Why I started coaching

coaching scaling Sep 28, 2019

It all began when I moved to Canada and joined a startup.
I was quickly promoted to Director of Engineering at Syncapse, one of the first social media management product and consulting firms, which launched in ~2008 and scaled up like crazy, raising $45M, expanding globally until it’s demise in 2013.
During my 2+ years at Syncapse (2009–2011), I had the opportunity to see a lot of crazy startup growth happen. We were all trying to keep up with the “just hire people and we’ll figure it out later” mentality, and rationalize away the multitude of nonsensical directives which rarely made any sense. Trying to apply process and rules to the organization was like trying to catch a chicken while blindfolded — not even Chuck Norris can do that.
While there were many problems , I realized that for me, there were a couple of really big issues: one was a lack of transparency and communication about where we were trying to go — which led to misunderstandings about why things were happening, which led to a lot of assumptions being made. This didn’t align with employees and management.
I spent a lot of time trying to help keep engineering morale high as well as delivery on schedule, which basically meant running interference on a daily basis, while working hard to avoid micromanaging and getting the right people in the right places. I try to look at organizational issues from a systems perspective -making a change someplace can sometimes have “ripple effects” across the organization. And it was always clear to me that decisions made by the executive team would not be received and executed without lots of ill-effects. This was something I worked hard (and still work hard) to try and mitigate in my day-to-day.
I remember one day the CEO took me out for a cocktail and said :” Remember you work for me, not for them”. And while this was true, they were the ones delivering the work, and I’m not going to treat them like cattle because I don;t work for them. The goal is always to find the best implementation which gets the job done without breaking the system. Some of these decisions made it very difficult because they were not well thought out and they didn’t get the proper level of feedback. This would be a common theme throughout my next 10 years as a manager.
Ever since then, I’ve found myself time and time again..in similar position, constantly trying to solve this problem of executives not understanding how the systems below them work and taking it out on the system. Even today, while talking to CEOs, I still come across the attitude of “to be honest, I don’t really give a shit what my employees think”.
I’ve come to realize that it was a two way street — front line employees, team leads, department heads, directors — who don’t always understand why a company is moving in a certain direction and aren’t given the information to come to terms with why stuff is happening. And even in the case of this lack of transparency from the executive team, it’s always good to try one’s best to put yourself in their shoes: “what would you do it if were your company?”

This led me work hard and ultimately understand what I believe are the  tenants of success and happiness for employees of startup and small companies: empathy, perspective, scaling, strengths and shipping.

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