Design Leadership Through Uncertainty
2026-01-15
In the months before Fiserv acquired BentoBox, the designers on my team were asking the questions designers always ask in those moments. What happens to my role? Does the acquiring company even value design? Am I going to be managed by someone who has never shipped a product?
These are rational questions. They are also questions that, if left unanswered, will cause your best people to leave before the deal closes. And the deal needs your best people to close well.
What does not work
Reassurance does not work. "Everything will be fine" is a statement the leader cannot guarantee, and the team knows it. Saying it erodes trust rather than building it.
Charisma does not work. People do not stay through turbulence because they like their boss. If the system around them feels unstable, a likeable manager is a likeable manager on a sinking ship.
Transparency about things you do not know does not work either — or at least, it is not sufficient. "I don't have answers yet" is honest but does not give people a reason to stay.
What works
Systems work. Specifically, systems that give people evidence that their future is being designed with the same care as the product.
At BentoBox, I published a career ladder in week six. Not because the company needed one operationally — it had survived without one. Because the team needed to see, in writing, that their growth path existed independent of the org chart changes that were about to happen. The career ladder was a design artifact. It was designed to solve a retention problem the same way a checkout flow is designed to solve a conversion problem.
The career ladder had explicit IC and management tracks. It had clear criteria for each level. It had been reviewed by leadership before publication. It was not a gesture. It was infrastructure.
100% of the design team stayed through the acquisition. I attribute that mostly to the framework, not to my personal relationships with the team.
The skill gap
Most design leadership conversations focus on craft leadership — design reviews, quality standards, creative direction. These matter. But they are not the hardest part of the job.
The hardest part is keeping your people through the moments when the company around them is uncertain. Reorgs, acquisitions, layoffs, pivots — these are the events that determine whether a design function survives or scatters.
The skill that matters most in those moments is not vision. It is infrastructure. Can you build systems — career ladders, decision-making frameworks, communication cadences — that give people stability when the org chart cannot?
If I were interviewing a design leader candidate, the question I would ask is not "what is your design philosophy." It is "how do you keep your people through uncertainty." The first question tells you how someone thinks about design. The second tells you whether they can actually lead.