Why leadership development feels useless (but is quietly saving your business)
by Chloe Field.
We've had a number of conversations lately where leadership development quietly gets deprioritised. Always for the same reason - there is just too much work to do.
I couldn't disagree more.
The busiest leaders, the ones with no time to grow, develop, or actually lead, are usually the ones who need it most. Not the overpriced, content-heavy stuff. The kind that makes a real difference - not just a personal difference, but to the whole business.
So I've climbed onto my (very) high horse, pony if we're being generous… to share a few truth bombs on what Kristen Gallagher and I are hearing and seeing right now. Strap in, because it's a long read 👇
If you've worked anywhere in corporate or scaleups, you've probably met leadership development in one of its more questionable forms.
Maybe it was a three-day virtual summit with breakout rooms named after mountain ranges. Maybe an e-learning module that felt like it was written by AI or some lengthy PDF template.
Whatever the format, a lot of leadership development feels kind of like corporate kale - presented as essential, hard to chew, a bit bitter, and rarely something anyone actually wants.
Okay, let's be real about this. When done badly, leadership development is forgettable and expensive, and, worse, it bakes in outdated or plain wrong habits that make leaders, their teams, and the business perform worse.
Done well, you barely notice it. Because things just work better. Leaders feel invested in. Teams collaborate differently, share a language, and sing the same song but in their own voices, no cookie-cutter ones. People perform better, and so does the business.
Leadership development might be the most undervalued competitive advantage in your organisation.
So why the bad rap? And why, underneath the jargon and the off-sites, it’s absolutely critical to scaling a high-performing, happy organisation.
You can’t just hire ‘good leaders; and call it a day
There's a persistent (and rarely proven) hypothesis in business: we'll fix our leadership gaps by hiring from outside.
Cool, cool..but a shiny external hire dropped into a business with no internal development is like installing a new kitchen in a house with no plumbing. Looks great, until nothing flows. It may feel faster, but speed isn’t everything; velocity is!
Wharton's research found that external hires take about two years to match the performance of someone promoted from within, while getting paid 18–20% more and leaving at higher rates.
When a senior hire doesn't land, Gallup puts the cost of replacing them at up to 200% of their salary. Meanwhile, your internal people (the ones who already understand your customers and your complexities) ramp faster and tend to stay roughly twice as long.
That's not a soft, feel good benefit. It's money quietly walking out the door while your best talent sits in career purgatory wondering what it takes to move up.
Leadership development isn’t about turning every manager into a visionary guru. It’s about systematically growing people who can navigate complexity, lead change, and build trust from within your own walls.
Leading people is a completely different skill set
It should be no surprise that around 82% of managers are deemed "accidental" - promoted into leadership with no real training and 77% of businesses report leadership gaps.*
Therefore, it’s not shocking, but also it isn’t right, how often companies promote people into leadership roles with the confidence of someone handing the keys to a car to a child and saying, “You’ll figure it out”.
Great ICs become team leads. Reliable operators become department heads. Then they're left to fend for themselves with the odd check-in.
It's not that they're unqualified - you promoted them for a reason. It's that nobody taught them how to lead. And leadership isn't intuitive. It's a set of behaviours: giving feedback, coaching performance, managing conflict, holding people accountable without ruling by fear.
And no, these skills don’t magically appear during onboarding. They require intentional development.
*2025 WorkLife Digital Report, Chartered Management Institute, eLearning Industry
Middle managers are your most underpowered engine
If the executive team is the brain, middle managers are the nervous system. They connect strategy to action, feedback to improvement, and change to actual adoption. They're also where your culture genuinely lives - not on the mugs and screensavers, but on whether a manager will have the hard conversation your values say they should.
So why are they so often the least supported 🤷♀️
Middle managers get caught in the crossfire: shifting priorities, tight resources, managing up and down at the same time. We ask them to lead transformation, run performance cycles, look after wellbeing, and hit quarterly targets - then expect them to do all of it on instinct.
That's not a strategy. That's a stress test, with burnout waiting to happen 🔥
Get this layer right and strategy moves. Get it wrong and even your most airtight plan dies quietly in the middle of the org chart.
The best companies don't just hand middle managers more process. They give them practical skills and a shared language. "Shared language" isn't as soft as it sounds.
In practice, it might mean every manager gives feedback the same way (for example): situation, behaviour, impact. "In yesterday's stand-up, you spoke over Sally twice, and the room went quiet" lands very differently than ten managers improvising ten versions of "hey, got a sec?"
When the method is shared, feedback stops feeling personal and starts feeling normal and people can lead through ambiguity with some actual clarity. Remember, clear is kind.
So why does it still feel like a box-ticking exercise?
Because too often, leadership development is missing four things (and conveniently for my love of alliteration, they all start with C):
Context - generic content with nothing to do with people's real world.
Continuity - delivered once, then left to collect dust.
Credibility - led by facilitators who haven't run a team in yonks.
Community - a single teaching moment with no dialogue, no different perspectives, no honest conversations.
When it works, it's because it's real, relevant and reinforced. Not jargon - just human skills, practised in context, with accountability over time.
How to make it stick? (and not suck.)
Make it behavioural. Focus on what people do, not just what they know. Ask: Are we talking about what this looks like in our business - not in theory?
Make it layered. Build support from brand-new managers to seasoned directors (they need reminders too). Ask: Is there a shared language everyone can use, and can senior leaders mentor across it?
Make it experiential. People learn by doing, reflecting and getting feedback - not by watching keynotes. Ask: Is there real time to practise and discuss?
Make it embedded. Tie it to actual business priorities. Don't train just because there's a budget. Ask: Are leaders bringing real challenges into the room, and can they use this tomorrow?
Make it social. Small cohorts, peer coaching, shared problem-solving. Community builds capability. Ask: Are we hearing from everyone in the room?
It’t not a ‘nice to have.’ It’s infrastructure.
Look, leadership development will never be the flashiest initiative in the budget. But done well, it's what holds a business together under pressure: resilience when things are uncertain, alignment when things are complex, performance when you're trying to scale.
Your managers are your number one lever for performance. Don’t let the business run on instinct alone.
Here's some homework for you - pick one middle manager and ask them a single question: What's the hardest part of your job that no one ever trained you for?
Then listen, like, really listen! The gap they name in the first ten seconds is exactly where development should start.
The smartest thing you can do is invest in your people so they can do their best work, and the business gets to as well.
Real change takes time, but it makes work so much better. And that's the whole point!
If turning that gap into something structured is where you get stuck, that's the work Kristen and I love to do. But that question needs to come first.