Michelle Flink on "Dealing with Ambiguity, Getting Out of Your Comfort Zone, and Working at a Startup"

Michelle Flink Headship.jpg

I am pleased to feature a career Q&A today with my longtime friend, Michelle Flink. When I met Michelle in college, she was fascinated by entrepreneurship and interested in pursuing her own venture someday. Over the past decade, she has made significant contributions to the dreams of other organizations, both mature companies and startups, to prepare herself for future entrepreneurial opportunities, and is someone whose opinion and experience I respect. Here, she shares her perspective on a number of topics, including how she learned to handle ambiguity at a young age, networking tips, and what it was really like to work at a startup in the Bay Area.

What people and events during your childhood played a major role in how you approached your career?

There are three people that come immediately to mind - my parents and my tennis coach growing up. 

Very early on, my parents instilled in me that a solid work ethic was the foundation to any success. I learned early on that anything you wanted in life took effort and hard work to achieve; nothing should ever be taken for granted and nothing comes without hard work. For example, I had to do chores growing up and for me, it was more about contributing to the family (a team so to speak) versus doing chores to earn money. I learned that being part of a family and a team meant that everyone had to pull their weight, and while I know many people do chores growing up as a way to earn money, for me, it was an important lesson in contributing and not letting your family/ team or commitments down. I also kept very busy, between sports, music lessons, school, etc., I learned how to stick to a schedule and how to prioritize school and homework with many other activities. This was a huge help in preparing for college and my career beyond school. I feel like being successful in your career is all about knowing where, when and how to prioritize and organize your ever-growing list of projects and 'to dos'. It was great to have this foundation built into me from a very early age.

My tennis coach was also my first boss growing up. He was the tennis director at the tennis club I trained at, and I started working for him right before my freshman year of high school.  Interestingly, I learned more about hard work, having a good work ethic, problem solving and just getting the job done than I have in any subsequent job. He was one of those bosses where he gave you a vague task and said, 'I need you to get this done by next week'...no other instructions or directions. I remember one of my early jobs was him asking me to order trophies and t-shirts for an upcoming tennis tournament we were hosting. That was the extent of the request... 'Michelle. We need to order trophies and t-shirts for x tournament. Get it done'. My 13 old tentative, somewhat shy and not yet confident self, had so many questions...'Where do I get trophies & t-shirts'? 'How many'? 'What size'? 'How much can we spend'? I had no idea where or how to start. I asked these questions and my coach's response was, 'Figure it out'. This was just one example where I panicked, cried and got angry about not knowing exactly what to do. I was great at following specific directions, but found the high degree of ambiguity, especially with so little experience, daunting.  Later I realized that my coach could have easily given me all the answers, but the true lesson I learned in that job and took with me my entire career was that I can problem solve and figure anything out on my own. I learned that there is no task too great to accomplish; the task at large may seem overwhelming, but with research, preparation, hard work, and problem solving you really can do any job that is given to you. I've taken this lesson with me in my career and always think about how my coach helped prepare me for the work world and life's challenges better than any boss and job I've had thus far.

What did you study in undergrad? Did you intern or work somewhere in your chosen field before graduating?

I was a Business Marketing major with a minor in Entrepreneurship. I had many internships and jobs that focused on work related to my major and minor before I graduated. I worked for my first boss and tennis director throughout high school and early in in college. I then interned for a smaller start-up company focusing on building out Marketing, Sales and Advertising tactics for their growing business, and also did study abroad programs that were tied to internships working for companies while also furthering my education.

What were some of the most important things you did during college that helped you land your first job?

I think the activities and classes I had in college helped me to be successful in my first job, but honestly found the most important thing I learned was the importance in networking. This is what ultimately helped me 'land my first job'. There are tons of really smart and successful people out there that will have resumes that look equally as impressive as yours, but so much of business - making deals, getting into closed doors, etc. is done through your past experience and work, your reputation, and the networks that you make along the way. I truly believe that networking is equally important as being a smart and hard worker. You can be brilliant, but it's hard to continue to be successful and have more doors open to you without making real and true connections with the people you interact with.

I find the best sort of ‘networking’ is when you are authentic in your intentions. It’s taking the time to really get to know someone. It’s taking time out of your day to grab coffee or lunch. It shouldn’t be forced, instead it should be wanting to truly get to know and spend time with that person and know who they are both at work and outside. Asking questions about how work is going, what are they proud of, what are they struggling with as well as asking about their family, friends and hobbies outside of work. Networking is building lasting friendships and truly being authentic in your interactions.

You started your career in healthcare with the Advisory Board Company, and were quickly promoted to a leadership role, working as the Chief of Staff and a manager within the marketing group.  Were you prepared for this role when you started? If not, what were some things you did early on to make your transition more successful? What did you learn along the way?

