All Articles Leadership Management Losing a great employee? Here's your best chance at retaining them (and understanding why they’re leaving)

Losing a great employee? Here’s your best chance at retaining them (and understanding why they’re leaving)

You might not be able to keep a departing employee, but you can learn from why they're leaving.

6 min read


Losing a great employee? Here's your best chance at retaining them (and understanding why they’re leaving)

Renee Fisher/Unsplash

Exceptional leaders depend on great teams, and great teams are full of great people, which is why it’s so painful when one of your strong contributors decides to leave. This can be demoralizing and made worse if their departure catches you unprepared. 

Is it possible to change their minds? Maybe. Like breakups, someone saying “I’m leaving,” is unlikely to be talked out of it. You should assume great consideration went into this decision. Few make these changes lightly. However, it costs you nothing to explore any deeper reasons behind their departure and explore the possibility they might stay. 

Why are they leaving?

There are simple places to start when evaluating an employees’ motivation for leaving.

  • Is the employee leaving because of you? Is the employee dissatisfied with your relationship, your management style, or other underlying personality conflict?
  • Are they leaving because of their role? Are they burned out? Do they feel like they’re doing meaningful work?
  • Are they leaving because of fit within the company? Do they believe they have a future here? Do they want to be a part of where the company’s headed?

Ask for a 30-minute exit interview where you can explore these topics. Consider these questions:

  • What can you tell me about how you decided to leave?
  • Was there a specific moment or situation that cemented your decision?
  • Have you thought about options where you might be able to stay?

These questions should give you the information you need. Try to keep the employee talking for as long as possible. Think of it like a therapy session where your job is to take notes, listen, nod politely, and allow the other person to share as much as they feel comfortable. Avoid reacting to anything you disagree with. They might say “I’m leaving because I hate you,” and you need to respond with “tell me more about that.”

Your job is to understand, not to be right.

Do they want to stay?

End your conversation by simply asking: “If we could find a way for you to stay that fits with your needs and the company’s, would you be interested?” This doesn’t commit you to anything and cuts to the heart of the matter. If their mind is clearly made up and they’re already determined to leave, then that’s ok. You need to hear that from them. Don’t be surprised if you get this answer; most resigning employees are already beyond your reach.

But there are situations where they’ll doubt their decision. Maybe they feel like they should leave but don’t really want to. That gives you an opening to explore. The employee will hesitate when you ask or will say “I need to think about it.” Tell them that’s OK, and give them a day or two before checking back in.

What are the realistic options?

Do you want the employee to stay enough to make sacrifices? Are you willing to expend political capital on figuring out a situation that might work for all parties?

The biggest risk in retaining an employee who’s resigned, especially if it’s public knowledge, is unintentionally messaging that the best way for an employee to get what they want is to make a big show of quitting. Is retaining this person worth the potential cost? In some circumstances, it’s better to cut your losses, let this employee go, and focus on the great employees you have left.

If you decide it’s worth it, then start thinking about a proposal for staying that might entice this person. A resignation is a statement to the world: “I want change.” Your job, as their advocate, is to show them they can achieve the change they want without leaving the organization. What is it they’re looking for? Are you in a position to help them get it? If you’re not sure, ask them.

Some solutions to consider:

  • A different job within the same team or department
  • Same job in a different department
  • Different job within a different department

The above considerations assume that this isn’t simply a matter of money. Resolving employee departures originating in financial disputes are straightforward to resolve. However, you should take extra care in the message you send by retaining these employees. You may send a message that the way to win a financial negotiation is to threaten to leave. 

Once you have an option or options you feel comfortable proposing, be sure you have support from HR and upper management (if applicable). Set aside another block of time to talk with the employee. Talk through the potential solutions and the benefit and trade-off to both parties. Ideally, give the employee more than one option to decide between. This will show that you’re giving them a real choice and working to come up with a solution that they feel meets their needs. 

After you both have settled on an acceptable solution, give the employee another day or two to be sure that it’s what they really want and think of a plan to internally communicate the outcome, especially if people already know about the resignation.

Employee departures are an opportunity for self-reflection. You may find a blind spot in your culture, how you treat employees or other key insights. Being willing to explore these questions and take responsibility for the answers shows courage and humility that many leaders lack. By taking ownership of factors that lead to employees leaving and working to change them, you inoculate against losing other star employees in the same way.

And if you aren’t able to retain a valued employee, don’t let the departure get to you. People leave, it’s not the end of the world. One day you’ll leave your company and will go through the same thing your star employee did. It’s important for people to feel like they have mobility.

The best thing you can do is to make their departure as warm as possible. People will relate how you treat outgoing employees to how they’d be treated in the same circumstance. Warm departures allow the door to swing both ways, empowering the person to return if they change their mind down the road. For every 10 employees who leave, you’ll find that one or two explore a potential return.


Patrick Figures (@patrickfigures) is an executive at Village Health Partners, a progressive primary care medical group. He writes about leveraging empathy and authenticity towards a meaningful career in leadership. Read more of Figures’ writing at his website.