Insight December 1, 2021 Lisa Sacchetti

9 Great Questions to Ask to Retain Your Top Talent

There are few things more frustrating than having a strong employee leave your company suddenly, in a way that you didn’t expect. You’ve done all the hard work to hire them and then out of nowhere (or so it feels) you lose that talent. In today’s incredibly hot labor market, the probability of talent flight is higher than ever.

Failing to retain these people can be very expensive. Studies show that replacing an employee can cost between 6-9 months of salary, not to mention the psychological damage to morale and team cohesiveness if your turnover is too high.

Typically, this happens because of an underlying pain point that you weren’t aware of and it can cause a serious rift throughout your organization. As one person leaves, there’s a higher probability that others will leave as well, so it’s crucial that you are proactive in order to avoid these types of situations.How do you be proactive? Well, you ask the right questions of your employees so that you can obtain the information you need to retain them. Here are 9 questions that can be especially valuable in this regard.


1. What do you like about your job?

This is simple but very effective. By leaving the question open-ended like this, you can create space for your employees to talk about the best parts of the working environment without being led in a specific direction. Then you can double down on those strengths to create an even better environment going forward.

2. Describe a good day of work you had recently.

Walking through an employee’s good day can provide a lot of insight into the little things throughout the day that make a difference. Listen for the subtle and indirect points and that can open your eyes to what truly matters for a positive holistic working experience.

3. What does your dream job look like?

Encouraging your employees to dream a little can unearth opportunities for improvement when it comes to keeping them happy. Often, there are components of their ‘dream job’ that you can take action on right away and that will make a big difference to how they feel about the current role and their future with the organization.

4. Do you feel that your skills are being utilized to the fullest?

This question is designed to uncover parts of the job where your top talent might feel constrained or unappreciated. Once you’ve identified these, be sure to take action and rectify this situation so that your people feel maximally engaged and acknowledged for the skills that they have.

5. Do you feel like you are treated with respect?

This is a difficult one but it’s paramount for nurturing a healthy relationship and culture. As a leader, it’s likely that your employees are hiding certain feelings from you – so it’s up to you to draw out that honesty and tackle any problems as quickly as possible. If your employee doesn’t feel respected, it’s only a matter of time until they go somewhere where they do.

6. Do you feel like you get properly recognized for doing good work?

One of the biggest contributors to workplace satisfaction is due to recognition for work that gets completed. The feedback loop where a leader expresses their appreciation for hard work is crucial to maintaining the morale and productivity of employees. If your top personnel doesn’t feel that they’re getting the credit they deserve, you’re in trouble.

7. What would make you leave your position?

Direct and to the point, this question helps to weed out the negative aspects of a job that might be a risk to your top talent. Getting open and honest answers requires open communication though, so this is something that you can build over time. Don’t just take them at face value – dig deeper to understand the nuances and what lies beneath the surface.

8. When you are contacted about another job, what do you tell them?

A question like this aims to get at the reputation of your company and what is being said about it. It’s a nice framing to understand how things are perceived inside your organization and what can be done to improve things. See if you can identify any hidden pain points that the person is not telling you about directly.

9. What advice would you give management in order to retain your peers?

Here, the indirect framing works again to make things less personal and more general. This gives your employee the opportunity to make a sweeping statement that won’t affect their standing with leadership directly. Often, this cover helps them to be more honest and upfront with their feedback, which is worth its weight in gold for you as a leader.

Those are just a few of the questions that can be helpful when you’re trying to retain your staff over the long term. Ideally, they should be included organically in conversation and you should continually be probing to understand what keeps your top talent happy and engaged with the company mission.

Here at The Renaissance Network, we can help you source this top talent and we continue to support you in retaining them as they onboard. If you’re looking for a professional firm to assist you in building a world class team, be sure to get in touch. We’d love to see how we can help.

Lisa Sacchetti Headshot

Lisa founded The Renaissance Network in 1996 with the mission of building world-class teams and quickly developed a focus on the growing Education and Technology vertical.

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