There is a question that has surfaced many times in my management career and I’m finally convinced it’s one of the best ways to gauge your employee’s happiness.

“What would cause you to leave?”

This simple question opens up a few avenues to collect feedback from your employee.  Here’s what to listen for:

  1. “Nothing, I’m fine.”

Throw up the red flag.  It’s likely rare (unless you hired them within the past 6 months) that anyone is 100% completely happy in their role.  If you get this answer, dig a bit by asking some follow-up questions like “What do enjoy most about your role?”  and “What do you wish you could delegate to someone else?”  This gives the employee an opportunity to decipher between what they enjoy and what they simply tolerate, in their current role.


  1. “I am hoping for a promotion / a raise / a new challenge.”

This is a great start!  This allows you to discuss growth potential, performance issues, professional development and mentorship opportunities.  If they are a high performer, and you have them mapped for a promotion, you can focus on specific and measurable items for them to work on over a set amount of time.  Example: “It sounds like you are hungry for growth.  You continue to be a high performer on our Sales team and I think it may be great for you to partner with the team lead and learn more about his role.”


If the question is focused solely on money, be sure to ask more questions so you can get to a specific amount or a competitor that they may be considering.  Do this with finesse…you don’t want to punish them for being honest with you.  Here’s an example of how to gather more information, if needed: “Thanks for letting me know.  Pay is important to us.  You’ve been here a few years now, and I see that you’ve received the annual merit increase and a small bump in pay.  What kind of salary do you have in mind?  Are you looking for increased responsibility with that pay or are you hoping to stay in the same role with more pay?”


  1. “I don’t like my boss.”

There are two things to listen for when you get this response.

  • Is the boss impeding their opportunity to succeed?

It is ultra-important that an employee is aligned with their manager most of the time.  Personality conflicts arise, but if the boss is impeding the ability for someone to be successful, there are multiple issues at play.  To ask more about this, try: “I see that you have been reporting to this manager for a few years now.  Has something recently changed in the way you can work with him/her?  Can you share with me what you think could be improved to make your job more enjoyable?”

  • Is the individual unhappy with the boss, or do you have a sense that the whole team is unhappy with the boss?

If you get a sense that this individual is speaking on behalf of a group, be sure to zero in on what, specifically, makes them unhappy and avoid making a group assumption.  You should, after this meeting, schedule time with other members of the same team to vet whether there is a disruption in the team culture.  Questions to ask: “Thank you for bringing this up.  What type of boss would you want to work for, if you left our organization?”. This questions will show you the gap between their current manager and their ideal manager. Keep in mind that no manager is without flaws. What you want to decide is whether this employee can be successful in their role given the misalignment with their manager.

By taking a pulse check on your employee’s happiness on a regular basis, you can avoid losing top talent while opening a channel of communication.  Keep track of this question over time, and you will start to see when an employee becomes less engaged and thus, more vulnerable to a competitor’s offer of employment.