Happy Tuesday, we’re officially in challenge open week, and I can’t wait to meet so many of you inside! There’s lots of filming and finessing happening over here at FLWHQ. See some of you inside VERY soon.

The 6 secret traits of a truly respected leader

I got this so very confused at the start of my leadership journey, but being liked and being respected are not the same thing. And most of us, myself included, find that out the hard way.

When I first stepped up to manage people, I reallyyyy wanted my team to like me. I said yes too often, softened feedback until it meant nothing, and covered for people when I should have had the conversation.

And the strange thing was, the more I tried to be liked, the less anyone actually listened to me.

That’s beacuse respect works differently.

You can’t ask for it, and a job title doesn’t hand it to you.

It gets built, or chipped away, in hundreds of small moments that nobody writes down.

After training more than 20,000 leaders (wth), I’ve noticed the ones who earn it tend to share the same 6 traits.

And ALL of them are learnable.

1. They’re the same person on a Monday as on a Friday

The worst manager is the mood-driven manager. Your team is constantly reading you, and if your mood decides whether an idea gets heard, people just grind to a halt.

Respected leaders are predictable in the best way. They practice emotional intelligence, meaning they hold the same standards, same tone, same reaction to bad news whether it’s a good week or a terrible one.

People know where they stand, so they can stop managing you and get on with their work.

2. They tell the truth, kindly

Respected leaders say the hard thing, and they say it early, because they’ve worked out that silence isn’t kind.

Letting someone walk into a performance review blind is the unkind option. Telling them three months earlier, with a plan and some belief in them, is the caring one.

3. They hold people accountable because they care

Accountability comes from a true place of care. Respected leaders hold the bar high precisely because they believe their team can reach it, and they never apologise for holding their standards high. It might be tough, but it means the entire team gets built and consistently levelled up together.

4. They give the credit away and keep the blame

It sounds simple and it is. It’s also rare. Every time a leader stands in front of senior stakeholders and takes the hit for a missed deadline, then fixes it privately with the team, they bank a huge amount of trust. Every time they quietly claim someone else’s idea, they spend it all at once.

5. They make it safe to disagree

Respected leaders actively go looking for the dissent.

They ask “what am I missing?”, they don’t get defensive and they don’t let their ego get in the way.

They thank people for challenging them (especially in front of others). The result is a team that tells them about problems while they’re still small enough to fix.

6. They grow people, even if it means losing them

The best leaders I’ve worked with measured their success by where their people went next. They put team members forward for opportunities that would take them out of the team and talked openly about careers and development.

It feels counterintuitive. Why would you train someone to leave? But people don’t respect the manager who kept them comfortable. They respect the one who made them better, and they tell everyone about it for years.

Respect is built in the tiny moments

Notice that none of these six are big gestures.

Nobody earns respect with one brilliant all-hands speech.

They earn it in the follow-up email they didn’t have to send, the awkward conversation they didn’t put off, the credit they handed over in a meeting when nobody would have noticed if they hadn’t.

That is actually great news, because it means respect isn’t reserved for the naturally confident or the effortlessly charismatic.

It’s a set of habits, and habits can be practiced.

Peace,

H

PS. Respect is a set of habits. The Strategic Leadership Challenge gives you one to practice every day for six weeks.

Doors open tomorrow, early-bird pricing won’t hang around, and enrolment closes 4th November. Come and join us?

I had a message from one of our In The Making community members, Libby. She said something to me that really struck a chord:

“I think managers get a bad reputation online, and it can sometimes feel like a battle trying to prove you’re not a bad manager, that you’re genuinely trying to be a great leader.”

And she’s right.

As someone who creates leadership content online, I see it constantly in my comments. “Bosses are all on a power trip.” “Middle managers are just pen pushers.”

GRR.

But, I need to help us help ourselves.

I know that most weeks, we’re all just trying to get through the day and tick enough off a to-do list that never seems to shrink. But that means, that conversations that really matter, about trust, expectations, growth and support etc, keep getting pushed to next week. time and time again.

So this week, we’re doing something a little different.

Below are 21 things great managers wish their team knew, but don’t always get the chance to say.

I’m writing it as a list so you can use them as a starting point for a conversation with your team.

Choose the ones you most want your team to hear from you, and say them out loud before Friday.

Quick one before we get into today.

Imagine, 6-weeks from now… Your team brings you problems early, you’ve finally had the conversations you’ve been putting off, and you’re no longer the bottleneck.

That’s what The Strategic Leadership Challenge™ is built for.

It’s 3 minutes a day, with 1 small challenge you can do alongside your work (not adding extra hours into your day). I’ve used this approach with over 20,000 leaders, from Amex to Sony Music.

Doors open next Wednesday, 28 October, and everyone on the waitlist gets early-bird pricing plus a free Day 0 challenge tomorrow, so you’ll get your first win before we even start. More info.

Let’s get back to it…

While this list is written from a manager’s (our) perspective, it’s also a good moment for a bit of reflection too, as some of these are things our own leaders might wish we understood too.

So with that in mind…

21 things your manager wants you to know

1. If you’re stuck, tell me earlier rather than later. Small problems are easy to fix.

2. When you bring a problem, bring an idea for a solution too.

3. I do notice the effort, even when the result isn’t perfect.

4. If you disagree with something, I’d much rather hear it than have you quietly resent it.

5. You won’t lose respect by asking questions, but you might by pretending you understood something you didn’t.

6. If something takes longer than expected, letting me know before the deadline goes a long way.

7. You don’t need to CC me into everything to prove you’re working.

8. I’m juggling more context than it probably looks like. If something seems odd, there’s often a reason behind it.

9. Not every piece of feedback is a huge deal. Sometimes it’s just a small tweak.

10. I genuinely appreciate it when someone takes initiative without being asked.

11. When meetings run well, it’s usually because you came prepared.

12. If something feels frustrating to you, chances are it’s frustrating to me too.

13. If you tell me what you want to learn or get better at, I’ll look for opportunities to help you practice it.

14. Your attitude on difficult days has more impact on the team than you might realise.

15. When you own a mistake quickly, it actually increases my trust in you. Please don’t try to pretend it didn’t happen.

16. The people who progress fastest are usually the ones who ask for feedback, not just wait for it.

17. I want you to succeed here. Your growth makes the whole team stronger.

18. If something feels confusing in a process, it’s probably confusing for others too. Pointing it out helps us improve the system.

19. The small things you follow through on are often what build the most trust over time.

20. Sometimes I’m under pressure from above too. I’m doing my best to balance that while still backing the team.

21. Just like you, I’m learning as I go too.

Drop a comment, I’d love to know which one resonated with you the most and why…

Leave a comment

Peace,

H

P.S. Want a nudge to actually have these conversations, not just think about them?

The Strategic Leadership Challenge™ opens next Wednesday, 28 October: six weeks of quick daily challenges to help you lead with more confidence. More info.

In yesterday’s blog post I told you about our exciting new, 6 week The Strategic Leadership Challenge™ kicking off at the end of the month, then I shared how you can join the waitlist.

And then sent you to a page with NO form on it. Woops.

So if you clicked, scrolled, and thought “erm… where on earth do I put my name down?”

