How to have one-on-one development conversations

Last week, I was coaching a newer leader whose team is expanding. He was exploring proactive ways to develop his team through rapid team growth and to develop his successor for the future. This coaching topic comes up often. There is clearly a specific need for leaders to be guided through their first few development conversations with team members.

Why have frequent development meetings?

One-to-one development conversations help you keep informed on how things are going with each of your team members, including how they feel, their professional development, their interests, even their life outside of work. These conversations can also help you find out about your team members’ emotional states, including morale and stress levels, which can give you insight on any specific ongoing issues: either the employee’s, the manager’s, or both.  

Staying informed and aligned can help you solve challenges while they are still small. Through these conversations, you not only track the status of a team member’s performance and how their goals are coming along, you may also learn if there are any obstacles in the employee’s way that need to be removed, or if their goals need to be adjusted. 

Finally, these meetings help to build trust because they demonstrate to your team that you care about their development and your relationship with each team member. There have been numerous research studies over the last decade that point to employee motivation being tied to the relationship with their leader and their leader’s investment in their development. One-on-one meetings are key to understanding what is challenging each team member, and to recognize team- or organization-wide challenges that may be emerging.  

What a development meeting could look like

There’s no one perfect formula or framework for one-to-one development meetings, but here are some suggestions for how you can structure your meetings in order to maximize the value for both you and your team members. You can adapt these to fit your unique relationships, team and work environment.

Before the meeting:

  • Book a recurring meeting at least 30 minutes once a month or every two weeks. Never cancel, but you may reschedule if something urgent does come up. Discuss expectations around rescheduling together in your first meeting.

  • Tell your team why you are holding the meetings, the intent to focus on their development, challenges and other non-tactical agenda items.

  • Prepare ahead of time so you can come to the meeting with feedback and examples, whether positive or course corrective.

  • Notice your employees’ accomplishments and come prepared with specific examples to help them understand how they created a positive impact.

During the meeting:

  • Meet somewhere comfortable for your team member. For example, a coffee shop can make the meeting less formal. Sharing food together creates some magic in the relationship and a change of scenery can offer a new perspective. Make sure the space is private - for example, a coffee shop can be private with a table away from others 

  • Begin with a check-in. Break the ice by catching up on things important to them like their family, interests outside of work, and other things happening in their life.

  • Set the agenda and ask what challenges they are facing or what they want to discuss. These could include: professional development goals, team dynamics, self-improvement, personal challenges, interpersonal challenges in the workplace.

  • Recognize wins, and give feedback on misses. Ask them: “What can I do differently to help you be successful?” You can get honest value-added feedback from them, and find opportunities and ways for you to coach them. 

  • Talk about performance, coaching and career or learning progression. Avoid status updates on tactical issues. By making time to have regular conversations beyond everyday to-dos and business strategies, you can address topics prone to getting lost in the shuffle, such as career development.

  • Ask for feedback about your leadership. These meetings are a valuable opportunity to expand your self-awareness and development as a leader and demonstrate your commitment to self-improvement, not just your team’s improvement.  One starting point could be: I’m continually looking to improve myself as a leader.  What is one situation where I may not be aware of the impact that I had either positive or negative that you could help me understand from your perspective?

  • End meetings with a recap of what each of you took away from the discussion. Providing mutual feedback helps each other grow.

After the meeting: 

  • Keep notes and keep them in one place for all team members and follow-up on any action items or check ins during the next meeting.

  • Follow-through on any commitments you have made.

  • Make sure to schedule your next development conversation.

Your first meetings may feel a little awkward as you start navigating this new approach in your relationship. By committing to regular meetings, you’ll begin to develop your own natural style to create maximum value and you’ll both soon look forward to these development conversations.

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