The Questions We Couldn't Answer

A follow-up to Tuesday’s webinar, and an invitation to continue the conversation in Bergamo, April 9–12.

Last Tuesday, we ran the webinar. Sixty-something people joined from Stockholm, New York, London, Oakland and a dozen places in between. We walked through the three traps that keep senior design leaders stuck - Permission, Reorg, Identity - and for about half an hour, the conversation was exactly what we had hoped for: people recognising themselves in each other, in real time.

Then we ran out of time.

There were two questions we couldn’t get to. We have been thinking about them since, because they are hard and honest about the situations design leaders are actually in right now. This post is our attempt to answer them properly.

If you want to go deeper in person, we are running a small leadership retreat in Bergamo, Italy, April 9-12, designed for exactly the kind of conversation we didn't have enough time for.

What we did cover

The quick version, for those who weren’t there.

On the Permission Trap: organisations that hire design leaders are running an experiment, and nobody is coming to hand you a mandate. The role is yours to define or yours to lose by default. Waiting for clarity is how you cede territory you were hired to own.

On the Reorg Trap: restructurings are not events to survive. They are windows to act in. The two months after a reorg, when everything is uncertain and alliances are dissolving, that is when the most durable relationships get built, by the people who move first.

On the Identity Trap: your confidence as a designer was anchored in what you made. Leadership doesn’t work like that. The feedback loops are long, the wins are hard to point to, and the temptation to retreat toward craft under pressure is almost universal. The unlock, as Andy frames it, is recognising that leadership is slow-motion facilitation, a skill designers already have, stretched across a longer timeframe.

There was also a sharp exchange about design leadership training. Marzia’s position: skip the MBA. Spend that time having coffee with people in finance, marketing, and sales, and learning how they get their bonuses. That organisational ethnography is worth more than any case study. Andy added something that got a laugh but wasn’t entirely a joke: the literature on couples therapy and family therapy will teach you more about navigating leadership relationships than most business books. Leadership is relational, almost entirely. Understand how you relate, and you understand most of the job.

That was the conversation we had. Here is the one we didn’t.

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Question 1: What happens when you claim your space and no one follows?

“How do you handle the situation where you’re claiming your space and moving toward role clarity, but the rest of the leadership team isn’t doing the same work and wants to keep the experiment’s status quo? In the worst case, you will end up singling yourself out as the difficult one. No amount of trust-building is going to fix that. How do you avoid becoming the system’s antibody target while still walking alongside your peers?”

This question contains a distinction that most advice in this space quietly sidesteps. So let us name it directly.

There is a version of becoming an antibody target that is, at least partly, your doing. You arrived leading with design as the message rather than the method. You framed the work as design versus the business, rather than design as how the business gets somewhere it wants to go. You claimed space in a way that registered as a threat rather than a contribution. That version is addressable. Talk about design less. Lead with outcomes. Do the organisational ethnography. Build relationships before you need anything from them. Position yourself as a student before you position yourself as a peer.

But there is another version that has almost nothing to do with your approach. The organisation hired a design leader as a signal - to investors, to the board, to the market - with no genuine intention of letting design touch anything structural. The status quo suits the people who built it. The experiment was never meant to succeed. In that version, doing everything right still makes you the difficult one, because your success would threaten an existing order that is working well for the people currently in charge.

These two situations look identical from the inside, especially early on. That is what makes the question so hard.

The first move is diagnostic. How was your role created, as a genuine strategic bet, or as a symbolic hire? Who championed it, and do they still have power? When you push, does the resistance feel like friction or like a wall? Friction means people are uncertain and need convincing. A wall means the decision not to let design matter was made before you arrived.

If it is friction: the approach that consistently works is what Marzia calls ego-first relationship building. Not positioning yourself as a peer immediately—that framing requires acceptance, the other side may not be ready to give.

Instead, get genuinely curious about how your peers do their work. Ask to learn from them. Let them feel they are the authority, because in terms of their own role, they are. This is not flattery, it is a real way of building the kind of rapport that eventually earns you the right to be heard. From that foundation, look for the small win that makes design legible in their language: the problem that already exists, in their terms, that design can visibly solve. Andy calls it carrying an umbrella on a sunny day. Everyone thinks you are strange until it rains, and then they all want to be your friend. Find the small patch of rain first.

If it is a wall: the honest answer is that your options narrow, and it is worth naming them clearly rather than dressing them up as a resilience challenge. You can play a longer game, building relationships below and around the people blocking you, creating quiet coalitions, waiting for structural change to create a new opening. You can reduce scope and accept a smaller version of the role while preserving your energy. You can do good work for the people who do want it and let that build slowly. Or you can recognise that this organisation was never going to let design lead, and decide your energy is better spent somewhere it is actually wanted.