That’s on us. But it’s fixed now, so here’s the working link…

👉 Join the Strategic Leadership Challenge™ waitlist

Being on the waitlist gets you priority access when doors open on Wednesday 28th October, and it’s the ONLY way to get the early-bird price.

There are just 500 spots and over 5,000 people already waiting… so don’t let our broken link be the reason you miss out.

Thanks for bearing with us (you know we like to keep it real with tech issues around here)

Peace,
H

The Strategic Leadership Challenge™️ opens soon.

6-weeks, 1 short daily challenge, 100s of managers across the globe.

The waitlist gets first access, make sure you’re on it here: [Join the waitlist]

Now, on to today’s topic...

6 words the greatest leaders NEVER use

Earlier this year I was running a workshop with a senior leadership team.

An incredibly talented group of middle managers, but with some big old pressure to perform from their seniors. And within the first ten minutes, I’d heard one leader on the phone say three times:

“I just need to check…”

Just.

It’s one word. But I winced a bit, because it was sneakily dismantling everything this manager was trying to say before she’d even finished her sentence.

And I don’t want to sound preachy here, because for years, one of my biggest insecurities as a leader was my vocabulary. I would avoid speaking in meetings because I was convinced I sounded stupid.

But over the years I learned, the way you speak is a skill. And like every other leadership skill, it can be practiced and improved. So I started small, editing one word at a time.

And here are the 6 I started cutting first.

[Quick disclaimer: Not all of these are single words. Some sit inside phrases, but it's usually one word doing all the damage]

1. “Just”

“I just wanted to check…” “I just thought maybe we could…” “I just need five minutes…”

Every time you use it, you’re shrinking yourself before you’ve even made your point.

Cut it entirely. Say what you mean and own it.

2. “Always.” “Never.” “Everyone.”

This one changed how I communicate at work and at home.

In psychology, these words are called ‘absolutist language,’ and they’re one of the most well-documented triggers for defensive behaviour in human communication.

Therapists flag them in couples counselling, and managers use them every single day without realising the damage they’re doing.

When someone hears “you always do this”, their brain immediately goes hunting for evidence to disprove it.

For example:

“You always miss deadlines.” gets the response → “Actually I hit the deadline in March.”

And just like that the conversation is no longer about the behaviour you needed to address. It’s about whether your word choice was accurate, and you’ve handed them an escape route and the real issue got buried.

It’s just as destructive at home by the way. “You never listen.” “You always do this.” The moment an absolute lands, the other person stops hearing the feeling behind it and starts building a defence case.

Swap it for the specific.

“In the last three weeks I’ve noticed…” “This is the third time this month that…”

Specific is harder to argue with, and it keeps the conversation on the behaviour.

Which as a leader, is exactly where you want to be.

3. “Sorry”

Apologising for asking a question, having a thought or for existing in a meeting.

I see it constantly (especially in women). Sorry should be one of the most powerful words in our entire vocabulary. It should mean something. But when you use it forty times a day as a social reflex, it stops meaning anything at all and it starts eroding all the authority you’ve worked hard to build.

Save your sorry for when you genuinely mean it.

4. “Does that make sense?”

This one is sneaky because it sounds like good leadership. Like you’re making sure everyone’s with you. But what you’re actually doing is asking for reassurance.

Does that make sense? translates as: I’m not sure I explained that well. Please tell me I did.

Swap it for: “Let me know if you have any questions?”

Same intention but with different energy.

5. “I don’t mind”

Ok I must admit this is one I have a personal vendetta against. When I ask Char what she wants for dinner and she says:

“I don’t mind.”, then I suggest doing a salmon pasta and she says “mm I’m not sure about that”.

So… You minded, Char. You minded the whole time!! haha. Love ya really.

But back at the office, this looks like:

“Which approach should we take?” “I don’t mind, whatever the team thinks.”

“Should we go with option A or B?” “Honestly, I don’t mind either way.”

But you do mind. Even if you need a little longer to think about it, you do have an opinion and that opinion is valid. But every time you say “I don’t mind” you’re just opting out of making a decision.

6. “Hopefully”

“Hopefully we’ll hit the target this quarter.” “Hopefully the team will get there.”

Every time we say hopefully, we’re handing our power to chance. We’re telling our team (and ourselves) that outcomes are out of our hands and that we’re a passenger.

Great leaders don’t hope. They plan, act, course-correct, then communicate. Replace hopefully with “We’re on track to…” or “Here’s what we’re doing to get there.”

Yoda said it best. "Do or do not. There is no try."

Final thoughts

Language is one of our greatest leadership tools, and most of us are using it against ourselves without even knowing it.

But reading this email won’t change the way you speak, only practice will do that.

That’s exactly what The Strategic Leadership Challenge™️ is for.

It’s 6-weeks, with one short challenge a day. Some reflection, some action, all designed to turn the leadership stuff you already know into things you actually do, and leadership language is a big part of it.

Doors open soon, don’t miss out: Join the waitlist.

Peace,

H

The job of a manager has changed, and it’s imperative we keep up.

We’re no longer just leading teams. We’re navigating AI, remote and hybrid work, managing different generations with whole new expectations, supporting wellbeing whilst still keeping standards high.

All on top of doing the actual job.

Running a few 1:1s and keeping work on track is no longer enough.

That’s why, after training 10,000 managers over the last three years, I’ve built the exact thing I wish every manager had access to… practical training that matches the reality of the job we’re doing today.

So it is my honour to announce…

The Strategic Leadership Challenge™

My brand-new six-week challenge for managers ready to finish this year equipped to lead, so you and your team can make 2027 your most impactful year yet.

We open on 28th October. Places are limited. Join the waitlist.

The WHY

For the first few years of my management career, I was desperate to learn.

I signed up for the leadership programmes, read the books and filled notebooks with frameworks.

And every single time, I came away thinking this was the moment everything would change.

Then Monday would come. I was straight back in the weeds and all the knowledge I’d consumed was pushed to the side.

It took me far too long to realise that knowing wasn’t the problem. I already knew what good leadership looked like.

What actually changed me was the doing:

• Delegating the thing I’d normally take back

• Having the difficult conversation

• Setting the boundary

• Choosing respect over approval

Small, uncomfortable moments, repeated until they stopped feeling uncomfortable.

And yet, so much leadership training still asks managers to sit, listen and take notes… and somehow become better leaders afterwards.

The Strategic Leadership Challenge™ flips that completely.

The HOW

• 6 weeks

• A new challenge unlocks every weekday morning

• Each challenge is a quick, 2/3-minute video from me explaining exactly what to do

• One small but powerful action to take in your real working day

• You’ll be in a community of 100s of managers across the globe, completing the challenge alongside you, so you actually stay accountable

• If you miss some days inside the challenge, don’t panic. You have access until the end of the year to complete them

By the end of the six weeks, I don’t want you to simply know more about leadership.

I you will be managing more powerfully and confidently.

This challenge is fast, practical, easy to fit around your already-busy full-time job.

Doors open on Wednesday 28th October, with 500 spots available. The waitlist is open now, and everyone on it gets priority access (+ early-bird discounts 💸)

🚀 Join the Strategic Leadership Challenge™ waitlist

Less consuming, more doing.

