#16: Leading Through Humility

Ryan_NameEver since I set foot on the plane out to Hawaii I went through a lot of self reflection trying to determine what pushed Alison to the edge. The conclusion I came to was me. I’m the problem and I’m the only one who could fix it.

Jason Hamilton once told me that CEOs and founders aren’t ingenious creators who do everything on their own in a sterile vacuum of innovation. They are leaders in a world plagued with too few leaders. They make choices on where their business should go and they convince their team to follow them forward.

I forgot that and pushed forward without trying to gain the buy-in of the team. I ignored their thoughts. I dismissed their suggestions. And, I devalued their contributions.

There are countless mantras and schools of thought that pull at your mind as you look to improve your leaderships skills and it’s impossible to incorporate all of them. The one thing that I’ve decided I need to implement into the way I lead is to start leading through humility.

I have tried a laxed approached to leading, tried to bring more vision, and even threaten my team to pull the most out of them. The one thing I haven’t done is opened up to them and act meekly. When I think of a leader I think of someone confident, forceful at times, and decisive. And that’s how I was when I led my first startup, Shippd. But this is a different team. My partners are different and need more out of me.

When left Toronto to head to Maui I was angry. I was thinking about how to fix this mess with Alison by bullying or manipulating her into coming back to Kitchener and start working towards my plan for Merge. By the time I landed in Maui and stood waiting in line for a rental car for what seemed like two hours, I was calm, collected, and apologetic.

I landed in the early afternoon and reached the far west side of the island around dinner time. After grilling Alison’s software lead, Heather, over email I found out where they were staying and what their rough schedule was.

I had once spent a month living in Maui and know the place fairly well so the drive was uneventful. As I approached the town of Kapalua and drove past Ritz-Carlton located beach side I started to think about what I’d say to Alison when I saw her. Nothing in particular was coming to mind. My hands actually started to shake as I parked near the beach.

The steps to the beach were filled with people heading back to their condos for dinner. It was about 6:00 PM when I finally set foot on the sand. Molokai was visible in the distance and I looked out to the beach scanning for the only person likely to be on a laptop at the beach. Heather assured me that Alison’s routine would put her on the beach right now.

After a couple seconds I spotted a woman to my right staring out at the last surfer paddling out. There was a laptop next to her. I started off towards her and it only took about ten feet of walking to know that it was Alison. She hadn’t seen me yet. I still didn’t know what I was going to say as I approached her.

Before I reached her Alison looked over with her right hand over her eyes shielding her eyes from the sun that was nearing the horizon. She said nothing. I dropped to my knees, stared right into her eyes as I sat between her and sun, and said, “I’m sorry, Alison. Please come back to the team.”

Alison turned away and continued to look out at the waves that slowly crashed into the beach. We stayed like that for about a minute. The whole time I wasn’t sure what she was going to do. But she hadn’t gathered up her things and left, so I figured she was thinking about how to respond.

“Is anything going to change?” Alison asked as she continued to look away from me.

“Yes,” I said simply, still on my knees. “We’re a team. You, me, and Jasper. I forgot that and–”

“Just stop talking,” Alison said, interrupting me and turned to look at me. “You’re going to do two things. One, you’re going to stop drinking for the next month, and, two, you’re going to ensure we don’t get bought out for at least a year.”

“That’s really not my–” I began.

“Yes or no, Ryan?” Alison asked.

I thought for a moment and finally said, “I’ll do what you ask, but I’ll need your help with both.”

“Good,” Alison said. “Now get off your knees like a hooker and sit here with me. I could use the company.”

Next Post – #17: Done Isn’t Always Better Than Perfect – An Interview with Jasper

Previous Post – #15: Decisions and Board Meetings


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