• Aug 11, 2025

Leadership Readiness: Are You Solving for Now or for Next?

  • Sam Harvey & Charlotte Stebbing-Mills

 "You don’t rise to the level of your goals. You fall to the level of your systems." — James Clear


In Today's Issue:

  • Why readiness for change is the hidden factor behind failed leadership initiatives

  • How to match your leadership solutions to where your leaders actually are

  • Real examples of maturity mismatch (and what worked instead)

  • A reflection question to future-proof your next big move

  • Event sneak peeks and waitlist updates


Readiness Trumps Ambition

It’s tempting to throw bold solutions at big problems.

New leadership frameworks. Bold rebrands. Culture sprints. But here’s the kicker: transformation doesn’t stick if your leaders aren’t ready to change.

Change readiness isn’t about ambition. It’s about capacity, safety, and maturity.

Too many orgs launch leadership programmes that look great in a deck… but flop in real life. Why? Because they’re solving a Level 3 problem with a Level 1 foundation.

The result? Eye rolls. Low uptake. The classic "we tried that, it didn’t work."

Before you go big, go real. 

Ask: “Where are our leaders now…and what do they need to get ready for what’s next?”


Meet Them Where They’re At (Not Where You Wish They Were)

Think of leadership maturity like fitness. You wouldn’t run a marathon without doing any training….right? You’d start small, meet your fitness where it’s at, maybe (depending on your fitness level) even with a walk or short run. 

Same with leadership growth. The best interventions meet leaders at their current capacity, not their title, tenure, or what HR wishes they could do.

Some signals to spot:

✔️ SURVIVAL MODE
❌ Bad fit: Strategic visioning workshops
✅ Better fit: 1:1 coaching, practical tools for stress and delegation

✔️ STRIVING MODE
❌ Bad fit: Deep systems change with no groundwork
✅ Better fit: Peer learning circles, psychological safety foundations

✔️ THRIVING MODE
❌ Bad fit: Endless “training” on things they’ve already mastered
✅ Better fit: Bold experimentation labs, co-created leadership charters

This is less about slowing down and more about starting at the right speed. Match pace with place.

Practical Tip:

Ask your leaders: "What’s making change hard for us right now?"

Their answers will tell you if the issue is clarity, culture, confidence, or capacity.

Then choose the next move that builds readiness, not resistance.


Big News - Save the Dates!

🗓️ Save the Date – September 25th
An morning of real connection, strategy swaps, and a few surprise experiments. Details soon. Pencil it in.

🎟️ November Full-Day Event – Accouncment: 20th of November The countdown is on for our biggest community gathering of the year. If you're into culture, change, and doing wellbeing differently, this one’s for you.

💥 Think immersive experiences, bold convos, and ideas you’ll want to steal.
👉 Join the waitlist now

🎙️ Podcast Conversations

We’ve wrapped on Season 1 of the Wellbeing Leaders Podcast 🎧

Massive thanks to every guest who showed us what real leadership looks like.

🔥 From sleep science to stress, retention to inclusion, we covered it all.
Catch up here: youtube.com/@wellbeingleaders

Got a guest or theme in mind for Season 2? Hit reply—we’re all ears!

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