Eek I’m so excited about this,

H

Happy Tuesday! We’re full in the swing of Q4, and I can’t wait to see the 1000s of you registered for my live, online masterclass later today. See you there?

But today, we have an important discussion to have…

Are ‘core values’ just corporate bullsh*t?

I had a brilliant call with a business owner yesterday. He leads a team of 6 people and has had a set of core values in the business for a couple of years.

They sound good, they’re written down and everyone technically knows they exist.

But he said something I hear all the time: “I’m not actually seeing them show up in how the team works.”

Then, he asked me:

Are core values even useful? And if they are, how do I actually get my team to use them?

My answer was:

No, core values aren’t bullsh*t. But the way most companies use them absolutely is. Because if you spend half a day coming up with words like:

Integrity. Excellence. Collaboration. Ownership.

Then stick them on a wall, add them to the onboarding deck and expect everyone to start behaving differently...

Then they’re hella useless.

Core values ONLY become useful when they start influencing real decisions and real behaviour. That means you actually have to use them.

Core values matter because they give you a standard for how people are expected to work, not just what they deliver. So when someone is hitting every target but their attitude is damaging the team, you have something concrete to hold them accountable to.

My core values project with SMP

I’ve had the honour of working with Sony Music Publishing over the last year on a long-term global core values implementation project.

And I mean i.m.p.l.e.m.e.n.t.a.t.i.o.n… not a few nice words on a slide.

So, after a year of seeing what it takes to bring core values to life inside a huge global organisation, here are 4 of the biggest lessons you can steal for your own team:

Lesson 1: Build them with the team

I’m a huge believer in involving the team in defining what your values actually look like in practice. For example, if you have ‘ownership’ as a value, decide together,

• Does it mean raising problems early?

• Coming with solutions instead of dumping problems upwards?

• Following through without being chased?

The word itself doesn’t matter anywhere as much as the behaviours underneath it. We need everyone in your team to be able to clearly explain what each value means in practice.

Lesson 2: Talk about them in your 1:1s

In order to keep the language at top of mind, they should come up in your 1:1 conversations in a structured way too…

Ask:

• “Which of our values do you think you’ve demonstrated really well recently?”

• “Which one could you demonstrate more strongly?”

• “Where do you think we’re not living up to our values as a team?”

This way, they stop being words written somewhere and become part of how people actually relfect on their performance.

Lesson 3: Reward people for living them

Most organisations say culture matters and then reward people almost entirely on output?? That sends a VERY clear message.

If somebody delivers brilliant numbers but makes everyone around them miserable, and you keep promoting them because they hit the target, your actual values are not whatever is written on your website.

Your actual value is: Results at any cost.

People pay attention to what gets rewarded, so recognise the people who live the culture you’re trying to build.

Then praise and promote it as much as possible.

Lesson 4: Leaders have to go first

This sounds obvious, but it’s where so many companies lose credibility. You cannot have “candour” as a company value while senior leaders avoid difficult conversations.

You cannot have “ownership” as a value while managers blame everyone else when something goes wrong.

Your team watches what leaders tolerate far more closely than what leaders say. So before asking whether your team is living the values, ask…

Am I?

So no, core values aren’t bullsh*t

But they are completely useless unless you’re willing to actually use them to manage, reward, challenge and make decisions.

Peace,

H

And NTW if delegation is one of the things keeping you stuck in the weeds right now, I’m running a free live workshop at 2pm BST today on how to stop doing everything yourself and build a team that takes real ownership.

If you want in, grab your spot now and I’ll see you at 2pm 👀

I’ve had two FULL weeks off for wedding/honeymoon, and I’m finally back in the office full of energy. I have an important question for you…

How many times in September have you done something for your team because you thought:

“It’s quicker if I do it myself.”?

Maybe you avoided delegating because they’re already busy and you didn’t want to add more to their plate?

Or you knew that by the time you’d explained it properly, you could have finished it yourself?

Or maybe you did delegate it, but it came back below the standard you wanted, so you fixed it yourself anyway?

This is one of the most common struggles I hear from managers.

And the annoying thing is… It probably IS quicker if you do it yourself.

Today.

But do that for six months and you build a team that relies on you for everything.

You become the person answering every question, checking every detail, fixing every mistake and carrying work you shouldn’t be carrying anymore.

Meanwhile, the strategic work you were actually promoted to do gets pushed further and further down the list.

Early in my leadership career, I started noticing that the brilliant leaders around me operated differently. They weren’t doing everything themselves.

They knew how to delegate in a way that built ownership, accountability and incredibly high standards without micromanaging their team or burning everyone out.

I started putting what I saw into practice in my own teams, refining it over the years into what is now my 5-step Strategic Leader’s Delegation System.

And I want to hand the whole thing over to you.

So, on 6th October, I’m running a free, live 45-minute masterclass where I’ll teach you exactly how to use it.

Go from Stuck in the Weeds to Strategic Leader

📅 Tuesday 6th October
⏰ 2pm BST / 9am EDT
👉 [Save your free spot]

You’ll also get The Delegation Engine™ download to keep, so you can turn everyday delegation into clearer ownership and stronger results.

I only run these free, live workshops a handful of times each year so you don’t want to miss it.

See you there,
H

As of today, I’m officially OOO for two weeks to go and get married in Seville, then honeymoon in Greece, and I am sooo excited.

But, I also run a business and lead a team, and September is technically the start of our busy season. So stepping away now has forced me to practice something I believe deeply in as a leader… Rest and time away is not something you earn once everything is finished, and your team should not need you to be permanently available in order to succeed.

I know I need proper time away to come back with energy, perspective and ambition.

And I know how much it matters that my team sees me take that time properly too. Not half off or checking Slack from the pool. Fully gone.

Back in 2022, one of my team members, who was a manager himself, was supposed to be fully off on annual leave with his family. But throughout the week, I kept seeing him popping up in Slack and sending messages.

So when he came back, I called a meeting with our full management team and said…

”When we’re on holiday, and the team is getting messages from us, what kind of message do you think it sends?”

They agreed, it says to our team:

• I don’t have my shit together

• I don’t prioritise rest

• I don’t think you can handle the work without me

• And subconsciously they make a note, thinking ‘when I’m on holiday, I still need to be checking in’

Negatives all round.

Taking time away from work to rest and recharge has always been crazily important to me.

I love my work. It excites me, fulfils me and inspires me. But when I don’t get regular, proper rest, the kind where my brain is fully switched off, I start to feel chained to it.

What usually feels exciting and ambitious starts to feel heavy, and eventually, like a prison I’ve built for myself.

And rest means properly gone. No laptop, no “just checking in,” no Slack notifications lighting up my pocket whilst I’m laid reading my book by the pool.

But I know it’s terrifying for a lot of us leaders. We have alot on our plate, a lot of people relying on us. So I want to walk you through exactly how I’m handing over the business and work to the team, because the handover isn’t really about the two weeks off at all… It’s what it proves to them and to me.

Start with your mindset

A sentence I had to cut from my own vocabulary: “I’ll be there if you need me.”

