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Start-up CEO Spotlight: How to fire your best friend

Posted December 1, 2016 • Emotional Intelligence,Leadership,Organizational Culture • by Jennifer Goldman-Wetzler, Ph.D.

Several of the start-up CEOs I’ve coached recently have struggled with this question: Should I fire one of my co-founders (who is also one of my best friends)? If so, how can I do this while maintaining my integrity as a leader and as a friend?

Here are six steps to help you navigate this situation:

  1. Acknowledge multiple choices.  Many CEOs are so loyal to their co-founders that they forgive bad behavior beyond the point of rationality. Other CEOs are concerned about seeming biased towards an employee (because he happens to be a friend), and they decide to cut the cord without considering all the options. As a first step, acknowledge that you have multiple options—not just one or two. He could stay in his current role, leave the company, or serve the organization in a different capacity, either in another role, or as a full- or part-time consultant or Board member. Which of these options might work best?
  1. Conduct a rational analysis.  How much conflict does your co-founder have to stir up before it’s clear that it’s time for a new role? How in over his head does your co-founder have to get before you replace him with someone else?   List all the current costs and benefits associated with keeping your co-founder in his role, and assign “importance” points to each. Add them up. Which column is higher? If the benefits outweigh the costs or they’re equal, keep him in his current role or shift his role in the company. If the costs outweigh the benefits, ask him to leave the role or the company. (Advice below on how to do this skillfully.)  You could also compare the benefits you and the organization would receive if he stays in his current role, versus the benefits you and the organization would receive if you reconfigure his role or if he leaves (and gets replaced by someone else). Follow the same guidelines as above, assigning points to each benefit, adding them up, and seeing which column is higher.
  1. Provide direct, timely feedback. As soon as you realize that your friend is not a good fit for his role or for the organization, discuss it with him directly. Let him know how he adds value, and also share your concerns. While no one likes to hear negative feedback or bad news, people overwhelmingly appreciate honesty and directness. This builds trust between you, even as you have disappointing feedback or news to deliver. And if you communicate as soon as you identify a small problem, this may allow him to do something about it before the problem becomes larger.
  1. Help him improve his performance. If you believe he can improve, offer to help him do it and check on his progress (for example, in 3 or 6 months). Provide him with a mentor or coach and increased opportunities to discuss his work directly with you.
  1. Help him understand what you are saying, and listen to him. He may never have thought about it this way before, and it may take a while to sink in. He may need to take a break or finish the conversation another time. Or he may be as unhappy as you are, and welcome the chance to discuss what hasn’t been working. Be open to what he has to say. You will likely learn a lot from listening to his point of view.
  1. Deliver your message with kindness. Tell him how much you have appreciated, and still value, his friendship, hard work and loyalty. If you have already decided to let him go, let him know that this has not been an easy decision and that you will understand if he is not happy with you. Then ask him if he has any feedback for you.

Knowing deep down that someone is no longer the right fit for his role but not doing anything about it prolongs the pain. To do what is right for the organization and your friendship, make informed decisions and communicate swiftly, directly and kindly.

Jennifer Goldman-Wetzler, Ph.D. is the Founding Principal of Alignment Strategies Group, a NYC-based consulting firm that helps CEOs and their teams maximize their organizational growth and vitality. She is also Adjunct Professor at the International Center for Cooperation and Conflict Resolution at Columbia University.




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