Management That’s a fascinating question

How It’s Worked So Far

First job. Scotts Valley, California. Zero clarity what a manager did, but Rick seemed like a nice guy and he pointed me in the right direction. Mostly. Rick was demoted after we didn’t ship for three years and Linda showed up and OH MY a solid opening lesson in credible and effective leadership. Thanks Linda. We shipped quickly. I received my first promotion, but Microsoft.

Left the first gig. Two bad career choices. Two horrible jobs in a row – bad judgment, but good people at the second gig. Let’s not talk about it, yet. Let’s move on.

Second high growth company. Inventing the Internet in Mountain View. These humans are fired up and people are randomly becoming millionaires. That’s a new thing. Tony walked in my cube and asked me to look after Harry, Bob, and… someone else. I asked for advice and he told me, “Schedule a team meeting. Do 1:1s.” Ok. Leadership?

Busy. Really busy. Microsoft again. I go to Tony and asked for help and he says, “Open a req.” Cool. Yeah. “What’s a req?” Walking around the hallway looking for examples of good leadership. Jon, Tom, and Toy. Smart humans who value the humans. Acronyms everywhere. Microsoft increasingly… hostile. I switch jobs internally. Bye Tony. Hello Java. Hello new manager who… didn’t really care? Bummer. Microsoft seriously now. We’re retreating now. Bad internal job transfer, but someone during that gig said, “Your superpower is reading the room and synthesis.” That stuck.

First start-up. Sunnyvale. You’ve never heard of it. First manager hired at the company. Employee #20. Promoted me to Director (Thanks Gary) which felt like an achievement at the time, but… what a joke. Took it to 250 humans and then back to 70. Most. Learning. Ever. Wish I could blame Microsoft, but going to blame myself. Really looking for leadership help now and finding nothing that speaks to me, so I start banging on the keyboard and documenting what I consider to be obvious things. You tended to agree, so I kept banging.

Start-up failing. The bubble burst. Drunk at Chevy’s with the CEO when the mothership called. I HAVE WANTED TO WORK AT THE MOTHERSHIP SINCE I WAS KID. Worried about being a little fish in a big pond, but Steve kept teams… hungry. Never felt little. No one asked if I used a Mac during the interview. Whoops. Eight and a half years there and title never changed but never stopped learning. Typography, operating systems, the power of having a defensible opinion, and the force multiplication of diverse teams. Take that Microsoft. Thanks, Laura.

I bore easily. Change of scenery. Left a sure thing for a Palo Alto thing no one understands, still. My first free electron gig with a relatively prompt promotion to Director. Real Director now. Good people. Looking at you Joshua. Wrong role, though. Whoops. Time to get back to building product.

San Francisco now. VP now. Head Of, actually. Achievement unlocked again but finally learning that with each significant advancement in leadership it will take three years to learn the new gig. Three years. Minimum. Advertising-based business now. Big time. Watch as the product design process is twisted and turned… by advertising. Responsible for all of engineering and learning my technical strengths and weaknesses at scale. Forgetting to ask for help. Whoops.

VP again. Closer to the Golden Gate Bridge. Pure product. Gosh, I love when the customer transaction is a simple, “If you like what we build, pay us. Otherwise, do not.” Not just amazing product-market fit, but best product-Rands fit. Talking to a talented group of humans. One asked, “What’s your leadership arc?” I told her, “That’s a fascinating question. I should write that piece.” Three and half years. Best boss ever? Best leadership team ever. Tired of almost a decade of rapid growth.

Back to the mothership. Laura still here. How will the start-up playbook work here? Still figuring that out. Still debating. All. The. Time. All of my favorite parts of being an engineer except, ya’know, a multi-year pandemic, but we still build, we build well.

Learned two things along the way.

  1. Remember the people that helped you along the way.
  2. There is always more to learn.

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6 Responses

  1. I’ve always wondered, and now I know. I enjoyed the writing style of this piece.

  2. Laura 5 years ago

    You are welcome

  3. Thank you for sharing. Loved it. A single tear in my left eye. You moved me.

    22 years on this path. I find leadership where I can.

  4. JohnD 5 years ago


    The thing that stuck with me in the early years, I kept thinking the next job will be the one to show me “what to do”, so far it had been mostly “what not to do”. Now many years later the ratio is better but I still think there are more “what not to do” lessons than the other.

  5. Dear Michael. Nailed it.
    I love following your fast track mind through a complex and challenging career path. So happy that you did choose to share your wisdom as you discovered and invented it. Know that you have made a lot of difference to people who think better because of you.

  6. Barry Williams 5 years ago

    Amazing journey, thanks for sharing. My journey has been similar in many ways. Thanks to the good and bad bosses I have learned so much and keep evolving every day.