12 Coaching Questions for 1:1 Development Meetings


Are you having one-to-one development conversations with your employees each month?

Working in this field for more than 30 years, probably the most effective habit I have seen for leaders to develop and retain employees is this 1:1 development meeting.

Your job in a 1:1 meeting is to ask, listen, and coach. This small investment of time each month shows your interest in the employee as a person. Try to keep these meetings. Reschedule if you must, but don’t cancel them. Over time, these meetings produce career results for your employees. And that produces results for your team.

Following up from last week’s topic, here are 12 coaching questions for 1:1 development meetings.

Monthly 1:1 Development Meetings

Where the focus of the 1:1 check-in meeting is on the past and current period, the focus of the development meeting is on the future.

This is where you pull back the camera for a bigger picture view. Ask about longer-term aspirations and goals. Most managers find it helpful to schedule development 1:1’s on a monthly basis.

The development 1:1 is structured the same way as the progress check-in meeting. But you have to take stock every now and then. I recommend doing a full development conversation every six months.

Try these questions for that full conversation:

  • “What do you like about your current job?” - Get the good parts, first, and learn more about the employee. Keep this question open-ended and just listen.
  • “What do you not like about your current job?” - Handling their answer to this question with grace can build trust with your employee. Some employees will give you a very blunt answer. Some will dance around this question. Be prepared to hear things that you don’t want to hear, and just take it in. Do not explain, respond, or defend yourself. Accept their point of view. This is valuable information about the employee that you can keep in mind when making work and development assignments.
  • “What skills and interests aren’t we tapping enough now?” - This question can help you discern the employee’s engagement level and spot opportunities to get them involved with things that could help them, you, and the team.
  • “What is your next big career goal?” - Depending on the current level of the employee, this could be a promotion, a big project assignment, an entirely new job, working on a certificate or degree, or many other things.
Side Note: But what if they don’t have a career goal? There are usually two cases here. They may be comfortable where they are right now. This is fine. Focus on how they can stay up to date in their current role. What could they do to keep building knowledge, skill, and experience to help themselves and the team? They may not know where they want to go. In this case, help them think about and explore the options in their career field or related areas, based on their skills, interests, and motivations. They may decide that they are fine in their current role for now. They may start thinking about advancement. Follow their lead in either case.
  • “What will it take to get there?” - By asking this, you acknowledge that the employee is in charge of their destiny and that you aren’t pushing or dictating. You are getting them to think about what it will take. Give your perspective here and offer advice if asked, but don’t tell them what they should do.
  • “What obstacles will you need to overcome?” - This gets them thinking at a deeper level about the path to their goal.
  • “How can I help?” - This is the simple ask. If the person isn’t sure, exploring some things from your own experience might be useful. Offer, but don’t push. It’s their plan and they have to own it.
  • “What can I do to get out of the team’s way and help everyone be most productive?” - Some variation of this question gets you feedback by asking the employee to talk about how you could help the team. It avoids forcing the person to give you blunt, personal feedback about your leadership behaviors. (Although some will do this, anyway!) Asking this requires some trust and you will have to put that feedback into action if you want to keep getting it.

On an ongoing basis, use the same approach you would for progress check-ins (see this article), but with the focus on the person’s personal and career development. Consider using these questions for your monthly conversations:

  • “What are some ‘wins’ over the past month?” - Ask this for the same reason as in progress check-ins: To start off with positive things and acknowledge successes.
  • “What did you want to accomplish with your development this month?” - Here, we are following the same structure as the weekly check-ins. The main topic is the employee’s development progress.
  • “What did you do? How did that work? What did you learn that is helping you with your current role? What did you learn that will help you reach your next career goal?” - These are all questions about what they learned. Explore this with the employee so that you are informed and they can lock some of the learnings into memory by explaining them to you.
  • “What’s next? What can I do to help?” - Turn it future-forward and ask about their goals for the next month. This is also a chance for you to offer insights and opportunities that you know about as a manager to help the person move toward their goal.

Okay, this was more than 12 questions. But you get the idea.

Again, you can see that the 1:1 development conversation is mostly you asking questions and then listening. Make the meeting about them. Help them succeed. Make it a habit. Invest a little of your time and help your employees grow!

You can request more information from me here, if it would be helpful.

Cheers,
–Steve

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