When You Have to Fire a Friend

Hey Founder,

Of course you hired your friend. You are ramping up your business and who better than one of your closest friends to help? She is fired up about your business, willing to wear any hat, and works her tail off without complaint. 

Boy, do the two of you have some war stories….

As the business grows, however, it becomes clear that her skills and experience just aren’t the right fit. This hurts because you care deeply about your friend, but something has to change.

[SIDE NOTE: I have written about the “strategy gap” that many founders face as they scale—a gap that arises because growing companies require new kinds of leadership that may be beyond the capacity of those, including friends, who were there with you in the beginning. Here’s an article I wrote on this topic that may help you understand and explain this transition pain. 

I also recommend an article to help you articulate how fast-growing companies can outgrow their leadership teams, resulting in moving people into different positions within the company—or moving them out of the company.] 

Bottom line: one of the hardest things you will have to do as a founder is fire that friend. I’ve had to do it and have advised others on handling this most difficult of conversations. 

Obviously, the spirit in which to approach it is one of compassion and empathy. But beyond this I would add a few other observations to consider. 

First, it’s common for all of us to build up stories in our heads about another person that influence how we might approach such a discussion. One thing you might do is an exercise called “fact versus story,” which helps you get past any stories you may have been telling yourself about how your friend might react and ground your discussion in facts. The point of this exercise isn’t to win points but to clear the air in your own head of false narratives. 

In the end, the termination is about your friend in that moment. Not about you. I recommend processing your feelings with someone other than the person being let go before you have the conversation. 

Then make the conversation about them, delivering the message clearly but with love and caring and in the full expectation that your friend will go through phases of shock, anger, fear, sadness (not necessarily in that order) that need to be processed. Give them time to process their feelings, even if it means arranging to circle back after the weekend to finalize some details. 

Please know that everything after, “I am truly sorry about this, but I have to let you go,” will not be heard. Things like terms of the dismissal should be emailed to them in clear, simple language, as trying to talk them through them rarely works. 

Your friend will want to know the “whys,” but focus more on the “what,” as in what this change means for her or him. If your friend insists on knowing why in that moment, keep the focus on the needs of the business but try to be firm on recommending a later meeting time, perhaps over coffee, to go deeper on learnings after emotions settle. 

Letting a friend go is never easy, but you will emerge stronger—and so will your friend—if you maintain your presence of mind and 

  1. Stay calm and clear (e.g., send the simple, next steps and termination details in writing).

  2. Make the discussion about them not you (e.g., they are the ones being let go, how sad you feel is not relevant to them in this moment).

  3. Give them lots of oxygen to feel their emotions and work through them.

  4. Do all you can to support them to their next engagement.

  5. Process your own feelings with a trusted friend/advisor (not with the person being let go).

I am open to any other ideas or questions you might have on my approach. Here’s hoping these tips can make this difficult transition a little less stressful.

Sincerely,

Rob Craven, ScalePassion


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