It sounds supportive but it’s actually quite egotistical.

Underneath it is a belief that something might go wrong that only you can fix. There isn’t. Our team is far more capable than we give them credit for, and every time we stay half-reachable, we’re taking away their chance to prove it.

Hand over ownership (not tasks)

A task list tells someone what to do. Ownership tells someone they’re in charge adn they decide what needs to happen.

So, before I go, I’m writing up:

• Who’s leading the meetings I normally lead

• Who owns each client relationship while I’m away

• Who’s making which decisions, and who they escalate to if it’s not them

If the answer to any of those is “everyone kind of does it together,” that’s not a strong enough handover.

Agree the decision-making boundaries

This stops everything from grinding to a halt. I need to communicate clearly:

• What can they decide without me?

• What can they spend without asking?

• What genuinely has to wait until I’m back?

Without this, people freeze, because they’re often fearful of making the wrong call and having to explain it to you later.

Clear boundaries remove that fear. All you need to do is write them down at the top of your handover document, which leads me to…

Get it out of your head

Key dates, context, contacts, priorities, the stuff people would normally just ask you.

All of it gets written down before I leave, it cannot exist in my head.

The goal of a good handover was never for your team to survive without you, but for them to realise how much they can handle without you.

I’ll be back in two weeks. Married, sun-drunk, and hopefully having proven myself completely unnecessary for a fortnight. Woop.

Speak soon,
Heather

P.S. Thank you to all our members inside Custard. I’m seeing all the incredible results you’re having with your teams and it blows my mind.

Not already with us? Start your Custard 14-day free trial today.

8 years ago, my team member (let’s call her Jane) found out from someone else.

We were in a client call, three of us, and the client casually said “yeah we did flag that a few weeks back, thought you two had already spoken about it.”

Jane went quiet. I felt my stomach drop before she even looked at me.

Because I hadn’t said anything, but I’d been meaning to. For weeks.

It wasn’t a big thing on its own. Some of her client updates had gotten thin, dates slipping without a heads up, that kind of thing. But it was something I needed to mention so she could adjust before it became a pattern someone else noticed.

I’d noticed it myself, actually, months previous. I even wrote notes on my phone once to jot down what I wanted to say to her.

But in every 1:1, something more urgent came up, or I told myself it wasn’t quite bad enough yet to raise, or I didn’t want to make a whole thing out of something small. So I sat on it. For weeks.

Which meant the first time she heard about it wasn’t from me, in private, with context and care. It was in front of a client, as a throwaway line, like it was old news everyone already knew about except her.

She wasn’t embarrassed about the feedback. She could handle feedback. She was frustrated that she’d lost months she could have used to fix it. Months where she just kept doing the same thing, thinking it was fine, because nobody had told her otherwise.

She told me she’d rather hear it small and early every time, because it meant she could actually get better at her job in real time instead of finding out months later that she’d been getting something wrong the whole way through.

She started asking for feedback more often after that, not less. Within the year she was the one giving it to newer starters on the team, the same way, quick and early, before it became a big deal.

When we ignore delivering the small, but often tough feedback, it doesn’t feel risky in the moment because nothing actually happens right away.

But the risk is that the other person keeps operating without the one piece of information that would have let them grow sooner. Every week you sit on it is a week of growth they don’t get back.

This is the exact gap we built Custard to close.

Not a once-a-year survey that tells you what everyone already knew months ago. A weekly pulse that surfaces the small stuff early, while it’s still a two-minute conversation and still early enough for someone to actually do something with it.

Take Jennie for example:

One of our pilot customers, a director running her own team, put it better than I could.

Seven questions, sixty seconds, and she’s already had conversations she wouldn’t otherwise have had, the small ones, before they turn into a Jane moment.

Her score’s sitting at 8.2, strong, but the real value is that asking for feedback stopped feeling scary and started feeling normal, on both sides.

So if you’ve ever sat on something small for too long, go see what it feels like to catch it while it’s still small.

Start your Custard free trial today.

I think about this every time I catch myself finding a “better time” to say something.

There is no better time. There’s just less time for the other person to grow from it.

Peace,

H

I have some very exciting updates from HQ this week:

• This time next week, Custard, our platform giving all leaders the rocketfuel the need to lead their team well, opens again. Make sure you’re on the waitlist to join us.

• And more of a personal one, in just 3 weeks, I’m headed off to get married eee. It’s a slightly surreal feeling. I’ll be doing something I’ve never done before on this newsletter, so keep your eyes peeled.

But today I just had to bring our focus back to such an important topic…

Am I too friendly with my team?

I read through hundreds of messages from managers every month, and the biggest pattern of all sounds a little something like this:

• “I got promoted and I don’t know if my team take me seriously.”

• “I’m managing people who used to be my friends and I feel like I’m falling apart.”

• “I’m worried I’m being too nice and friendly to my team”

This is the problem. More than burnout, more than Gen Z, more than any single skill gap… This transition from peer to manager is wrecking more leaders than anything else I see.

Because when we move into that leadership role, we don’t only get a new job, we get a new relationship with every single person we used to eat lunch and gossip with.

Growing pains

I want to take you back to October 2020, I’d just got the news I was being promoted to ‘Operations Director’ at GoProposal

We were a small company at the time, only a team of 12. I was excited for a salary raise, fancy title. I’d been working so hard for years to get there.

Then Monday rolled around… And after the announcement to the rest of the team, the dread quickly set in.

Now I actually…. had to do it. Eek. These people who had all been my peers, shared drinks with, told secrets to, and who I viewed as a ‘friend’, I now had to manage them.

The process stuff I found simple, the increase in responsibility and technical expertise of the role… Fine.

But I now had a team of 11 under my wing. And just the week before were mates.

I’d actually done this transition once before when I’d moved into a marketing manager role, but this time felt serious. So I started fiercely watching YouTube, dusting off my old notes, and made a plan of how I could transition from ‘mate’ to ‘manager’, as quickly as possible.

I felt like:

• I had to prove I was worthy of listening to

• They were thinking ‘who is she to tell me what to do’

I was in the Ops Director role for 3 years, as the team grew, nobody ever left, we had incredible results over the years, my salary went from about £45k to £120k+£40k bonus, all because of the results I was having with this particular team.

I figured this out the hard way, but imma tell you all you need to know in less than 300 words…

The 7 things that worked the best for me going from ‘peer’ to ‘manager’

1. Be curious

   “Take time to be interested, not interesting”
   A lot of the imposter syndrome we hold in this situation comes from the fact we feel as though we need to know all the answers. Like somehow being the ‘boss’ rightaway means we have to know everything.
   Give yourself 30 days to ask questions and listen, instead of dictating meetings and giving answers.
   

2. Stop hiding
   I had a tactic of always sharing a few insecurities of mine with my team. As soon as you say an insecurity out loud, it loses half of it’s power.
   It also brings your team closer to you and helps them come along this journey of progression with you.
   You don’t need to share all the gory details, but something like
   “It feels a little strange for me, going from your peer to your manager, and it’s an entirely new feeling that I’m currently figuring out. So if you feel the same or have any questions, I’m an open book so let’s talk it out”
   

3. Pledge your allegiance
   Your team need to trust that you’re on their side and that you have their best interests at heart, that you’re going to find them new opportunities and advocate for them when they’re not in the room.
   
