8 Questions You Should Ask A Key Employee Before They Quit


You depend on your team. So when a key staff member tells you that they are considering moving on, it’s usually an unexpected (and unwanted) surprise. We asked eight members of Young Entrepreneur Council (YEC) what questions they should ask in this situation. Here’s what they had to say:

What Are You Not Getting Here?

Ask what need they’re fulfilling by moving to a different position. Is it pay? Responsibility? Respect? Often there is a problem that’s easy to solve, but both sides have made false assumptions about what the other is looking for.

This is your last chance to have an honest, frank discussion with your employee before they leave. You should try to keep them there depending on what they’re looking for. Maybe they would like a shift in responsibilities, or to learn more about a new area. But if they aren’t happy in the work environment, can’t keep up, or don’t feel like they’re a match for the team, it’s probably time for them to move on.

Lauren Roeder, LKR Social Media

If You Had a Magic Wand, What Would You Have Changed?

If someone is ready to move on, it’s likely because they no longer feel motivated or inspired. Asking what they would “magically” change can yield answers that are more telling than if you simply say, “Why are you unhappy?” Hopefully the feedback they give will be helpful in addressing any issues for other employees.

Unless there is a very clear problem with a simple solution, it’s not a great idea to negotiate to try to keep someone on your team. Even key team members are replaceable. You should staff your company with people who are excited to be part of it and believe in your mission, not people whom you begged not to jump overboard.

Brittany HodakZine Pak

What More Do You Need to Stay On?

Depending on how key the staffer is, I would analyze their value to the organization and run a cost/benefit analysis. I’ve been known to double or triple compensation in situations that warranted it. This is particularly true with sales staff who are worth their weight in gold and their contribution is easily quantifiable.

My advice for entrepreneurs is treat everything as “all business.” Don’t take it personally if a staffer wants to leave. If it makes sense on a business level to keep them around, then get ready to negotiate.

Charles MoscoeScumbag.com 

What Can Someone Else Offer That We Can’t?

If someone discusses their interest in moving on, there’s still a part of them hoping to stay. This is their way of starting the conversation. Ask them what someone else can offer that you can’t. Talk through it to come to the best decision for everyone involved.

—Brooke Bergman, Allied Business Network

How Can I Improve?

Whether or not their resignation is coming from anger, their options opening or their goals changing, asking what you can do to improve your work approach for other employees is extremely important. It establishes your own humility and openness to developing your leadership skills, and chances are they’ll provide you with extremely honest feedback.

Rob Fulton, Automation Heroes

What is the Root of the Problem?

Begin with asking why. Find out if there is a problem that you can fix, and if you can’t fix it with them, make sure that you apply it to your business in general. If the issue is simply monetary, see if there is a way you can work with that person on sustainable goals and solutions.

—Ashley Mady, Brandberry

Does This Decision Serve You Well?

The one question I would ask one of my key staff members is, “Does this decision serve you well?” I would try to learn where they’re wanting to go in life and confirm with them that whatever decision they’re making is going to help lead them to that end result.

—Dan Price, Gravity Payments

Can You Help Me Understand?

I find this question to be enlightening in all sorts of conversations. Thankfully, we have never had a key staff member choose to leave our organization, but if someone expressed the desire to leave, I’d want to understand why. There may be situations where we could find a way to meet their needs without them leaving the company, but we won’t know unless we understand the reasoning behind it.

Chris Cancialosi, Gotham Culture

Images courtesy of Shutterstock, YEC 

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