons and I honestly wouldn’t change a thing. I know many young people, especially at this time, are feeling very uncertain about their future amid a global pandemic and economic uncertainty. I think now, more than ever, it is particularly important to take time to invest in your mental health and well-being and give yourself permission to not have all the answers, to not know what comes next, and to be okay with that.

So, I guess on that note, the advice I would say to ignore is the old mantra of “fake it till you make it.” Don’t fake anything. Be authentically you, don’t stress too much about the future, and know that life is a journey and some of my best moments came out of the times where I had no idea what was going to happen next. 

What’s something unexpected that has happened in your career, and how have you responded?

I have been given several unexpected opportunities throughout my career, opportunities that I did not have the skill set nor the experience for at the time. But I had the courage to seize those opportunities, and ultimately, I used these experiences to build up my confidence.

I knew I was great at being an executive assistant, so I was hesitant at first when the opportunity to join the marketing department came up. I knew I wanted a change, but I didn’t know if I would be successful at it. So much so that I told my boss at the time, “let’s just try this for six months” fully expecting her to fire me at the end of that test. 7 years later, under her mentorship, I was the VP of Marketing. I could never have predicted that but because I took a chance on something that scared me, it opened even more doors which, eventually, put me on the path to becoming Chegg’s first CCO.

I think being able to articulate what it is I want to do and, equally as important, knowing what I don’t want to do, being willing to take risks, and embracing failure has really helped me excel through my very non-traditional career path.

Since entering the workforce, how have you changed or transformed?

Well, I started working full-time at 18 so I have grown tremendously over the course of my career in so many ways. I think one of the more obvious places of growth is that I had to learn how to accept not being good at things, at failing, and being transparent about that. Early on in my career, I thought that failure was not an option and that it would be catastrophic for me professionally. Now, my attitude towards failing is the exact opposite. I learned that failure can be a career accelerator because of the learning opportunities you get every time something doesn’t work.

In fact, Esther Lem, Chegg’s CMO and one of my mentors, really modeled that for me by celebrating failure every month in our marketing team meetings. She gave failure a central point in our team meetings, allowing people the opportunity to talk about the lessons they learned and so that others could see the failures across the team. These meetings taught us to take ownership of our failures and to be empowered, rather than hindered, by them. 

When have you felt stuck in your career? How did you break out of it or push forward?

I was an executive assistant for ten years. By the age of 30, I had reached the top of the career ladder for that role, having already worked for the CEO and Chairman of the company. I didn’t know what I wanted to do next and felt stuck in terms of professional growth. I actually tried to resign from Chegg because I thought there was nothing more for me.

Fortunately, another one of my amazing mentors, Dan Rosensweig, encouraged me to explore my other interests, such as philanthropy and creative storytelling, and recommended I give marketing a shot because it seemed like a fitting pivot in my career. It was like a lightbulb went off because I had never connected my degree, which was focused much more on creative storytelling for film or theater, to brand storytelling. He was able to offer me a perspective I wouldn’t have even considered on my own.

So, when you feel fatigued or lost or just that you have reached a plateau in your career, I think the first step is just being self-aware. I knew when I was at the end of one path. I just needed some guidance about finding my next one.

And, on that note, I think surrounding yourself with great mentors is really important because they can challenge you in ways that might surprise you. And then, when the opportunity to make a change presents itself, you have to be bold enough to take the risk at trying something new. When that door opens, ignore that self-doubt and just go for it.

Who is one person, dead or alive, who you admire? Why do you admire them? 

I feel like, on any given week, I would have a different answer to this question because I admire so many people for so many different reasons. I look up to the many amazing female mentors I have in my life, like Esther Lem, Lee Woodruff, Desiree Gruber, and Melanie Whelan. Right now, I am really in awe of Arlan Hamilton, because she is transforming the venture capital world.

I started my professional career in the corporate legal environment and then moved into private equity. But, unlike my peers at the time, I did not have a master’s degree from an Ivy League school. In fact, I attended community college, transferred to a local state school, and did not pursue a higher degree afterwards and, because of that, for a long time I felt like I was always underestimated. It weighed on me a lot but also made me work much harder than everyone else around me. I always felt I had to hustle to prove my worth.

Arlan seems to have a similar mentality. She experienced so many setbacks but has still shown the world that it doesn’t matter where you came from or what your background is. What matters is where you are going and your ambition to get there. I admire how she hasn’t let anything hinder her success and how she stays focused doing what she is passionate about and having such a positive impact on the people and communities around her. She’s a rock star.  

What habit or practice helps you manage stress?

I find I have to invest in both my physical health and my mental health to really find balance in my life – especially these days. I make it a priority to find time to work out, even if that just means a walk with my kids or the dog, or a quick HIIT workout if I am short on time. It’s really evident, to everyone around me, when I don’t have any exercise in a given week. Let’s just say, I don’t even like being around myself then.

I also find connecting with my family and friends to be a great stress-reliever. That’s been particularly challenging during the COVID-19 pandemic, but I have been finding creative ways to spend time with people, such as hosting Sunday family suppers over Zoom and playing online games or doing virtual wine tastings with friends. It is important for me to feel connected with my friends and family, and I’m so grateful for the technology that enables us to do so.

For more Career Q&As, click here, or you can check out my monthly newsletter and podcast.

Career Q&A with Tami Forman, Chief Executive at Path Forward (#11)

The next Career Q&A is with Tami Forman. Tami offers great insight into the power of setting low expectations (yes, you read that right), how our obsession with “passion” can lead us astray, and how having a child helped give her confidence in her career.

Tami M. Forman is the chief executive of Path Forward, a nonprofit organization that creates mid-career internship programs to ease the transition back to work for women (and men) after taking a break for raising children or other caregiving responsibilities. Before founding Path Forward, Tami spent a decade as a tech marketing executive with data solutions provider, Return Path. Before that she worked in book publishing at Simon & Schuster and Houghton Mifflin and held senior-level web editorial positions at iVillage and News Corporation. She is a frequent speaker on issues related to women’s participation in the workforce, writes a career column for Forbes, and was named by Flexjobs as one of the top 20 career experts for working moms. Tami lives in New York City with her husband and two kids, aged 10 and 12. 

What’s a book that has influenced your career or life, and why? 

I am a big fan of Laura Vanderkam, especially her book on working women titled I Know How She Does It. She offers different ways to think about our relationship to time which, especially in a knowledge job, is really helpful for breaking out of old habits around work and life. I don’t believe women or men should have to choose between a fulfilling career and a life. Vanderkam’s work offers frameworks that help you figure out how to make that idea a reality. 

Was there an experience you had before age 21 that shaped who you are? What was it? 

My parents are not college graduates so, for me, college was a very disorienting experience. It was very apparent to me that many of the kids around me had access to a set of unwritten rules and practices that I had to figure out. And that carried over when I entered the corporate world. Because my parents didn’t have professional jobs I am not a native to the folkways of corporate culture. Much like an immigrant to a new land I’ve had to learn the customs and language without the benefit of having grown up in it. I think it’s made me resilient and given me the confidence to take a leap into the unknown—I know I can figure things out.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours? 

I started out my career in media—book publishing and then digital media—and I didn’t do great in that field. Part of it was loving books and writing is not enough to carry you through a career. But also, it was a world I just didn’t fit into. Part of it was being a corporate “immigrant”—I didn’t understand how the white-collar world worked in general. But media, specifically, is an industry where a lot of emphasis is placed on where you went to school, what neighborhood you live in, and what connections you have. Some people are able to overcome that and find a way to fit in—or find a way to stand out!—but I couldn’t really do either of those. Took me awhile to figure out that it just wasn’t the right fit. 

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore? 

I would say, “Just start somewhere.” So many of us starting out want to pick the “right” job to lead to the “right” career but there’s no way to really know if you are good at something or will like it unless you start doing it. Take a job that seems aligned with your interests and then go from there. I generally tell people to ignore the advice to “Find your passion.” If you really have a passion you will know it and you really won’t even have a choice but to follow it. But most of us have a lot of different interests and could fit well in any number of careers. Our obsession with “passion” can lead people down dead end roads. 