   Now’s time to dig out the suggestion box, and just like when Ted Lasso increased the shower pressure for Roy Kent, try to fulfil one wish of each person.
   It could be a small payrise, getting rid of one of the responsibilities they don’t love, or even something as small as reguarly ordering soy milk into the office
   Whatever it may be, start making little moments of magic happen.
   
   (and if you’re confused on the reference because you haven’t watched Ted Lasso you’re seriously missing out on all the greatest leadership lessons in life).

4. Growth > Perfection

   Stop focusing on being right, focus only on getting better. That way, if you f*k up, it doesn’t matter.
   Ultimately, you’ll become way less scared of failure, and stop letting that fear hold you back from all the growth you deserve.

5. It’s going to be scariest at the beginning
   The 1st time you have a difficult conversation with them will be hard.
   The 10th time will feel like second nature.
   The 1st time you have to set new rules, you’ll be shaking and nervous at the announcement.
   The 10th time, you’ll go in there like a confident machine and command the room like the incredible leader you are.
   But you can’t get to the brilliant 10th time without doing the bad 1st.
   

6. We’re not put on this earth to be liked by everyone
   
   Being a manager means making tricky decisions that might piss people off
   So guess what most people do? They try win the approval of as many as possible, and just never make a decision
   Never grow and move forward
   
   Remind yourself, we absolutely cannot excel in our work and life if we’re afraid of being disliked
   So long as you’re being kind, acting in the best interest of your business and team… It doesn’t matter if you don’t win instant approval
   Because you will win the long-term respect

7. Please don’t change that much

   The truth is, you don’t need to change all that much. You’ve been given the position ‘manager’ because of who you are right now. You don’t need to become 10x better overnight. You are enough exactly as you are.
   
   You don’t need to change how you communicate, how you dress or how you present. You don’t need to magically become someone else. You are enough.

What would you add? How did you manage the transition from peer to manager? 👇

Leave a comment

Peace,

H

Have you heard of Project Aristotle?

It was a study ran by Google from 2012-2015, in which they proved one of the most expensive assumptions in leadership dead wrong.

Google’s People team studied 180+ internal teams to answer the question… What actually makes a team perform well?

They wanted to stress test the theory that if you have a team filled with the most talented people, you technically get the best team. If you have the best engineers, CVs, individual track records, you’d have the best outcome, right?

Well, spoiler alert… It wasn’t.

They found that some teams full of brilliant, proven, high-performing individuals were mediocre.

And some teams nobody would have picked on paper were consistently excellent.

They dug through everything from seniority to personality types. Whether teammates were friends outside work or not. And NONE of it explained the gap.

Then, mid-research, they found the missing piece.

The consistency in all successful teams was, in fact, whether people on the team felt safe enough to say “I don’t know,” admit a mistake, push back on the loudest person in the room, or ask the question that might make them look stupid.

AKA, psychological safety.

But let’s take a look at my favourite example of this in action.

Enron, an energy company based out of Houston, TX, was named Fortune's America's Most Innovative Company six years running, with a market value near $70 billion.

They were stacked with talent and unlimited budgets.

But behind the scenes, the Enron team was using an accounting trick that let them log estimated future profit as if they’d already earned it, so the numbers on paper looked far healthier than the cash actually coming in.

The team knew it wasn’t working, but their CEO had built a culture where questioning the numbers or challenging a superior got you managed out, so the people closest, the ones who could see it clearest, stayed quiet.

By the time third-quarter losses came out, it was too late.

Enron collapsed. And the cause of the failure wasn’t actually the accounting, it was a room full of smart people who felt unable to push back or challenge what they all knew to be wrong.

But here’s the good news…

Psychological safety isn’t a personality trait and it definitely isn’t luck. It’s built through specific, repeatable behaviours. Managers who get this right tend to do three things consistently:

• They admit to their own mistakes and let go of perfection

• They react to mistakes with curiosity, not punishment. The first response to an error is “It’s all good, how are we making sure it doesn’t happen again?” not “who did this?”

• They change their own mind in front of the team. Being seen to update your view when someone challenges you tells people disagreement is welcome, not risky.

That’s what a high-performing team actually is. Not the most traditionally talented people, but the people who trust each other enough to tell the truth.

So if you’ve been telling yourself your team’s culture problem will sort itself out once you hire better, or more people, it won’t.

And this is the exact issue we built Custard to solve. Custard gives every manager the data and the actions to actually build a team with a high level of psychological safety.

On Psychological Safety alone, we built in 22 data points and 18 specific actions, assigned to managers over a 12-week period, levelling up every single manager and their team.

You don’t need a bigger team. You need the smaller, harder thing… People who trust you enough to be honest.

We open Custard again on the 25th August. Join the waitlist to learn more.

Best,

H

Back in 2024, I surveyed over 100k of you on Instagram and here on this blog, with one question: “What do you actually think of your Gen Z team?”

The same three answers came back, over and over:

Entitled. Lazy. Difficult to manage.

I don’t think any of that’s true, but I do believe the rules of the game have changed, and most managers are still playing by the old ones.

GenZ didn’t invent wanting clarity, autonomy, and a reason to care about the work, they just stopped pretending they didn’t want it.

Every generation before them wanted the same things and learned to perform compliance instead.

So here’s how I actually keep my Gen Z team engaged at work, and why I’ll happily call this “controversial,” even though none of it feels remotely radical to me.

I am as transparent as possible

GenZ has a very low tolerance for vague communication and BS.

I give them the full context, explain exactly why decisions have been made and never make promises I’m not prepared to keep.

When someone on my team asked for a pay rise a few years back, my honest answer was no, not right now. I didn’t soften it into “let’s revisit that soon” or some vague gesture towards “budget conversations.”

I gave them the real numbers and the real reasoning, and then I told them what would need to change for the answer to become yes.

They didn’t love the answer. But they respected it, because it was true, and because I treated them like someone capable of hearing the truth.

I stopped performing corporate

Your team does not need a leader who performs perfection and pretends to have all the answers.

They need one who is credible, self-aware, and honest.

I own my mistakes & say when I don’t know something.

I give flexibility (with clear expectations)

GenZ values more ownership over when, where and how they work (me too). But flexibility should never mean lowering the standard.

Practically, that means clear KPIs and clear ownership. Everyone knows exactly what they’re accountable for and what “good” looks like when they hit it. What I don’t dictate is how they get there.

The KPI is the fixed point. Everything underneath it (the process, the tools, the order they tackle it in) is theirs to own. I’ll never micromanage the method, but I will always be clear on the target.

I find them progression at every turn

Progress doesn’t always mean a promotion or a pay rise, but our team do need ot feel as though they’re moving forward.

I look for opportunities to build a new skill, or remove the work that’s holding someone back. Sometimes progression is a title change. But more often, it’s someone finally not doing the admin task that’s been killing their motivation BTS for six months.

I build safety into every conversation

This is the biggest one.

