Most companies that realise they need to transform imagine it will be a project. Something tidy. A managed process with a start and an end, owned by a program plan and a Gantt chart. They believe the core product will keep running while the change happens somewhere else.

It never works like that.

The moment you start, the transformation leaks into the core. Releases slow down. Customers notice. People start looking at each other in a different way. What looked neat on a slide turns into a problem in the product, in the backlog, in the support queue, and in the faces of the people who have to keep the lights on.

I remember walking into a company that swore their product was off limits. Two weeks in, the release rhythm had collapsed and the leadership team met me with the kind of eyes that asked who had cut the power. That image has stuck with me. Transformation does not glide in quietly. It barges in, kicks the furniture, and then asks you to keep the lights on.

When people talk about resistance, they treat it like an abstract enemy. I do not. I see four concrete pressures that will push back at you every time.

Technology. A senior developer once said to me, if you ask us to change this component it could collapse the whole tower. He was not being dramatic. Systems are often held together by years of compromise and duct tape logic. When the tech changes required are dramatic and risky, the objection is rational. You need technical governance and interim solutions, not slogans.

Process. Teams defend their ways of working like family heirlooms. I have sat through meetings where a team agreed to try a new board and then immediately asked if they would still be measured by the same delivery calendar. If your expectations for predictability remain unchanged you will have no room to experiment. And if there is no room to experiment you will not create anything new.

Capacity. Leaders consistently underestimate how much work transformation actually is. It is not a side hobby you do in the evenings. It is not something you can switch on overnight. You cannot reasonably expect the old work to continue at full speed and simultaneously ask people to build a new way of working. Without real slack, people burn out and the change dies a slow, demoralising death.

Fear. This is the most human one. People whisper to themselves, will I be safer or less safe when this is over. The blunt truth is that almost everyone will feel less safe at first. If you do not name that out loud it becomes an underground current that undermines every plan. The only effective response is to talk about safety, to create room for honest conversation, and to show how mistakes in the change process will not be punished.

And then there are stakeholders. They come from every direction. Product managers who are juggling promises to sales. Innovation leads waving an AI prototype like a flag. UX people who have sat in the corner and quietly promised themselves that one day they will finally delight the customer. Add years of frustration and impatience and you have a highly combustible atmosphere. Step into that room with a neat checklist and you will turn it into a battlefield of winners and losers. If you present yourself as the one who decides who wins you will be fought. The only way through is ruthless transparency. Show the trade offs. Make priorities visible. Explain why the choices are made today. Trust grows by repetition, not by proclamation.

Culture is its own paradox. Tech companies are proud of their bottom up DNA. People do things because they can, because they care, because they found a better way. Transformation by definition requires direction from above. You cannot fix that paradox. You must hold it. Your job is to be clear about the goal at the top and to make sure teams feel in charge of the solution. Direction from above. Problem solving from below. If you try to bulldoze either side you will break the organisation.

I have been burned by ignoring that balance. Early in my career I pushed a structural change without spending enough time earning the trust of the teams. The change delivered technically, but the social debt was massive. People resisted quietly, productivity fell, and I spent months repairing relationships. That lesson has shaped everything I do since. Better to earn the micro victories than to demand the macro one.

There is one more thing people do not often say aloud, and it is the piece where you can either surrender to the tide or try to surf it. Change the systems and, given time, the organisation will reshape itself around them. Most leaders treat that as a problem. I treat it as an opportunity. If you know where the architecture needs to go you can, at great risk, nudge the organisation into the future before it arrives. You can reorganise some teams early, you can create new integration points, you can staff for the future shape rather than the present chaos.

This is not a guaranteed trick. It can explode. Sometimes it backfires spectacularly. But when it works, it flips the inertia. The architecture starts pulling the organisation in the direction you need. Conway’s Law becomes an ally rather than an enemy. Being willing to take that risk, and doing so with clear communication and staged experiments, is one of the rare ways to gain real momentum.

So here is the blunt truth I tell leaders. Transformation is not a project. Calling it a project is how you get surprised. Real transformation is an iceberg. The slide is the tip. The real work is under the surface, where technology creaks, where processes are defended, where capacity is thin, where people feel unsafe, and where dozens of stakeholders tug in different directions. Your job as a leader is not to present the perfect plan. Your job is to keep the core alive, be ruthlessly transparent about trade offs, hold the culture paradox without trying to resolve it, and when the timing and courage are right, use the shape of the systems to pull the organisation forward.

I am curious: have you been part of a transformation that went horribly wrong, or one that actually worked? What did you see under the surface of the iceberg? Share your experience — I would love to hear it.

And if you are facing transformation yourself and want to talk it through, don’t hesitate to book a call with me: calendly.com/mansen66/jorn-1on1.

#Transformation #Leadership #ChangeManagement #DigitalTransformation #OrganizationalChange #TechLeadership