The older I get, the better I remember I was

Someone asked me recently how many businesses I'd started. Four, I said. Then I wrote them down. There were six.

I also know a restructure I led won a business award. I can picture the evening. I couldn't tell you what the award was called.

If my memory is that careless with the facts, I can't help wondering how careful it is with the reasons. And I don't think I'm unusual. The more successful someone is, the more often they tell their story: to boards, to investors, to new hires, to conference audiences. Each telling edits it a little. The luck drops out. The team shrinks to "I". The scaffolding disappears. The near-misses vanish. The edited story then gets used to make decisions. Worst of all, success in one place is taken as proof of success in the next.

Brilliant there, ordinary here

Being highly successful at one thing doesn't make you good at the next. Some talents are real and remarkable, and they belong to a context. Move them to a different kind of business, a different stage or a different role, and they stop working. The person often doesn't notice, because their memory of being brilliant is still vivid, and so is everyone else's.

I've seen this many times, and I can't name anyone, because they'd all recognise themselves. So here are the types, each drawn from more than one person.

The permanent pitch. I'm in awe of good salespeople. Their ability to spot an opportunity, pursue it, look after an account and close a deal worth having is a talent I don't have. I've watched several of them promoted to run the business. In one case a top salesperson became managing director and brought their methods with them. They were something of an expert in persuasion techniques, the neuro-linguistic programming kind, and the people closest to them knew it. They could sense when the techniques were being used on them. Trust broke down and the business faltered. It didn't fail, but it stalled, and in time they moved on. Persuasion that works on a customer you see once a quarter doesn't work on a team that sees you every day. Customers meet the technique. Colleagues learn to recognise it, and a leader who never stops pitching stops being believed.

Phantom departments. This one is a particular beef of mine. Plenty of corporate executives founded something earlier in their lives, but if most of their career has been spent in blue-chip businesses, their knowledge of how to lay a startup's foundations is thin at best. In a large company the gaps are filled for you. IT systems are already in place, or a team is lined up to build new ones. There are HR, finance, training and wellbeing departments, and people whose job is to design policy and business process. Take all of that away and they keep reaching for departments that aren't there, like a phantom limb. You find out how much of your success they were carrying.

A startup needs people who can do almost everything in the early days, or people who have set up a company's foundations before. Those foundations won't be perfect, and they'll be built on a tight budget. What matters is that they can be developed to match the business when the time comes to scale. I once watched a corporate-led startup fill its key roles with other corporate executives, every one of them used to a business that already worked. One told me they needed two analysts and a project manager to do their job. I asked what they had done before they had those people. There was a long pause, and then, honestly, they said they couldn't really remember: it had been fifteen years. I've told the rest of that story before. It cost the company around £1.5m and years of delay before it finally broke through.

The ten-fingered business. The founder, technical or not, built the company by doing everything, and can't quite stop. They hire well, and the business can reach a good size. But every area still has the founder's fingers in it, and the business can only grow as far as ten fingers reach. The specialists they hired never quite get full ownership of their areas, or full accountability for them. The businesses I've been close to where this happened didn't fail. But the tension was palpable, and they grew more slowly than their markets would have allowed. The talent that built the company had become its ceiling.

The weather-matched leader. Businesses need different leaders at different stages, and I think of it as weather. Some leaders are at their best in a storm, some in fair weather, some in a steady breeze. I'm a strong-wind leader. I'm most comfortable where change is moderate to fast: a startup, a scale-up, a scale-down, and the odd turnaround (I've done two). Put me in calm water, a steady business with modest growth, and I'm a sailor with too little wind. I won't sink the boat, but I won't be at my best. Put a fair-weather leader into a startup and you get the opposite: someone doing everything right for conditions that aren't there. Neither is better. The mistake is assuming that success in one kind of weather proves you'll succeed in another.

