What? A key leader is leaving?

32-Key Leader Leaves-Pic#1“When people leave…as a CEO and Founder…it’s easy to take that personally.”

That was Tim Fargo, Founder & CEO of Tweet Jukebox, on a recent episode of the “From Founder To CEO” podcast.

Can you relate? 

I know I can. It happened to me early in my tenure as Founding CEO.

Unless you’ve been a Founder & CEO, you may not know the depth of the feelings involved. Many thoughts flood your head when you learn that one of the people on your leadership team is thinking of leaving or has made the decision to do so. You probably recruited them, or were part of the recruiting process. You probably sold them on your business idea, your strategy to disrupt your key sector, or your big dream. You probably suffered and celebrated together. Now you stomach is in knots.

What did I do? What happened? Why? Why now? Where are they going? To a competitor? Who else knows? Who else is leaving? Will there be an exodus? What will my investors think?

How You Handle This Has A Huge Impact

Tim’s story is a familiar one. I’ve been around long enough to see how a range of leaders, founders, and CEOs react to this situation. Years ago when I left the military, my brigade commander was mandated to have a meeting with me when I officially made it known I intended to leave active Army service.

He asked no questions. He really didn’t seem to care. The meeting lasted about three minutes. He said, “Well, I guess you’ve made up your mind. So, good luck to you.” I left the Army a few months later.

I guess that’s why Tim Fargo’s story really struck a chord with me. He had a key member of his team being recruited away by another organization. Here’s what he told me during the interview, “We put up signs everywhere, Julie don’t go…I know it may sound crazy, but she stayed.”

How you react to a departing key leader has a big influence on the situation and your company. The person may not have fully committed to new plans. Or, they may have. Either way, Tim shares some key advice.

He says, “Learning to understand…if somebody is leaving, not to take it personally…but try to figure out…are they leaving for good reasons…try to be real about it.”

In my experience, this is sound advice. However, there’s another approach too.

Here’s what Greg Sausaman, the CEO and Co-founder of fast growing Topper’s Creamery, told me during a recent podcast interview:

“We had one of our GMs…she had been with us for a year…I thought she was leaving. So, I jumped into my car…and drove over to the other side of the state…so I could spend a half an hour, shake her hand and look her in the eye, and tell her thank you so much for working with us, I just deeply appreciate your service. If anything happens that you change your mind, we’d love to have you…I just wanted to tell her thank you…and she ended up changing her mind.”

Greg did not drive to the other side of Florida in an attempt to change his GM’s mind. He drove to see her because he wanted to express his thanks for all the work she gave the company over the year. It was appreciation, not persuasion. But, the by-product was that she stayed.

Some Considerations

As a Founder & CEO, people will leave your company. It’ll hurt. It will be painful. But, it’s the cycle of life. What can you do to make the best of the situation? Here are some things  you may want to consider.

1 – What if you just decided to help? Not everyone has this all figured out. They may still be thinking about it. They may be reacting to short term circumstances. They may be frustrated with something at work. They may be the target of an aggressive recruiter and it’s the first time they are dealing with the flattery that comes with that experience.

What if you just decided to help them think through it? What if you just asked them some questions to make sure it’s a better opportunity? It actually may be a better opportunity. What if you took a “coach” perspective?

If you take this approach, you may learn some things about your organization, help them out, and bolster your employment brand as a company who wants the best for its people.

2 – What if it’s a compensation issue? There are a lot of human resource statistics on this topic. Bidding wars aren’t always fruitful exercises. But, so what? What if they have an opportunity to make more money somewhere else? Maybe they’ll gain some additional skills that make them a good fit to come back to your organization at a later time when you have more resources to compensate them. Just help them ensure they are comparing apples to apples.

3 – What if you asked them to help you find a replacement? They may be willing to do so. Or, they may be hesitant because there is something about your organization that needs attention. Wouldn’t you want to know about that sooner rather than later?

4 – What if you used this as an opportunity to engage your team? It’s likely your team will have a range of emotions. Helping your team process their emotions can be helpful. The bigger gift for you, the CEO, may be some deeper insights and feedback about the team, the company, and the mission that you may not have discovered without this key leader’s decision to leave.

5 – What if they are leaving because of you? Admittedly, this can be painful. Lack of faith in your leadership. Lack of faith in your concern about them. Lack of trust in you as a person. The list can be long and the odds are you will not hear this from them directly. But, it shouldn’t stop you from asking. A startup is a fragile, dynamic, whirlwind of constant change, and a roller coaster of highs and lows. If you can get some feedback about you as a leader earlier, from a key leader who may be opting out, it just may save your company.

It’s never easy to lose a key leader…especially for a startup. You and I know the impact is magnified. Just ask questions. Be curious. Be kind.

Try to take the possible personal feelings of hurt and channel them into genuine personal concern for the other person. After all, they are probably emotional and confused just like you. Your kindness just might encourage them to stay just like Tim and Greg’s key leaders decided to do so.

In the end, I think great CEOs handle this with grace.

What are your experiences? What are your recommendations? Please share them below so our growing community of Founding CEOs can learn from you too.


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