My team can admit when they’ve made a mistake and challenge me without first worrying about how I might react. I work hard to create a culture where people can question decisions, own mistakes, and tell me what I may not want to hear.

If someone only tells you what you want to hear, you don’t have a team. You have an audience.

Want to learn more?

I broke down exactly how I lead Gen Z without lowering my standards in this week’s episode of my podcast, The Boardroom.

🎧 How I manage Gen Z at work (without lowering my standards)

Listen on YouTube, Spotify or Apple Music

Peace,

H

Big update from HQ, we’re opening up Custard today to another 50 teams, which feels so crazy/exciting that we’re already on the full second cohort. I can’t wait to meet some of you inside.

Eventually, Custard will be open full-time, like most tech products. But right now, I’m making a very intentional choice to grow it sustainably.

I’ve got an incredible audience ready and waiting to buy. I could open the floodgates today. But I’d rather build out our support, onboarding, and tech properly first, so that everyone who comes in gets an exceptional experience (not a rushed one).

But today I’m coming back around to my FAVOURITE topic… The 1:1

We cannot escape them as managers. Infact, they’re one of the single most important levers we can pull to improve our culture.

However, the traditional ‘appraisal’ system is wildly outdated and if we don’t switch it up we’ll get left behind. Instead, we need a system that runs seamlessly to understand your team, so you can continue to challenge and fulfil them at work.

Luckily for you, I have spent years testing and refining this system, experimenting with the questions, the frequencies and more, so it’s now literally plug and play ready for you to start using.

Today I’m laying out my 4 step 1:1 system, and I’ve linked out an agenda below so make sure you scroll to get those.

The mistakes

I train leaders inside some of the planet’s most successful organisations, and the mistakes I see over and over are:

• The 1:1 turning into a regular status update, or just a task check-in, without making the space to talk about deeper stuff

• The manager cancelling

• Assuming our team's priorities are the same as our own (eg. You want promotions & pay rises, but they prioritise creativity or rest).

• Only doing ‘appraisals’ annually (Bottling up feedback, praise and general performance improvement work until it’s all way too late).

• Just saying ‘my door is always open’ (This isn’t enough, our team naturally don’t want to ‘bother’ us).

The method

Each employee should have:

Every year - Salary Review

The annual review exists to make sure each employee is paid fairly and has a real space to talk through their wins and the reasoning behind them, so the leader has the full picture and the employee has the best possible chance of a fair outcome.

One tip: ask the employee to bring a short written case beforehand, covering their wins and impact, so the conversation starts from evidence.

But what if they ask for something I can’t give them? Transparency is your best friend here. Be honest. Set realistic expectations from the get go.

Every 90 Days - In-depth 1:1

A successful 90 day 1-2-1 is a space that is dedicated to, and properly used for 2 people to open and honestly discuss performance, personal development, and feedback. Both parties will prepare answers to each question

Here’s the agenda I use.

Every fortnight - 30 mins

No agenda needed here. Just some simple rules:

• 30 minute calendar entry, regularly occurring every 2 weeks

• You (the Leader) can NEVER cancel it. The team member may, but never you.

• No agenda needed, this is just space being held for you and your team member to bring anything important to you

Every day - Regular, unignored praise & difficult conversations

Challenge your team at the time, never bottle it up. Don't discourage emotion (It isn't weak. It shows that you care). And never, EVER ignore the difficult conversations.

What’s next?

It’s not actually helpful for you to consistently nurture each of your teams wishes & priorities, if someone prioritises spending time with their children, you shouldn’t be figuring out how they can do the school run, that’s on them.

But you need to build a workplace that creates a healthy and fulfilling environment for all, that works for your company and your values. Rather than having different rules for different people.

You need to KNOW these priorities, you need to ensure your team are consistently working on them, and you’re holding them accountable to pushing towards them.

So ultimately, you’re not pushing them in the wrong direction.

What do you struggle with most around 1:1s? Let’s chat in the comments

Leave a comment

Peace,

H x

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.

The sun is shining woop, and next week I’m bringing our community together for a live workshop that could completely change how you lead for the rest of 2026.

I’ll be teaching my powerful 4-part system to reset your authority, earn more respect and step into the leader you know you can be: reserve your free spot here.

But something has caught my urgent attention…

PwC’s latest ‘Workforce Hopes & Fears Survey’ confirms something I’ve seen play out for over a decade so we really need to chat about it.

I have seen that, for years, middle managers (anyone who sits in between SLT and non-people managers) have been quietly carrying organisations on their backs.

And now the data has finally caught up:

Yep, you read it correctly. Employees trust their direct manager far more than they trust senior leadership.

They feel safer speaking openly with them.
They believe them more.
They go to them first when things feel uncertain, confusing or unfair.

Which tells us something most businesses still don’t want to fully face:

Culture does not live in the C-suite.
It cannot be dictated from the top.
It lives in the day-to-day relationship between a middle manager and their team.

Middle managers are our translators.
They turn direction from the top into clear outcomes and priorities.
They keep teams focused when pressure spikes.
They translate strategy into day-to-day decisions.

And yet…

They are still the most undertrained and overstretched layer of the organisation.

We are asking them to carry the emotional weight of the business without giving them the skills, systems, or support to do it well.

If you are a middle manager, do you feel genuinely equipped to carry that responsibility?

Do you know how to set clear expectations, handle difficult conversations and hold people accountable without losing trust?

And if you lead middle managers, are you giving them the skills, systems and support they need to succeed?

Because whether you are carrying that pressure yourself or supporting someone who is, middle management cannot keep being treated as the forgotten layer of the business.

It is where culture is translated, trust is built and performance is won or lost.

Peace,

H

P.S. This is exactly why Custard exists. Investing in our middle managers is officially absolutely crucial.

Custard is my new culture intelligence platform, built specifically for people operating in this middle space, where pressure comes from every direction.

It’s practical, grounded tech that helps managers to:

– Collect honest, anonymous team feedback
– Spot culture issues before they escalate
– Turn insights into clear, practical actions
– Get AI-powered coaching to lead better

Our next 50 free trial spots open on the 28th July, and the waitlist is filling up verrry quickly.

Happy halfway-there!

If you’re anything like me, this point in the year feels a bit... foggy. Not the fresh-start energy of January or the sprint-to-the-finish of Q4. Just... The middle.

And at this point in the year, the managers who end up feeling calm, respected, and in control heading into H3 are using the mid-year point to reset the fundamentals.

They’re revisiting their standards, treating July like a second start line (not just the middle of a long slog).

And they’re making sure the second half of 2026 feels intentional (not just a continuation of whatever habits crept in over the last six months).

So if you’re heading into H2 wanting to stop carrying everyone else’s problems, lead with more authority, and actually find some joy in managing again…

I’m running a free live workshop, back by demand: How to be a respected leader in 2026 (The mid-year reset version)

It’s the same framework I’ve used with thousands of managers to help them regain control of their time, decision-making, and standards.

👉 Save your spot

I’m only running this session once and attendance is capped. So join me live on 22nd July 3pm BST / 10am EDT, save your spot here

This won’t be boring leadership theory. It’ll be fun, whilst still being verrry practical (as always). A strong way to reset together as a leadership community before things ramp up again in autumn.

