He should have fired my ass

Giff Constable management, startups


Bijan Sabet of Spark Capital today posed the question of how a startup maintains speed once it hits adolescence. His conclusion is that “speed is really the result of a having the company aligned.”

Howard Lindzon, the colorful CEO of Stocktwits, responded with the following comment:

we deal with this today. managing feature creep is key.
obviously being aligned is good as long as you are aligned around the right path.
just a real tough question but a real belief in the model ahead is what does keep things aligned.

Howard’s line, “obviously being aligned is good as long as you are aligned around the right path,” really hit home with me.

The last startup I was involved in, wearing various VP hats, was highly “non-lean”. It started out as a land grab on a new, fast-growing technology platform, and while we sold some incredible customers, grew revenue, and built a leadership position in our sector, about 2 years into the business we realized that the core strategy was not going to work. We needed to downsize quickly and pivot.

Downsizing was painful but necessary. We got it done and kept the ship from foundering. The real problems emerged with the need to pivot. We had been a team on a mission, backing up a CEO with a strong vision. Now, we found ourselves with a fundamental disconnect as to how the business should re-define itself, and the disconnect existed across the board-seated investors, CEO & founder, those of us at the VP-level, and across the entire organization.

What do you do when a bunch of smart, talented people simply cannot agree? When the differences aren’t incremental but fundamental?

In this case, we stuck it out for a while. We all retained the hope that we could regain the greatness of the first two years.  We believed in the talent of the team.  I personally was not ready to give up on the company after working so hard to get it off the ground. It’s not a unique startup story by any means.

But this post is about alignment.  For better or for worse, I am hard-wired to fight, and fight hard, for my beliefs. I’m open to being convinced of a better path, but nothing was convincing me in this scenario. Whether I was right or wrong back then is irrelevant. I had some good ideas and some stupid ones. What I do know, however, is that my disagreements on direction hurt organizational alignment and I went from being a force and productivity multiplier to, at times, the opposite.

We were never going to agree on direction, but with that in mind as I look back, I still puzzle over what I, and the CEO, should have done.

Putting myself in the CEO’s shoes, I probably would have fired me. He’s a very loyal guy (to a fault), and I had played a big role in building our initial success, but the world had changed and we were no longer on the same page. If he and the board had truly made up their mind on direction, I now think that they should have shed everyone not 100% in agreement. They would have lost a lot of the remaining talent, but they would have cut the cash burn way down and bought more time to see if their ideas were the right ones. (of course, the reality was more muddled and complex)

Looking back at my own shoes, I still puzzle over whether I did the right thing by sticking it out for another 18 months. Since I didn’t have control over direction, and I fundamentally disagreed with the chosen direction, perhaps I was an idiot for staying. My intuition says that yes, I should have left and started my own company much earlier. But with loyalty to colleagues, inherent stubbornness, not wanting to chalk up huge amounts of effort to “Fail”, and my wife expecting a baby, it was all rather complicated. I stayed. For the record, I don’t regret it as I grew in some useful ways.


At the end of the day, you need people aligned. The CEO needs to make his or her best judgment as to the right path, and the board should either back that up or replace the CEO. If as CEO, you cannot get all the members of the team on the same page, you probably need to change up the team.

Yes, he should have fired my ass.

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(image cropped from Tug Of War – Colour Edit, by tj.blackwell, Creative Commons)