It was a long time coming, but business leaders finally get it. Design matters. So now what? Design leaders have been fighting for a seat at the table for so long and the acceptance seems to have come so fast that it’s freaking confusing to know what to do next.

To get feedback from the front lines, I reached out to the design leaders in the Bureau Community to ask them what was the biggest challenge they saw to design leadership? And with over 100 responses we definitely saw trends. But more than that we saw challenges that were both related and contradictory. And it all makes sense.

In the words of Hamilton’s King George III, “What comes next? You’ve been freed. Do you know how hard it is to lead?”

And when I shared the list back out to the community I heard the rumblings that some things weren’t problems any more, and others would fix themselves when certain issues were addressed, and the challenges were contradictory and the order was spot on except for being completely wrong.

So sharing this list doesn’t really accomplish anything except getting your attention. (Hey there!) Instead, let’s look at the themes that rose to the top and how they’re impacting not just design leaders, but the perception of design leadership itself.

Whenever there is rapid acceptance of a skill or role as a business advantage it’s going to create a vacuum as every company decides it has to have it in place today. And that causes a major supply and demand issue so everyone makes do with the best people they can find. And in an industry where being a designer gave you limited room for advancement, this was a new level. So designers rightfully applied for design leadership positions. And they were hired.

Think of it like content strategy. Same thing happened when it was accepted as a solution to a better content experience and improved communication across a growing number of channels. Copywriters handle content, but they weren’t content strategists. Or were they? These content strategists had to come from somewhere.

And now all the designers who were hired but didn’t have business experience are enjoying a little trial by fire and burning the midnight oil.

Meanwhile the experienced design leaders are trying to help their green teams catch up on their design education while at the same time trying to educate the C-suite on how design improves the bottom line.

As a result, they find themselves in the old maker-versus-manager trap where they are trying to do the work with, or for, their teams and they can’t lead and create so other things start to fall apart.

Even the most seasoned design leaders are worried that a backlash may be coming because the design magic that was expected isn’t happening fast enough.

Which also leads to a dissatisfied team that has a lot of opportunity to jump ship. And they often do. As do the design leaders themselves. In the last two years it seems like everyone is working somewhere new.

So the company has to keep filling roles with new people, sometimes with great experience and often with less because the cost to hire new people is growing by leaps and bounds. As is the cost to retain them.

Depending on where you are in the cycle, and where the company is, it’s going to be a different version of this whirlwind of people in and out that makes it hard to get anything settled.


On a recent podcast with Chris Wilkinson, he made the analogy comparing the western expansion across the U.S. to design leadership. “The challenge for design leadership right now is to get out of that machete-through-the-jungle mode and start to build up that sustainable foundation…I think we're already there and I think that the challenge isn't to progress further. The challenge is to change the way we talk about it. And to talk about it as this established discipline and this established practice.”

Are there challenges for design leadership? Absolutely. Is it about qualified talent and experience and proper education in both business and design? Yes. But the biggest challenge to design leadership may be realizing that the fight for acceptance is over. Now it’s time to shift our mindsets to one of integrating design in with the other established business disciplines while maintaining a touch of disruption. Because customers are humans, and they will continue to want different things. Things that design will be able to deliver.

So what do you think? Is this the biggest challenge to design leadership?