I was nervous about the conversation. After searching for several months for someone to lead our growing engineering team, we had settled on Michael. Michael, if he agreed to take the job, would be easily the most experienced leader on our team. I was hoping his experience at renowned startups would help with recruiting and fundraising in the years ahead.
I find there is this funny moment in any recruiting process where my mind shifts from hoping I will like the candidate to hoping the candidate will like me.
I found myself doing something that I feel to be quite shameful recently. I was kneeling down, getting in the face of my eight-year-old son, and raising my voice to him.
I found myself saying these words:
Why do you have to be like this? I really wanted to have a good night tonight. I just wanted to relax and enjoy time together. Why do you have to be like this?
Thinking back on these words, I feel a sense of shame and self-judgment.
If I let that pass by for…
I found myself in a coaching session recently blurting out the following sentence, “I am not talented enough to work 80 hours a week. Neither are you.”
The client had shown up for the session on two hours of sleep.
I asked her about her weeks in general; how many hours did she work?
“80 hours or so,” she replied.
I paused. A flash of insight came.
This woman is so damn talented. If I had invested in this company, I would think our most valuable asset is this founder/CEO. …
There was a five year period in my life where a lot of painful stuff happened. I lost a child. My father and step father both passed away in the same year. I went through a difficult divorce. As a CEO, I found myself having to lay off 80% of our staff as a result of financial challenges.
Those five years paralleled my experience of life in my teens. In my early childhood, my family was close and life felt secure. Summers were spent sailing and winters skiing. My grandparents lived…
“As of this week, my personal net worth has hit nine figures,” my client said.
It took me a moment to sort what that meant.
One hundred million dollars!
Wow, I thought. That is a big number.
In coaching, part of what we train for is to notice our thoughts, reactions, and emotions in sessions. We are taught to identify them so we can set them aside and remain present for the client.
At this moment, what I noticed was I felt simply happy for my client. It was not happiness…
Matt needs to shore up his communication patterns in 1:1s and in smaller group settings. Being able to refine and get a bit better in those smaller interactions will make a pretty distinct impact on the company. It is a combination of things that would be helpful (active listening, truly giving off the feeling of being receptive, and having the other person feeling heard or valued).
Wow, that makes me cringe to read. That quote is snipped from a 360 review of me, as CEO, in the summer of 2016. …
I sat at the bar alone. The beer next to me half gone as the waitress set down my salad and asked if I needed anything else.
I felt utterly alone.
“Who am I going to tell?” I asked myself. “How am I going to get through this alone?”
The day before, my (now ex) wife had told me she’d had an affair and that our second child was not mine. Suddenly, I found myself contemplating single parenthood with an 18-month-old.
I was also pondering how I might start over again…
I was trying to hide the tears welling up in my eyes. It had been a tough day in the midst of a tough week, month, and year.
The Series B we had been preparing for the last year was not coming together the way we hoped.
We were living on debt.
Our revenue, which had been growing steadily for over a year, had suddenly cratered. Our best acquisition channel imploded when our domain got dinged and our email deliverability rates went through the floor.
Even now, sitting in a cabin…
Destroy the idea that you have to be constantly working or grinding in order to be successful. Embrace the concept that rest, recovery, and reflection are essential parts of the progress towards a successful and happy life.
- Zach Galifianakis
We were 20 minutes into a coaching session aimed at sharpening my client’s company’s goals for the year. I was challenging her to begin by zooming way out.
“What do you most want to have achieved 10 years from now?” I asked.
“I want us to have built one of the…
It was my very first board meeting, and I had no idea what I was doing.
Although I had been running my startup for three years, I had never had a board before. To be honest, even with an MBA under my belt, I did not really know what a board was supposed to do or how it was supposed to work.
As the meeting started, I walked my one board member through the long deck I had meticulously prepared.
I spent the next two hours trying to convince her…