Category: Leadership

I have been involved in transformation programmes for most of my career. I have seen some work. I have seen more fail. The ratio is not flattering.

The post-mortems on failed transformations tend to blame the same things: lack of executive sponsorship, poor change management, technology that didn’t deliver. These are true, as far as they go. But they’re symptoms. The root causes are less comfortable.

The transformation is the strategy, not a programme of it

Most organisations treat transformation as a discrete programme with a start and end date. The technology gets delivered. The “change” gets managed. The programme closes. Six months later, people are using the old spreadsheets again.

The organisations where transformation actually takes hold treat it as a continuous operating model shift — not a project to be delivered and signed off. The difference in framing changes everything: governance, resourcing, measurement, and what success looks like.

The business case is written to get approval, not to guide delivery

I have reviewed hundreds of business cases. Almost all of them are written to get investment approved. The benefits are optimistic. The risks are understated. The delivery assumptions are best case.

Then the programme starts and the real world arrives. But the governance framework is still tied to that original business case — so you spend the next two years managing against projections that were never realistic, explaining variances rather than making decisions.

Good transformation governance separates the investment case from the delivery framework early. The case gets you started. The delivery framework has to evolve with what you learn.

The people who know where the bodies are buried aren’t in the room

Every organisation has people who know how things actually work — which processes are workarounds, which dependencies aren’t documented, which teams will resist and why. They’re usually not the people in the transformation steering group.

The organisations that avoid the worst delivery surprises invest heavily in operational discovery before they start designing solutions. Not a two-week current-state assessment. A genuine, sustained effort to understand how work actually gets done, by the people who do it.

Change management is an afterthought, always

I know this because I have said “we need to bring in change management resource” at roughly the midpoint of every programme I have ever worked on. By then, the design decisions are made. The technology choices are locked. The change manager is handed a solution and asked to make people want it.

This doesn’t work. Change capability needs to be in the room when you’re deciding what you’re building and why — not when you’re trying to land it.

The few things that actually work

A clear problem statement that people believe in. Not a transformation vision. A specific, honest articulation of the problem you’re solving and why it matters.

Governance that makes decisions, not reports on status. A steering group that meets to resolve issues and make calls — not to receive RAG updates.

A delivery team with real authority. Programme managers who can say no, change scope, and escalate effectively. Not coordinators.

Measurement of outcomes, not outputs. Not “we delivered the system.” What changed because of it?

And the thing nobody wants to hear: time. Real organisational change takes longer than any business case will tell you. Build that into your expectations from the start.

Radical Candour has become one of those terms that people deploy without doing the reading. I have sat in leadership development sessions where it was used to mean “I’m going to be blunt with you now.” That is not what it means.

Kim Scott’s framework is more precise and more demanding than most people who cite it seem to realise. Understanding it properly changed how I manage — and how I receive feedback.

What it actually is

The framework has two axes. One is whether you challenge directly. The other is whether you care personally.

Radical Candour sits in the quadrant where both are true: you care enough about someone to tell them something difficult, and you’re direct enough to actually say it rather than hint at it.

The three failure modes are:

Obnoxious Aggression — high challenge, low care. Being blunt without the relationship or the genuine concern to back it up. This is what people often mistake for Radical Candour. It isn’t. It’s just aggression with a framework attached.

Ruinous Empathy — high care, low challenge. Caring so much about how someone feels that you don’t tell them the thing they need to hear. This is the most common failure mode among well-intentioned managers. You let someone walk into a performance review unaware of a pattern you’ve been watching for six months, because you didn’t want to have the difficult conversation. That’s not kindness. That’s a failure of care, disguised as it.

Manipulative Insincerity — low on both axes. Saying what you think someone wants to hear. Giving vague feedback that doesn’t actually land anywhere. Most performance management conversations in most organisations.

What it looks like in practice

The hardest part is the timing. Radical Candour is most useful when it’s immediate. Feedback given three months after the fact is not feedback — it’s a history lesson.

I have had to learn to say the thing in the room. When a senior stakeholder presents a plan that has a significant gap in it, saying “this looks good” and then flagging the gap in a separate email is not Radical Candour. It’s Ruinous Empathy at the senior level — and it’s actually disrespectful, because you’re protecting yourself from discomfort at their expense.

The receiving end

This framework also changed how I ask for feedback. The question I used to ask — “do you have any feedback for me?” — is almost designed to produce a meaningless answer. Nobody wants to think on the spot about how to critique you.

The question that gets useful answers is: “what’s one thing I could have done differently in that meeting?” Specific. Bounded. Easier to answer honestly.

The qualification

Radical Candour is not a licence to say whatever you think. The “care personally” axis is load-bearing. The framework requires you to have done the relationship work first — to have shown genuine interest in the person, their development and their context. Without that, challenge without care is just blunt criticism.

If you haven’t read the book, it’s worth reading before you try to apply the framework. The nuance matters.