How to Talk to Your Manager About AI Strategy

There's a conversation you need to have with your manager. You probably know this. You're probably avoiding it.

The conversation is: "What's the AI plan for our team, and where do I fit in it?"

Most people don't ask this because they're afraid of the answer. Or because they think raising it might draw unwanted attention. Or because they assume their manager doesn't know either. All three might be true. But not asking is worse than any of those outcomes.

i didn't have this conversation before my redundancy. I assumed everything was fine because nobody told me otherwise. Turns out, quite a lot of people knew things weren't fine. They just hadn't told me. If I'd asked, I might have gotten a heads-up. I definitely would have been better prepared.

Why this conversation matters

Your manager almost certainly knows more about the company's AI plans than you do. They might not know everything. But they know more than nothing, which is what you currently have.

More importantly, having this conversation does three things:

It signals that you're forward-thinking. Managers remember who asked smart questions about the future. When restructuring happens and they're asked "who should we keep?", the people who showed awareness and initiative are the ones who come to mind.

It forces your manager to include you in the conversation. If they haven't thought about what AI means for your role, your question makes them think about it. Better they think about it with you in the room than without you.

It gives you information you can act on. Even a vague answer tells you something. "Don't worry about it" means either nothing is happening (unlikely) or your manager doesn't want to tell you (more likely). "Actually, there are some changes coming" gives you a head start. Either way, you know more than before.

The script (yes, literally a script)

i know some people want exact words. So here they are. Adapt them to sound like you, obviously.

The opening: "Can we spend 10 minutes talking about AI and how it might affect our team? I've been thinking about it and I wanted to get your perspective."

This is low-pressure. You're asking for their perspective, not demanding answers. You're framing it as a discussion, not a confrontation. You're giving a time limit so they don't think it's going to be a massive emotional conversation.

If they say "sure":

"I've noticed the company has been talking more about AI recently [or: I saw the announcement about the new AI initiative / the transformation programme / the Head of AI hire]. I wanted to understand what that means for our team specifically. Do you know if there are any plans to introduce AI tools in our area?"

Then listen. Actually listen. Don't interrupt. Let them talk. What they say and what they don't say are both informative.

Follow-up questions:

"Is there anything I should be doing now to prepare for those changes?"

"Are there AI skills or tools you think would be valuable for me to learn?"

"If there are AI pilot programmes happening, could I be involved?"

These questions position you as proactive, engaged, and adaptable. They also generate specific, actionable information.

If they seem uncomfortable or evasive:

"I understand you might not be able to share everything. I'm not trying to put you on the spot. I just want to make sure I'm prepared for whatever's coming and that I'm as useful to the team as possible."

This gives them an out while still making your intent clear. And it leaves the door open for them to come back to you later with information they couldn't share in the moment.

What the answers actually mean

Let's decode the likely responses.

"Nothing's changing, don't worry about it." Either nothing is changing (possible but increasingly rare) or something is changing and your manager can't or won't tell you. Either way, take action independently. Start building AI skills regardless.

"We're looking at some AI tools but nothing definite yet." Translation: AI implementation is being planned but hasn't been finalised. You have time. Use it. Get ahead of whatever's coming.

"There are some changes coming and I'll tell you more when I can." Translation: restructuring is being planned. Your manager knows about it but is bound by confidentiality. This is actually a generous response because they're telling you to prepare without telling you to prepare. Take the hint.

"I don't know, honestly." This might be true. Middle managers are often the last to know about restructuring plans. If your manager genuinely doesn't know, that's useful information too. It means the plans, if they exist, haven't reached your level of management yet. Or your manager is being kept out of the loop, which might tell you something about their position as well.

"Actually, let me tell you what's happening..." This is the best outcome. Your manager trusts you enough to share real information. Whatever they tell you, act on it immediately.

When to have this conversation

Now. This week. Not next month.

The best time is during a regular one-to-one, so it doesn't feel like a special occasion. Drop it in as one of your agenda items. "I had a couple of things: the project update, the client issue, and I wanted to chat briefly about AI plans."

Making it one item among several reduces the weight. It becomes a normal professional conversation rather than a scary existential one.

Don't have this conversation:

• Immediately after a town hall about efficiency (too reactive)
• In a group setting (too public)
• Over email or Slack (too easy to dodge)
• When your manager is visibly stressed (bad timing)
• During your annual review (wrong context)

The follow-up is more important than the conversation

Having the conversation once is good. Following up is what makes the difference.

After the initial chat, do something. Build a small AI project. Learn a tool. Apply AI to a real task. Then go back to your manager a few weeks later: "Remember we talked about AI? I've been experimenting with Claude for our report drafting process. Here's what I found."

Now you're not just someone who asked about AI. You're someone who acted on it. That's the difference between being a passenger and being the driver.

Keep the conversation going. Every few weeks, mention what you're learning or building. Ask if there are updates on the team's AI plans. Stay visible. Stay engaged. Make sure that when decisions are made about the team's future, your name is associated with AI capability, not AI anxiety.

The conversation you have with yourself

Before you talk to your manager, have an honest conversation with yourself.

What's your actual fear here? Is it that AI will replace your job? That you'll be made redundant? That you'll have to learn new things? That you're too old or too non-technical to adapt?

These are all valid fears. But they're also all manageable. AI literacy isn't what you think it is. You don't need to become a technical person. You need to become someone who can work alongside AI tools. That's a much smaller shift than it feels like.

The conversation with your manager is partly practical and partly psychological. It's you deciding to engage with the change rather than hide from it. That decision, more than any specific tool or skill, is what protects your career.

The one thing to do today: book 15 minutes with your manager this week. Put it in the calendar now. Not next week, this week. Write down the three questions you want to ask. Then ask them.