16 hard decisions every growing manager must make

(and a big day for the business)

Hey team, happy Tuesday,

I want to start off by thanking you for all the support whilst we’ve been in the sales campaign period for Fresh Start the last 4 weeks. As you know, I’ve always felt a little icky about selling (I think most of us do), and in the past it’s held me back a lot.

But since seeing the very emotional and wildly successful results of almost 500 managers inside Fresh Start, I know that selling this bootcamp to it’s full potential is my duty. Also, it becomes much easier to sell a product that you so deeply believe in and have put heart and soul into building it.

So thank you for the support, the replies and the trust. It never ever goes unnoticed. And I’m very excited to see the 150 of you join us when we open the doors at 10am today.

I’m glad you’re here. Now, to the point…

16 hard decisions every growing manager must make

Over the last few years, I’ve worked closely with leadership teams across global corporates, scale-ups and founder-led businesses, delivering talks and workshops to managers under real pressure to perform.

I’ve also spent the last 10 years managing teams myself. And across thousands of conversations, workshops and leadership rooms, the same patterns show up again and again.

Different industries.
Different titles.
But the exact same 16 tough decisions every growing manager eventually has to face ( and usually avoids for far too long).

That repetition matters to me. Because when the same decisions are being delayed everywhere, they stop looking like personal weaknesses and start looking like predictable pressure points in leadership.

And with every one of these decisions… both paths are hard.

Not making the decisions is hard.
It looks like staying stuck, carrying too much, firefighting, quiet resentment, and burnout creeping in while telling yourself you’ll deal with it later.

Making the decisions is hard too.
It means discomfort, difficult conversations, letting go of control, and acting before you feel fully ready.

Leadership doesn’t offer an easy option.
It only offers a choice about which hard you’re willing to live with.

The 16 decisions below sit exactly at that turning point. They aren’t designed to make you feel good.

A few may land uncomfortably, because they ask you to let go of stories that keep you comfortable but stuck. But these are the decisions that sit underneath calm, confident, respected leadership and the ability to shape culture intentionally, rather than by default.

I ask you read this with openness rather than armour.

And if you strongly agree (or disagree) with any of them, hit reply or comment with the number and your reasoning. I love nothing more than getting into these conversations with you in the comments.

Let’s go.

The 16 hard decisions every growing manager MUST make:

1. Making the decision to stop being liked
   Seeking approval from others will keep us stuck, and slowly erode the respect we’re able to build.

2. Making the decision to address a small issue now instead of managing a much bigger one later.
   Delay doesn’t make problems disappear, it just gives them time to grow teeth. Honesty saves everyone’s time.

3. Making the decision to take the fall for your team if they mess up.
   It can feel a little hard in front of seniors at first, but it signals you’re a true leader who can be trusted and depended one.

4. Making the decision to notice when your involvement is creating dependency.
   If everything runs through you, nothing is truly owned.

5. Making the decision to prioritise standards over harmony.
   Pulling someone up for bad behaviour may not keep the peace today, but it increases the performance of your team in the long run.

6. Making the decision to question your management before questioning their ability.
   Under-management is often mistaken for underperformance.

7. Making the decision to truly give credit where credit is due.
   When I was in a meeting with seniors and they say ‘great work from your team here Heather’, I would always say ‘Thank you, Danielle was a true star in XYZ, and John really smashed XYZ too, they’re real standouts at the moment.’
   Shine a spotlight on individuals where they deserve it.

8. Making the decision to act before you feel ready.
   If there was one magic pill I wish I could give all managers, it would be the courage pill. I can’t tell you the number of times I get asked, “How did you find the confidence to do X?”
   But I didn’t find any confidence, I just did the thing, scared, nervous, unsure if I’d get a positive outcome. Then eventually, I earned the confidence.

9. Making the decision to read your calendar honestly.
   It will always tell you what you prioritise, and what you avoid. If you’re in B2B meetings all day, why are you not pushing back more? Be more ruthless with your time.

10. Making the decision to be direct with feedback instead of diluting it.
    Do you leave a conversation thinking ‘did I actually say what I needed to? Or did I sugarcoat it?’

11. Making the decision to set expectations clearly enough.
    A task may come easily to you because you’ve been doing the job for years. But you need to be patient and clear with others, take time to coach and give clarity to people.

12. Making the decision to own confusion as a leadership failure.
    If people are unclear, something wasn’t explained well enough.

13. Making the decision to let go of work that just serves to make you feel competent.
    Growth means giving up the things you’re best at. I’m great at creating content, but it takes me hours and hours every day and I know it’s not scalable for me to keep doing it. So I had to train someone else up to do it and stop being so involved.

14. Making the decision to lead for tomorrow’s organisation, not just today’s team.
    Those 2 things are rarely aligned. For example:
    Today’s team: Needs you to urgently respond to a question in order to fix a quick issue.
    Tomorrow’s org: Needs you to push back and ask “Where is the process doc we should be following to ensure you don’t need me to jump in in the future?”

15. Making the decision to let go of the identity that built your success.
    You can no longer be the star individual contributor, your success is now tied to the collective success of your team. So coach, delegate, nurture and spotlight them. The aim is to create a team of star individual contributors just like you were.

16. Making the decision to stop proving your value through busyness.
    The greatest leaders are often the least busy. They’ve delegated, empowered and systemised so well that stress isn’t their default. Aim to make yourself redundant. You never will be, but getting closer means letting go of control and stopping the need to prove your value through busyness.

Which number do you agree with most? Or disagree?

Let’s chat…

Peace,

H x