What are the bad recommendations you hear in your profession or area of expertise?

Along the same lines as “find your passion,” I really hate when people say “Do what you love and the money will follow” and “Love what you do and you will never work a day in your life.” First, there are lots of things people love doing that simply do not pay well. Second, I love my job and there are days that are hard and awful. Work is still … work. Expecting to love every minute, and get paid handsomely for loving that super gratifying, totally fulfilling work, is just setting people up for massive disappointment.

I believe in keeping relatively low expectations. You can have big goals and still not have such ridiculous expectations that you are almost guaranteed to be disappointed. By the way, this is also where I think my upbringing helps me out. I have already far exceeded all expectations I could have imagined for my life—at this point everything is really gravy. 

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be? 

“Your first job won’t be your last job.” I knew that, of course. In 1993 there was no longer an expectation that you’d spend your whole career at one company. But I still think I was too worried about making a bad choice. I wish I’d embraced the idea of exploring different jobs earlier in my career. The idea of design thinking—trying something, figuring out what is working and what is not and then tweaking—is something I came to later. But if I’m being kind to my younger self I have to admit that it’s easier to feel comfortable with the idea of experimenting when you have had some success and seen things work out!

What’s one of your proudest professional accomplishments? 

I’m really proud of starting Path Forward from scratch. We’ve now worked with 70 companies, including large employers like Walmart, SAP and HPE, we’ve seen more than 400 people employed through our returnship program and we’ve truly established ourselves as experts in our part of the workforce development space. And everything I’ve done in the last 4.5 years is something I had never done before which makes these accomplishments feel even more incredible.

I think part of the courage to do that came from having to figure out a lot in college and my early career. But the final push that convinced me that I could really do anything I wanted to do was having children. Babies are the ultimate start-up experience. The hospital sends you home with one and says “Good luck!” And as soon as you start to get good at your job, it changes. More moms should start businesses. We are experts at figuring things out and learning on the job.  

What’s something unexpected that has happened in your career, and how have you responded? 

I never expected to start and run a nonprofit! I was working in corporate communications at a private software company when the HR department decided to start a returnship program to bring former stay-at-home mothers back into the workforce. I thought it was a great idea and as the head of PR I also felt it was a great story! We got an article in the San Francisco Chronicle. That led to other companies becoming interested in what we were doing and looking for support and consulting.

Eventually our CEO, Matt Blumberg, felt like the program could have a big impact as a nonprofit to work with employers to create more of these programs. When he told me his idea it was as if a light bulb went off over my head—I thought “I have to be a part of this.” I’d never thought about becoming an entrepreneur. But the cause felt so important to me. And I like the challenge of doing things I’ve never done before. 

Since entering the workforce, how have you changed or transformed? 

There is a scene in the third season of The Crown where the Queen is lamenting the new image of her as an older woman and someone refers to her as “the settled sovereign.” I found that to be such a compelling phrase, noting the complete lack of humility I may be showing by comparing myself to the Queen of England! But that phrase is a good way to explain how I feel now—I feel settled. I know what I know, I know what I don’t know and can figure out how to learn it. I also know what I’m good at and feel far more comfortable not trying to be “perfect.” I don’t feel the need to “appear” confident—I am confident. I feel like I have a firm foundation on which to build the next phase of my career—which feels very exciting. I know I can make mistakes and recover from them. I don’t feel as focused on what I might lose so I can stay more focused on what my team and I can win. 

When have you felt stuck in your career? How did you break out of it or push forward?

I definitely felt stuck when I was in media. I’d love to tell some great story about having a grand epiphany, quitting media in a dramatic fashion after having landed a great new job and riding off into the sunset. In fact, I got laid off. It was the beginning of 2003, the economy was still rocky after the dot-com bust and I lost my job at News Corporation. I spent six months looking for a job—any job—in media. But it was a rough time and I actually ended up losing out on three jobs to people I knew! It felt like the walls were closing in. I then landed at Return Path—a small software company where I ultimately became the VP of Corporate Communications. The rest is history! Sometimes the universe really does need to give you a shove. 

Who is one person, dead or alive, who you admire? Why do you admire them? 

Julia Child. I’ve read her biography and also the autobiography that she started and was finished by her nephew. Interestingly the biography is much more hagiographic. But I have a few reasons I love her. First, she is a late bloomer. She didn’t even take her first cooking class until she was 38 years old! She was in her 50s when she became the star we all came to know and love. When I was struggling in my early career I kept reminding myself that not everyone is a wunderkind. Second, she was an unapologetically ambitious woman. That really comes through in her autobiography—she was very driven and she wasn’t always nice about it! I admire that—we don’t expect men to be “nice” on the road to success. In the waning days of my media career I was working as a food editor and I got to talk to her on the phone. It was late in her life and she wasn’t well but it was such a thrill to talk to her! And she was quite humble. She said she “got lucky,” in her career, which, while true, is clearly not the whole story. 

What habit or practice helps you manage stress? 

I get up early every morning and go on a 3-mile walk. It gets me moving, clears my head and gives me an instant feeling of accomplishment. I also have dinner every night with my family. This is much easier now that we are in quarantine, but even when I commuted I prioritized getting home for dinner. Sitting around the table and reconnecting over a shared meal recharges me. 

For more Career Q&As, click here, or you can check out my monthly newsletter and podcast.

Career Q&A with John Mayfield, General Partner at Album VC (#10)

The next Career Q&A is with John Mayfield. I’ve had the good fortune of knowing John for more than 10 years and he’s one of the most genuine and kind people that I know. I love his advice on adopting a give first mentality, the power of developing soft skills, and why people shouldn’t over-index on compensation in the first 15 years of a career.

John Mayfield is an early stage investor at Album with investments in Route, Neighbor, Filevine, Podium, Divvy, Weave, Qwick, and Homie, as well as a board member with the Rocky Mountain Venture Capital Association. Prior to Album, John was an early employee at Qualtrics and pre-IPO Instructure where he worked in sales, marketing, and new product launches. Prior to that, he spent several years in Silicon Valley working on M&A valuations for top software companies such as Oracle, HP, Yahoo, Cisco, and Amazon.

What’s a book that has influenced your career or life, and why?

One book that has had an influence on me that I almost never hear people talk about is The 15 Commitments of Conscious Leadership. The book is a must-read for anyone working with other humans. The concepts in the book have helped me identify in myself some of my unconscious reactions to work and life situations, it’s helped me in my approach to relationships, and overall improved the way I find energy to go after my goals. 

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

Don’t underestimate or forget the power of your relationships. I have loved watching friends and acquaintances from my past reemerge in my life in different contexts and being a resource to open up new opportunities for them and them for me. It’s something you have to live through to fully appreciate and I’ve found it very rewarding. 

Early in a career, it can feel like you don’t have a network but I’d challenge that and advise a college student to look around and develop relationships with those in your classes, clubs, and social groups. There are always people you can build friendships with and help out. Adopt a give first mentality and look for ways to help, it will come back around and it just makes life more enjoyable. The power of compounding is alive and well in the relationships you form early in your life and career. 

Advice to Ignore: I think most colleges have a built-in incentive to minimize risk and find the most expedient way to get people jobs–makes sense right? For some yes, for many or most I’d argue no. My experience is that colleges care very little about how fulfilled or meaningful your work will be and more about graduation and placement statistics. 

I believe that for college students, embracing uncertainty, tolerating more risk, being okay with developing networks and skills over steady pay, and having a more open aperture for opportunities creates more serendipity and many times more meaningful paths for a fresh graduate. 

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Salary is the primary focus for many people from the start and can lock you into a path that has limited upside, or worse, into a life you hate. Focus the first 15 years of your career on finding the right mentors, networks, experiences, and skills. After the first 15 years, you can start optimizing more for pay grade. 

What’s one of your proudest professional accomplishments? 

I’m most proud of the partnership we have at Album, the culture and brand we’ve built so far, and the incredible founders we’ve been fortunate to back. 

Since entering the workforce, how have you changed or transformed?

Growing up, school and early jobs teach you that it’s all about memorizing the right answers and doing tasks correctly and fast. I think I entered the workforce having that same mindset. 

Through years of experience and struggles, I’ve learned that it’s much more important to have softer skills like persuasion, critical thinking, and human relationship skills. While hard skills are important and have their place, at some point, you have to learn how to persuade other people to join your point of view after you’ve taken the time to think through something deeply. I now focus much more on how I effectively create accountability both in myself and others and find ways to create leverage in my day and structurally in our business.

When have you felt stuck in your career? How did you break out of it or push forward?

This is where a good mentor comes in. Find someone who is two steps ahead of you in an area where you’re interested who can help you navigate. I also get a lot of value out of reading books and a number of podcasts. A few podcasts I’d recommend whether you’re in the investment world or not include: Invest Like the Best, The Knowledge Project, and Naval Ravikant. 

What habit or practice helps you manage stress?

I’ve recently picked up a daily breathwork practice. Breathing is something that we rarely think about but can create a massive shift in our state if used deliberately. There are techniques for anxiety, general stress, lethargy, sleep, and more. There are many apps out there but I use Breathwrk and Wim Hoff.

For more Career Q&As, click here, or you can check out my monthly newsletter and podcast.

Career Q&A with Mia Mabanta, Head of Talent and Growth Initiatives at Y Combinator (#9)

Our next Career Q&A is with Mia Mabanta, Head of Talent and Growth Initiatives at Y Combinator. Mia provides excellent advice on how to view career opportunities with an abundance mindset, the power of long walks, why ‘fake it ’til you make it’ is bad advice, and how immigrating to the US taught her to be scrappy and resourceful. I hope you enjoy her insights as much as I did.

Mia Mabanta runs talent and growth initiatives at YC Continuity, Y Combinator’s growth-stage fund. Prior to YC, Mia led product marketing at Quartz, the business news startup, as the company grew 10X in revenue and headcount. She also cofounded a fintech startup, HelloWallet, which sold to Morningstar and spun out of research she had been working on at the Brookings Institution, where she began her career as an analyst. Mia has an MBA from Stanford.

What’s a book that has influenced your career or life, and why?

My Kindle is full of highlights from business/leadership-type books, but the book that has stayed in my consciousness longer than any other couldn’t be further from that genre. The Meadow by James Galvin is made up of poetic, intricately written vignettes chronicling a hundred years of life on… a meadow. The elegance with which he describes sensory details is almost meditative. Almost 20 years after I first read it, I still find that it helps me stay calm and centered in my life and work.

Was there an experience you had before age 21 that shaped who you are? What was it?

I immigrated to the US at 17 (for college) and have been largely independent ever since. At the time, I didn’t have much of a support base and had to figure out a lot of basic life things on my own: financial hurdles, visa lotteries, the DMV. I probably sent my resume to 100 companies before I got my first job offer, and had more brushes with deportation than I would have liked. I learned how to be scrappy and resourceful. It built up my resilience and taught me how to plan for the worst-case scenario.

How has a failure, or apparent failure, set you up for later success?

My biggest career misstep was hastily taking a job for the wrong reasons. On my first day, I knew I’d made a mistake. It made me seriously question my ability to make good decisions. But I then spent a lot of time thinking deeply about what was important to me in a job and company. At one point, I was printing out companies’ values and stacking them up against my own. Going through that exercise cemented how important culture and mission are, and within a few months I landed at a startup that I felt deeply connected to and (I think) had a lasting impact on, even years after I left. 

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

Don’t “fake it ‘til you make it.” Ask all the questions you need to understand a problem deeply. The best people, no matter their seniority, are the ones who ask questions to get the information they don’t have and work through problems instead of talking around them.

Also: Read a lot, especially about things that have nothing to do with your job. Find a great boss to work for. Spend time on relationships. There’s something to be learned from everyone you meet, whether it’s something to emulate or something to avoid. Learn how to think, speak, and write with clarity and conciseness. It’s amazing how much that sets people apart. 

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Ali Rowghani, my current boss, gives this piece of advice that I wish I’d had when I was just starting out: View career opportunities with a lens of abundance. There is so much to do and learn, so many problems to solve. When see your career this way, you start to focus more on the expansiveness of your own potential rather than the little distractions—job title, status, organizational politics—that inevitably come up.

What’s one of your proudest professional accomplishments?

My proudest professional accomplishment is probably the people I’ve hired. I love building teams and get a lot of fulfillment out of working through challenges together and celebrating wins. Whenever I’ve created an environment where people are working hard, having fun doing so, and genuinely care about one another, I feel like I’ve done a pretty good job.

Since entering the workforce, how have you changed or transformed?

Besides all the usual growth that one goes through as they advance in their career, one big change is that I’ve become much more adaptable to people’s different working styles, and better at communicating my own. It’s not that I was intolerant of different styles before—but with time and experience, I’ve gotten better at seeing where people are coming from and minimizing friction along the way.

What habit or practice helps you manage stress?

Every few days, I go on long music walks to decompress. I’ll listen to an album or two front to back while walking around. It creates this sensory experience that I find really soothing and quietly epic. Some albums I’ve been walking with lately are Put Your Back N 2 It by Perfume Genius, Historian by Lucy Dacus, Little Creatures by the Talking Heads, and Suddenly by Caribou. 

For more Career Q&As, click here, or you can check out my monthly newsletter.

Career Q&A with Ryan Seamons, Co-founder and Chief Product Officer at Sprintwell (#8)

Our next Career Q&A is with none other than Ryan Seamons, Co-founder and Partner at Sprintwell. There’s a lot of goodness throughout. I’ve always been impressed by Ryan’s commitment to learning and how intentional he is in living his life. Enjoy!

Ryan Seamons is co-founder and partner at Sprintwell. They help teams build habits of innovation without burning out. Ryan believes that everyone can do meaningful work, and that people growth and product growth go hand-in-hand. 

After a decade working in product management, Ryan loves helping others understand the mechanics and mindset that drive great product teams and save companies time, money, and energy. Ryan created the first internal version of LinkedIn Learning and led product teams as Director of Product at Degreed. 

He is passionate about education and family. He and his wife write about intentional family living from their experiences homeschooling their 5 children. He also created the “What do you really want?” newsletter with weekly conversations about getting what you want at work and in life.

ryan seamons

What’s a book that has influenced your career or life, and why?

First, Break All the Rules. This book got me into organizational behavior. It was eye-opening to realize that many people go into management not because they would be good at it, but because of the additional income and power. 

Gallup calls this the “blind, breathless climb”. This explains a good percentage of incompetence and friction at work. Just because someone was a good individual contributor doesn’t mean they will be good at managing other people doing that thing. We promote people just beyond their capabilities. 

That book was the beginning of my finding the problems I care deeply about — the reality that:

  • Most people don’t like their jobs.
  • Many managers aren’t ever equipped and enabled to guide meaningful work.
  • Often companies have no idea how to build sustainable habits of innovation.

There’s a better way. We should all be able to find meaning in our work. Management can be a noble profession. And innovation is more like math than magic. 

Was there an experience you had before age 21 that shaped who you are? What was it?

I served a 2-year mission for my church in Bangkok, Thailand. While the entire experience was incredibly formative, the most impactful part was 9 of those 24 months spent living with native Thai companions (missionaries pairs are called “companionships”). 

It’s incredible to spend 24/7 living with someone from a different cultural upbringing. To speak their language and learn about their country and culture by observing them. I made too many mistakes to count. My world view was challenged over and over again. But not a day goes by that I don’t use the skills of empathy, observation, patience, and compassion that I learned from my time with them. 

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

Lots of failures to choose from. 😂

My favorite failure ended up being the best thing that happened to me. I dated this girl in high school that broke my heart, per my mother’s encouragement (my mother didn’t want me dating seriously so young). I was hurt and discouraged but moved on. 

A few years later that girl and I reconnected, had a quick engagement and got married. We were both a little older and wiser and the time allowed us to both grow up. A decade of travel, entrepreneurship, and 5 kids later I realize the best thing in my life probably wouldn’t have happened had it not ‘failed’ first. 

Thanks, mom. 

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

1) Never stop learning. Most people get stuck because they stop learning. 

2) Spend time early and often deciding what you really want. Too often we choose a path for the wrong reasons. It’s easy to accept the script of others but it ends up being the #1 regret at the end of people’s lives

3) Be Bold. I got my first internship by first being told that a recruiter “wasn’t looking for interns, only full-time”. I was about to leave, but then turned back around and asked, “well, if your company were to recruit an intern, who would I talk to about that?” He sized me up for a few seconds, then handed me his business card with the email of a colleague written on it. That one moment of boldness turned into an incredible experience where I first got exposed to applied bioinformatics, web development, design, consulting, database, etc. Many skills I have used in my career came from that moment of boldness. 

What are the bad recommendations you hear in your profession or area of expertise?

“The Product Manager is the CEO of the product.” It’s a horrible mindset that leads to a lot of stress and poor expectations. Too many people go into product management because they think they will be in charge or be able to call the shots. That’s rarely the case. 

A product manager is a lot more like an American football quarterback or a pirate captain. You have to be a master of influence without authority. Your job is a lot more about alignment, inspiration, and communication than many expect. The hard skills of market research, analytics, prototyping, etc are important, but if you don’t build trust with your stakeholders and team, you’ll never deliver value to customers in the way you hope.

So many teams grind to a halt because product managers don’t prioritize the people side of product management. 

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Optimize for learning. Learning compounds just like money. Given the choice, choose the opportunity where you’ll learn most.

This has driven my choices in schooling, switching teams/companies, and how I spend a good deal of my free time. More than ever you will stand out by intentionally learning (vs binging on Netflix or social media). There is so much knowledge out there. Spend a few minutes each day consuming in a high-quality way and you’ll stand out with your ability to help others and lead change.

Who is one person, dead or alive, who you admire? Why do you admire them? 

Stephen Covey. I love the stories about how he prioritized his children, even while working hard. I hope to influence just a few people the same way he influenced millions.

What habit or practice helps you manage stress? 

Whenever my wife and I are stressed out or overwhelmed, we have a “whiteboarding session”. 

This is a technique we use in our consulting at Sprintwell to help teams get clarity and alignment. But it works incredibly well for individuals or couples as well. 

We pull up a whiteboard (or document) and go through the following steps:

  1. Write down what’s going well. 
  2. Write down what’s not going well, stressful, or needs to get done
  3. Organize the list, putting like items together and then sorting by priority. 
  4. Make some quick decisions about next steps. 

This always gets us unstuck and facilitates positive conversation and action.

When have you felt stuck in your career? How did you break out of it or push forward?

I had a boss who once told me that I didn’t have what it took in the career path I was hoping for. I remember being devastated. I was pretty mad walking out of that 1:1. I distinctly remember realizing that I could decide how I responded. I decided to ask myself, “what can I learn from this?”

Suddenly I realized how much I could learn. I did have a long way to go. So, I got to work learning. Now, years later, I’m sharing the knowledge I learned with product managers and leaders at some of the world’s most successful companies. I might not have built that expertise if I hadn’t been “challenged” by that boss. 

For more Career Q&As, click here, or you can check out my monthly newsletter.


Career Q&A with Lisa Lee, VP of Global Culture, Belonging, and People Growth at DoorDash (#7)

Our next Career Q&A is with my friend and colleague Lisa Lee, VP of Global Culture, Belonging, and People Growth at DoorDash. Lisa provides fantastic advice on bouncing back from failure, creating stronger and more inclusive teams, and the need to continually invest in building relationships.

Lisa Lee is the VP of Global Culture, Belonging, and People Growth at DoorDash. She oversees Employee Connections, Diversity & Inclusion, Internal Communications, and Learning & Development, weaving together these four critical areas to create an interconnected strategy so DoorDash’s employees can do the best work of their careers.

Lisa joins DoorDash from Squarespace, where she led the creation of its first diversity and inclusion strategy. Before Squarespace, Lisa served as Pandora Media’s first Director of Diversity and Inclusion Strategies. Prior to joining Pandora, Lisa was at Facebook where she led initiatives in User Operations, Product Operations, and Diversity Programs.

Lisa served as the publisher of Hyphen magazine, an award-winning publication about Asian American arts, culture, and politics, co-founded Thick Dumpling Skin, a positive body image community for the Asian American community. Most recently, she co-launched The Margin, making space for people of color at conferences around the world.

lisa lee

What’s a book that has influenced your career or life, and why?

Bryan Stevenson’s Just Mercy is a book I will forever remember not just for the important message it has for all of us, but also for the way it made me feel. 

Just Mercy documents Bryan Stevenson’s life long quest to free wrongly convicted people from death row. The majority of his clients being poor people of color from the South who were targeted in a justice system that is systematically unjust. 

I remember the day that I finished the book, I went to a meeting for a nonprofit organization that I volunteered with and just cried the whole drive there. In doing diversity and inclusion work, one can easily become so well versed with the data and “the business case for diversity” that it’s easy to forget about the lives of real people who are impacted as a result of racism, sexism, and other forms of bias. Bryan Stevenson’s message reminded me that if we want to solve the problems that we see, we must become intimate with the people impacted and the system that perpetuates those persistent problems.

Was there an experience you had before age 21 that shaped who you are? What was it?

I was born and raised in Taipei, Taiwan. At the age of nine, my family immigrated to South Africa and we immigrated again to Los Angeles, California when I was 15. Throughout, my parents weren’t always with me and my siblings because they worked abroad to provide for us. 

The experiences of assimilating within such vastly different cultures without a traditional family unit had a profound effect on me in my understanding of the world and myself. I learned to be independent and to trust myself (as much as this is a lifelong journey). I learned to be resilient and to acknowledge my differences. I also learned that you can learn from everyone around you, especially those who don’t look like you or reflect your upbringing. 

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

Earlier on in my career, I prided myself on being principled. I had a strong sense of right and wrong. Frankly, I probably felt like I was right most of the time! While this served as a guiding light for me in my life, it didn’t help me to be a great listener and I didn’t always make room to understand other people’s perspectives. Rather than asking myself, “how can I make sense of this?”, I would double down and become frustrated. 

This lack of curiosity on my part resulted in some major failings with internal partners and stakeholders, where even as I wanted to lead, I was getting further and further away from that goal. 

Looking back, the failures helped me to learn a few things: 

  • Listen, and do not listen to speak or defend. Listen to understand the other person’s perspective and the impact that you had on them through your actions 
  • Hone and master your craft. Deliver excellence always, even when it is hard. If you’re thinking that people have different standards of excellence, sure. Then go back to #1 and also ask yourself “am I putting out work that I am proud of?”
  • It’s ok to feel ashamed, but don’t let it erode your faith in yourself. We all have our good days, bad days, highs and lows. Take the time to acknowledge, “I could’ve handled that better” and even sulk for a few days is absolutely ok! But don’t beat yourself up to the point when you’re so down on yourself that you can’t see clearly. 

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

Graduating from high school, I didn’t get accepted to any of the schools I had my heart set on. Growing up in a community where mostly many people in my circle touted their prestigious school acceptance like a badge was especially tough. It was around that time that my dad told me that life is a marathon, so don’t let one milestone (or the lack thereof) be the determination of where you’re going. This stuck with me. We all have our own timeline, even if you don’t know where that destination is. Focus on being the very best at what you get to do every day. Be prepared, do your homework, and ask questions. Be open to all possibilities, and friendships, because you never know what doors people can open for you. 

This may be an unpopular opinion, but I would ignore the advice around “don’t worry about money,” or “just follow your dreams.” Financial independence for me was incredibly important since my family was far from well off. At a young age, I knew that my parents were under a lot of pressure for taking care of their four children and I knew that I wanted to 1) not be a burden on my parents financially, and to 2) take care of them one day. Depending on your circumstances, money could be a very real reality for you. Find ways to feed yourself and your family (literally), as well as your soul. It may mean putting in more work, after work hours, but know that the two are not mutually exclusive. 

What are the bad recommendations you hear in your profession or area of expertise?

These are more common mistakes that get shared out as good practices rather than bad recommendations.  

  • Start with “gender diversity”: Gender diversity is oftentimes, in action, synonymous with increasing, promoting, and retaining white women. This is dangerous because it implies there’s a pecking order in how a more diverse and inclusive workforce can and should be achieved, and it further ostracizes and excludes women of color (and men of color) by not addressing experiences that they’ve had. 
  • Setting up Employee Resource Groups as (the start to) a company’s diversity and inclusion (D&I) efforts: Employee Resources Groups can only be as successful as the leaders of the company want them to be. They’re oftentimes seen as fun extracurricular activities that only the employees themselves care about, yet companies like to tout them as a badge of honor. It’s important to remember that Employee Resource Groups are oftentimes formed to yes, build community, but also to address gaps that underrepresented employees feel, whether that is a lack of representation in the company’s leadership or practices that could be improved to be more inclusive. Therefore an incentive and reward structure needs to be created to sustain Employee Resource Group participation, and funding, as well as leadership involvement, needs to be built into the structure from the beginning. 
  • Focusing D&I efforts mostly on recruiting, or at the talent attraction level: Many companies think of D&I as a recruiting problem, and think that investing in recruiting is a good start, instead of looking at the employee lifecycle holistically. While it is important to set goals around increasing underrepresented people in the applicant pool, it is just as important to ensure that people can come into your company and grow to have meaningful impact. 
  • Learning and Development efforts being separate from D&I efforts: “Unconscious Bias Trainings” have traditionally been divorced from manager trainings and other curriculum offerings at a company. Amongst training topics, such as coaching and delegation, where unfair treatment often happens, it is important to educate how bias can cause us to give disparate amounts of time to people of different backgrounds and how we may inadvertently delegate more “house” work to women, such as note-taking and planning team offsites. In order to correct unhealthy power dynamics at work, especially if your company has had a more homogenous workforce, it is key to embed D&I training into all L&D efforts because it is incumbent on everyone to create an inclusive culture that will enable diversity to grow. 

What’s one of your proudest professional accomplishments? 

In addition to purchasing my own home before I turned 30, I’ve been able to support my parents and siblings in their home ownership. As an immigrant and a child of immigrants, I’ve spent most of my life being obsessed with the idea of “home” and I love that we’ve been able to find it and create it for our family.  

What habit or practice helps you manage stress?

A few years ago I made physical fitness a priority to help me manage stress and to feel more balanced. I work out with a kettlebell trainer twice a week and go to yoga about twice a week. During the summer I love biking in New York as a form of (fun) commute. 

I also set reading goals every year to get through a number of fiction books. To reach the goal, I go down the rabbit hole of finding my “next book” and it can be fun researching. 

One of the greatest benefits of living in New York is, of course, experiencing great art! I was a theatre and performance studies major in college so I make sure to attend theatre performances, live music, and even comedy. It’s always inspiring to be wow’ed by other people’s creativity, which helped me to think about how I can be even more innovative in my own work. 

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Invest more time in relationships. Given that I had a lot of interests outside of work, I didn’t spend a lot of time getting to know my coworkers because I always had somewhere to go, whether that was volunteering or my existing friend circle. Many people that I used to work with are doing absolutely incredible things now with their lives and I could be learning more from their journeys.

For more Career Q&As, click here, or you can check out my monthly newsletter.

Career Q&A with Kelly Palmer, Chief Learning Officer at Degreed (#6)

Our next Career Q&A is with Kelly Palmer, the Chief Learning Officer at Degreed. Kelly offers great advice on managing career transitions, developing confidence, and the three “power skills” that will make you successful in the future of work.

Kelly Palmer is on a mission to change the way the world learns. A well-known thought leader on learning, business, and career development, she is currently on the executive team of Degreed and was formerly the chief learning officer of LinkedIn. She is the co-author of the book The Expertise Economy: How the smartest companies use learning to engage, compete, and succeed, which was named one of the best business books of 2019. Kelly speaks regularly at companies and business conferences around the world, has been featured in Harvard Business Review, the Financial Times, Fast Company, Entrepreneur, Inc, and Barron’s among others. Kelly lives in San Francisco.

Kelly book photo high res may 22 2018

What’s a book that has influenced your career or life, and why?

This may sound cliche, but “To Kill a Mockingbird” really influenced my early life as a child and then again when I was older. I remember watching the movie with my mom when I was a child and realizing for the first time that there was injustice in the world and that there were people like Atticus Finch who stood up for what was right even when so many were against him. Later in high school we read and analyzed the book and then again in college as an English major I studied it extensively. It has always held a huge place in my heart and in my thinking about life.

Was there an experience you had before age 21 that shaped who you are? What was it?

My mom was diagnosed with cancer when I was 17 and died when I was 19 and a freshman in college. I was incredibly close with her and losing her at such a young age (she was only 39) and at such a formative time in my life forever shaped my worldview and my perspective on life. For the first few years after her death, I was angry, lost, and confused, but then I was determined to embrace life’s opportunities because, after that experience, it seemed that not much in life could ever be so tragic. There is a certain strength that comes with early loss, and I think that’s influenced so much of my life.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

It’s interesting in retrospect to see what choices or events in life change the path you are on. For example, when I was early in my career, I applied for a job at Microsoft and didn’t get that job. If I had gotten that job, I would have moved to Seattle and been on a different path. Instead, I got a job at Sun Microsystems where I spent 20 years of my career, met my husband, and stayed in the Bay Area.

Later in my career when I was running a large product development organization, I interviewed for a job in a different group in engineering at Sun and didn’t get that job, but ended up going into the learning field instead. At the time, not getting those jobs seemed like huge failures to me, but over time I realized those “failures” just set me up for different opportunities in my life.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

I actually talk to quite a few recent college grads (my son and his friends are in that category). There is so much pressure to get a great job and be on a career path and to move up quickly, and my advice is to instead look for experiences that will help you build your skills and not focus so much on promotions and the job that pays the most money.

Those things can come over time, but if you get experiences that show that you have and are learning skills that are critical to the future of work, that’s what is going to help people be successful in the long run. For example, if you demonstrate learning agility (the curiosity and motivation to learn new skills over the entirety of your career); if you show that you can communicate and collaborate effectively; and, if you have emotional intelligence and empathy, those things will take you far in your career. Those uniquely human skills are what I call “power skills” that will make you the most successful in the future of work.

What are the bad recommendations you hear in your profession or area of expertise?

I hear executives and leaders at companies try to solve business problems by suggesting we just send everyone to a training class! It really drives me a bit crazy. We write in The Expertise Economy an example of one company wanting to send all managers, at every level, through a training class that will help them make better hiring decisions because a few managers were making bad hiring decisions. This one-size-fits-all approach does not work. Many managers already have that information and know what they should be doing, but are just not applying it; other managers may be really great at this skill already; and others may not be hiring people at all at this time, so the information is not relevant. This is not a good approach, but it’s the first thing people jump to when trying to solve a problem. As people in my profession know, this might not even be the real problem you are trying to solve.

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Have more confidence. When I was mid-career, I had a leader at Sun Microsystems coach me on going after new opportunities and having more confidence in my abilities and it really made a difference. I’m not sure he even realizes what an impact it made on me and my career, but I’ve tried to pass on that advice and coaching to people I’ve managed and mentored over my career. The research shows that women in the workforce feel they need to have 100% of what is needed when they apply for a job and that men feel they need about 60%. That’s about confidence in your abilities and the mindset that you will be able to do that job.