If you want the rest of 2026 to feel calmer, cleaner, and more intentional than the first half did, join us. Let’s reset 🚀

Peace,
Heather

Before I get into today’s topic, I want to say thank you.

This time last week, we opened Custard up to our waitlist. 50 spots. Gone in just over an hour.

We’ve been building Custard behind the scenes for 6 months, and last week was the first time it went out into the real world. Hundreds of team members are now inside it, and today, their managers got their very first culture scores. Eek.

Thank you to everyone who jumped in and trusted us with it early. It means more than you know.

And because of how fast those spots went, we’re planning to open a second round in a few weeks, so if you missed it, read more here.

Right, onto today’s topic...

There’s a moment from my early management days that still HAUNTS me. I was an Assistant Manager at Harrods, managing people who were older than me, more experienced than me, and seemed farrr more confident than I felt.

One team member kept turning up late. But not dramatically late, I told myself, nothing that felt “serious enough” to warrant a conversation. Ten minutes here. Five minutes there. The kind of thing you tell yourself you’ll pull them up on “next time”.

So I didn’t say anything, I told myself I was being empathetic and I didn’t want to be nit-picky.

But then very quickly, lateness became the norm. What I ignored didn’t disappear, and the rest of the team started to take note. Then slowly, it lowered the bar for everyone else (why wouldn’t they now turn up late too??), and not to mention damaged my authority with the team.

By the time I finally addressed it, that conversation ended up being ten times harder than it ever needed to be because I’d left it so long.

Over the years, I’ve had some brutally difficult conversations.

• I’ve fired people.

• Explained that someone isn’t ready for the promotion they expected.

• Telling a long-tenured employee that the role has outgrown them.

But as I became more senior, eventually working as an Ops Director, I realised that the conversations that feel the hardest in the moment aren’t the ones that cause the biggest damage. The big damage comes from the conversations you avoid.

That’s why the most important rule I’ve learned in leadership is this:

Never ignore it.

I didn’t build this framework in one go. It started as a few scribbled notes before conversations I didn’t want to have. Then I refined it, stress-tested it, and stripped it back to what actually worked when emotions were high and stakes were real.

I’ve now used this framework hundreds of times. I still use it today. And I’ve yet to find a difficult conversation it doesn’t help with.

I call it the 4P’s Framework.

Please steal it. Screenshot it. Print it. Write it down. Take it into the room with you if you need to.

Because the more of us who stop avoiding these conversations, the healthier our teams, our standards, and our working lives become.

The 4P’s framework for having difficult conversations

1: PURPOSE

Firstly, explain why are you having this conversation? What’s the outcome you actually want

“I want you to have more ownership, and I need to be able to trust the updates I’m getting.”

This stops the conversation becoming a rant and it anchors it in intent.

2: PROBLEM

What specifically needs addressing? Keep it factual and contained.

“I’ve had to chase progress several times after we agreed deadlines.”

Not “you’re unreliable”. Not “you don’t care”. Just the issue.

3: PROOF

What evidence makes this objective, not personal?

“On Tuesday I was asked for an update I didn’t have, and we then missed Thursday’s deadline.”

This is where defensiveness softens, because you’re not attacking character, you’re naming impact.

4: PATH

This is the part many managers skip, but it’s the part that actually creates change.

What happens next? What’s the expectation, and what changes?

“From now on, I need a weekly update with what’s done, what’s next, and any blockers. That’s how I stay hands-off without losing visibility.”

Final thoughts

Don’t be hard on yourself for struggling with this.

I know after training thousands of managers now, that the managers who earn the most respect STILL don’t find this easy. It’s not supposed to be easy, they still feel the same nerves, the same hesitation, the same discomfort.

The difference is they don’t let that stop them.

See you next week,

H

Most managers sit in one of two camps.

We either:

• Avoid the hard conversation entirely, softening the message so much that the person walks away with no idea anything was wrong.

• OR we overcorrect, come in too strong, and the conversation lands as an attack rather than a redirect.

Neither works.

What we need are phrases that do both things at once. That hold the standard without making someone feel small, are clear without being cruel, and move things forward instead of just making a point.

So here are the four phrases I come back to again and again:

1. “Help me understand your thinking here.”

I use this one constantly, especially when something lands on my desk that doesn’t make sense and my first instinct is to jump straight to “that’s wrong.”

It slows me down and it keeps the conversation open. Instead of leading with a challenge I lead with curiosity, and more often than not the person either explains something I’d genuinely missed, or they talk themselves to the realisation without me having to say it.

Example: if someone has gone completely off-brief on a piece of work, this is my opener. Not “this isn’t what I asked for” but “help me understand your thinking here.” Same message, but with a completely different energy in the room.

2. “If this keeps happening, here’s what I’d need to do. But I’d rather not get there.”

This is the one I had to learn to say out loud because for a long time it felt too direct.

But I've learned that naming a consequence clearly is one of the kindest things you can do for someone. It removes all ambiguity about where things stand. I use it when I've had the same conversation more than once and I need the person to understand that we're at a different stage now.

Example: if someone has missed a deadline for the third time and I've already addressed it twice, this is how I open the next conversation. I'm not threatening them. I'm being honest about where we are and making it clear I'd rather find a way through together.

3. “Here’s what I need from you going forward.”

I reach for this one when I want to close a difficult conversation cleanly without leaving it messy or open-ended. It's forward-facing, which really matters because the goal of any hard conversation isn't to make a point… It's to change something.

Example: if someone has been letting things slip and we've just had a frank conversation about it, I don't end with "so just try to do better." I end with "here's what I need from you going forward" and I get specific. E.g. The report in by Thursday. The update sent before you leave on Friday. Something concrete they can actually act on.

4. “The impact on the team was X. I don’t think that was your intention, but it’s worth knowing.”

This is probably the phrase I'm most glad I learned. I used to make the mistake of focusing on what someone did without separating it from why they did it, and the conversation would shut down almost immediately because they felt accused.

Now I lead with the impact and I actively separate it from the intent.

Example: if someone has been venting about a decision to the rest of the team before I've had a chance to address it properly, I don't go in assuming they were being deliberately difficult. I say "the impact on the team was that people started to feel unsettled before we'd had a chance to talk it through. I don't think that was your intention, but we need to discuss the impact."

The conversation stays open. And they can take responsibility for the impact without feeling like they're being painted as the villain.

Final Thoughts

Today is an increidbly exiting day for us here Fresh Leadership World HQ because it is the day we finally open up the doors to our brand new tech product, Custard, to the world.

6 months In The Making. Ans I’m so excited to see some of you inside.

So if phrases like these, along with 1:1 agendas, manager actions, team scores and a full library of resources to help you lead better week on week, sound like something you need, this is your last chance.

We open Custard to 50 businesses later today.

This is your last chance to join the waitlist to get all the info in a few hours time.

I can’t wait to see you inside,

H

I was a manager of a team at the age of 21. By 26 I was an Ops Director in one of the biggest tech companies in the world. Fast forward to this week, I’m 1 week away from launching an entirely new business. A tech product. And we have nearly 2 thousand people on the waitlist eek.

