How Proximity Makes Leaders Better Decision Makers

When a CEO or founder dives into the frontline work, it often stirs up discomfort. You’ll hear whispers:

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“Shouldn’t they be delegating more?”
“Do they not trust the team?”
“Why are they in the weeds instead of focusing on big-picture strategy?”

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But these reactions reflect more about how we perceive leadership than the leaders themselves.

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For too long, we've equated leadership with detachment, as if keeping a distance somehow equates to maturity. We’ve put strategy on a pedestal, so much so that any hint of rolling up your sleeves and doing the actual work seems like a failure.

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Here's the truth: You can’t lead effectively unless you truly understand the work.

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Sure, you don’t need to be involved every day. But if you've never done it, or haven’t been close to the action for years, your decisions are based on what you think work is, not what it actually is.

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When Leadership Gets Uncomfortable

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In Uncommon Service by Frances Frei and Anne Morriss, there’s a powerful story about a bank leader who becomes a teller for a day. Not just shadowing or observing, but actively doing the job.

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In just a few hours, she uncovers challenges, inefficiencies, and broken policies that no amount of strategy talk could have revealed. It wasn’t about proving a point; it was about gaining clarity.

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When you're on the ground, answering phones or handling customer complaints, strategy is no longer just a boardroom discussion—it’s real. The problems become personal. Decisions become more grounded. Empathy isn’t assumed; it’s earned.

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Why I Still Manage Clients

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I’m incredibly proud of my team. I trust them deeply, and I delegate tasks daily. Yet, I make it a point to manage at least one client directly.

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It’s not about trust. It’s about staying connected. That client keeps me grounded, reminding me what it’s like when expectations shift, deadlines pile up, or communication falters. The challenges we face aren’t theoretical—they’re real, and they hit hard.

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Managing clients isn’t always easy, but that’s the point. Those tough moments force me to reassess our systems, question assumptions, and confront the same issues I help my team navigate.

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The Difference Between Involvement and Interference

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There's a fine line between staying involved and overstepping. Some leaders hover because they don’t trust their team. Others get too close because they don’t know how to let go.

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What I’m talking about is disciplined involvement. It’s staying close enough to the work to understand it—not to micromanage, but to keep your perspective sharp. You can’t identify what’s broken if you’ve never touched it. You can’t guide others if you haven’t walked in their shoes.

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Proximity Is a Leadership Discipline

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Too often, we value elevation over connection. But leadership isn’t about floating above the work—it’s about being present, shaping the process, and guiding your team from a place of understanding.

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Sometimes, that means logging into a client meeting. Other times, it means answering a customer support ticket or sitting in on a launch. It’s not about checking on your team; it’s about staying informed and relevant.

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If that makes some people uncomfortable, let it.

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That discomfort usually stems from a belief that leadership must be detached or that involvement means failure to delegate. But both are misconceptions. True leadership means creating a team that thrives while keeping your perspective close enough to evolve with it.

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Ask Yourself the Harder Questions

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• Can you step into your team's shoes for a day and still thrive?

• Do you truly understand what their daily work looks like today—not just what it was five years ago?

• Are you making decisions based on real insights or outdated assumptions?

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I’m not suggesting you take on everyone’s workload. I’m asking you not to lead from a place of abstraction. Because when you're too far removed, you'll only spot the cracks after the system breaks—and by then, it's too late.

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At StringCan, we understand the power of staying close to the work. Our approach to leadesrship helps businesses thrive and adapt, ensuring decisions are grounded and impactful. Let’s work together to elevate your leadership and your team.

Reach out to us today!