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Prevent Turnover of Your Best Employees With Stay Conversations

Prevent Turnover of Your Best Employees With Stay Conversations

Prevent Turnover of Your Best Employees With Stay Conversations

In every organization, there are “star” performers. These are the top contributors, those with long legacies at the company, or those who are on track to build incredible teams. When we picture long-term success, these individuals are always part of the vision. But, imagine if your top contributor left….what would you do?

Many leaders have no idea their top performers have one foot out the door. As a result, they assess turnover by asking themselves “why.”

Why did this employee leave?

Why were they unhappy? 

Why did we not know?

These questions are important to consider, but are retroactive - they occur after the star employee has already left. An important element of understanding your workforce, minimizing turnover, and increasing retention of your top performers is understanding how you can retain your employees. This is done through intentional, thoughtful, and regular Stay Conversations.

Key Takeaways

  • A Stay Conversation is a conversation between an employee and two members of leadership, designed to acknowledge key performers and evaluate barriers preventing employees from staying.
  • Stay Conversations should be conducted annually with the top 10% contributors in your organization, and last about 15 minutes.
  • The formula for Stay Conversations includes: acknowledging unique contributions, highlighting the impact on the mission, and identifying barriers to staying.
  • Effective Stay Conversations are specific, safe, intentional, and timely.
  • Stay Conversations have several positive outcomes, including identifying employees who are at risk of leaving or planning to leave, helping senior leaders identify themes and common barriers organizationally, and promoting trust and accountability for leaders and employees.

What is a Stay Conversation?

A Stay Conversation is a conversation between an employee and two members of leadership (usually the manager and a senior-level leader). The purpose of these conversations is to demonstrate value to employees and evaluate if there are any barriers preventing employees from staying.

Looking at the whole of the organization, Stay Conversations are typically done annually with about 10% of the workforce. These are the people in your organization who carry the DNA of the organization, have a deep history, and bring substantial value; they are people you can’t afford to lose.

This isn’t to say that only 10% of your workforce is worth having meaningful conversations with. Rather, mid-level managers communicate value with remaining employees through ongoing one-on-one conversations. What is unique about a Stay Conversations is its intentionality. Not every employee needs to have a meaningful conversation with senior leadership, but for the top contributors (the 10%), these intentional conversations are extremely meaningful.

The Fundamentals of a Stay Conversation

Stay Conversations should be done annually. Oftentimes, senior leadership identifies candidates for Stay Conversations after an annual talent review. This is an opportunity for leadership to look at people’s development opportunities and capacities, identify candidates for promotions, and make a plan for underperforming employees. Another opportunity is after conducting an Employee Engagement Survey. Both exercises open up dialogue about who the key contributors are and who you can’t afford to lose.

Keep in mind, that Stay Conversations are only effective with the foundation of regular, one-on-one meetings with managers. Without regular communication with one's manager, a Stay Conversation with senior leadership is going to feel out of place, impromptu, and uncomfortable. It is important employees understand the why when going into these kinds of conversations.

A Formula for Successful Stay Conversations

In a sense, a Stay Conversation is like a pulse check. Through interpersonal connections, senior leadership and employees can partner together toward long-term success. The environment you create for these conversations will foster truthful and honest conversations. It's important employees feel comfortable.

Here is a simple formula to use when preparing for Stay Conversations.

  1. Unique contributions - “This is what I’m hearing about your contributions.“
  2. Impact on the mission - “You are making an impact on our overall mission in this way. We have a desire for you to stay.”
  3. Barriers to staying - “Are there any barriers in your way that are preventing you from staying?”

How to have effective stay conversations

Let’s look at a practical example to unpack this further.

Karen has worked in marketing at your nonprofit for 5 years. She was a key contributor during a recent rebranding project. Additionally, she has expressed interest to her supervisor in moving into people management. Her development plan focuses on preparing her for a management position in the next year. Karen has been a loyal team member with valuable company knowledge. Losing Karen would have a substantial impact on her immediate team as well as organizationally. Senior leadership has identified Karen as a key contributor and a stay conversation is scheduled.

You say:

“Karen, we are so thankful for the work you have done at our organization for the past five years. I am hearing from your manager about how you were influential in the success of our recent rebranding project. You are making an impact on our organizational mission by accurately portraying our company values to our audience, reaching more people, and expanding our ability to serve our constituents. We value you as a loyal team member and we are so thankful for the way you care and serve our audience. We would love to see you stay at the organization. Are there any barriers in your way preventing you from staying?”

