How to Ask Whether an Employee Is Happy at Work

People quit jobs all the time — for a better pay or a more exciting opportunity, to escape a toxic culture, or because they’ve reached an impasse in their current job. Some feel because they don’t feel valued by their manager or organization, or because their managers don’t spend enough time understanding their level of job satisfaction. And all this comes at a cost. The cost of replacing an employee can range from one-half to two times the employee’s annual salary. But this is more than just about losing money. It’s about losing your good people, dampening the team’s morale, and may be even losing customer relationships along with the employee. While you can’t make everyone stay, you can improve your attrition rates by investing time now to keep your team members by really understanding any underlying issues. The author offers recommendations for how to have effective “stay conversations” with your employees.

One mistake leaders often make is assuming that because a team member isn’t complaining, they are happy at work.

Take my client Rana (not her real name), a member of a senior team at a large international organization. By every measure, she was highly engaged in her work. She proposed fresh ideas in meetings, completed projects on time, and was responding to messages 24 hours a day as she had for the last several years. But, she was also applying for other jobs. Like many people, the pandemic caused her to reevaluate her priorities. In two years of working remotely, her well-intentioned but busy boss failed to make time to check in about anything other than work, did not talk about her career development, and ignored requests for support. As a result, frustrations built up and she left, and with it went her institutional knowledge, client relationships, and contribution to the team’s culture.

Could Rana’s departure have been avoided? Perhaps. According to research conducted by Gallup, 52% of voluntarily exiting employees say that their manager or organization could have done something to prevent them from leaving their job. While you can’t make everyone stay, you can improve your retention rates if you take the time to check in with your people.

Most people are familiar with the concept of an exit interview, where someone in HR interviews an employee who has given their notice to understand why they’re leaving. A “stay conversation” is when a leader checks in to make sure an employee is having an experience at work that makes them want to stay. I recommend having these conversations quarterly and also setting them up around key milestones (like work anniversaries). Research shows just how important it is to keep these “career risk triggers” in mind. The largest risk happens when an employee experiences a change in manager or responsibility, with job search activity going up by 17%.

Here’s how to prepare for these conversations and what to actually say when you meet with your employee.

Set the context

Let your employee know this is not a performance conversation or a meeting to talk about projects, but instead a check-in to understand how they are doing and how you can best support them. You could say:

I wanted to let you know that I really appreciate having you on our team. As we start the new year/quarter/etc. I wanted to set some time aside to just check in to make sure you’re having a good experience at work. There is no specific agenda, but I would love to have you think about the following before we meet (choose 3-4 questions from the list below):

  • How have you been feeling about work in general?
  • What part of your job are you enjoying the most?
  • What aspect of your job do you enjoy the least?
  • How have you been feeling about being able to balance work and home?
  • What has been the biggest challenge this year/quarter and is there anything I can do to better support you?
  • What can I do differently to support you and the team?
  • Is there anything you want feedback from me on?
  • Do you feel like you are learning and growing here? If not, is there anything I can do to improve your experience?

Mentally transition to the conversation

Our ability to listen and connect is largely impacted by our frame of mind when we enter a conversation. If you are scrambling to finish a project, or rushing from another meeting, it is unlikely you will be present and empathetic with your team member. When you schedule your conversation, make sure you have a buffer before you meet. When advising leaders, I recommend they take a few minutes to reflect on the below questions to help them get present to the person they are meeting with and why.

  • Who is the person I am speaking with and what does it take for them to do their job each day?
  • What would be the impact on me and our team if this person left tomorrow?

Start the meeting off right

Whether you are meeting in person or via phone or video put away any distractions. Turn off notifications, put away your computer and phone, and close out your email and any chat functions. Intentionally or unintentionally, nothing closes down sharing faster than someone looking away or responding to something else when they are sharing.

Then, express the context of your meeting in the beginning. Remind the person that you are here to listen, understand their experience and see if there is anything you can do to improve it. Start by asking one of the questions you listed in your email to them. I recommend you start with a more general question to get the conversation flowing and then move deeper.

Probe, then really listen

When training leaders to have stay conversations, they will often express the concern “What if my team member brings up a problem I can’t address, or asks for a raise or promotion I can’t give them?” My response is always, “Isn’t it better to understand what is going on than to ignore it?” And, in most cases, the act of authentically listening to a person’s concerns often addresses them or, at a minimum, helps you identify a path forward together.

In my experience, nervous leaders will enter conversations expecting the worst, when things are actually going well.

As your team member shares their experiences, (really) listen. Then probe by celebrating and reflecting on what’s working.

“I have been really enjoying working from home, I feel like we are much more efficient as a team.”

  • Celebrate: “That’s great to hear, I feel the same way.”
  • Reflect: “What do you see has been making the difference?”

“I have really been enjoying working on the launch of the new app!”

  • Celebrate: “I am happy to hear that. I love the passion you have put into it.”
  • Reflect: “What have you enjoyed most about working on it?”

Look for hidden commitments

If the person starts sharing frustrations or what comes across as complaints about their work, working remotely, lack of childcare, etc., remember that behind every complaint is a commitment. Avoid the temptation to try and propose solutions, instead, listen for their commitment, reframe it, and ask about what you could do to address it together.

“I feel like I am in non-stop meetings every day and I am up until midnight every night to get my actual work done.”

  • Reframe: “I get you’re committed to doing great work and it is frustrating when you don’t feel you have the time during the day to get it done.”
  • Reflect: “What do you feel we could do that would make a difference for you?”

“I feel like I am doing the same thing every single day and I am not getting anywhere in my career.”

  • Reframe: “I get you are really committed to growing and, right now, you feel like that is not happening at all.”
  • Reflect: “What do you feel we could do that would make a difference for you?”

Agree on next steps

In the last ten minutes of your conversation, shift your discussion to the next steps. If there are multiple things you did not have time to discuss, schedule a meeting to continue the discussion. If there are follow-up actions you will each take, put them in writing so your team member knows you really heard them out.

“Thank you for your openness in our meeting today, I really appreciate you sharing all that you did. As promised, I am going to (list follow-up actions), and send you an invite now for another conversation in two months. And, if anything comes up prior, please know we will always make time to check in.”

While this may feel like “extra work” that you may not have time for, in reality, you don’t have time not to have a stay conversation. Remember, it is the simplest actions that often have the biggest impact.

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