start ups

Ask the Damn Questions

I’m writing this in response to a conversation between Tim Ferriss and Mike Maples. Before I start, if Mike or Tim is reading, I want this part to be unmissable: THANK YOU. To Mike for being inclusive and kind and generous. To Tim for his endless curiosity.

I was flipping through Tim Ferriss’ new book, Tribe of Mentors, and saw that Mike Maples is featured. It’s cool to see someone you know on the pages of a best-seller. A couple weeks later at a book signing in Austin, Tim told me Mike is one of his favorite people. That makes perfect sense to me. I see Tim as the ultimate learner and Mike is the consummate teacher.

Not long after that book signing I listened to the recording of an event Tim and Mike did in San Francisco. It’s been years since I’ve seen Mike, but hearing that conversation brought back a flood of memories from when he and I worked together at Tivoli, a very long time ago.

That trip down memory lane also sparked a bit of regret. Actually, it started as regret then shifted into more of an understanding of assumptions I had made that led to me blowing a couple opportunities. Digging into these stories is harder than I expected. It’s not personal, per se, but we all have our tender spots and this is a big one for me.

Here goes.

The Ranch

I was an entry level worker bee in the marketing group and Mike was Director of the product marketing team. It was just after IBM had acquired Tivoli and we were all adjusting to going from rebel Texas start-up to being swallowed by Big Blue. Mike was held an off-site team meeting at his family ranch in the Texas Hill Country and for reasons still unknown to me he invited me to attend. It felt like I had won the golden ticket.

I was in full-on sponge mode that day — listen, observe, absorb — and there was a lot to take in. I got to see first-hand the value of a team having shared experiences outside the office. There were no forced team building activities, just good people in an incredible setting, sharing a meal and getting to know each other better.

At the end of that day I had absorbed a hell of a lot about our products and some important insights about team dynamics and leadership. It was an exceptional experience for the new kid, but it’s the missed opportunities of the day that linger in my mind.

Observing was the exact right approach, but I stopped short and missed the critical next step: ask questions.

First, I showed up that day without knowing why I was there. The most important thing I could have said was, “Mike, thanks for the invitation. I am honored and thrilled to have this opportunity, but I’m not sure why you invited me.” Asking that question required a level of courage I did not possess. My logic went something like…if I ask he’ll surely know I’m clueless and un-invite me. But what a powerful piece of information to have, right? To have insight into his thinking process. To arrive with a goal in mind. To understand what was expected of me.

Second, imagine having unfettered access to an entire team of A+ product managers and not asking one question about their jobs. I was plenty curious — what did it take a be a good product manager, what would they change/do differently, what was the next career step for them — but I didn’t have the courage to act on that curiosity. No one in that room expected me to know a damn thing about product marketing, but I hadn’t yet learned that there’s no shame in being a novice. I let my fear of what others thought about me stop me from taking advantage of the learning opportunity in front of me.

The Lunch

Fast forward a few years. Mike and I had both moved on to other companies. Mike invited me to a lunch meeting. I’m pretty confident Mike will have no recollection of this meeting, but it stands out in my memory, unfortunately, because of what it wasn’t and what it could have been.

Mike was curious about how we were doing life-cycle customer marketing at the company I was working. I froze. Now, so you get the full picture, customer marketing was about 80% of my job and I was excelling beyond expectations. Yet, here I was with nothing coherent to say.

Mike was too kind to let on, but I knew he was disappointed. I don’t know why I didn’t understand what he was asking. Maybe he used jargon I didn’t understand? Maybe I was nervous? But if I had simply paused to clarify what he was asking I am certain we would have had a much different conversation. Or imagine if I had asked ahead of time why he wanted to meet?

So, why the fumble? I walked into lunch that day with the self-defeating assumption that I didn’t have much to offer. I mean, here was the co-founder of a hot new start-up in town. Who was I? I didn’t have a fancy title. I was “just” the person executing our programs. I hadn’t yet learned that being on the front lines gives you invaluable insight.

Being Honest

I’m embarrassed. Embarrassed that I blew it, twice. Embarrassed that I just admitted my mistakes publicly. Embarrassed that I’m writing about something that happened almost two decades ago.

I’m not re-hashing the past to beat myself up. It’s the opposite. I remember these events because they had a positive impact on me. I learned something. And maybe my mistakes can be useful to someone else. That’s worth a little embarrassment.

Truths Emerge

It’s so easy to overlook these small moments of failure. But here’s the thing. A mistake that we keep repeating is trying to show us something. It’s pointing us to a fundamental truth we’ve yet to learn.

Three truths emerged from my early mistakes.

  1. Seeking understanding is a strength. Ask the damn questions.

  2. Execution is an equal partner to vision. Don’t dismiss your in-the-trenches knowledge.

  3. Play your own game. Worry less about what other people think.

These truths have stood the test of time and have served me well. Every good thing I’ve accomplished professionally has come when I’ve remembered to ask the questions, to play my own game and to not dismiss what I already know.

I hope you too can find service in these.