As demonstrated in the example with Karen, effective Stay Conversations are specific, safe, intentional, and actionable. Let’s look at these characteristics deeper.


Notice the specific contributions mentioned - contribution to the rebranding process, loyalty, saving the team time and money, etc. During a Stay Conversation, be sure to highlight specific contributions. This demonstrates to the employee that senior leadership has an understanding of how they are contributing. In larger organizations where senior leadership may not know every employee, meeting with managers in advance of a Stay Conversation to identify these contributions is crucial for success.


Encourage employees to share openly and honestly about their experiences. No matter what employees share - positive or negative - be careful to not jump immediately into the problem-solving mode or try to negate the experience. Instead, Stay Conversations are an opportunity for employees to be honest and leaders to validate their experience.

Some employees may need some time to think about their responses. Allow space for thoughtful answers, and if the employee needs more time, schedule a follow-up conversation.


At the heart of a Stay Conversation is the opportunity to listen intentionally to your employees. You may learn new information about the employee experience that is hard to hear. An appropriate response, whether the feedback is positive or negative, is “Thank you for sharing honestly about your experience.”

Even if it’s hard to hear, leaders should develop a posture of thankfulness and gratitude and avoid trying to negotiate toward a different outcome or threaten employees into changing their perspective. As a leader, a Stay Conversation isn’t your opportunity to wave a magic wand and solve all the problems. It is, however, an opportunity to evaluate what is going well and what barriers and obstacles are in the way.


Stay Conversations are revealing for both employees and leadership because you'll identify barriers along the way. Some barriers are easy to remove, while others may need deeper exploration and planning. Even still, some barriers may be impossible to remove. Either way, timely follow-up is key. Whether this is a follow-up conversation or email, let your employees know you hear them, and will assess the barriers presented, regroup, and share an action plan in a specific amount of time.

Outcomes of Stay Conversations

You may learn as a result of a Stay Conversation that an employee is planning on leaving. These employees often fall into three camps:

  1. The employee is thinking about leaving but hasn’t taken any action steps.
  2. The employee is actively looking for new opportunities.
  3. The employee is facing barriers that can’t be removed (for example, a necessary move or a family crisis).

If you learn an employee is looking to leave but hasn’t taken any action steps, be honest about the barriers they are facing. A good question to ask is, “If there was a possibility we could remove a barrier, how much time could you give us to make that change?”

If you learn an employee is actively looking for a new opportunity, be sensitive to their experience. First, thank them for their honesty and affirm their decision. This is not the time to convince them otherwise. More times than not, the employee has made the decision to leave long before this conversation and not much is going to change their decision. Then, use the remaining time to ask discovery questions designed to learn more about how, together, you can make this transition as graceful as possible.

Some good questions to ask include:

  • How far into the process are you?
  • Do you have an estimated timeline?
  • What can we do in the meantime to make sure you leave well?
  • How can I best support you in this process?

Sometimes, helping someone exit gracefully can be just as important as helping someone stay.

Beyond lowering turnover rates, or better understanding why an employee may choose to leave, Stay Conversations also have positive outcomes organizationally. Stay Conversations help senior leadership identify themes and common barriers across the employee experience. In a sense, Stay Conversations can be like a focus group, exposing the areas of greatest need organizationally. If even your top performers are expressing similar concerns, these are most likely triggers for the rest of your workforce as well. Any kind of feedback - positive or negative - is valuable information for senior leadership to better support all employees.

Additionally, Stay Conversations promote trust and responsibility. Stay Conversations allow both leaders and employees to take accountability for their expectations and experiences of work and provide a safe space for feedback. They also provide space to encourage employees and show appreciation, which promotes a shared culture of trust.

Take the next step

Turnover is costly, but open communication and the right questions can prevent turnover. Through ongoing communication and Stay Conversations, leaders can effectively gauge the employee experience and remove barriers, ultimately retaining their best employees.

In addition to annual Stay Conversations, an effective one-on-one meeting strategy is a crucial element in understanding and minimizing turnover. Our toolkit, Supervisor Essentials: Effective One-One Meetings, provides valuable insight for managers to begin incorporating this practice with those they lead.