Design leaders: If you haven’t talked to a user in the past two weeks, you’re cooked.
As design leaders assume more responsibility, one thing often falls through the cracks: direct connection with the user.
It’s understandable. Your calendar is packed. You’re thinking about hiring, team morale, headcount plans, design systems, research roadmaps, cross-functional alignment, showing impact—the list never ends.
But here’s the truth: If you’re not deeply connected to the user’s challenges, none of it matters.
Most design leaders think the job is running a design team. It’s not. Your job is staying obsessed with user problems.
You were put in this position to solve problems. Real ones. You were probably promoted into your position because you’re really good at solving user problems. But if you drift too far from those problems, you risk leading a team that is active but ineffective—busy, but not impactful.
Success Tracks Directly to Time with Users
Want clarity on what matters? Want to empower your team to focus? Want to show meaningful business impact?
Spend more time with users.
It’s that simple. Staying close to their frustrations, goals, and realities gives you the clearest line of sight into what your team should build—and why. It’s how you avoid chasing vanity projects and start delivering real value.
If your team is always shipping but it’s hard to articulate the impact, chances are you’re solving problems that don’t matter. And the fix? Time with users.
How to Stay Close to Users (Even When You’re Busy)
Here are practical ways to build a consistent user connection into your leadership routine:
💬 Executive Sponsorships
If your company assigns executive sponsors to major accounts, ensure you’re included in the rotation. These relationships offer a high-fidelity line to customer needs, especially for strategic, high-value users. If your org doesn’t do this yet, advocate for it—it’s a game-changer.
🧠 Sit in on Discovery Research
Not just validation. Discovery. You want raw, unfiltered user pain. Shadow your research team on calls or listen to recordings. Ask to be looped in on early-stage work where users talk about goals, frustrations, and context, not just how they’re responding to a prototype.
🆘 Listen to Support Calls
Customer support is a goldmine of insight. Join live support sessions or watch call recordings. You’ll hear the real pain points in users’ own words—and start to notice repeat patterns fast.
🎧 Join the Support Rotation
If your company allows it, work a shift. Triage tickets. Answer chats. Escalate bugs. It’s humbling—and enlightening. You’ll quickly see the delta between what you thought users struggled with and what they experience every day.
💼 Sit In on Sales Demos
Sales calls give you the unvarnished first impression. What makes people lean in? Where do they get confused? What promises are being made? You’ll understand how your product lands with new users and how your brand story is being told.
📹 Watch User Call Recordings (But Don’t Stop There)
This is the easiest path—but the least rich. Recordings are helpful, but they lack nuance and depth. You can’t probe or dig deeper. Use them as a supplement, not a substitute.
🔑 Tip: Not sure where to begin? Talk to your heads of Research and Customer Support/Success. They can plug you in right away.
So… How Much Time Should You Spend?
Let’s look at the math.
One 30-minute user call per week? That’s 1.25% of your workweek. That’s not enough. Your calendar reflects your values—whether you like it or not.
Years ago, John Chambers (former Cisco CEO) said something that stuck with me:
“Show me your calendar, and I’ll show you what you value.”
He’s right.
If understanding user needs is at the core of your team’s success (and it is), then you need to block meaningful time for it.
I recommend aiming for 20% of your time.
That’s about 8 hours a week, spent actively listening to and learning from your users.
Is that a lot? Sure. But so is the cost of working on the wrong things.
Final Thought
Being a design leader means you’re no longer just shaping pixels—you’re shaping what gets prioritized, why it matters, and how your team makes an impact.
And the only way to do that well… is to stay close to the people you’re building for.