How to make a transformation work for you

Two candid conversations with C-level leaders who ran transformations from the front

I enjoyed writing the article on what makes founders and hires succeed so much (and especially the interviews I did for them) that I decided to do another one, in the last semi-quiet summer week. I wanted to write something real, not another recycled thought-leadership post. This is me sharing what interests me and what I’m learning from the people around me.

This article is about transformation – and it comes from two leaders who didn’t just witness one, they designed and ran it, at real scale, more than once. Both spoke on condition of anonymity, and both were direct about it: no corporate polish, no consultant-speak, just what really happened and what they’d tell you if you worked for them.

Who we spoke to

Respondent A: a serial entrepreneur turned transformation leader, who has built and sold his own consultancy, helped scale a rapid-growth venture from zero to over 10,000 people, and later led global digital transformations for large corporates, including growing an e-commerce business from roughly €200 million to nearly €3 billion in a few years.

Respondent B: a technology leader with more than 20 years of experience, including CIO roles and senior advisory work for companies ranging from around $100 million to multiple billions of dollars in revenue, who has led transformations spanning aggressive cost restructuring to full digital overhauls.

From the trenches: Where these lessons came from

Neither respondent was theorizing. Both have run transformations under real, public pressure, and the specific situations are worth spelling out because the lessons only make sense against them.

Respondent A was once asked to replace every single system at a major retailer, webshop, CRM, ERP, everything, in six months. They finished with just one week of delay, landing it right before the peak holiday season. During the pandemic, with physical shops closed, his team had to invent new ways to move product before it turned into low-value commodity stock. That included setting up scooter-based delivery networks in markets like Ghana, essentially from scratch: “just making it happen.” Years earlier, he’d built an AI company betting on using camera feeds to predict security threats before they happened — a good idea sitting on hardware that wasn’t ready yet. The company eventually relocated to London and was acquired by a US defense group. He walked away from a global transformation role he’d used to grow an e-commerce business roughly fifteen-fold, the moment a new CEO signaled a return to “business as usual”. “I knew it would mean a year of analysis and standstill. I get a burn-out from doing nothing, so I left.”

Respondent B’s proudest transformation was inside a roughly $100 million revenue company whose share price had already collapsed. He pushed heavy outsourcing to Vietnam, Malaysia, and China and ran a ruthless downsizing of the home team, a decision that tripled the share price and, a decade later, earned him an unprompted thank-you message from someone in the new team who’d since become CEO.

What makes a a success of a transformation

Both respondents pointed to speed and iteration over planning and perfection, but they arrived at it from very different angles.

Respondent A’s clearest lesson came from a rapid-growth US venture he joined after business school: “As a Dutchman, my idea of growth was maybe 250%. They were talking about 1500% growth… That’s where I truly learned that time is more important than the amount. If you can deliver successfully in a short time, the price becomes secondary.” He carried that principle into the retailer system overhaul and the pandemic scooter networks above: aim to get things 90% right, move, and let the last 10% come from learning in the real world : “by then, the world will have changed again anyway.”

Respondent B measures success less by the plan and more by what happens ten years later, the $100M restructuring described above being his clearest example: “It’s a lovely thing to happen, to know you gave two companies a future.”

What triggers a transformation

Respondent B was blunt about this: companies rarely act until the math forces them to. “There’s an old adage that a $4 billion company should have 11.000 employees, and a $6 billion company should have 13.000. Companies see their growth projections and realize they’re going to spike massively in headcount, so they need to do something about it.” The other classic trigger, in his experience, is a merger that leaves a company structurally bloated overnight: “An M&A experience where they suddenly have 15.000 employees when they should only have 11.000. In my experience, companies tend not to act unless they have to.”

Where transformations are built to fail

Respondent A puts the root cause at the very top: “It starts at the very top.” Three failure modes, in his words:

• A board that doesn’t understand what it’s overseeing: “The board and the supervisory board often lack genuine, hands-on experience with transformation, technology, and innovation. They look at it through a lens of risk, not opportunity.”;
• Ownership handed off instead of held: “A CEO will quickly say, ‘my transformation guy is the CIO or CTO.’ They don’t take full ownership themselves. It’s not just an IT project.”;
• Chasing a risk-free transformation that doesn’t exist: “Things will go wrong, but learn from them quickly and adapt. In our culture especially, ‘failing’ is seen as a mistake, not a positive learning experience. When something goes wrong, they hit the brakes, which kills momentum.”

