A Tale of Two Bosses: Why Culture Matters

When I started my last job, I was thrilled about the opportunity. The product itself was something I could see myself using. The team was incredibly smart, filled with the type of people that you knew would be successful because they’re already been at least somewhat successful. And beyond that, they were an environment of respect and even those at the top kept their egos in check. So why didn’t it work out?

In my interview for that job my soon-to-be boss asked me a really interesting question — there are two type of people — are you a builder or a fixer? I immediately jumped, as a serial startuper, to say I’m a builder. How could I not be? I landed the job in convincing him that was true.

In that environment I was surrounded by highly structured, very organized individuals, mostly of Indian decent, who were very kind, intelligent, and did I mention highly-structured thinkers and doers? I still have great appreciation of that team and can see them being a huge success. However, my mind didn’t fit in. Even a personality type test showed that we weren’t a fit. While they tried to explain that difference was appreciated, in the end it was my difference that had me undone. In a culture so structured and organized my more free-flowing style stood out like a sore thumb and didn’t fit. When I was expected to lead and build I felt lost and overwhelmed in a culture that rewarded left-brain thinking and had little respect for creativity or bigger picture thinking. I did a lot of things wrong that quickly led to my parting, but ultimately the culture fit just wasn’t there. I think both my boss and I at the time looked at each other a bit like aliens, with that gaze of respect and bewilderment. I realized in order to be successful culture fit, especially in a startup, goes a long way.

My new company is much more like the one I came from before my last one – built by creative, passionate people with a fairly good mix of right and left-brained individuals. But what’s more interesting is the fact that for many of the same reasons my boss at my last gig disliked me is the reason I’m doing well in this environment. With a CEO who is more visionary and creative, he isn’t off-put by my lack of structure (although, of course, I still have to deliver!) In fact, I can’t see someone who would perform well in the other environment being able to handle the style of a company where meetings frequently start late, plans change rapidly, and everyone is moving at a million miles per minute, sometimes all in different directions. I’ve realized what I do best is help environments like this filled with brilliant yet more unstructured people come together and see eye to eye. I’m a fixer after all.

That’s not to say it’s been easy. I’m still feeling overwhelmed but in a very different way. At the moment my boss sees me as someone who can be very successful and thus is investing his time to help me learn how to be a leader, not just expecting me to magically be one out of the box. I know to him this helps motivate me to be my best and the best for the company, so it’s a win-win all around. I don’t expect this from every boss in the future, but at this point in my career it is so vital to have a coach help me understand the wonky transition from individual contributor to executive/leader (especially when you’re expected to play the role of both.)

I think as a woman who was raised to not take risks, to take orders, to do as I’m told, to play it safe, it’s very hard for me to break out of this mindset. I don’t think it’s genetic, but I do have a nurturing, even, I guess you could say, mothering mindset about me. I see problems and I like to fix them. I like to be in an environment that appreciates that it needs a mother-like figure to come in and give it guidance. I don’t know if that’s a sexist thing to say, and I know some women leaders who aren’t like this at all, but for me – I like to go where what I provide beyond my deliverables is of value.

Today, months after failing at a job where I clearly wasn’t a fit for being too unstructured – told I should clearly not work for small companies anymore, I sit bringing value to the leadership team of another small company where I’m the one in a large part helping to establish structure (along with a few other awesome new hires who are more used to companies with certain types of more standard process.) The environment fuels me to be my best. I realize now I never should have taken my last short-lived position because it clearly wasn’t a fit from the beginning. This, on the other hand, is an entirely different ball game. And hopefully, this time around, I can become a champ for years to come.



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