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The 3 Stay Conversations: The best way to improve employee retention

Improve employee retention by having these three one-on-one meetings with your staff once a month.

improve employee retention

We all want to improve employee retention. The question is how?

Our knee-jerk answers to this question can feel opaque. Pay, perks, and promotion opportunities could matter… but to what degree? Employee recognition programs or more social activities could be helpful aspects… or will those efforts feel superficial? Training for new managers could also be beneficial… but who needs to be trained, and on what skillset areas?

The fog begins to lift when we have a conversation with our team members themselves. We must talk one-on-one with our team members to best understand what their current experience of work is like, and how it can be better.

Sure, a survey or two can be helpful for giving data points of general sentiments – but when we sit down in-person or in front of a video call, face-to-face with our team members, we capture the nuance for what is encouraging that specific person to stay. Rather than broad generalizations of our own projected assumptions, a conversation shines a light on what we can do for each particular person we want to stay. Only then can we understand exactly what steps to take. 

What conversations should you be having to improve employee retention?

I’ve identified 3 conversations in particular that you as a leader can be having with your direct reports to improve the likelihood of employee retention.  I call them “The Three Stay Conversations”  as they focus on identifying the aspects of the work itself that encourage someone to stay.

Stay Conversation #1:  Work Clarifying Questions

Ask these 3 questions around work motivation to understand what might encourage your employee to stay:

  • In the past few months, when have you felt most motivated or energized in your work (if at all)?
  • Is it clear why the work you do matters to the organization?
  • Which of your skills do you feel is not being used in your current role? 

From the answers of these questions, you’ll learn how to better adjust projects and areas that an employee is working on, along with what the employee’s role is, so their work is aligned with what your employee might be most motivated by.

Stay Conversation #2:  Dynamics Questions

Ask these 3 questions around team dynamics to understand what might encourage your employee to stay:

  • Is there any part of the team you wish you got to interact with more?
  • How do you feel about the current level of social interaction across the team?
  • How do you prefer to be recognized for work well done?

These questions help reveal the degree of social interaction, team closeness, and positive recognition that an employee desires. From this, you can then consider how to craft opportunities for rapport and connection to be fostered throughout the organization.

Stay Conversation #3: Context Questions

Ask these 3 questions around organizational context to understand what might encourage your employee to stay:

  • Is there any aspect of the organization that you wish you knew more about?
  • What’s felt confusing or frustrating for you lately?
  • To what degree would you say the vision of the organization is clear?

The answers to these questions can give you an accurate picture of how informed an employee feels in their current work environment, and how that might be affecting their experience of work. From this, you can then change how and what context you’re sharing (or not sharing) in the workplace.

💡 All three of these stay conversations can be found in our one-on-one template in our One-on-Ones Tool in Know Your Team. 

Try holding these Three Stay Conversations in your one-on-one meetings once a month, or at the very least, once a quarter. Alternatively, you can try interweaving these questions into your weekly one-on-one meetings, in whatever order feels right to you. 

However you might look to implement the Three Stay Conversations, know that it’s the quality of these conversations that will help you improve employee retention in a meaningful way.


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Written by Claire Lew

CEO of Know Your Team. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.

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