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Stay Conversations to Increase Retention


Stay Conversations to Increase Retention by Rebecca Boartfield

We all have (hopefully) key team members who are excellent at their job and incredibly valuable to the practice – whose departure would create stress and challenges, and their talent would be nearly impossible to replace. Retaining these employees is critical to your overall success.

While you may feel that way about them, when is the last time you’ve asked those individuals how they’re doing? Are they as committed to the practice as you think they are? Are you making assumptions about their overall happiness simply because you’re happy with them and they’re one of your top performing employees? Bottom line: are you taking them for granted?

Maybe it is time for a “stay conversation.” A stay conversation is when a leader/manager checks in with their current staff to make sure they’re having an experience that would support staying. Ideally, these conversations should happen on an ongoing basis. It is also good to align these conversations with key milestones (e.g., anniversaries) and “career risk triggers” such as a change in responsibilities, a change in management, or promotions of other employees. 

To start, be sure you let your employee know this is not a performance review; it’s a check in to see how they’re doing and how you can support them. Let them know they’re valued and appreciated, and that you just want to be sure their experience at work is a good one. 

When having this conversation, here’s a few questions to consider to drive the discussion:

  • 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?

Try to avoid making it feel driven by an agenda – it’s a conversation, not a test, and does not need to meet any specific goal other than hearing and discussing their experience. 

Schedule these conversations to occur when your head will be clear, and you can focus. Ask yourself, “What would the impact on me and our team be if this person left tomorrow?” And approach it with the mindset of preventing that. 

Other pointers:

  • Turn off notifications and put away all distractions. Focus 100% on this conversation. 
  • Set the context of the meeting; start with a general question to get a flow before probing deeper.
  • Actively listen.
  • Know that not everything will be solvable (e.g., asking for a raise), but understanding what’s going on is better than ignoring it and can help identify a path forward together. 
  • When something is working, celebrate it (“That’s great to hear, I feel the same way.”), and then reflect on it (“What do you see has been making the difference?”).
  • When they’re sharing frustrations or complaining, listen for their commitment, reframe it, and ask about what you could do to address it together. For example, “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 together to make a difference for you?”
  • Close out the conversation by establishing the next steps in writing and expressing gratitude for their willingness to share. 

Hands down, this is more work than just assuming everything is okay, hoping for the best, and doing nothing. But, is it more work than finding and onboarding a replacement for these individuals? Wouldn’t you rather spend your time (and money) on keeping good employees rather than replacing them? Don’t bury your head in the sand. Refocus your efforts on being proactive rather than reactive – it’s better for everyone!