None of these feels like winning. But the worst outcome, the one we see most often, is staying in a wall situation while treating it as a friction situation. Pouring more relationship investment into a system that has already decided. That is how you end up genuinely worn down, genuinely marginalised, and genuinely wondering what you did wrong. The answer, in that case, is often: nothing. You were in the wrong place.

“How do I avoid becoming the antibody target?” is sometimes the wrong question. The right one is: “am I already inside an organism that was always going to reject me, and what do I do with that information?”

Finally, and related to the MBA point, design still has a role to play as a counter-cultural voice. If you just become another MBA talking business jargon with a focus on shareholder value, there’s no real point in you being there with a design background. Instead, you can use your different perspective, your skills in making abstract ideas tangible, and design as a risk mitigation methodology to question and provoke. But that does not mean conflict. Think of design more in the role of a personal trainer or guide-by-the-side than a know-it-all.

Question 2: Design leadership is declining in demand. How do we make it matter again?

“In Sweden, designers are experiencing a huge decline in demand for design leadership and design competence within companies. At the same time, in an age of massive technological change, we understand that our competences are more needed than ever. To make things fit their purpose. How do we make design attractive and demanded again?”

This question names something the design community has been reluctant to say plainly: the design leadership moment, in its current form, may be over.

The wave of Chief Design Officer appointments, the design thinking era, the D-suite moment, it crested somewhere around 2019 and has been receding since. The layoffs that hit design disproportionately hard over the past few years were not random. They reflected a reassessment at leadership level of what design had actually delivered relative to what it had promised. Sweden is feeling this acutely. It is not only Sweden.

And now AI is doing something complicated to the picture. It is accelerating the commoditisation of the executional layer, the production work that junior and mid-level designers have occupied. At the same time, the deeper work, making sense of complexity, understanding what people actually need, helping organisations navigate change with intention, is more necessary than it has ever been. The problem is that the field spent a decade arguing for design in terms of aesthetics and process. The aesthetic and process layers are now automating. The argument that was never made clearly enough is the one about judgment and discernment. About meaning. About what it takes to shape something that genuinely serves the people it is supposed to serve.

So the challenge is to stop making the argument for design and start making the argument for the outcomes that only this kind of thinking, at a senior level, can produce. Not “organisations need design leadership because design matters.” But: here is the specific class of problem your organisation cannot solve without someone who thinks this way, and here is what happens when you try without them.

This is a harder, more specific case than the field has typically been willing to make. It means identifying the exact decisions where the absence of design thinking has cost money, created friction, or produced something nobody actually wanted. It means being willing to point at failures, not just celebrate successes. It means getting concrete about what design leadership is for, rather than what design leadership is.

There is also a structural argument worth making. Most of the organisations that have cut design leadership in recent years are not ones where design was embedded, where strategic decisions get made. They are organisations where design was a department, reporting to product or marketing, producing outputs on request. That version was always fragile, because it never had real structural power. The question is not how to make that version attractive again. It is how to make the case for a different version: design as a capability distributed through leadership, not a department that can be cut when budgets tighten.

That is a different conversation to have, with different people, in different rooms. And it requires exactly the kind of organisational intelligence and political fluency that the permission trap, the reorg trap, and the identity trap are all, in different ways, about.

The role of AI and the collateral damage of the bubble bursting post-hype are still to be fully determined. What is already clear is that AI amplifies structural and process issues within organisations. It does not solve them.

The building part of design—at least in digital—is faster and easier and this affects product and engineering people, too. But the questions of what should be built, whether something should be built, and the human experience of it all are still ones design is well-placed to contribute to answering.

Why we launched the Leadership Renewal Retreat

Both of these questions have something in common. They cannot be answered from the outside. They require you to actually be in them, sitting with the specific texture of your specific organisation, your specific peer group, your specific moment, and thinking it through with people who understand the territory.

That is the conversation a webinar cannot hold. It is the conversation the retreat in Bergamo is designed for.

The Leadership Renewal Retreat, April 9–12, is a small group of senior design leaders stepping out of their usual context and into an ancient building in a valley outside Bergamo, Italy. No keynotes. No performing expertise at each other. Marzia and Andy cook on the first evening. Over the days that follow, there are sessions with a professional theatre actress on presence and voice, and with a professional chef on leading under pressure. There is group coaching, there are paired walks, and there is time, actual uninterrupted time, to think about your own leadership in a way that most of us haven’t done in longer than we can remember.

The questions above are exactly the kind that need a room, not a screen.

Secure your place at the Leadership Renewal Retreat, Bergamo, April 9–12.

A €150 deposit holds your spot. Spaces are limited.

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Marzia Aricò is a leadership coach, author, and founder of the Organisational Intelligence Institute. Andy Polaine is a design leadership coach, educator, and author. The webinar recording is available at the top of this page.