What’s one of your proudest professional accomplishments? 

For a while, I’ve had a dream of writing a business book to help impact the way people think about learning, and last year that book was published: The Expertise Economy: How the smartest companies use learning to engage, compete, and succeed. The thing I’m most proud of is the feedback I’ve been getting from people in the industry that it’s helping them in their companies move to a new paradigm in learning.

What’s something unexpected that has happened in your career, and how have you responded?

I was asked to move completely out of my comfort zone and area of expertise to integrate one of the companies we were acquiring at Sun. At first, I was thrown off balance wondering if I could actually do it. But, then I gained some confidence and got some coaching and mentoring along the way and I realized I not only could do it, but I could do it quite well. That turned into a career move to corporate strategy at Sun where I ran the acquisition integration function for all the companies we were buying at Sun.

Since entering the workforce, how have you changed or transformed?

That’s a big question since I think throughout my career I’ve been changing and transforming. Probably the biggest area where I’ve changed is that I’m more confident about working on new and interesting challenges that I haven’t tackled before and that learning about new things keeps life interesting.

What habit or practice helps you manage stress? 

I have two golden retrievers and I take them for long walks so we all get some exercise and get the endorphins going. Getting outside and walking (sort of like a walking meditation) always helps me think and reflect on both my personal and professional life and is a great way to manage stress.

Who is one person, dead or alive, who you admire? Why do you admire them? 

I just watched the documentary “Inside Bill’s Brain: Decoding Bill Gates.” What an amazing human being. When I was at Sun Microsystems he was always painted as the bad guy since Microsoft was one of our biggest competitors, but I’ve got a completely different view now. What he’s doing to try to solve some of the world’s biggest problems (climate change, world disease) is so admirable and I also admire his relationship with his wife, Melinda, and how they are working on these challenges together. While some use their fortunes for their own personal gain, he has devoted himself to higher causes and that I greatly admire.

When have you felt stuck in your career? How did you break out of it or push forward?

I felt stuck for a while after I moved into corporate strategy. I was always open to new opportunities but didn’t feel like I was necessarily doing what I was personally and professionally passionate about. That’s when I completely changed my career and went into the learning field. I thought maybe I should quit the tech industry and move into non-profit and focus on education, but realized I had no experience in either non-profit or education! Then I got an opportunity to move into an executive position at Sun to lead part of a large learning organization — the leader then took a chance on me. It was the turning point in my career and I’m forever grateful for it. I ended up going back to school to get my master’s degree while working and studied adult learning theory and education technology. It’s been my passion ever since.

For more Career Q&As, click here. Or you can check out my monthly newsletter.

Career Q&A with Ann Hiatt, Leadership Consultant and Former Executive Business Partner to Jeff Bezos and Eric Schmidt (#5)

I recently kicked off a series of Career Q&As with successful leaders. The goal is to provide practical advice and insightful lessons you can leverage to further your career. Next up is Ann Hiatt, a leadership consultant, and the former Executive Business Partner to Jeff Bezos and Eric Schmidt. Ann offers great advice on taking career risks, trusting your intuition, and effectively managing stress.

Ann Hiatt received her initial business training during 15 years as the Executive Business Partner to Jeff Bezos (CEO of Amazon) and Eric Schmidt (CEO and Executive Chairman at Google/Alphabet). Ann now consults with executives of Fortune 500 companies as well as European and Silicon Valley startups and is on several advisory boards. Ann has recently relocated from Silicon Valley to Europe and brings with her a unique perspective on what it takes to succeed in business today and how to apply that to any organization. She is also a sought-after international speaker having spoken at conferences across five continents.

Ann is a native of Seattle and studied International Studies at the University of Washington before moving to California to begin a Ph.D. at UC Berkeley. She speaks Swedish fluently and Spanish conversationally among other European languages. In her elusive free time, Ann enjoys running, scuba diving and traveling.

ann hiatt

What’s a book that has influenced your career or life, and why?

I love anything written by Adam Grant. His book, Originals, is a favorite of mine since I’ve spent 15 years of my career surrounded by and collaborating with truly original thinkers and am fascinated by them. His insights and research really ring true for me. Also, he’s a spectacular human being. If you’re not already following him, you should!

Was there an experience you had before age 21 that shaped who you are? What was it?

My first job ever was at a startup in Redmond, Washington in 1995 (back before anyone knew what a startup was). I learned from the entrepreneur founders (who were also brothers) what it’s like to start your own company, land your first clients and grow your first team. I had no idea how much that job was preparing me for my future career at Amazon and Google and beyond. 

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

I almost killed Jeff Bezos two months after being hired at Amazon in 2002. Seriously. Luckily that isn’t the end of the story or my career.  While it was the worst day of my professional life, it taught me that no matter how spectacularly you fail you always learn something. When the helicopter that I hired for Jeff Bezos crashed with him inside I learned that I am really good under pressure and with crisis management.  I just hope to never need to use that skill in that way again!  

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

I would say to take big risks early on. Don’t be afraid to ask the “dumb” questions or to show lots of ambition.  You will never ever receive anything if you don’t ask, so be bold! I wish I had learned that lesson 10 years earlier than I did.  Oh, and max out your 401k savings contributions every year—especially in those early years. Compound interest is your best friend! 

What are the bad recommendations you hear in your profession or area of expertise?

I have been lucky to work in very innovative companies and teams. With that said, there have been times when even those people told me no when I wanted advancement. I had to trust my gut, rather than listening to advice to be happy with what I had, and push harder to find creative ways to accomplish my growth goals. Eventually, that meant taking the scary step of starting my own venture.

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Be bold! Aim much, much higher than you can currently imagine. 

What’s one of your proudest professional accomplishments? 

Most of my proudest moments involve creating success within impossible circumstances. At the moment that means building a 6-figure consulting business in less than a year after leaving Google—all while in a new country, language and network.  I love helping global entrepreneurs thrive!

What’s something unexpected that has happened in your career, and how have you responded?

My very first job out of university was working for Jeff Bezos at Amazon. That came very unexpectedly and literally changed the course of my life. I learned not to fear failure, to be bold, and to trust my instincts. 

Since entering the workforce, how have you changed or transformed?

When I started at Amazon in 2002 I was timid and deferential. That didn’t last long!  In order to survive in that environment, you have to be daring and confident. Those lessons served me well when I left Amazon to start a Ph.D. at UC Berkeley and then in my 12-year career at Google as the Chief-of-Staff to the CEO. Now as an independent consultant I use those skills and experiences every day with my CEO clients. I am so blessed to have learned to be proud and confident whether I’m on stage, coaching a CEO or in a one-on-one mentoring session. I still have moments of doubt and imposter syndrome, like most high performing people, but I’ve learned how to combat.

When have you felt stuck in your career? How did you break out of it or push forward?

I loved every minute of working at Google but eventually decided to leave in year 12 because there weren’t opportunities for me to grow there. I had hit a ceiling that felt arbitrary and I wanted a bigger challenge. I realized that that kind of challenge would only come if I took a leap of faith in myself and started my own company. It’s been both terrifying and very satisfying.

Who is one person you admire? Why do you admire them? 

The notorious RBG! Ruth Bader Ginsburg is a pioneer who has broken glass ceilings for so many people. She is brilliant, clever, quirky and unapologetically herself. 

What habit or practice helps you manage stress? 

I had a full-on midlife crisis a few years ago and found that exercise is my very best form of therapy. (Although I did talk therapy as well!) I find now, even when life is happy and calm again, that I need protected time every single day to move my energy out of my head and into my body.  I need the sunshine and fresh air and relentless pace to keep me grounded so that I can then do my best mental work. In true Silicon Valley form, several years ago I signed up to run a half marathon to raise money for charity before I had ever even run a 5K. I am happy to say that I completed that goal (several times over now) and felt very strong and proud at the end—which was exactly what I needed at that moment in my life. I have continued these physical challenges to myself which helps my drive and confidence in all areas of my life.