The deep end. The Peter Principle says people are promoted to the level of their incompetence. I've seen more examples than I can count. A great engineer doesn't automatically make a great engineering manager, and a great salesperson doesn't automatically make a great sales director. The talent that earned the promotion isn't the talent the new job needs. More often than not it isn't a flaw in the person. It's a lack of readiness: nobody trained them, and there was no smaller role in which to practise. Sometimes it's simply the wrong temperament for the job, but less often than the people around them assume. Often nobody notices, the person included, especially in smaller businesses, which tend to have less formal management training and fewer roles in which someone can try managing before it really matters. The first management job is the test, and by then it's a very public one. The Dilbert Principle is the cynical version: promote the people who are bad at the work into management, where they can do less harm. I've seen that too, more rarely, and in some places more than others.

I became a managing director at 30. I've occasionally wondered which principle explains it.

My own blind spot

What I can tell you is that being senior let me sidestep my own weakness: admin. I'd love to say I overcame it. The truth is, I solved the problem the expensive way. I got promoted.

To be fair to myself, and I've only just remembered this, which rather proves the title, I'm not useless at admin. I can do it. It just takes me far more time and energy than it should, time and energy better spent on the things I'm actually good at.

I've been lucky. For most of my career there have been excellent people around me filling the gaps I leave: project managers who turned my plans into dates, PAs who knew where everything was, and my wife, a talented and very focused administrator, and a great deal more besides. If I'm honest, some of what I remember as my success was their organisation.

These days I work as an independent adviser, and my wife still backs up my admin deficiencies. When she runs out of time, there are part-time PAs who are very good. I have no desire to grow another business, which is partly wisdom and partly knowing exactly who would end up doing the paperwork.

That's the point I'd most like a reader to take away. A weakness is often not something you can't do. It's something that costs you more than it should. Track records never show that cost. They show what got done, not what it took, or who quietly did it more easily.

Memory keeps the drama

In the run-up to 2000, the consultancy where I was chief operating officer had a whole department working on Y2K. The work succeeded, so nothing happened, so almost nobody remembers it. I've called those engineers the heroes nobody noticed.

Successful people's memories work the same way. The crisis at two in the morning grows with every telling. The dull system that stopped it happening again shrinks. When my off-grid manufacturing business was close to being overwhelmed by its own orders, the near-collapse is the better story. What actually saved it was a touchscreen Kanban system on the shop floor that let people see the work and set their own priorities. Output rose by 30% with the same people. It makes a much duller anecdote. It mattered far more.

We rewrite our failures kindly, too

Successful people don't only inflate their wins. They soften their failures into lessons, which makes them nicer to tell and less useful to hear.

I'm no exception. In The cost of endurance I wrote about pressing ahead with an expensive first production run before we were ready, and I described it like this: "It was not recklessness. It was a failure of discipline under sustained pressure."

Reading it again, I notice how kind I was to myself. A failure of discipline under pressure sounds almost noble. The plainer version is that I wanted to keep moving, I didn't want to hear that we weren't ready, and the business paid for finding out.

Organisations forget the other way

There's an irony here. Individuals over-remember their own part. Organisations under-remember the knowledge. The field lead who remembers which fault pattern came before the last warranty spike leaves, and the company forgets. Meanwhile, one senior person's polished story takes the place of the messy record that would actually have helped.

What I should do about it

This is where an article like this usually tells you what to do. Write things down at the time. Keep what you remember separate from what the documents show. Ask someone who was there before you tell the story again. I'd recommend all of it, and I do almost none of it. I suspect most people don't either, until it's time to write their memoirs, by which point the story has had decades to improve.

So the useful advice is for the listener, not the storyteller. When someone's track record is being used to make a decision, mine included, ask three questions:

• What was the weather? What stage was that business at, and is this one the same?
• Who else was in the boat? Who did the work that the story leaves out?
• What did it cost? Not just what got done, but what it took.

I'm fairly sure I was very good. I have an award to prove it. I just can't remember what it was called, and if it was ever written down, I've no idea where I filed it.

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Related: The average said build. The odds said sell. · After the idea · Not all CTOs are created equal · The cost of endurance · Confidence, ego and the cost of not listening · all writing