500+ managers confessed their biggest struggles to me

Which do you share?

Hey team happy Tuesday,

I’m back on the train to London today to deliver my 3rd and final full team workshop of the month, very excited for this one I’ll keep you updated.

You only have TWO days left to get your ticket to my online event…

💥 How to Hold People Accountable (Without Being the Bad Guy) 💥

Over 400 people have now signed up, and I’m gifting you a free ticket when you buy my debut book, Your Boss Era.

But don’t wait - You now only have 48hrs. Once you’ve placed your order for the book (on any site), just reply “purchased” to this email, then i’ll check and send you the free ticket.

But back to the matter at hand…

Do you ever get that sinking feeling like you're trying to do everything right as a manager, but somehow… things just still aren’t clicking?

You’re not imagining it. And you’re definitely not alone.

Over the past few months, I’ve read through over 500 anonymous email and DM responses from real managers, ranging from new leaders to experienced heads of departments, spilling their biggest daily leadership struggles.

I asked them all one simple question:

“what is your greatest struggle in your leadership role right now?”

Some of them broke my heart. Others made me shout “YES!” out loud because they were so relatable. But all of them pointed to one truth:

The struggle isn’t because you’re not smart enough.

The struggle is usually rooted in self doubt, people pleasing and a lack of confidence in our abilities (even though you’re amazing).

So in today’s blog, I’m going to walk you through the five most common (and most frustrating) leadership struggles, (with real-world fixes) you we start using them today.

And I’d love to know in the comments, which manager do you resonate with the most?

Let’s jump in.

And you can either read the blog below, or watch the YouTube version of me explaining each of these in much more detail here.

Manager 1: The Accountability Trap

“I don’t want to be labelled a micromanager, but I keep having to chase people to get the work done to a good standard and on time. I ask nicely and I give them space. But things are still late.”

Let’s discuss.

No matter what we think, micromanagement doesn’t stem from the frequency of our check-ins.

It begins with unclear expectations.

We don’t get labelled a micromanager because we check in. But we become one when we fail to create clarity, so then have to scramble to fix it at the last minute.

Here’s what’s really going on: Most managers think they’re being respectful when they say, “Can you try to get this done by Friday?”

But that language creates wiggle room and uncertainty. Instead, use language like:

“Can you let me know a good deadline for this work?
”Then if anything might block it, let me know 48hrs before so we stay on track.”
”Are all the expectations of the work clear to you? Is there anything further you need support with?”

Why it works:

• We hand over ownership

• It adds a check-in moment that feels helpful, not controlling

Manager 2: From Peer to Boss

This transition can feel brutal.

Here’s what one manager told me: “I got promoted to lead my old team. I haven’t addressed the shift. I want to stay friendly. But now I feel awkward, and people keep overriding me or ignoring deadlines.”

Here’s the uncomfortable truth: You can’t lead people effectively if you’re still trying to be their friend.

You don’t have to become robotic or aloof, but you do need to reset expectations. Otherwise, people will keep relating to you the way they always have and you’ll start to resent it.

Try this soft-reset script:

“As you know, my role has changed. I want to make sure I’m supporting the team properly, and that means shifting how I work with you. Here’s what that will look like…”

Then calmly explain:

• What you’ll now own

• How decision-making will work

• How you’ll support them differently

The awkwardness doesn’t last as long as you think. But you need to create clarity. That’s what will earn you the long term respect.

Manager 3: My team relies on me for everything

This issue came up in every industry. One manager summed it up perfectly:

“I feel like I’m the bottleneck. Every question comes to me, even the basic ones. I worry when I go on holiday or even step away for a few days they can’t handle it.”

Here’s the problem: If you always answer, they’ll always ask.

You need to break the cycle with a default coaching script. Something like:

• “What’s the goal here?”

• “What are three ways you could approach it?”

• “What do you recommend, and why?”

Yes, it’ll take a minute longer than just giving the answer. But the long-term ROI is massive. You’re building decision-making muscle. You’re teaching them to own their work.

Autonomy doesn’t happen overnight, but it only starts with your refusal to rescue every time they panic.

A client of mine who runs a team of product managers said implementing this was the single biggest shift they’d made all year. Suddenly, people were showing up with proposals. Not just problems.

Manager 4: Feedback That Feels Like a Personal Attack

This one hurts, especially when your intentions are good.

One manager said: “I gave feedback once, and now she avoids me completely.”

And another said, “I told someone they needed to be more organised. Since then, I feel like they’ve stopped trusting me and talk badly about me behind my back.”

The biggest lesson I’ve learned here is this:

Feedback isn’t usually the problem. The way we deliver it is.

Most feedback is too vague or too emotionally loaded. So instead, try this formula:

The [specific action] had [specific impact]. What do you need to stay on track going forward?

Example:

“The report was late, which delayed sign-off for the project. What would help you hit the deadline next time?”

This reframes the conversation from criticism to collaboration. It keeps it about the work, not the person.

If someone does shut down, follow up later. A simple, “Hey, I noticed you were a bit quiet after our chat. Do you want to talk anything through?” opens the door.

TL;DR - Here’s Your Manager Cheat Sheet

• Deadlines slipping? → Use clearer ownership language with check-in triggers.

• Drowning in your first 90 days? → Slow down. Observe, then implement.

• Struggling with a peer-to-manager shift? → Reset expectations with calm clarity.

• Team too dependent? → Start coaching, stop rescuing.

• Feedback backfiring? → Get specific. Make it about the impact, not the person.

Peace,

H

P.S. If you prefer to watch the YouTube version of me explaining these in much more depth, here you go: