September 27, 2016
From, with love.

Your Work Personality

Hi everyone,

I often tell people I learned a lot by playing in a weekly poker game at Yahoo. More than just learning the game, I learned more about human interaction and negotiation than anything else I've done. One of those lessons related to personality. You see, in poker, there are two extreme player personalities: loose and tight. Loose players play a lot of hands and bet high (considered aggressive) while tight players only play when they have a good hand and bet moderate amounts (considered passive). While many players fall in between the two extremes, players are typically described as being either loose or tight based on their performance over a series of games.

However, if there's a new player at the table who is unfamiliar with you, your personality may not immediately be apparent. You may be a tight player, but yet on that day, you keep getting good cards hand after hand so you end up playing a lot more hands. To the newcomer, you are a loose player because all of the available data indicates it to be true. If you play several more times with that newcomer, your true playing personality will be revealed, but for that initial game, an inadvertent deception occurs. The same thing can happen at work.

I was at Yahoo for almost five years, and during that time I rose from software engineer to tech lead and architect. In order to do that, I had to become more assertive, and I could get away with that (for the most part) because I had built strong relationships with my colleagues. They knew that just because I was being tough on them (playing loose) didn't mean I wasn't a good teammate (generally playing tight), it was just the role I had to take in order to get things done. Although I did need to soften my approach along the way, fundamentally I was very assertive and comfortable giving short, decisive answers to important questions. That served me well at a large company (over 13,000 employees while I was there) with a bureaucracy that oftentimes made it difficult to get things done.

When I joined Box, I started out acting the same way I had at Yahoo: assertive, direct, disruptive. However, I noticed people were not reacting the same way they had at Yahoo. I seemed to be making people uncomfortable, and that's a difficult way to lead (they had perceived me as a loose player). After a couple of weeks, I decided that I needed to modify my personality to better adapt to my new environment. Whereas at Yahoo I was dealing with peers around my age with roughly the same amount of experience, at Box I was dealing with engineers who were sometimes more than 10 years younger than me with a lot less experience. I realized that the best personality for this role was to act as a teacher of a class (playing tight) rather than the captain of a ship. I would have to tone down the assertiveness until people got to know and trust me, at which point I'd be able to introduce that part of my personality again.

The point of these stories is that you need to understand how you're being perceived by your colleagues, as it may not necessarily be the reputation you want to have or believe you do have. Building strong relationships with others requires a certain degree of self-awareness, and a willingness to adapt your behavior to the current situation. Don't be afraid to experiment with altering your personality a bit at work to discover the version of you that performs best.

Be well.


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