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Leaders: Stop Assuming Your People Are Doing Okay

By Perry Holley | September 20, 2023
Leaders: Stop Assuming Your People Are Doing Okay

On a coaching call this week, I learned that the executive I am coaching lost one of their most talented team members to a competitor. While there are many reasons why this may happen, it is essential to know why it did happen. Retaining your top talent is something leaders cannot leave to chance. Retaining top talent requires intentional actions from every level of leadership in your organization.

Don’t Assume Your People Are “Settled”

While listening to an episode of the Craig Groeschel Leadership Podcast, I heard Craig use the term “settled” when talking about people on his team. Initially, this term did not resonate with me, but when Craig suggested the opposite of settled is “restless,” it made perfect sense. Are the people on your team settled or restless? This is a question that leaders cannot afford to avoid. It’s easy to assume everyone is doing well based on outward appearances, but that is not always true.

Becoming unsettled can happen quickly. One week, your team member is doing well, feeling valued, contributing, and feeling a sense of belonging. The following week, after a difficult client presentation, a snarky comment from a teammate, and zero encouragement from the leader, the person begins questioning if they are in the proper role. Questions arise about their value to the organization, and they begin to feel the sense of belonging slipping away. Feeling settled is not a permanent state for any of us. This is why it is imperative that you, as the leader, never assume someone is settled and become intentional about genuinely understanding where each person is on the scale of settled and restless.


When leaders stay close to their teams, the signs of potential restlessness become easier to recognize. In the 5 Levels of Leadership, we teach that you may go up a level but never leave the previous level behind. This means that when you achieve Level 3 (producing results), you cannot forget to maintain Level 2 (building relationships). We can become so focused on managing the business that we can forget to stay connected to the people.

Some signs that someone on your team is experiencing restlessness might be changes in behavior like decreased productivity, lack of focus, and complaining. They may take more time off than usual. They may appear disengaged from their work and less connected to their teammates.


To ensure your teammates remain settled, a leader must invest time in knowing them personally and professionally. The best way to do this is to schedule one-on-one meetings with everyone on your team. These can be weekly or bi-weekly, depending on the size of your team. These meetings are the perfect time for you to connect with your team members and hear how things are going for them.

Things to consider for a productive one-on-one meeting:

  • Get them scheduled at a regular day and time each week or every two weeks.
  • Encourage the team members to own the agenda – what would they like to discuss?
  • Be present. Turn off your phone and remove other distractions.
  • Ask open-ended questions about their work. What do they love? What do they not love?
  • Ask open-ended questions about ways to improve their work experience.
  • Ask open-ended questions about work/life balance and how they feel about their work.
  • Inquire about ways you can help them.

People don’t mind working hard and understand there will be good days and bad days. But they also want you (the leader) to know they are working hard and value your encouragement to keep going when things get tough.

When people feel like they are valued, psychologically safe, and part of a team, they will feel settled and less likely to look for ways to leave.

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