The Five Retention Questions You Need to Ask

Your most talented employees need to feel truly seen and heard.
By: | August 13, 2018 • 3 min read

Leaders spend a lot of time working and interacting with their employees—team meetings, one-on-one meetings, email exchanges … the list goes on. Yet how much time do they spend actually communicating with them, in a meaningful way? Retaining top talent is critical to any good organization, and to do so, these employees need to feel truly seen and heard. Employers must go above and beyond to get to know their employees. Here at Fierce Conversations, we recommend all leaders, at their earliest convenience, take the time to ask their employees these five essential questions, and the one they should avoid.

#1 Question to Avoid: How’s it going?

While this may seem inconsequential, simply asking “How’s it going?” does very little to further your relationship, and by not being more specific, makes it nearly impossible to get to the heart of any issue. The question is generic, and employees who hear it may shut down, assuming the only answer you want in return is, “fine.” The next frontier for exponential growth in leadership today is the ability to connect on a deep level. This question does not get you there.


Five Essential Questions To Ask:

What difference do you want to make here? Sure, there are times when a job is only a means to pay the bills, but all of us benefit from roles where we believe we can make a true impact. The act of asking it alone recognizes that a leader does in fact believe the employee can make a difference. It gives the employee the opportunity to think, perhaps for the first time, about the answer. This can help build a greater connection to their individual purpose and to the purpose of the organization, and ideally drive them toward greater success within their current role, and beyond.

How do you like to be recognized/rewarded? In work and in life, we all make assumptions based on our beliefs. If you feel great when your boss gives you kudos publicly, you may assume others want the same. The truth is, sometimes individuals would rather have a personal, in-person recognition vs. something more public. And while a bonus is always nice, perhaps some on your team would prefer a few extra days off instead. Understanding what motivates your employees on a personal level will ensure you can use these forms of reward to continue to get the results you want.

What is something that you feel is holding you back?  This is a loaded question, but one that’s worth asking. It quickly gets to the heart of any issues in a way that opens up the conversation to a number of possible barriers to success. These barriers could include  a process, an employee feeling overwhelmed with their workload, or even issues with their team members or team leader. Your job is to take these answers and try to smooth the way for that employee to be even more productive and self-aware. It’s critical for you to be able to ask many probing questions, even focusing on “What else? What else? What else?”

What would you like to be doing 2 months from now? A popular interview question is, of course, “Where do you want to see yourself in 5 years?” However, by crunching that down, you can get some insightful answers. Two months isn’t long, but it’s enough time to set short-term, attainable goals. These answers can help focus an employee–whether it be greater work/life balance or finishing a project that’s been on the back burner. This question helps the employer get a sense of where the employee wants to be, and gets the employee thinking about the future.


Do you feel you have successful work/life blending? This question is different than simply asking if your employee has a good work/life balance, and the subtle wording is key. Work/life balance is different for everyone, and issues come when there is a disconnect between what someone needs and what they’re getting.  Blending is a different way to look at it. This question opens up the ideas around how you can support them specifically, including where you, or other team members, may be overstepping. The key here is to ensure that they feel supported in what they’ve created, or possibly, need to create. It will solicit greater feedback and the action items needed to improve your relationship and their commitment to the organization as a whole.

Stacey Engle is executive vice president at Fierce Inc.