What does a workshop actually look like? Here's an honest account.

The morning of day one with Calvin Klein's loyalty team did not feel like it was going well.

The room was full; a mixed group of stakeholders from junior to senior, representing different parts of the business with different priorities and different ideas about what the problem actually was. The challenge they'd brought was real and genuinely complex. And for the first few hours, it felt like it. Everyone had context to share, assumptions to surface, constraints to name. The conversation was rich but sprawling. The problem kept expanding rather than sharpening.

This is normal. It's actually necessary. But it doesn't always feel that way from inside it.

What I've learned, running sessions like this over many years, is that the complexity of the morning is doing important work. Every assumption that gets named, every constraint that gets surfaced, every "yes but" that gets voiced; all of it is the group clearing the ground. Getting the real shape of the problem visible before they start trying to solve it.

By the end of day one, something had shifted. Not because of a single moment or a clever exercise, but because the group had done the hard work of actually understanding what they were trying to achieve. The question they'd arrived with had been refined into something sharper and more specific. And with that clarity came something else: a shared sense of what good would actually look like.

The next day was completely different. The same group of people, the same challenge; but with a defined question to work against, the thinking became focused and generative. Ideas that would have felt vague and untethered the day before now had something to attach to. The abstract became concrete. The complicated became workable.

That's the shape of a well-run workshop. Not a straight line from problem to solution, but a process that moves deliberately through complexity toward clarity, and then from clarity toward something you can actually do something with.

It doesn't always take two days. Some challenges are sharp enough to work through in a single focused session. Some need more time. But the shape is always the same: understand the context properly, define the real question, then bring your thinking to bear on something worth solving.

The thing that surprises people most, every time, is how much the group already knew. The answers are almost always in the room. The process just creates the conditions to find them.