3 Design Stakeholder Archetypes and How to Work with Them
#021: Inviting business partners into design and making it work for everyone.
Welcome to issue #021 of System & Signals. I post two issues weekly that feature practical tips for designers and design leaders and examine design from higher altitudes. I also post free downloadable resources, including guidebooks and templates, on occasion. Be sure to subscribe to get the latest in your inbox.
In many organizations design feels like a vending machine. A stakeholder drops in a request, waits a few weeks, and something shiny comes out the other side.
It works, until it doesn’t.
When people can’t see how decisions are made, trust starts to fray. Conversations shift from evidence to opinion, from “here’s what the research says” to “I just don’t like it.” Soon, you’re defending your work in meetings that should be about outcomes, and the process turns into a slow grind.
The fix isn’t more slides or longer explanations — it’s letting stakeholders into the process itself. Not as passive observers, but as collaborators who share in both the problem-solving and the discovery.
The Allies
The easiest place to start is with the people already curious about what you do. These allies — the ones who lean forward in meetings and ask good questions — can be your early wins.
I’ve had business leads spend an afternoon in a co-design workshop, sketching checkout flow ideas alongside designers. They didn’t just contribute; they brought in fresh insights about in-store impulse buying that shifted our thinking for online carts.
Or take the time we invited a finance manager to observe three back-to-back usability tests. She saw the same pain point appear in every session — customers failing to find pricing information — and by the end of the day she was making the budget case for a content overhaul.
Even something as simple as opening your experimentation backlog to them can change the dynamic. When an ally adds their own hypothesis, they’re invested in seeing it tested. If it works, they get a win. If it doesn’t, they see firsthand the value of testing over guessing.
The Skeptics
Skeptics are a different story. They’re not hostile, but they need to see proof that design can move the needle. With them, it’s about earning trust in small, visible steps.
One of my go-to approaches is the “5 Whys.” A stakeholder once came to us insisting on a chatbot. By the fifth “why,” we’d uncovered the real problem: customers abandoning their carts because they couldn’t get quick product answers. That reframing opened up multiple possible solutions — better product copy, live chat, and a phased chatbot test — rather than locking us into a single feature.
Quick wins matter here. On one project, a tiny tweak to a payment button label reduced drop-offs by three percent. We made sure the skeptical stakeholder saw the before-and-after data. That single success gave us the credibility to take on a much larger checkout redesign.
And sometimes, it’s about lowering the barrier to entry. Instead of asking them to commit to a full design sprint, I’ll invite them to a single playback session where we connect research insights to the next iteration. It’s a low-risk way for them to see the value without feeling trapped in a “design process” they don’t fully buy into yet.
The Directive-Givers
Then there are the directive leaders — the ones who walk in with a fully formed solution and expect it to be executed exactly as described.
Pushing back head-on rarely works. Instead, I’ll reframe their idea as a hypothesis and place it alongside alternatives in the experimentation backlog. We test them all and let the data decide. One sales VP swore a hero carousel would boost engagement; testing proved the opposite, but because it was framed as a hypothesis from the start, the conversation shifted from “you were wrong” to “here’s what we learned.”
Sometimes it’s about giving them a side-door view into the customer experience. I’ve invited executives to “just observe” a research session, no strings attached. In one case, a leader watched a shopper struggle to find store hours in the app and approved a navigation redesign the same day.
The key is to avoid public confrontations. Let the evidence do the heavy lifting, and keep the conversation future-focused.
Making It Stick
No matter who you’re working with, the goal is to build a shared understanding. That’s where a few key practices help. Keeping a visible experimentation backlog turns abstract discussions into concrete, trackable work. Running the occasional co-design session blurs the line between “your idea” and “our shared solution.” Creating a live insight wall — whether it’s sticky notes on a physical wall or a digital board in Miro — makes it hard to ignore what customers are actually saying and doing.
Even the “5 Whys” isn’t just a tool for skeptics; it’s a habit worth bringing into every intake conversation. It keeps everyone honest about whether you’re solving the right problem.
Closing
Design isn’t a black box. It’s a shared space where customer needs and business goals intersect — and it works best when the people responsible for those goals are in the room, seeing and shaping the work as it happens.
The way you bring them in will differ. For allies, it’s about tapping their energy. For skeptics, it’s about showing results they can measure. For directive leaders, it’s about turning their certainty into curiosity.
Do it well, and you won’t just improve the products you ship. You’ll build the kind of trust and partnership that makes design influence stick — long after the current project is done.