Over the past few weeks, I’ve had several conversations, like these:
- A team member adjusting to a new leadership role, learning how to manage evolving relationships and navigate lingering resource gaps
- A prospective client sorting through next steps to support their growing organization and emerging need for executive-level leadership
- A new hire at a nonprofit stepping into a role without the former staff member available to answer questions
- And a recurring client exploring how to build capacity as CEO by bringing on additional help and delegating key details with care
Different people, different contexts—but one familiar theme kept coming up:
New territory. No clear playbook. And that quiet pressure to get it right from the start.
There were questions, ideas, uncertainties, and vision in every conversation. And in each one, I found myself saying something I’ve come to believe deeply:
You’re not supposed to get it perfect the first time.
Progress Over Perfection: How to Lead With Confidence Through Uncertainty
When you’re navigating something new, it’s normal not to have it all figured out. You’re working with the information, capacity, and context you have right now. The goal isn’t to perfect it out of the gate—it’s to stay engaged, pay attention, and give yourself the space (and grace!) to improve as you go.
If you find yourself caught between wanting to do better and wondering if what you’ve done is good enough, here are five simple, practical ways to lead through the uncertainty—without getting stuck.
1. Get Clear on Expectations to Avoid Missteps
Whether you’re setting them yourself or they’re coming from a boss or client, take time to understand the goals, timelines, and why behind what you’re doing.
Clarity on the non-negotiables allows you to move forward with confidence, knowing what truly matters—and where there’s flexibility to figure things out.
2. Ask Questions Early and Often During Uncertainty
You don’t have to wait until you feel 100% ready. Start with what you know, and ask questions along the way. Some things will naturally sort themselves out, and the most important questions will rise to the top.
It’s a smarter (and faster) way to lead—especially when things are changing or unclear.
3. Learn From What Works (and What Doesn’t)
Make a habit of jotting down what went well, what felt clunky, and anything you’d do differently next time. That reflection turns experience into insight—and insight into growth.
We can only learn so much in theory. Doing teaches us faster and with more clarity.
4. Adapt Your Leadership Approach as You Learn
You’re allowed to change your mind, shift gears, or try something new as you learn more. That’s not a failure—it’s smart leadership.
When you give yourself permission to pivot, you also give your team permission to do the same. And that flexibility can open the door to new solutions, stronger collaboration, and better outcomes.
5. Build Trust With a Simple Apology (When Needed)
Stepping into something new comes with a learning curve. Most people understand that—and if a misstep happens, a genuine “I’m sorry” is often more than enough.
Here’s the good news: You probably won’t need to use it often. But knowing it’s available takes the pressure off and lets you focus on progress, not perfection.
“Good Enough” Is Often Better Than You Think: What Effective Leaders Know
In that recent conversation, the recurring client mentioned they might go about $200 over budget the first time through on a coverage plan. But after reframing it—realizing they gained a clear path forward for just $200 and a few minutes of decision-making—it became obvious:
They didn’t overthink it.
They did what needed to be done.
And they now know exactly how they’ll handle it next time.
That’s good enough. Move on.
And if you manage others, this mindset matters even more. When someone on your team is stepping into something new, they don’t need pressure to get it perfect—they need clarity, space to ask questions, and your support as they figure it out.
Remind yourself: their first version doesn’t need to be flawless, it just needs to be headed in the right direction.
Ask yourself: what context do they not have yet? What would I be wondering if I were in their shoes?
When in doubt: try to name the expectations clearly and then stay accessible as they work through it. A check-in and a bit of encouragement go a long way.
One more thing: when the work starts to wobble a bit, it’s tempting to pull it back and just do it yourself. I’ve felt that pull too. But resisting the urge is key to long-term growth. Delegating is a process, not a transaction, and giving someone space to learn is one of the best investments you can make. You can read more on this in our post on delegating successfully.
Encouraging progress over perfection creates space for real growth—and stronger contributions—in the long run.
Ready to Lead With More Clarity?
If you’re navigating something new in your business or your leadership role, you don’t have to figure it out alone. My work is centered around helping small business owners and their teams grow with clarity, confidence, and people-first strategies.
Check out The Full Leadership Profile if you’re looking for a fresh perspective and a practical plan to move forward—no pressure to get it perfect the first time.
Katie Taylor is the founder of The Outsourced COO and the LMRCA’s Young Professional of the Year in 2023. She helps businesses move from overwhelmed to in control by identifying what’s working, what’s not, and what’s next. Specializing in operational leadership, Katie guides business owners in shifting from doing to leading—so they can focus on growth without getting lost in the details. With a people-first, business-smart approach, she helps organizations strengthen their operations, delegate effectively, and build the right support to continue delivering exceptional service to customers. Katie works alongside growing businesses to ensure they don’t just run efficiently but thrive with intention. You can reach her directly here.
