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When should fire yourself?

The boss decides who to let go, but does he ever think about why they should leave and not himself?

We’ve all heard this story before. So you and your awesome start-up team built a great product, hits the jack-pot and starts on a trajectory of exponential growth. You just can’t believe your luck, everything is picking up at full speed and every day feels like a victory.  But soon, you as the CEO, starts to realize what used to work doesn’t work anymore, things change, costs sky rocket and soon it is time to let go even the most stellar members of the founding team who helped you build the company from ground up. All because the times have changed and the company no longer needs them. As you sit across the table from the guy who pulled countless all-nighters with you figuring out prototype #126, you look down at your script for firing him, and a little voice at the back of your head goes, “Why is he going but not me? Is it just because I own the company? Has my company outgrown me, too?”

It is hard to fire long-term employees whose skill sets are no longer applicable to the company’s growth, but what’s even harder is seeing the same restraint in yourself. So when exactly should you fire yourself? Here are some tell-tale signs that it might be time for you to hand over the reigns.


The passion is gone:

Do you still jump out of bed every morning excited to tackle the day? Or are you dreading to leave the bed when you think about all the burning fires that seems to never go out? Running a company is never without challenges, but if you see each hurdle as an enemy who you are running away from, maybe it is time to stop running and go fight a different war that you’re actually excited about.

You’re struggling to keep your head above the water:

Does it seem like the behaviors that have gotten you to where you are today no longer works to take you to where you want to be? However, despite all the investigation and experimentation you’ve did, you still couldn’t find out what’s going wrong and it just seems to get more and more out of hand. If it just feels like you’re drowning under waves of new problems and couldn’t keep up and grow as fast as your company changes, that might be a sign that your company has outgrown your skill set to lead.

There is disconnection between you and your company:

Are you constantly making decisions that contradicts your board or your exec team? Is there a lot of tension in your meeting rooms about what direction the company should go? This could mean that the company is no longer growing the way you would like it to, or that you haven’t created enough buy-in for your vision. The reason behind this could be that you really had an unique vision that the common eye couldn’t detect, or that you are the one who is actually limiting your company’s growth. Sometimes it is just time to admit that your initial vision of what you wanted to build and what the market wants are two distinct things.


Nobody wants to admit that their company has outgrown their skill sets, especially when the company is their baby that they’ve nurtured from Day 1. If you are indeed not the most qualified to lead your company forward, the ultimate question becomes: “Do you want to be remembered as the boss who stayed beyond his ability to lead? Or the leader who recognized his limitations, have the courage to step down when needed and ensured the company is in good hands?”  Your choice.

2 thoughts on “When should fire yourself?

  1. You’ve raised an interesting question, a question that I’ve asked myself a few times while working on my startup and a question that I think almost every other entrepreneur asks him or herself at some point. I think the three questions you’ve asked your readership to answer are good ones, but I’d caution you and other entrepreneurs to look more deeply at a few of these areas before leaving your baby for the following reasons:

    1. Just because your passionate about your company’s mission doesn’t mean you’ll be passionate about all the work required to fulfill that mission. I’m passionate about the mission of my startup, but this summer I lost a lot of fervor for it for a few weeks and dreaded going into work. It wasn’t because I was over the company, but rather because I was unexcited about the arduous, but important task that I was working on, web development. These rough weeks working on the site taught me that in startups there are lot of peaks and pits. Thus the question to ask yourself is whether you have lost the passion for your mission or your project. If it’s the former, then this is absolutely a red flag.

    2. You will often be trying to keep your head above the water and feel like you’re hitting a wall. Entrepreneurs have to be generalists and that’s not always easy. Before working on my company’s website this summer, I didn’t even know what a domain was (embarrassing ..I know). I felt way under qualified to be talking to different companies about API’s and other technical issues we were looking to address, but I picked it up eventually. Thus, I think it would behoove readers to think about the tasks required of them and determine whether they are competent enough to either complete or learn how to complete them. If they don’t think they’ll be able to do either then I’d agree that it’s probably time to recuse oneself.

  2. Interesting post. The challenge that isn’t entirely encapsulated here resides in the type of person who starts a business.

    There’s a saying that an entrepreneur is crazy enough to jump off a cliff without a parachute, but has enough confidence in himself/herself to build one before he/she hits the ground. When I think of that analogy and overlay some of the advice here, I feel a disconnect between theory and reality. With the exception of “the passion being gone”, the reasons highlighted in your post will often lead someone to think “it’s not me. It’s you (e.g. the market, a co-founder etc.). Realizing that you yourself are the problem is one that most founders will do everything in their power to ignore. I know I did.

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