If you are continuing to push yourself and grow in your career, I feel like you are never 100% truly 'prepared'. In any new job or role that you are promoted to, there are always opportunities to learn, grow, improve and get better. Yes, there are things you can do to help you be more confident for the next step, but you have to go into it knowing that you will have a lot to learn along the way and once you are in the role for some time and have honed-in and perfected that new skill set, then it's time to push yourself again and step into a new role and start over. 

There are things you can do along the way to set yourself up for successful instead of failure. For example, know what the ‘next job’ is about. Know what your strengths and weakness are before going into the role and how those play into that new role so you know where you may need to work harder and focus more in the beginning. Find mentors both inside and outside of your company - they can help you in different ways. Shadow, mimic and learn from others that have gone through that role before or who are currently in the role and who are successful.

After starting in Washington D.C., you moved to San Francisco with your husband while continuing to work for the Advisory Board Company on a remote basis, with some travel as well.  How did you approach and agree on this remote work arrangement? Did this reinforce or change your opinion on the practicality of remote work situations?

Luckily, I was working at a company that was very supportive of remote workers so long as you had proven yourself to be a self-motivated worker who has historically had a good reputation of having a good work ethic. I had been with the company for four years before asking to work remote. Since I had established a solid and reliable career, my manager and colleagues trusted that I would take that same work ethic outside of the four walls of our current D.C. based office. While I worked the majority of the time remote, I also traveled at least once every two to three month based on the nature and responsibilities of my job.

I am a huge proponent of allowing people to work remote so long as you can prove that you are just as efficient working remote, the workplace should allow for more flexibility for their employees. I believe that good talent is good talent no matter where they are based. Companies should be more focused on hiring and retaining the best talent instead of settling on others just based on physical location.

What was it like to transition from a more mature organization to the startup environment at Gainsight? What did you enjoy about it, and what did you not like?  Would you recommend that young professionals try to work for a startup if they have an interest in this type of work or are interested in becoming an entrepreneur themselves?

It was definitely a transition, however, one I was looking forward to. At my previous job, I had always sought out more opportunities that lent themselves to a more 'entrepreneurial' feel in nature, for example, products that were recently launched, or being re-launched, etc.  I’ve seen that you can find those entrepreneurial experiences and opportunities even at bigger, more established companies. I took these opportunities and it helped make the transition to 'startup' life a lot easier. I loved the amount of responsibility you get at a startup - you truly learn so much and have much more responsibility that you might at a bigger company. With that comes a lot less established processes and organization. You are essentially helping to create the process and organization at a startup which can be a lot of fun for some people, but others might find this a bit frustrating if you've been used to or expect order. In start-up life, you need to be able to make order from the chaos. I think it's a great idea for many people who are interested in being an entrepreneur - you will definitely learn a lot, but I also do not think it's necessary either. You can learn just as much at a bigger company if you find the right opportunities. The one piece of advice I will give is to join a start-up for the learning and opportunity, not to 'be at the next unicorn company'.

A couple years ago, you decided to pause your career and stay home with your daughter.  How do you feel about this decision two years later, and what advice would you give to other parents or soon-to-be parents who are wrestling with this decision?

It's honestly been the best decision I have made. I feel fortunate enough to have been able to stay home with my daughter - I find it so rewarding that all my time, work and effort is going into supporting and raising our little girl. I feel the time I am investing in her and our family are and will be so much more rewarding to me personally than investing in someone else's company or dream right now. I have the opportunity to invest in my dream right now - my family, and I feel so lucky to be able to do that. I also have other dreams - I would love to go back into the workforce and/or own a business of my own, and know one day I will focus on that again. Life will continue to evolve and change and a career in business I'm sure will be back in the horizon for me, but for now, I am right where I want to be. 

My advice is whatever decision you make, have no regrets! You have to do what is best for you and your family, but don't allow yourself to feel bad one way or the other for the decisions you've made or have had to make. You should never make yourself feel guilty or compare yourself to others and the decisions they have made. You don't know their full and complete story and they could never fully understand yours. Do what is right for you and what makes you happy! In the end, that's what life is all about ;o)!

About Michelle Flink

Michelle Flink brings a combination of marketing, entrepreneurship, and leadership skills to help organizations grow and thrive. Her professional experience includes a series of rapidly progressive leadership roles with the Advisory Board Company, a healthcare consulting and technology company, as well as a Senior Manager role with the customer intelligence startup Gainsight. Michelle earned her Bachelor of Science in Business from Miami University and gained additional experience in marketing and entrepreneurship life through a variety of internships and study abroad experiences with startup organizations. View more about Michelle here.