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If you’ve ever found yourself thinking, “I swear I’ve already answered this,” while a team member pings you yet again, this episode is for you.
Today, I’m unpacking one of the most exhausting leadership moments I see with designers — when your team keeps asking the same questions over and over, and it starts to make you wonder if you’re doing something wrong as a leader. I want to say this clearly right out of the gate: this isn’t a sign that you’re failing. It’s feedback. And when you understand what that feedback is actually pointing to, everything starts to shift.
In this episode, I talk honestly about why repeated questions usually aren’t a communication problem or a documentation problem — even though that’s where most of us go first. More SOPs, more explanations, or even questioning whether you hired the wrong person often feels like the logical next step. But in my experience, that approach only reinforces the dynamic that’s burning you out.
What your team is really asking — whether they realize it or not — is whether they’re allowed to decide without you.
We dive into the idea of decision ownership and why so many creative leaders accidentally hold onto it longer than they should. I share how being the fixer, the closer, and the safety net can quietly train your team to outsource judgment back to you — even when they’re capable of more. I also walk you through the leadership shift from “doing” to “designing,” and how your role as CEO is less about approving every choice and more about building confident decision-makers.
I also get very practical in this episode. I share how we’ve handled this inside my own firm, including why we clarified decision lanes, created clearer reporting structures, limited unnecessary visibility in project management software, and normalized thoughtful mistakes instead of punishing them. We talk about why mistakes — when made inside clear guardrails — actually build confidence instead of eroding it.
You’ll hear how hiring ties directly into this, why you’re not hiring extra hands but judgment, and how we’ve refined our hiring process over the years to make sure people are truly set up to succeed. I also explain why the 90-day review period is one of the most powerful tools you can use to build trust, clarity, and alignment on your team — without fear or drama.
We also talk about seasons. Sometimes the issue isn’t that someone is a bad hire — it’s that their season has changed. Learning how to recognize that, have honest conversations, and adjust roles accordingly is part of real leadership. I share a recent example from my own team where a simple conversation created massive relief, clarity, and momentum for everyone involved.
And if this conversation hits close to home and you want help untangling it, I offer a free 15-minute problem-solving session where we focus on one real leadership challenge in your business. No pitch, no pressure — just clarity. You can book that at fixmydesignbiz.com.
As always, remember: your business should be working for you, not you working for it. If that’s starting to feel out of alignment, it’s time to redesign how leadership shows up inside your fir
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