For more Career Q&As, click here. Or you can check out my monthly newsletter.

Career Q&A with Scott Smith, CEO of CloudApp (#4)

I recently kicked off a series of Career Q&As with successful leaders. The goal is to provide practical advice and insightful lessons you can leverage to further your career. Next up is Scott Smith, CEO of CloudApp. He has a lot of good nuggets throughout and I particularly like his advice on spending as much time as possible feeling uncomfortable, how he balances work and family life, and the power that comes from assuming positive intent.

Scott Smith is CEO of CloudApp, whose mission is to enable instant business communication through quick shareable videos and images for its 3 million users. Before CloudApp, Scott spent three years at Facebook developing and launching the ‘Workplace’ collaboration tool. He joined Facebook through an $85m acquisition of Parse, a YC-backed developer tools platform. Before that, he spent three years at Dyn building its sales and partnership channels. Dyn would eventually be acquired by Oracle for $600m. He’s a dad of three of his own, and foster dad too. You can find him on Twitter at @scotcha1.

Scott Smith headshot

What’s a book that has influenced your career or life, and why?

“The Hard Thing About Hard Things” by Ben Horowitz. In the book, Ben tells a story about when he joined a brand new startup. His daughter had just been diagnosed with an illness, and he was extraordinarily busy and stressed. He spent a lot of his time thinking about his job, and himself. One day his father came over to visit, and as they sat and talked, his father said: “Ben, do you know what’s cheap?”. Ben replied, no, and his dad said flowers. He then said “Ben, do you know what’s expensive? Divorce.” 

His father was reminding him to refocus on what was most important — his family and their well being. This idea of family as a focal point in life has always been important to me. The idea that “No other success can compensate for failure in the home” is something that motivates me, and Ben’s book really resonated with this on a very practical level. 

My family keeps me grounded and focused. But frankly, the idea of family is often understated or shied away from in Silicon Valley. Most of us here are desperate to win, succeed, or to gain some level of notoriety. I loved the honesty and vulnerability that Ben showed in sharing that story. And it’s helped me throughout my 10+ years of marriage to always be reminded of how I got to where I am, and what’s most important.

Was there an experience you had before age 21 that shaped who you are? What was it?

When I was 19 I left the United States for 2-years to do a service mission in Birmingham England and Cardiff Wales. I can still remember my very first day as a full-time volunteer. I was picked up from our training center and I was immediately taken to the Birmingham City Center “Bull Ring”. The ‘Bull Ring’, was a popular shopping center booming with tens of thousands of people walking around. My leader said “Okay, go find someone to talk to” and he quickly disappeared. I looked around shocked, and very concerned, but made the decision to say “Hi” to the next person who walked by. From the moment I entered the UK, I was perpetually in a place of discomfort being asked to do hard things. And while it was hard, this experience allowed me to learn to embrace discomfort and try things that made me uncomfortable.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

At the age of 11, I tried out for the 11 & 12-year-old Milburn All-Star baseball team. For years I had been a well recognized, and fairly successful pitcher throughout our local little league, but when the list came out showing who had made the team — my name was notably absent. That team went on to play in the Regional Championships just shy of the Little League World Series. The team traveled all over the Northeast Region, stayed in hotels, were featured on TV, and they played against some of the best teams in the nation. 

I was really discouraged and disappointed to have not made that team. It was one of the first times in my life where I really felt the weight of what a future could look like where you might not be good enough despite your best efforts. While I can’t say that moment was the catalyst that led me to be the greatest pitcher in MLB history, that memory and moment has left an indelible mark in my mind and life of a feeling I just hate to experience. Failure is important, and it helps us grow, but I absolutely hated the feeling of coming up short, and ever since then it’s motivated me to work harder.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

My advice would be to spend as much time as possible feeling uncomfortable. Stretching yourself to try new things, and to say yes to things you might not have all of the information for.  One of my favorite moments as a very new sales rep at Dyn (my first full-time job after college) was when they invited me to work at their booth at a conference in Santa Clara, California. I had only just recently joined the company several weeks earlier, knew almost nothing about the product, and the first person I spoke to at the booth was a high ranking technology officer at Cisco (I’m pretty sure it was the CTO!). 

As I looked around me, hoping to receive help, no other team member was jumping in to help me, and I realized I was all alone. I stretched the knowledge I had about the product as far as I possibly could, and surprised myself when we ended the conversation several minutes later. Reflecting back on this experience, it all started from saying ‘Yes’, when my VP Sales, Kyle York, asked if I’d be willing to attend this conference last minute and fly across the country.

What are the bad recommendations you hear in your profession or area of expertise?

I hear bad recommendations all the time. But I also have a career behind me full of perspective. I think the worst kinds of recommendations are given without any context. These are recommendations that someone you are meeting with tells you before they understand your situation. Silicon Valley is full of thought leaders and ‘yogis’ who tell you their way is THE way. 

I think rather than providing a list of bad recommendations, and the ones to avoid, I’ve always tried to follow a relatively simple process that my dad suggested to me years ago when I started playing little league baseball. While I was young, every year I had at least one new coach. Each coach had different suggestions. Some would tell me to throw curveballs, others would tell me to carefully avoid them because they would hurt my arm. Other coaches would recommend I change my batting stance (move forward, or backward, change my hand grip). All of the suggestions came from a place of good intent, but if I changed my approach to the game as quickly as I was asked to, I wouldn’t have been able to keep up and it would have severely affected my game. 

In the professional world, any time I hear what seems like a great idea that might require me to change, I write it down, think through it for a few days, and consider how it could fit into my current approach. I also always tend to be a Googler of new ideas. I love to find other people who might have tried out the approach and to hear their experience. But what I’ve found to be the most compelling and powerful, is to, over time, build a group of people I respect and trust, who I can ask and solicit feedback from. So my recommendation is basically to take recommendations carefully and thoughtfully but to always be open to them.

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Always assume positive intent. This is a philosophy that I now live by, that has largely changed my work experience. By positive intent, I simply mean, when someone does or says something, choose to believe that they are acting with the intent of good. That they are trying to provide good feedback, or they are trying to help improve your product. Never choose to be a victim. Rather than spending time or energy believing that the person hasn’t put in their best, or that they are trying to do something that is hurtful to you, spend your energy and time believing that they have your or your companies best interests in mind.

What’s one of your proudest professional accomplishments? (while this can include an obvious accomplishment, feel free to include a more personal one)

On April 25, 2013 Parse was acquired by Facebook for $85m. This felt like a significant event for me because it demonstrated that we, as a small 20-person team, had built something so incredible that one of the largest companies in the market wanted us to join them. We even received an email from Mark Zuckerberg welcoming us to Facebook, expressing his desire to include us in his larger vision for the future of their developer business. But, maybe even cooler, and on a personal level, was that Parse was mentioned during a segment of Facebook’s quarterly earnings call. On that day, I received a call from my father in law who had mentioned that it was ‘pretty cool to hear about your company in the Wall Street Journal today’. 

What’s something unexpected that has happened in your career, and how have you responded?

When Parse was acquired by Facebook, we were all very surprised. We were brought together at a small all-hands meeting, and our CEO, Ilya Sukhar, excitedly (and a little anxiously), described that we would be joining Facebook. The team instantly had a million questions. Would we need to move our office from SF to Menlo Park? Would Facebook shut us down, like so many companies before it? Did we all have jobs still? The questions were many that day, and even after our CEO patiently answered many of them, our team was unclear about our future, and you could sense a general feeling of discomfort. 

After joining Facebook, it became very clear that there were some incredible opportunities in different and adjacent parts of their business. Facebook, for example, had a larger, and more mature, developer partnerships team. Rather than trying to go about everything alone at Parse, developing relationships and partnering with that team seemed like an obvious way to continue to grow Parse within Facebook. 

