1. What have you found most challenging as a CEO or executive of a large enterprise?

As an individual contributor, I have always been good at seeing a path from where I am to the result I want to achieve. The path I see in my head has an outline or stepping stones that are clear enough to work toward but contain enough flexibility to handle any adjustments that I need to make along the way. This vision is clear enough to me that I often struggle to communicate it well to my teammates. It is difficult to find the right balance between vision and micromanagement. Using context takes a lot more trust than using control.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

I jumped straight from an entry level position to co-founding a company. I didn't get the benefit of climbing a corporate ladder to learn and practice managing people. I also got criticism that wasn't very constructive. I was doing a poor job of being a leader but wasn't getting help to improve until I set out to do it myself. My first team grew to about 20 and I learned a lot of lessons the hard way. During my next adventure I had 3 teams that rolled up to me and I got to put into practice the lessons I had learned from before. You come off a lot more valuable when people don't see the steps you took to get where you are.

3. How do you structure your work days from waking up to going to sleep?

I get up around 7am and check Slack for urgent messages from my European colleges. My son is usually up a few minutes later and my wife and I get him dressed and fed before I take him to daycare around 0815. I'm home around 0845 and I get some breakfast before conference calls start at 0900. The day is checkerboarded with calls that stop late in the afternoon. Some days I get a 10km run in before I drive out to pick up my son from daycare. We have dinner together as a family and then spend a few hours playing with whatever a 2 year old fancies at the time. After he is in bed, I spend a couple of hours doing miscellaneous things around the house. Often I spend time picking up the house and working my first book that I hope to finish in a few months.

4. What's the most recent significant leadership lesson you've learned?

I read Reed Hastings book "No rules, rules" and have been working to lead with context, not control. It boils down to a better way of explaining agile.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

I have learned a lot about product management and leadership from different books over the years but one book still stands out. "How to win friends and influence people'' was the book that changed the course of my career. I started out life as a prototypical engineer and "well actually" guy. I would happily correct anyone for the slightest technicality, even if they were right but for the wrong reason. Unsurprisingly that kind of behavior doesn't lend itself to successful team building. I took a long hard look at myself and concluded I had to change. Ever since then, I have made purposeful strides to grow into the person I wished that I was.

6. How do you build leadership capacity in a large enterprise?

Deliver. Make sure you have the capacity to deliver the things you and your team commit to. Make sure you deliver on the things you commit to doing for your team.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

As an engineer, I can confidently say that product management is the most important part of the business. Projects almost never fail because engineering can't figure it out, they fail because we made the wrong thing.
At my first company, customer feedback suggested that we add another download format. It was an easy ask so we knocked it out. Then we noticed from logs that people were downloading the same gigabyte files multiple times per day. More conversations with the sales team revealed that customers were having trouble naming the files so they would simply download them again whenever they needed them. An easy fix from the engineering team was to automatically create better file names that would be easy to find. Customers continued to download the same files multiple times and after even more questions, we discovered that they were simply trying to view two files side by side. our interface didn't have this feature but customers knew they could do it if they exported the data into another program.
Months were wasted because engineering did exactly what customers asked for, not what they needed. Good product management fills that gap.