What I’ve Learned Coaching Dozens of Design Leaders: The 5 Most Common Challenges—and How to Navigate Them

Here are the five challenges I see most often—and how I help leaders work through them.

1. Design Isn’t Valued (Yet)

You join a company with big ambitions, only to realise design is seen as a delivery service, not a strategic partner. Often, the founders have built the business without design at the table—and they’re not convinced they need to change now.

How to respond:
Don’t try to convince—demonstrate. Tie your work to tangible outcomes: improve onboarding and show the uptick in activation; streamline a broken workflow and reduce support tickets; upgrade sales collateral and help shorten the sales cycle. You’re not just fixing pixels—you’re driving progress. Make that visible.

2. You’re Flying Blind

Many design leaders are hired into loosely defined roles. The brief is often “fix design”—but with no clear definition of success, no prioritisation, and no shared understanding of what good looks like.

How to respond:
Create clarity. Sit down with your manager and stakeholders to define what success actually means in your first 6–12 months. What are the top priorities? What outcomes matter most? Where are the landmines? With that shared understanding, you can stop firefighting and start leading.

3. You’re Not in the Room Where It Happens

You’re brought in after the key decisions have already been made. You’re expected to “make it look good”—not shape the strategy. Frustrating, but common.

How to respond:
Start where the business already feels pain. Use that as your entry point. Speak in terms they understand—growth, conversion, efficiency—not “craft” or “delight.” Once you’re seen as a problem-solver with business impact, the invites to strategic conversations will come. Eventually, you’ll stop needing them.

4. You’re Leading and Doing

In many orgs—especially early-stage ones—design leaders are expected to do it all: set strategy, manage people, deliver work, and somehow avoid burnout.

How to respond:
You have to prioritise. Focus on what only you can do—like aligning with product and engineering leads, shaping team culture, and coaching others to own more. Build a team that can operate without you in every file. And be honest with your execs: they may think they’ve hired one person, but they’ve actually hired a multiplier.

5. You’re Pigeonholed by Your Past Experience

You’ve developed deep expertise in one sector—say, ecommerce or fintech—and now you’re looking for a new challenge. But the feedback is always the same: “You don’t have experience in our domain.”

How to respond:
Think like a strategist, not a job-seeker. Look for stepping stone roles—companies that sit adjacent to your domain but offer a fresh angle. Or take on crossover projects: mentoring, advising, or collaborating with startups in new industries. You don’t need to reinvent yourself overnight—but you can reframe your story.

One Final Thought

Most of these challenges have nothing to do with capability. They’re about context. Design leaders often have the right instincts—but the environment isn’t set up to support them.

That’s why I coach from both ends. A few days a week, I work directly with design leaders—helping them grow their influence and impact from within. The rest of the time, I advise early-stage founders as a VC—getting them to value design from day one.

Because when design is part of the founding story—not an afterthought—everything gets easier. For the team. For the product. And for the business.

If you’re a design leader looking for support—or a founder building your first design team—feel free to reach out.