#19 Courage (Part 1 of 2) — Why Nothing Starts

"We should be careful about starting something like this."

Some version of that sentence reaches me several times a year, and it's almost never about something large. The most recent case was 360-degree feedback: one department, a few weeks, software optional, entirely reversible.

Careful about a feedback pilot.

Nobody involved was blocking anything, and I want to be clear about that before I use it as an example. The caution was reasonable by the standards of the place. In organisations like that, nothing stays small: every initiative becomes a proper undertaking, a boulder to be set in motion. Capacity is thin to begin with, so anything new has to queue. By the time it reaches the front, the energy that started it has drained away. That's how most initiatives die in established companies. Not refused. Slowed until nobody quite remembers why they mattered.

Most conversations about AI in organisations are about capability: which tools, which use cases, which skills, what it costs, who governs it. Far fewer are about nerve, about whether anyone is willing to go first. And in that case, capability was never the problem. Nerve was.

Reading time: 10 minutes. If you take one thing from this: good ideas in companies are rarely rejected. They're slowed until the energy is gone, which makes this a cost problem rather than a character problem. Ahead: what Microsoft's 5Cs get right and wrong about courage, why boldness clusters at the top (the research is not what you'd assume), what the courage gap now costs, and a ten-minute diagnosis for your own team. Part 2, next week, is what to do about it.

Microsoft's 5Cs, and where this newsletter already stands

This newsletter has spent nineteen editions on human skills in the age of AI, so when Microsoft's WorkLab published a piece on that exact question in April 2026, it belongs in front of you. It's an excerpt from Open to Work by Ryan Roslansky, LinkedIn's CEO, and Aneesh Raman, its Chief Economic Opportunity Officer, and the argument is that as AI absorbs the technical work, the capabilities deciding your value come down to five: curiosity, courage, creativity, compassion and communication.

If you work anywhere near people development you'll meet this framework, because it's already shaping how large organisations talk about the subject.

Two of the five I've worked through here at length: communication got a double edition, creativity has been circling since Delegation. So I'll take the remaining ones over the coming editions, beginning with courage. Today, why so little of it reaches the point of action. Next time, what to do about that.

Two editions ago I warned against importing American playbooks unchecked, so in fairness I should test this one: it survives the crossing, because the 5Cs describe capabilities rather than mechanics. Mechanics are what break in translation. Capabilities travel.

One line in it stopped me. The 5Cs, the authors write, "aren't capabilities you can pick up from a weekend workshop or an online training module"; they develop "only through time, connection, and challenge." That's almost word for word the argument I made in the Communication edition about buying repetition instead of content — coming, this time, from the CEO of the platform you're probably reading this on.

What they mean by courage, and what they leave out

Their definition is clean: AI can calculate risk. Only humans decide what risk is worth taking. Courage, they write, is "the willingness to act without complete information and to move forward when the outcome isn't guaranteed. It's choosing to be the test case when everyone else is waiting for proof."

Their examples are Polynesian wayfarers and the crew of Apollo 13. Stirring, and unhelpful. Nobody in your organisation is deciding whether to strap themselves to a rocket. They're deciding whether to raise a hand in a meeting where the boss has already stated a preference. Apollo courage is one dramatic act with the world watching. Workplace courage is a Tuesday, repeated, unwitnessed, with a career attached. I'd argue that's the harder of the two.

Four minutes, or four months

Back to that feedback pilot, and to the scale-ups I work with, where a decision of comparable size takes four minutes. Is it safe enough to try? Yes. Then go, and we'll look at what broke afterwards. Same question, two organisations, and the gap between them isn't intelligence or appetite for risk. It's the cost of an attempt, and most of that cost is momentum.

Which makes the caution rational. Where a team can run a two-week experiment and adjust, courage is cheap. Where every move has to be a full undertaking, courage gets expensive, and rationing it is sensible.

That's the generous reading. Here's the one I've come to trust just as often: turning something into a big project is a way of not having to touch it. A proper undertaking needs a plan, a budget, a slot in next year's roadmap, and while all that is being arranged nobody has to change how they work on Monday. The size becomes the alibi. From the outside, diligence and avoidance look identical, and the person doing it often can't tell them apart either.

None of this is universal. Plenty of organisations move differently, which is a large part of why I enjoy working with startups and scale-ups. Caution is also sometimes the right call. Not every AI initiative deserves to happen.

So the skill worth building isn't speed. It's a team being honest with itself about which mode it's in: when are we quick and bold, when are we slow, and do we know which one we're doing right now? Which gives you a short question for your next meeting. Are we holding off on this because it's the smart call, or because nobody wants to go first?

A fair objection at this point: are American companies simply braver? I don't think so, and the distinction matters. What differs is the price of failure. Bankruptcy law is gentler, hiring and rehiring are faster, and a venture market that expects most bets to lose treats a dead project as tuition rather than disgrace. Make failure cheap and courage looks abundant, but it's subsidised by structure rather than character. That cuts both ways: cheap courage produces a great deal of waste, and a high tolerance for trying things is not the same as getting value from them. So the conclusion isn't to be braver in general. It's that where an attempt costs more, somebody has to lower that cost on purpose instead of waiting for people to turn bold.

A quick aside for HR and people-development leaders. If there's development budget still sitting in this year's pot, this is the moment to decide where it lands: on another event your teams will have forgotten by February, or on something that changes how they work. Getting a workforce to try things isn't a communications problem and it won't move with a kickoff email. It moves when the conditions change, which takes months rather than days — workshops, coaching, longer programmes, or a single culture offsite to start. Planning next year's budget instead? Then it's the same conversation, only earlier and cheaper. Twenty minutes and you'll know whether it fits, whether or not you end up working with me: book a call.