While on a developer relations trip in Europe, I had dinner with a Facebook director named Julien Codorniou. He was charismatic, energetic, and I felt like he had a great grasp of Facebook and its future. After meeting him, I reached out over email, and we developed a relationship that led to me joining his team. While my initial experience going through the Facebook acquisition was unexpected, I was able to leverage Facebook’s strengths to provide myself and Parse with a larger platform.

Since entering the workforce, how have you changed or transformed?

When I was in high school and college, I tended to frequently just ‘show up’ at classes, and tests. By ‘show up’ I mean to say that I either did little or no preparation. Looking back now, I’m not sure why. But I wouldn’t be caught dead doing that today. One of the biggest changes for me has been to realize that doing your best work takes an immense amount of effort and preparation. The workforce is a grind. You commonly hear the phrase, “Choose a job you love and you’ll never work a day in your life.” I don’t agree at all with that phrase. Work is a grind, and you need to be ready to grind. While I regularly get to experience the excitement and love for my work, I also regularly have to experience the deep troughs of failure, regret, and discouragement, and I still need to press on, prepare, and deliver what’s expected of me.

When have you felt stuck in your career? How did you break out of it or push forward?

9 years ago, I moved from the Manchester New Hampshire Dyn office, out to San Francisco to open a small west coast branch. I had, in large part, moved from the East Coast to the West Coast to be closer to family. My dad recently had back surgery and I wanted to be closer to support him in his advancing Parkinson’s Disease. 

Dyn provided a wonderful experience for me, but when I moved out West, I admittedly had underappreciated how hard it can be for a small branch to feel important to a primary headquarters. Not to mention the fact that I found it incredibly hard to transition from an incredibly beautiful 20k+ square foot office in Manchester to a literal 15×15 foot room with white walls and no windows. Just a small box for me to work in. My team and leadership were now remote to me, and it was a challenge to feel included, and supported. 

I pretty quickly felt like I was on an island, and I felt like over time there would be few opportunities for advancement given the low interest in growing that office by Dyn. As I started to go on more local sales calls, I frequently heard from the CEOs that were my customers that they would be interested in hiring me. I was admittedly a little surprised to hear this, but I started to become open to the idea of finding something better suited for my career track and interests. 

What habit or practice helps you manage stress? (the more specific you can be, the better)

For the entirety of my 10+ years of marriage, my wife and I have gone on a date night nearly every single Friday. The date night is pretty simple, and it usually follows some kind of template: whether it’s dinner and a movie, games and dinner, visiting a bookstore, or occasionally knocking off a few high priority to-dos at Home Depot. 

The main ingredient that I feel that is critical, and honestly the priority of the night, is the personal, devoted, and focused time spent building a relationship with my wife. We have 4 kids all under 8, and life can sometimes be pretty wild at home after work and there are few opportunities for quiet and peace. Quite literally, they seem to try and interrupt any and every conversation we try to have. 

The date night allows me to end the week, put down my phone and computer, and to begin to release and put down some of the stress I’ve been carrying. It helps me connect with a person that provides me with so much love and support, and it helps us put the week into perspective, and go into the weekend a little more slowly. Plus, and I think this is most important, it gives you time to find out how your spouse is doing, to find opportunities to do things with them that they love, and to remind them that even if you’ve been distracted a bit earlier this week, that this time is just for them, and you can show them how important they are to you.

For more Career Q&As, click here

Career Q&A with Eric Hass, Analytics Leader at Amazon (#3)

I recently kicked off a series of Career Q&As with successful leaders. The goal is to provide insightful lessons and practical advice you can leverage to further your career. The next interview is with Eric Hass, an Analytics Leader at Amazon. I love his advice on taking action without asking permission, avoiding the law of averages, and habits for managing stress.

Eric Hass is an Analytics leader at Amazon. He’s spent the past 10+ years in a mix of data and business roles, from leading teams to launch new products to driving growth in mature $100M+ businesses. He’s currently leading a cross-functional team (data science, software engineering, product management) to solve personalization and optimization challenges on Fire TV and Fire Tablets.

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What advice would you give to a smart, driven college student about to enter the “real world”?

One of the challenges to get the internship / job you want early in your career is that you may not have relevant experience for it. It’s a chicken and egg problem. This problem can also manifest itself later in your career if you want to change functions/industry, etc. My approach has been to find an opportunity to just start doing what I want to do before seeking a new job. A few years ago, I decided I wanted to transition from product/business management into data science and tech leadership, but I didn’t have a formal educational background in the area. I took on a project in my current role to develop a machine learning based product plan and did some self-study to learn the basics. I was able to leverage that experience to get an individual contributor role working closely with one of the most senior data scientists at Amazon. I focused on learning as much as I could in that role, and after a year was given the opportunity to lead a cross-functional team over science, engineering, and product management…So, my advice is to not wait for anyone to give you permission to do what you want to do. Just find opportunities to start doing it, and doors will open.

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be? 

I would have prioritized getting educated in data science and computer science while in school. Being able to work with and lead engineers enables you to create value for customers at great scale, even if you don’t end up becoming a scientist or engineer yourself. I’ve learned a lot of this on the job and self-study, but I wish I would have prioritized it earlier.

What habit or practice helps you manage stress? (the more specific you can be, the better)

I focus on three things: 1) Sleep, 2) Exercise, and 3) Boundaries and focus.

Sleep – Through trial and error, I found that I get more accomplished by getting a full 8 hours of sleep, than by sleeping less and having reduced energy and mental capacity throughout the day. I know others who seem to be productive sleeping much less, but a lot of research is coming out on the short and long term benefits of sleeping a full 8 hours. The Circadian Code by Sachin Panda was eye-opening for me.  I recently attended a presentation by a sleep doctor about the topics in this book and was fascinated.

A few things have really improved the quality of my sleep. 1) Time-restricted eating – I try not to eat after 6-7pm. 2) I try not to do any difficult thinking after 7pm (or else it’s hard to turn my brain off). 3) I try to maintain mostly the same bedtime / wakeup times 7 days a week.

Exercise – I used to tell myself that I didn’t have time to exercise regularly. However, I’ve found that it’s the best investment of my time that I make in a day. Last year, I re-worked my schedule so that I could exercise every morning and have felt more energized throughout the day to be at my best.

Boundaries and focus – I try to be disciplined about when I’m working / not working and don’t check work email after I leave work (except on rare occasions). When I’m at work, I do my best to block off time every day to work on high impact projects without distractions.

*This is still a work in progress for me and I’m always experimenting with ideas to reduce stress and boost my productivity. I’d love to hear any practices that have worked for others!

What’s a book that has influenced your career or life, and why?

7 Habits of Highly Successful People and How to Win Friends and Influence People were foundational for me. I think that by following the principles in these books you can be fairly successful in almost anything.

What are the bad recommendations you hear in your profession or area of expertise?

I think there is a tendency to focus too much on averages when making schooling/career decisions.  Common guidance I see is to pursue opportunities where the averages are favorable. What is the average starting salary of someone graduating from this program? What does the average career look like for someone in this industry? What is a typical career path in this company? However, this line of thinking misses the fact that there are often huge distributions of outcomes, and it doesn’t consider the opportunities you may have to be on the extreme positive end of the spectrum or how you could customize your experience. 

What makes this challenging is that understanding what your true opportunity looks like requires that you have several exploratory conversations with people in the school/industry/company you are considering to see what’s possible, do some soul searching on what you would want your path to look like, and then do some critical thinking to assess how realistic it is and what alternative options you might have if it doesn’t work out as you hoped. 

This was very real for me when I was deciding whether to get an MBA. I wanted to get an MBA, but the ROI wasn’t making sense when I was looking at averages in terms of future career prospects. However, after dozens of exploratory conversations, I developed a specific path of where I wanted to take my career, and the numbers totally changed. It ended up being a great decision for me. Since then, I’ve gone through this exploration exercise at least once every few years.