When Experience Becomes a Constraint
By Stephan Engelen ยท 2026-08-18
Experience has an interesting paradox. The longer you work in business, the faster you recognise situations you have seen before, and the easier it becomes to recognise a pattern that is no longer there.
Pattern recognition is what we call experience
A difficult customer negotiation reminds you of another one. A company struggling to scale looks remarkably similar to one you worked with ten years earlier. You recognise the tensions that appear when founders build their first leadership team, or when a product that once sold almost naturally suddenly requires much more effort to win the next customer.
This ability to recognise patterns is enormously valuable. Much of what we call experience is probably exactly that: a collection of situations, successes, failures and mistakes that allows us to make sense of a new situation without having to start from scratch every time.
When the pattern no longer fits
But there is another side to experience that I have become more aware of over the years. Sometimes we recognise a pattern that is no longer there. Or, more accurately, the pattern is still there, but the circumstances around it have changed enough to make our previous response less useful.
When a company is struggling, we naturally look for explanations in things we understand:
- Sales is not delivering, so we look at the sales organisation
- Growth is slowing, so we revisit the go-to-market strategy
- Customers ask for different functionality, so Product Management reviews the roadmap
- Margins are under pressure, so we look at pricing and costs
All perfectly sensible responses, and often the right ones.
But sometimes several of these things start happening at the same time. Sales cycles become longer. The people involved in buying decisions change. Customers start asking different questions. Competitors we once considered irrelevant begin appearing in deals. Features that used to differentiate the product become expected as standard.
At what point do these stop being separate operational problems and start telling us something more fundamental? This is one of the hardest judgement calls in leadership.
What Thomas Kuhn tells us about leadership teams
Kuhn was interested in how scientific thinking changes. Scientists work within what he called a paradigm: a shared way of understanding how the world works. When observations appear that do not quite fit, the first reaction is not to abandon the paradigm, scientists try to explain the anomalies within what they already know.
That makes perfect sense. You don't throw away an entire way of thinking because of one unexpected result. It takes an accumulation of anomalies before people begin to question whether the problem might not be the observations, but the framework through which they are interpreting them.
Something similar happens in companies. A leadership team develops its own paradigm, although we rarely call it that. It consists of assumptions about who the customer is, why customers buy, what makes the product different, how the company goes to market and where future growth will come from.
Those assumptions are not arbitrary. They were built through experience and, more importantly, they were validated by success. That is precisely what makes them difficult to question.
Improving execution inside a model that has shifted
When results begin to deviate from expectations, the natural response is to improve execution within the existing model. Sell harder. Improve marketing. Add functionality. Change pricing. Hire different people.
Any of those decisions may be entirely correct. But there comes a moment when leadership needs to ask whether it is still solving problems within the right frame of reference.
I have seen this in my own decisions as well. Experience gives confidence, and usually for good reason. The danger is not having experience. The danger is allowing experience to close the question too quickly.
Transitions where this matters most
- A company moving from early adopters towards a more pragmatic market may still have a good product and a capable sales organisation, but the reasons people buy have changed.
- A founder who successfully led twenty people may still have excellent instincts, but an organisation of two hundred creates different problems.
- A technology that once differentiated a company may still work perfectly well while becoming increasingly irrelevant to the customer's decision.
In each case, the temptation is to improve what already exists. Sometimes that is exactly what should happen. Sometimes it isn't.
Why no dashboard can make this call for you
Data can show that something is changing, but data does not tell you whether to improve the existing model or question the model itself. That requires judgement.
And perhaps this is where experience becomes interesting again, because the answer is not to distrust it. Quite the opposite. Without experience, many of these patterns would be impossible to recognise in the first place. The challenge is to hold experience lightly enough to question it.
Experience teaches patterns, judgement tells you when they expire
Looking back, some of the most important decisions I have made were not about knowing what to do. They were about recognising that what had worked before might no longer be the right reference point.
Experience teaches you patterns. Judgement tells you when those patterns no longer apply. And perhaps one of the hardest things about leadership is knowing the difference before the results make it obvious.