So I feel like if anyone is qualified to talk about imposter syndrome, it’s moi.

At the beginning, I had hugeee imposter syndrome. I struggled with:

• My team were older than me, why should they listen to me?

• I was new to manager world, I figured everyone else had so much experience, so why would they listen to me?

• If I made a decision that people didn’t ‘like’, I worried everyone was talking about me behind my back

But 21 year old me riddled with imposter syndrome Hev, could never have reached 28 year old, courageous, intentional leader Hev without getting some serious methods in place to NEVER let imposter syndrome get in the way of my growth.

The thing that really did it for me, the breakthrough moment, was realising…

There were people much less qualified than me, living my dream life, all because they decided to believe in themselves and take action

5 ways I never let imposter syndrome hold me back

If you want growth, the goal here isn’t to overcome imposter syndrome. If you ever feel you’ve ‘overcome’ your imposter syndrome, you’re actually just inside your comfort zone and you’ve stopped growing.

So the goal here isn’t to overcome imposter syndrome, but to use it to your benefit.

And BTW before I jump in, I did a full podcast episode on this where I go into imposter syndrome in much more detail. The mindset shifts, the practical tools, and the exact things that helped me stop letting it hold me back.

So if you’d rather listen properly on your commute, walk, or while pretending to answer emails, you can listen in. Here are the links: Spotify. Apple Music. YouTube.

Let’s go…

1. The things you feel most vulnerable about are actually your greatest strengths
   
   For me, alot of this was age and experience.
   I was worried everyone older than me was better, and I didn’t deserve a seat at the table as a result.
   But in reality, my age and lack of experience were great strengths.
   I wasn’t held back by ‘old ways’ or ‘pre-conceptions’ of how my role should look.

2. Focus on growth over perfection
   
   Don’t focus on being right, just focus on getting better
   That way, when you f*k up, it doesn’t matter
   When you seek growth, you’re not bothered about being perfect
   You instead figure out what learning needs to happen and lean into it
   Ultimately, you’ll become way less scared of failure, and stop letting that fear hold you back from all the growth you deserve
   

3. Know it’s going to be scariest at the beginning
   
   The first time you have a difficult conversation will be hard
   The 10th time will feel like second nature
   
   The first time you ask for a pay rise, you’ll be shaking and nervous
   The 10th time, you’ll go in there like a confident machine and ask for the exact number you deserve
   
   But you can’t get to the brilliant 10th time without doing the bad 1st
   So you need to just feel the fear and get the first 1st one over with
   Push through the barrier
   Shatter the ceiling
   

4. We’re not put on this earth to be liked by everyone
   
   Being a manager means making tricky decisions that might piss people off
   So guess what most people do? They try win the approval of as many as possible, and just never make a decision. They never grow and move forward.
   
   So remind yourself, we absolutely cannot excel in our work and life if we’re afraid of being disliked
   So long as you’re being kind, acting in the best interest of your business and team… It doesn’t matter if you don’t win the instant approval
   Because you will win the long term respect
   

5. Your final reminder:

Who’s with me?

Repeat after me.. I am never EVER going to miss out on an opportunity in my life because the voice in my head is telling me I’m not ready for it

I know it’s scary, trust me I’ve been there

But nobody is going to be a bigger cheerleader for your life and career than you, so you need to start smashing through these comfort zone barriers today

I believe in you

Peace,

H

P.S. We’re launching Custard 1 week today 👀

A few months ago I shared this list and honestly, the response blew me away. It became one of the most shared newsletters I’ve written. Since then, thousands of new managers have joined us here, so I thought it was time to bring it back.

So as a way of quick re-introduction… Hey, btw, I’m Heather, and I’ve spent the last 10 years managing teams, from the Harrods shop floor to Ops Director in corporate tech. I’m no leadership guru and will never claim to be. But I’m addicted to learning, and I know you are too, so I created this space to share my messy, real lessons of leadership in depth.

My hope is that these weekly emails bring clarity, growth and even joy to your work, and offer a quiet, precious realisation: ah, it’s not just me who feels this way.

If you’re here, you’re exactly where you should be. Because no matter what stage in your leadership journey, we’re all still In The Making.

I won’t do this big intro every time I’m just really glad you’re here. The more of us learning together, building a world where people can love the work they do, the better. And if you’ve been here a while, know I’m endlessly grateful.

Now, back to the point…

24 harsh truths all managers need to face

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

The 24 truths I’m about to share aren’t here to flatter you. They might sting a little because they ask us to let go of comforting stories about ourselves. But these are the truths that sit underneath confident, respected leadership. So if you’re willing to read with openness rather than armour, we’re cooking.

I want you to actively engage with this, so if you strongly agree or disagree with any of the points, please comment below which number (or hit ‘reply’ to this email and let’s chat).

24 harsh truths all managers need to face, let’s go…

1. Giving tough feedback is hard. But managing the same underperformance for months is harder. Choose your hard.

2. People pleasing is costing you respect.

3. If your team won’t make decisions without you, it’s becuase you’ve trained them not to.

4. You cannot scale effort. You can only scale systems.

5. The greatest leaders ask more questions than they answer.

6. Leadership isn’t about being in the spotlight, it’s about shining the spotlight on others.

7. Conflict avoided always returns, usually louder.

8. Your intentions don’t matter, only your impact does.

9. If each individual’s success measures aren’t clear, accountability can’t exist.

10. Nothing will lose you great employees faster than them watching you tolerate a bad one.

11. If everything still relies on you, you’re not leading, you’re just depended on (and it feels good to feel needed).

12. If you wait to feel confident before you act, you’ll wait forever. Leadership requires courage first.

13. Delegation only works if you delegate the ‘why’, not just the ‘how’.

14. Being busy is not evidence of value.

15. If you’re constantly firefighting, you’ve trained yourself to be the rescuer. Stop fixing and start coaching.

16. Avoiding discomfort always costs more later.

17. Most performance issues are clarity issues in disguise.

18. If feedback has been bottled up until an appraisal and lands as a surprise, it’s a leadership failure.

19. Respect is built through consistency.

20. If you protect people from consequences, you steal their growth.

21. Leadership isn’t being needed, it’s about becoming unnecessary.

22. If you’re exhausted, look at what you refuse to let go of (cough, meetings, cough).

23. Being clear will upset some people. That’s the job.

24. If the team can function without you, that’s not failure, that’s leadership.

Which number do you agree with most? Or disagree?

Let’s chat…

Leave a comment

Peace,

H x

P.S. If you’re ready to take this work beyond the newsletter, here are 3 ways we can do that:

1. Build a better culture with Custard
Our new AI-powered culture platform helping managers understand what’s really going on in their teams, spot issues early and get personalised leadership support. Join the waitlist here.

2. Become a better manager with Fresh Start 🚀
My 6-week leadership bootcamp for managers who want to build confidence, create accountability and lead a high-performing team (without becoming the bottleneck). We run 2 cohorts per year, next one in September. Join the next waitlist here.

3. Bring me into your business 🎤
If you’re looking to develop your managers or create a stronger leadership culture across your organisation, I deliver keynotes, workshops and leadership programmes for teams around the world. Find out more here.