The Leadership Advice That Changed My Career

Northern saw whet owl perching on a tree branch

It was the late 1990s and I was interviewing for a new position at a hot software company in San Francisco. The hiring manager was trying to convince me that I was perfect for the product management job, but I was not so sure. After sensing my hesitation he said something I will never forget:

You would be awesome for this role. Product managers are the engine that drive companies. But I don’t think that you know it yet, so you better go figure out what you want to do with your career.

You may be thinking — the greatest piece of leadership advice was someone telling me to take a hike and figure out my life? Yep, that was it.

More important, I actually listened. And in the process I discovered that he was right. I didn’t yet understand that product managers truly do manage the future of the companies they work at, but I soon would. That path led me to where I am today — product builder and founder and CEO of Aha!

The advice was transformative in another way. Once I was in a leadership role, I knew I had to pass the message along. I speak with a lot of people every month about where they are headed and my advice is always the same — it’s up to you to decide what you are aiming for.

The advice has informed how I approach the responsibility of my role. I have learned that my most important task in my job is to mentor. I listen and help people discover what is most important to them. I do the same thing whether I am speaking with a friend who has asked for career advice or working with the amazing team at Aha!

I care that the team at Aha! is working toward shared goals and fulfilling our vision. And of course I want us to be wildly successful. But I care even more that each person is doing what they truly want to do. Life is short and everyone deserves to be happy at work and to become better at that work with each passing day.

The hiring manager who shared that good advice with me cared enough to point me along the way. And I try to continue to pass that message along — from my interactions with others to the topics I write about.

Paying it forward is another important part of my role as CEO of Aha! — and the idea that you should constantly evaluate where you are headed and why is central to that work. Any advice worth heeding forces you to ask hard questions of yourself: Where am I going and why? The answers lead the way.

That is why I want to hear from you: What is the best leadership advice you have received — or shared? How did it shape or change your career? How did it help you pursue your true path?

Share the words of wisdom that most impacted your career in the comments below. I will collect the most compelling stories for a followup post so that we can all benefit from that great advice — and continue to assist one another.

About Brian and Aha!

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 roadmap software — and the author of the bestseller Lovability. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

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  1. Brad Lynch

    My very first job a age 15, retail. My manger would give me a list of tasks every night. As hard as I worked, I would never get the entire list completed, yet my manager was supportive, praised my efforts. It was frustrating, but I kept at it. I eventually moved on and 10 years later we had a chance encounter. During our conversation I asked him directly why he always praised my work when I never got the “list” completed. He explained his philosophy – if you want 5, ask for 10 and you’ll get 7. He explained it was less about the list and more about helping a person push their boundaries and grow both personally and professionally. He was a good “boss” in all respects and I will always value his methods and mentorship. He helped build my professional character and I try to pay it forward everyday.

  2. Deirdre

    The best career advice I got was from a senior exec while I was at Motorola. In my product management role there, I was responsible for multiple products and there was always so much going on, that it was easy to get buried in the weeds. He said to me one day “Stop spending 100% of your time fighting fires and start dedicating a set amount of time to figuring out where you want (and need!) your products to head.” From that point forward, I made the time to start each day reading industry news, paying attention to the latest trends, and finally building a real long-term strategy vs. just thinking short-term.

  3. Jeff Brantley

    The best career advice for me was from a seasoned enterprise sales leader who told me: “You’ve got two ears and one mouth. So act accordingly.” I was early in my career, so it was the first time I’d heard it. That quick statement stuck.

    It taught me to be much more attentive and intentional about how ‘active’ my listening really is. Too often I was (and sometimes still am) too quick to think of a response, instead of trying to digest, process, and restate what I heard. Then and only then would I suggest some thoughts about the context around the problems, the impacts, the current workarounds, etc. It helped me have a discussion about what the perceived problem(s) were rather than a debate. Because sometimes it matters not what I think the reality is, it only matters what this person (customer, salesperson, manager, exec, prospect, etc) perceives reality to be. (BTW – It’s was good marriage advice too! )

    This is really the root of what has become my continual and constant curiosity about why people (customers/users) behave the way they do? What drives them? How can I facilitate the understanding of that context and knowledge into the product team(s)? I love it.

    Thanks for the question. I enjoyed recalling that advice today!


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