The Leader Mindset #38

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Kick-off 2026 With Development Conversations Your Team Will Appreciate

Most managers skip development conversations because they assume they aren’t worth the time. If there’s no budget and no promotion to offer, they worry the discussion will fall flat.

Others avoid them because they don’t know how to make the conversation valuable in the first place.

But avoiding it is precisely why employees leave. People rarely walk out because they didn’t get chosen to attend a conference. They leave because their career is going nowhere, and no one seems to care.

Recently, a coaching client admitted that his team was frustrated by the lack of development support they were receiving. When I asked if he knew his employees’ career aspirations, he froze.

“Honestly, I have no idea,” he said. Then came the flood of doubts: I don’t know how to start… What if it feels awkward… What if they ask for something I can’t give? All valid concerns. But none can be solved without the conversation.

If you are wrestling with the same questions, this article is for you. What follows is a simple, repeatable process for starting development conversations that actually matter. In the next five minutes, you’ll have everything you need to guide a meaningful, impactful discussion your employees will truly appreciate.

Set-up the Conversation

If you want a development conversation to land well, treat it like a meaningful moment, not something you squeeze between project updates.

Give notice. Give space. And give context.

A short message is often enough or introduce it during a team meeting. Something like:

Subject: Your Growth in 2026 – Let’s Talk

“Hi [Employee Name],

I want to set aside time to focus on you and your career aspirations. I have scheduled a separate 60-minute meeting so we can discuss your development without rushing.

Before we meet, take a few minutes to think about:
• What parts of your job do you enjoy most and why?
• What strengths you feel proud of?
• Which skills, experiences, or projects are you curious about learning?
• Where you might want to be in the next year or two (even if it is in the same role)?
• Any ideas you already have for stretching or learning

No perfect answers required. Just bring your thoughts.”

It is short and warm. More importantly, it sets the expectation that this is a genuine conversation, designed specifically for them.

Run the Meeting That Feels Like a Real Conversation

A good development discussion is not complicated. It needs enough structure to stay focused, but also enough flexibility to allow them to think out loud. Here is a rhythm that has worked for me:

First five minutes:
Set the tone. Thank them for meeting with you and for caring about their growth and development. Let them know this is not a conversation performance or project updates. It is about their growth.

Next fifteen minutes:
Let them lead. Walk through what they reflected on. It may feel slow at first. Silence is not a problem. It simply means they are thinking. Feel free to ask questions to clarify their thoughts.

Next fifteen minutes:
Explore together. Ask coaching-style questions that help them uncover what they may not yet be able to articulate.
• “What part of your day makes you lose track of time?”
• “If you could spend more time on one part of your role, what would it be?”
• “Is there a skill you have always been curious about?”
• “What would make next year feel meaningful for you?”
• “If your role stayed the same for a while, what would help keep it fresh?”

You are not evaluating their answers. You are helping them explore.

Next fifteen minutes:
Share what you see. Name the strengths that stand out. Highlight possible paths or opportunities. Be encouraging and realistic at the same time. You can say things like, “Here is where I see you at your best” or “This step feels like a strong match for where you want to go.”

Final ten minutes:
Capture a few ideas you can refine together later. The goal is not to leave with a finished plan. It is to leave with momentum.

And keep this in mind. Some employees will tell you they love their job exactly the way it is. That is ok. Development is not always about climbing. Sometimes, it is about achieving a deeper mastery or gaining broader exposure. We must all continue developing in our own way.

Keep the Plan Simple and Straightforward

Most managers default to classes or training when considering employee development. Those help, but they make for a weak plan on their own. Adults learn by doing, which is why the 70-20-10 model matters: about 70 percent of growth comes from real work and stretch experiences, 20 percent from coaching and feedback, and only 10 percent from formal learning.

Your job is to help employees think beyond courses. The best growth opportunities are usually free:

• Taking on a small piece of a new project
• Presenting to a group they don’t normally face
• Shadowing a colleague briefly
• Partnering with a peer outside their comfort zone
• Asking for feedback more often

A strong development plan only needs a few meaningful experiences and consistent follow-through. Use the attached template to keep it simple.

Follow Up Like It Actually Matters

Once the conversation is over, ask them to draft their plan and send it your way. Review it together in your next 1:1.

Then keep checking in.
Quarterly is usually enough. Ask what is working, what is getting stuck, and what support they still need.

If you promise something, deliver it quickly. Introductions, project opportunities, visibility moments, you name it. Consistency builds trust far more quickly than grand gestures.

A Few Trust Builders That Make These Conversations Stick

Because people open up only when they trust the person across the table:

• Stay curious instead of trying to diagnose or judge
• Give feedback that supports their growth, not feedback that erodes self-confidence
• Be upfront about limits. If training dollars are gone for the year, say it plainly. Then explore free options
• Follow through every time. Predictability lets them know they can rely on you

Wrapping Up: No More Excuses

That’s it. You now have a practical framework to start meaningful development conversations. You have the warm-up message, the meeting flow, the coaching questions, and the resources. You don’t need a budget, promotions, or a big program to make this work.

Make 2026 the year of development. Fine-tune the kick-off email message today and send it out before the holidays. Let your team head into 2026 knowing you care about their future and career growth.

Andy Noon, PhD

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Thanks for reading and look forward to seeing you again next week.

Andy