The gate where initiatives die

Cost isn't the only thing holding initiatives back. I described the underlying pattern in the Profiling edition: some people are what I'd call worst-case sorters, and shown a new idea, their attention goes first and fastest to what could break.

That's a valuable pattern in the right seat. You want it in your risk function, your legal review, your security team. But put a worst-case sorter at the go or no-go gate rather than the how do we do this safely step, and nothing new ever starts. The questions get raised at the beginning, they're all legitimate, and the initiative dies of legitimacy.

That's what makes it so hard to see, and so hard to fix by asking people to be braver. There is no obstruction to point at.

We are not born cautious

I don't think most adults lack courage by nature. A good deal of it gets removed, gradually and with love, by people trying to keep us safe: parents who flinch first, teachers who reward the correct answer over the interesting one, early managers who punish the visible mistake more reliably than they reward the quiet win. Not one of them is acting badly. The effect accumulates anyway.

And I catch myself doing it. My daughter started at a school this month where the main subjects are taught in Portuguese, a language she doesn't speak. She walked in anyway. In the weeks before, my own instinct kept hunting for the softer landing, the smaller step: to protect her, and to spare myself the stress. Each of those decisions is defensible; the sum of them teaches a child that the safe option is the normal one. At her age the calculation isn't yet complicated by everything that might go wrong, which is more or less what we spend the following decades installing.

There's a second reason courage looks unevenly distributed, and it's the one I had backwards for years. The obvious explanation is character: bold people rise, so you find boldness at the top and less of it further down. The research points somewhere less flattering. Across five studies, Anderson and Galinsky found that a sense of power makes people perceive risk more optimistically and act more boldly — and they produced the effect by priming a high-power mindset in ordinary participants. Work on employee voice finds the same gradient: a sense of power predicts speaking up, its absence predicts silence.

Read that carefully, because it inverts the usual story. Boldness at the top isn't only the reason people got there. It is substantially a product of being there. The same person, handed authority and cover, becomes measurably bolder. Which isn't an argument that more boldness is always better; bold and wise are different things, and plenty of damage has been done by executives who felt very optimistic about risk.

But it does change the job. If courage were simply a trait, you'd hire for it and be done. If it tracks power, safety and how much an attempt costs, it's something an organisation can hand out. You're not installing courage in adults; you're removing what suppresses it and distributing what enables it. That's psychological safety, which Amy Edmondson defined as a shared belief that a team is safe for interpersonal risk-taking, and which sits in the middle of the Culture Design Canvas for exactly this reason. It gets built through what an organisation rewards and punishes rather than through what it announces.

Why this is now expensive

The courage gap has always cost organisations something. AI has put a price tag on it.

A much-quoted MIT report from 2025 claimed that around 95% of enterprise generative-AI pilots showed no measurable return. Treat that as directional rather than precise; the methodology has been criticised and I wouldn't build a business case on it. What sits underneath is more useful than the headline: the researchers put the gap down to organisational learning and integration rather than model quality, and found that the small group who succeeded worked through the friction instead of around it.

So the bottleneck is rarely the technology. It's the willingness to start something you can't yet prove and stay with it while it's clumsy. In the Atlantic Gap edition I argued that European AI adoption has to be led rather than pushed, since neither fear nor equity will do the pushing here. Leading it means someone goes first without proof, usually at a level senior enough to absorb the first failure.

Economics says something similar, more formally. Gustavo Manso's work on innovation incentives, published in the Journal of Finance, finds that the arrangements which do produce exploration share a shape: substantial tolerance for early failure combined with reward for long-term success, plus job security and quick feedback. Follow-up work with Azoulay and Graff Zivin found the same pattern in scientific funding, where grants that tolerated early failure produced more original research. The authors are candid that failure tolerance is hard to measure inside firms, so treat it as a well-supported principle rather than a settled number. The principle is the useful part: you don't get exploration by asking for it. You get it by making early failure survivable.

Your turn

This edition is diagnosis, so the exercise is too.

Your 1% this week. Take the last initiative in your area that never happened, and work out which of three deaths it died:

• Refused. Somebody decided against it. Rare, and at least it's honest.
• Slowed. It queued behind everything else until the energy drained out of it.
• Inflated. It became a proper undertaking, and then nobody could lift it.

The three have different cures, and organisations routinely apply the wrong one. Naming yours takes ten minutes and tells you where to start.

If you lead people, the harder version. Think back to the last visible failure in your team and ask what happened to that person afterwards, in real terms: in the room, in their next appraisal, in what colleagues learned from watching. That answer is your organisation's real courage policy. Everything else is a poster.

One last thing about that opening sentence. There is nothing cowardly in it. It's exactly what a certain kind of organisation trains people to say: think twice before setting a boulder in motion. The people hesitating in your company are usually behaving sensibly inside a system where trying something costs more than not trying.

Which is the whole problem, and it's a solvable one. Change what an attempt costs, and it turns out the courage was there all along. That's next week: what makes trying cheaper, where small steps are the wrong answer, and what HR can do about it that isn't another training.

Before you go: what's the last good idea you watched die at the gate in your organisation? I read every reply.

And if a name came to mind while you were reading — a leader or an HR colleague whose good work keeps stalling before it starts — send this to them. Word of mouth is how most people find this newsletter.

The Digital Leader Canvas is free for individual use. And if you're in HR or L&D and want to bring these themes into your organisation, here's that link again — book a 20-minute call. You can also explore the Leadership Essentials Workshop Series for teams.