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Tough Goodbyes: Five Questions to a Resigning Employee

Nobody enjoys losing a top performer. As a leader, it can be a heavy blow, particularly when the person is a critical player on your team. When faced with these tough goodbyes, we might ask ourselves – “What could I have done differently? Is there a chance they might stay?”

Over the course of my career in leadership I’ve had a number employees find their next great opportunity outside of the organization. When a talented individual who had significantly contributed to the team, receives an enticing offer from a major tech company and the salary bump is substantial, there’s not much I as a leader can do. Nor should I, I have always tried to build teams that are a great place to work and a great place to “have worked”. I want folks in my organizations to be able to look back and say, “I’m glad I worked there, look where it got me”. And we as leaders can look at that huge pay bump and say, look how great our culture was that they held out this long. However it’s still hard to lose top talent, all of the experience and context can be hard to replace. But instead of dwelling on the inevitable, decide to use this opportunity to learn more about why they are leaving and if there were factors beyond the salary that motivated this decision.

Here are five questions I find valuable during these tough goodbyes, which can help you understand your team member’s motivations and potentially reveal ways to retain them or at least retain the next employee.

  1. “What about this new opportunity excites you, aside from the salary?” By asking this, you’re encouraging them to discuss the elements they find appealing about the new role. It could be the nature of the projects, the company culture, or the learning opportunities.
  2. “In what areas do you feel your current role here could be improved?” This question aims to unearth possible areas of dissatisfaction or unmet needs. Is there something about their work, the environment, or team dynamics they wish was different?
  3. “What aspects of our team or projects do you think the new company might not offer?” This can shed light on the unique strengths of your team and the aspects they value. It can also highlight areas you should focus on preserving or enhancing.
  4. “Are there any growth opportunities you see at the new company that you feel you might not have here?” Their answer can provide insights into their ambitions and how they perceive opportunities for personal and career growth within your organization.
  5. “Beyond a salary increase, is there anything we could change or offer here that might make you reconsider your decision?” This is your direct route to finding out if there are non-monetary incentives or changes that could potentially sway their decision.

Of course, despite your best efforts, your employee may still choose to move on. This is an exciting time for them. Showing up for them with empathy and excitement even when they’re on the way out reveals a lot about who you are as a manager. It’s important to remember that this is a natural part of career progression. Nonetheless, these tough goodbyes can offer valuable insights to help you continually improve as a leader, foster a supportive work environment, and hopefully, make your team an even harder place to leave in the future.

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