What to Do When Good People Leave Your Organization

The Great Resignation has had a huge impact on teams and organizations. How do you respond as a leader when you lose a really good team member?

In this episode, co-hosts Richard Lindner and Jeff Mask talk about what happens when one of a leader’s biggest fears becomes reality: a key player on the team decides to leave. Instead of just speaking in generalities, Richard shares a very personal and recent story, and he and Jeff walk through these important questions:

  1. How do we process it internally?
  2. How do we communicate it?
  3. How do we make sure the company is better because they were here instead of worse off because they’re gone?

Listen in for some great tips to help you think about—and become better from and through—these experiences. 

Richard’s Team Loses a Key Player

Richard says their company was blessed not to lay anyone off during Covid, but they still experienced the Great Resignation to some degree this summer. He recently had the scary realization that his team was at the definition of a skeleton crew. Everyone was perfect for their job—right person, right seat, right attitude, right cultural fit. “If anyone here leaves,” he thought to himself, “we’re going to be in a bit of a bind.”

And then it happened. Someone who had been with the company for five years (in internet years, that’s forever, Richard says) put in her resignation. In the growth they had seen over five years, this person had been critical in figuring things out and ushering in that change. She was always smiling, had the best attitude, and owned her role. When Richard got the news, his mind went to “not her, not her.” This was going to hurt. 

Richard said this is when you start to spiral mentally, no matter how long you’ve been leading. He went immediately to a bad place, because he always processes the worst case scenario first. This person embodied their core values. The company could have written its values by following her around. When she left, we asked, where did we fail in leadership and vision? Where did we fail in growth and opportunity? What are the rest of the team members going to think? Will others leave because she left?

If “bad people” (an underperformer, someone who’s not a cultural fit) leave, we get it. But when a good person leaves, the fear is that other people will think, “Wait a second, if she’s leaving, should I leave? What does she know that I don’t know?”

How Do We Process It Internally?

Important question #1: how do we internally process the impact of this person leaving? How can we work through it in a way so that it’s a growth opportunity instead of something that paralyzes us? If we don’t work through it in our own minds in a healthy way, it has a negative ripple effect on everyone around us. A negative spiral is not helpful. 

Every failure is a failure of leadership. However. Good people leaving is not always a failure. It just means that, organizationally, their growth has outpaced your need. When done correctly, sometimes we grow people too good, too much. They outgrow the company. It’s a job well done. You’re called as a leader to grow people. You’re called as a leader to align that growth with the company. When they outpace it, you fulfilled your calling. If the company can’t support their growth, you let them go with your blessing.

Jeff summarizes Richard’s process. First, he went to a dark place, thinking “where did I fail? What will people think?” That’s totally normal, human, healthy. Where the unhealthiness comes in is when we stay there. We have to reframe. “Where’s the good in this? Where do we go from here?” It comes down to selflessness as a leader. Seeing the situation from the individual’s perspective and being happy for their growth. 

How Do We Communicate It? 

Once you’ve internally processed this person’s departure from the company, how and when and what and to whom do you communicate it? 

Richard says that, first, you talk to the person leaving. There’s an HR process they follow, but it needs to be collaborative. Create the tone and plan together. Be honest with the person. Say, “I’m concerned that other people will think there’s a problem. The story you told me, your truth, is awesome. I want people to hear that.” Partner with them on the truth. Jeff says that people’s BS meters are strong. When we spin it, people connect the dots. Truth and honesty is key.

After you talk to the person and make a plan, then you tell the people affected by this person leaving before you tell the company as a whole. One of Richard’s company’s rules is: no surprises. If someone is impacted by the change, don’t surprise them with the announcement at the company level. People who are unaffected should not be told at the same time as the people dramatically affected. 

The person leaving usually announces it at the team meeting. Keep it short and sweet. Don’t say goodbyes yet. Don’t be like the people who say goodbye in a restaurant, then walk out in the same direction. That’s awkward. Allow the person to say goodbye through a company channel—email or Slack—on their last day. 

Celebrate the person leaving, then dial in the critical areas of responsibility and functions of this role, and start the search for someone to step into that. 

How Do We Make Sure This Betters the Company?

You absolutely want your company to be better because someone was here, not worse off because they’re gone. And this can only happen if you put repeatable systems and processes in place. Hopefully, their replacement can take the company from great to greater because of what the previous employee was able to put in place.

Richard’s dad told him something when he was 13 that has stuck with him ever since. “Son, your job is to go further than I did, because my job was to give you a better starting point.”

When a great team member leaves, the next team member can go further because they had a better starting point. The first thing to do, after communication and timeline, is that the person needs to evaluate critical tasks they do. Is it documented? Is it up to date? Cross train someone by recording Loom videos of how you do this. Hand that playbook to the person who comes in, and they should be able to do it at 80% of the person who left—right away. How long did it take the person who left to get from where they started to where they ended up? A long time. The new employee just runs the playbook from day one. 

If the person does this the right way, they can’t wait any longer. They have to follow their dreams. Set up their successor for success. Then the only thing you should feel is gratitude and express it. Say goodbye on the last day, publicly or privately. Honor them in a powerful way. See this as your last opportunity to lead them. Then keep leading after they go.

Richard and Jeff want to hear from YOU. Was something in today’s episode a big aha moment for you? Anything you disagreed with? What have you discovered about yourself and your team? Email them here with your thoughts/questions: feedback@readytolead.com 


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