The power of one-on-ones and building a coaching mindset as a leader

September 24, 2026 By Kelly Bosak 0 Comments

Coaching isn’t a scheduled event – it’s a mindset that shows up in every conversation you have as a leader.

Whether you’re talking with a team member on the job, sitting down for a one-on-one or performance review, leading a team meeting, working through a corrective discussion or simply recognizing great work, each of these moments is a chance to coach.

The goal is simple: Bring a coaching mindset to every conversation, in every format, with everyone you lead.

Engaging in one-on-one conversations is one of the best ways to activate coaching every day.

Why one-on-one meetings matter

Meeting one-on-one is one of the most powerful ways to connect with your employees. Employees of managers who skip one-on-one meetings are four times as likely to be disengaged.

To quote researcher and author Brené Brown, “Daring leaders must care for and be connected to the people they lead.”

One-on-one meetings give you that connection – a dedicated space to care for the people you lead and celebrate their growth. Here are some tips to make your one-on-one meetings meaningful and productive.

Tips for meaningful one-on-ones

Frequency: Choose the right frequency for each person. At a minimum, meet with an employee once a month.

Length: Schedule for an hour and end early if you wrap up sooner. An hour is a good amount of time to broach thornier issues – that depth is where the real value of a one-on-one lives.

Don’t cancel – reschedule: If something comes up, reschedule rather than cancel. It shows your team you value the time together.

Location: Choose a setting that supports real conversation – a conference room away from your desk, a walk, a coffee shop or lunch together all work well. With remote employees, make sure you are in a private area.

Set expectations: Share your intentions and goals for the one-on-one with your team. Your employee should bring the agenda; you can offer a list of starter questions and always ask, “What else?”

Build rapport

It’s OK to build rapport when starting a one-on-one, especially early in the relationship. As your relationship progresses, you may not need to focus on rapport building with each one-on-one. Sample questions:

Which aspects of your well-being are or aren’t going well right now?
What is one thing we could change about your work that would improve your personal life?
What do you like to do in your free time?
What do you do to restore your energy?

Starter questions

Before the meeting, look through this list of questions and underline the ones that you’d ask.

What’s gone well for you since we last spoke?
What challenges have you experienced since we last spoke?
What’s on your mind today?
How can I better support you?
What part of your job energizes you?
What part of your job depletes you?
What are two or three new skills you’d like to learn on the job?
Where would you like more feedback?
How connected do you feel to your team?

Additional topics

It also helps to have a variety of other topics ready for discussion.

Talk about career development and personal development plans.
Give specific praise by being precise about what you like and give praise regularly. Studies show that getting praise or recognition for good work increases revenue and productivity by 10-20 percent, and those feeling unrecognized are three times more likely to quit in the next year. Give praise and watch them smile!
Ask for feedback. Feedback should be a two-way street. Ask about ideas they may have or learn how you can improve in their eyes.

Next steps

At the end of the meeting, take time to establish next steps by talking about what you can both do to make progress on what was discussed.

When you come to a one-on-one meeting with the right mindset and a few good questions, you help it push past any awkwardness and turn into a healthy and productive conversation.

Kelly Bosak is the chief people officer at Lettermen’s Energy, where she leads a small but mighty HR team supporting Lettermen’s employees nationwide. Kelly can be contacted at kelly.bosak@lettermensenergy.com or 816-679-1105.

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