Respondent B’s version of the same failure has a name he uses without hesitation — board-level incompetence dressed up as strategy: “They bring in people like McKinsey and Accenture who tell them what they want to hear. Very few of these companies will say, ‘your strategy is full of crap.’ It’s the Emperor’s New Clothes in real life.” The second, quieter failure mode is losing the workforce: “As a species, we don’t like change. If employees are not engaged meaningfully, they will silently sabotage the change.” He said the tell is in the small arguments ; teams pushing back on standardisation with “it’s always been done this way” and no board member competent enough to challenge it. His go-to example: a regional team insisting their market needs an exception to a new standard process, with no real justification behind it. “A competent board member should be able to challenge that and say, ‘Hey, this is how it’s done in Spain. It’ll work the same in Finland. Get on with it.’ If the board isn’t seeing or hearing these signals, it’s because they’re not competent board members, to be honest with you.”

Who do you need to hire?

Of everything Respondent A said, this is the point he came back to, unprompted, from multiple angles: Who you put in the room matters more than any process you design around them.

• At the top, that means refusing to let ownership get delegated away: “Transformation has to be owned by the entire executive leadership team. It’s not just an IT project.” A CEO who says “my transformation guy is the CIO or CTO” has, in his view, already made the hire that determines whether the whole thing fails.
• Further down, it means actively seeking out (and protecting ) a specific personality type that most organisations are structurally bad at hiring for: people who take ownership under uncertainty rather than waiting to be told what to do. His litmus test is a sentence, not a résumé line: he wants the person who says “I have no idea how we’ll get this done, but I will get it done,” not the person who says “this is difficult” or “we tried that before and it failed.” And he’s blunt about why these people are chronically underhired and underpromoted: “Managers are often scared of these people because they can’t control them, but they are the ones who will determine the future of your company. You need to give them space and trust.”

The upside nobody talks about

Both respondents pushed back hard on the idea that transformation is mainly a threat to employees, and both had specific stories to back it up.

Respondent B: “If people embrace it, they can do very well. Instead of thinking of it as falling out of a tree, they should see it as falling into a playpen full of soft balls; it can be fun!” He’s watched junior people move from frontline helpdesk roles into HR training roles purely because of how they engaged with a transformation, and made a point most people miss: “A good transformation is probably more beneficial to junior people because, to be honest, it usually reduces the number of senior roles.”

Respondent A frames it as a binary choice employees make, whether they realise it or not: “You can wait and see what happens, which is essentially letting yourself become obsolete. Or, you can choose to participate.” His advice is blunt: join the workgroups, even if it costs extra time, because it buys influence and knowledge and it’s exactly the behaviour he looks for when deciding who to bring up into the new structure.

Can you actually see a transformation coming?

Both respondents said yes, and both described it as something closer to instinct than analysis.

Respondent B: “It’s like you can go outside and feel that it’s going to rain in half an hour if you’ve been a farmer all your life. You just know. Emotionally intelligent individuals feel the change in the company’s internal weather system.” The problem, in his experience, is what leadership does with that instinct once employees act on it: “When you feed these sensitive, intelligent people bullshit by telling them nothing is happening, you lose them.” He compared it to looking outside at visible rain while someone insists, straight-faced, that it isn’t raining “the sad thing is, they kind of all do.”

Respondent A locates the earliest signal on the shop floor, not in the boardroom: “The signals often come from the operation itself. People on the ground see that competitors are faster or more efficient because they use newer technology. That information needs to flow upward.” Whether it actually does, in his experience, depends entirely on how many management layers sit between the floor and the decision-makers. This is also, separately, one of his biggest complaints about slow transformations: “These layers filter, translate, and often block critical information to protect their own positions. Speed is the most important asset you have, and these layers destroy it.”

The advice both leaders kept repeating

For leaders:

• Own the transformation as an entire executive team, not as a project handed to a CIO or CTO;
• Don’t chase a risk-free plan; it doesn’t exist;
• Cut the management layers that slow information down in both directions;
• Once teams are moving, don’t hit the brakes at the first hiccup: “Ask them for their learnings, but let them keep moving. If you stop them every time there’s a hiccup, the best people will eventually give up and leave.” ;
• Above all, don’t run a mushroom operation Respondent B’s term for keeping employees in the dark and “feeding them horse shit” about what’s actually happening.

For employees:

• Participate before you’re asked to. Put your hand up, join the workgroups, say “I’ll figure it out” instead of “we tried that before.”
• Trust your instinct about change even when leadership tells you nothing is happening and treat a transformation less like something that happens to you and more like the biggest opportunity you’ll get to shorten the distance between where you are and where you want to be, especially if you’re early in your career.

Respondent A’s closing line doubled as a philosophy for both sides of the table: “The moment when things become 100% clear will never come again… You cannot afford to stand still and wait for things to ‘land.’ That moment will never arrive.”

Two conversations, one pattern

Neither respondent knew what the other said. One came at this from founding and scaling his own ventures before leading transformation inside large corporates; the other came at it from twenty years in CIO seats and advisory roles for multi-billion-euro companies. They landed in almost the same place anyway: Speed beats perfection, ownership beats delegation, and the employees who lean in, rather than wait it out , are usually the ones who come out ahead.