Setting Your 2026 Leadership Goals with AI

You set goals for your team every year. You run the meetings, review the drafts, and make sure everyone has something meaningful to work toward. But when’s the last time you did that for yourself?

Most managers don’t. There’s no process forcing you to sit down and think about what kind of leader you want to become next year. So it doesn’t happen. Another year passes, and you’re the same manager you were twelve months ago – just more tired.

Setting leadership goals with AI can fix that, and the end of the year is the right time to do so. Before the chaos of January hits, before you’re buried in Q1 planning, take 30 minutes to figure out where you actually want to grow.

Tools like ChatGPT and Claude make this easier than you’d expect. Not because they know you – they don’t. But they give you a structured conversation when you’d otherwise be staring at a blank page hoping for insight. They ask better questions than you’d ask yourself, see patterns in what you tell them, and push vague intentions into something concrete.

Here are five prompts to set your 2026 leadership goals with AI.

Prompt 1: The Honest Reflection

Before you can figure out where you’re going, you need to look at where you’ve been. Not the highlight reel you’d share with your boss – the real version.

Most managers skip this part. It’s uncomfortable to sit with your own shortcomings. Easier to just pick some goals and move forward. But goals built on self-deception don’t stick.

The prompt:

I want to reflect honestly on my year as a manager. Help me think through this.

What went well: [List your wins - projects, relationships, growth]

What didn't go well: [List the misses - things you avoided, dropped, or handled poorly]

Where I felt stuck: [Patterns that kept repeating, frustrations that wouldn't go away]

Ask me follow-up questions to help me dig deeper on anything that seems surface-level or vague.

Why this works:

When you write this stuff down for yourself, you stay in your comfort zone. You gloss over the hard parts. AI doesn’t let you off the hook that easily. It’ll ask what you mean by “communication could’ve been better” or why that pattern kept showing up.

You’re not looking for AI to tell you something you don’t already know. You’re using it to pull out what you’ve been avoiding.

Spend ten minutes on this one. Don’t rush it.

Prompt 2: Finding Your Blind Spots

You just dumped a year’s worth of thoughts onto the page. Now let AI do something you can’t do for yourself – look at it with fresh eyes.

The prompt:

Based on everything I just shared, what patterns do you notice? What themes keep coming up? Is there anything I mentioned multiple times but didn't call out as a priority?

Be direct with me. I'm trying to see what I might be missing.

Why this works:

You mentioned delegation three times but didn’t list it as a problem. You talked about feeling disconnected from other teams but framed it as “just how things are.” You said a relationship with a peer was “fine” in a way that clearly means it isn’t.

AI catches this stuff. Not because it’s smarter than you – because it’s outside your head. It doesn’t have the same blind spots, the same rationalizations, the same reasons to avoid uncomfortable truths.

You might disagree with what it reflects back. That’s fine. But at least you’re looking at it instead of pretending it’s not there.

One warning:

AI doesn’t know context. It might flag something that’s actually not a big deal, or miss something obvious to anyone who knows your situation. You’re not looking for a diagnosis. You’re looking for a mirror. Take what’s useful, ignore what’s not.

Prompt 3: Picking 2-3 Goals That Actually Matter

You’ve reflected. You’ve seen some patterns. Now comes the hard part – picking what to actually work on.

The temptation is to list everything. Better delegator, stronger communicator, more strategic, more visible, more patient, better at feedback. You end up with eight goals and accomplish none of them.

Pick two or three. That’s it.

The prompt:

Based on my reflection, help me narrow down to 2-3 leadership goals for 2026. I want goals that:

Are within my control

Would make a real difference in how I lead

I'm likely to actually work on (not just aspirational)

For each one, tell me why you think it matters based on what I shared.

Why this works:

AI forces you to prioritize. It’ll push back if you try to cram in too much. And because it’s working from your own reflection, the goals it suggests are grounded in what you actually said – not generic leadership advice.

Real examples that aren’t BS:

• Building relationships outside your immediate team. You’re great with your direct reports but invisible to the rest of the organization.
• Having difficult conversations earlier instead of waiting until things get bad.
• Actually delegating instead of just saying you will.
• Asking for feedback instead of assuming you’re doing fine.

These aren’t flashy. They’re the real stuff managers struggle with.

Prompt 4: Making Them Concrete

“Build more relationships outside my team” sounds nice. But what does that actually mean? How do you know if you’re doing it?

Vague goals die quiet deaths. By March you’ve forgotten what you even meant. Concrete goals have a chance.

The prompt:

Here are my 2-3 leadership goals for 2026:

[List them]

For each one, help me define:

What does success look like in specific terms?

What's one small action I could take monthly or weekly?

How will I know if I'm making progress?

Keep it realistic. I don't need a complicated tracking system.

Why this works:

AI won’t let you get away with fuzzy intentions. You say you want to delegate more and it asks what you’ll delegate, to whom, and how often. You say you want to build relationships and it asks how many coffees, with which departments, starting when.

Example:

Vague: “Build relationships outside my practice.”

Concrete: “Have one coffee or lunch with someone from another department every two weeks. By end of Q2, I’ll know at least six people outside my team well enough to call them for advice.”

That’s a goal you can actually do something with. You’ll know in June whether it happened or not.

Prompt 5: The Quarterly Check-In

Goals set in December get forgotten by February. Not because you don’t care – because everything else gets loud and this feels optional.

Build the check-in now so it actually happens later.

The prompt:

I set these leadership goals for 2026:

[List your 2-3 goals with the concrete actions you defined]

It's now [March/June/September]. Help me check in:

What progress have I made on each goal?

What got in the way?

Do these goals still make sense, or has something changed?

What's one thing I can do in the next 30 days to get back on track?

Be direct. I don't need encouragement, I need honesty.

Why this works:

Quarterly is enough to catch yourself before the whole year slips by. Not so often that it becomes a chore.

Put a reminder in your calendar now – March 31, June 30, September 30. When it pops up, copy this prompt, paste in your goals, and spend ten minutes being honest with yourself.

You don’t need a perfect system. You need a simple one you’ll actually use.

Setting Leadership Goals with AI: The Bottom Line

That’s it. Five prompts, thirty minutes, and you’ve got something most managers never bother to create – an actual plan for your own growth.

That’s the whole process. You don’t need a leadership development framework or a fancy tracking system. You need two or three things you’re going to work on, specific enough that you’ll know when you’ve done them.

The managers who get better are the ones who decide to. Not because someone forced them. Not because it was on their performance review. Because they looked in the mirror at the end of the year and asked what they wanted to be different next time.

You just did that.

A year from now, you’ll be glad you took these thirty minutes.

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