Is AI coming for middle management?

What we *actually* need to worry about

Hey team, happy Tuesday

Tomorrow I’m running a live, online session on how to hold authority and earn respect without becoming the manager nobody wants to work for.

So if you haven’t reserved your spot, do it now, because I’m talking about something today that makes this session more urgent.

Is AI coming for middle management?

I did a keynote last week on my biggest stage yet, 600 people in the audience, and I was asked the same nervous question (twice) that keeps popping up a lot recently…

“Heather, is AI going to replace us managers?”

But we’re asking the wrong question.

The real question is: “Which parts of my job is AI coming for, and am I still attaching my worth to those parts?”

I’ve watched leadership evolve now for over a decade, and I can tell you exactly which managers should be panicking right now, and which ones are about to become more valuable than ever.

So let’s get into it.

A brutal stat for you: Managers spend around 54% of their time on admin, i.e.: status updates, chasing information, reformatting the same update for five different stakeholders, running meetings that exist to relay information that could’ve been a Slack message. Eek. (I can relate).

But we can’t actually call that management… It’s information plumbing.

And information plumbing is exactly what AI is built to do, only faster, cheaper, and without a lunch break.

So if your entire value and self-worth as a manager has been built on:

• Passing updates up and down the chain

• Running status meetings

• Chasing people for information

• Being the human middleware between SLT and the team

All of those things can be replaced.

And I’m not saying this to scare you (I promise, nothing pi**es me off more than fearmongering around AI), but I do need to lay it out clearly, because I think you already know, deep down, that this isn’t the right way to be a leader, and something needs to change.

Here’s what AI cannot touch (not even close)

I can no longer count how many times I’ve told you this stat, but it’s so important in the AI discussion…

Gallup has proved one thing over and over: managers account for at least 70% of the variance in team engagement.

Not the company, not the mission statement on the wall, not the free snacks… The manager.

And that engagement isn’t information pushing. It’s real, human, trust.

Put very plainly, AI cannot:

• Notice that someone’s gone quiet in meetings and ask them if they’re okay

• Build the kind of psychological safety where someone tells you the truth before it becomes a crisis

• Hold a difficult conversation with someone whose confidence is hanging by a thread

• Make a judgement call about when to push someone and when to protect them

• Earn respect

As I showed you in last week’s newsletter… Employees now trust their direct manager more than senior leadership (by a wide margin).

That trust isn’t sitting in a database somewhere AI can access. It’s built in hundreds of small human moments, things like a 1:1, hard feedback delivered kindly, and showing up consistently when things are messy.

“So how do I make sure i’m ahead of the curve with this?” I hear you ask

Forget waiting for your company to “strategise” about AI. If you do want to be ahead of the curve here, we can’t wait for permission to become more valuable.

Here’s where my team and I are starting:

1. Every week, find one dead task and kill it.
Pick the single most repetitive thing you do. Maybe it’s the status update, the meeting recap, or the report nobody actually reads properly. Draft it with AI instead of starting from scratch.
For example, a couple of months back, Levi used Claude Cowork to pull our weekly reporting data into Slack every Monday morning, so she no longer needs to spend an hour filling in reports.

2. Spend the hour you just got back on a person, not a task.
Have the 1:1 you’ve been putting off. Check in properly with the person who’s gone quiet lately. That hour is where your real value lives now, so don’t let more admin sneak back in and eat it.

3. Get visible outside your own team.
Post one honest thing on LinkedIn this week. Being visible, telling your stories and spotlighting your team not only fast-tracks your career, but makes you far more AI-proof because you’re building something human.

4. Practise the conversation AI can’t have.
Give that one piece of hard feedback you’ve been avoiding. Do it kindly, but do it properly. That’s the muscle that makes you genuinely hard to replace, and like any muscle, it only grows if you actually use it.

The line in the sand

If you’re an information pusher, you should be worried. That part of the job will be automated over the next 5 years, and no amount of “but I’ve always done it this way” will stop it.

But if you’re the person your team trusts with the truth, the one who has the hard conversation instead of avoiding it, the one who makes people feel safe enough to do their best work… You are about to become one of the most valuable people in your organisation.

The tools are changing but the job that actually matters isn’t.

So the question isn’t “will AI replace me?”

It’s now, “which manager am I choosing to be?”

Peace,

H

P.S. This is the entire thesis behind Custard btw. It isn’t there to replace the manager’s judgement… It’s there to systemise the admin, surface the pattern in the team’s feedback before it becomes a resignation letter, and hand the manager back their time so they can do the bit only a human can do.

We’re opening up to 50 more businesses next week, I hope you’re one of them. Join the waitlist.