💎 How to Get Out of the Weeds as a Leader, Without Losing Context

Leadership often feels like a constant balancing act. On one side, you’re deeply entrenched in the day-to-day, troubleshooting issues and ensuring smooth execution. On the other, you’re expected to look ahead, anticipate challenges, and steer the company toward long-term success. It’s easy to get stuck in the weeds, losing sight of the bigger picture—or worse, disconnecting entirely from the realities on the ground.

I’ve been in that exact spot—feeling pulled in a hundred directions and struggling to create space for strategic thinking. The good news? It doesn’t have to be this way.

Here’s what I mean:

Delegate Context, Not Just Tasks

Early on, I thought good delegation meant handing off a task and trusting my team to get it done. But “do this because I said so” doesn’t empower anyone—it just makes them dependent on me for every next step.

I learned this lesson the hard way when I asked a team member to analyze churn numbers. They came back with a beautifully detailed report, but it answered the wrong questions. The problem wasn’t them—it was me. I hadn’t provided the bigger picture: Why are we looking at churn? What does success look like?

Now, when delegating, I make sure to share the why. For example: “Our churn rate has ticked up in the last two quarters. I think it might be tied to onboarding. Can you figure out what’s happening in the first 30 days, and suggest where we might be dropping the ball?”

With context, your team isn’t just completing tasks—they’re solving problems. And when you delegate context, you free yourself to focus on higher-level priorities while building trust and ownership within your team.

Stay Close to the Frontlines

Here’s the paradox of stepping back: To lead effectively, you still need to stay connected to the day-to-day reality. The trick? Don’t do the work—observe it.

For me, this means joining a customer onboarding call once a quarter or listening in on sales pitches. It’s not about micromanaging—it’s about staying grounded in what’s happening at the user level.

I worked with a founder who had a brilliant approach: They’d join one support call a week. Not to take over, but to listen. Over time, this habit gave them a direct line to customer frustrations, which shaped product priorities far more effectively than any survey ever could.

Staying close to the frontlines keeps you connected to the real challenges without dragging you back into the weeds.

Protect Time for Strategic Thinking

Getting out of the weeds requires discipline—not just for your team, but for yourself. If you don’t carve out time to think strategically, no one else will do it for you.

For me, this means protecting my mornings. It’s when I’m at my sharpest, so I reserve that time for big-picture work: reviewing company goals, reflecting on priorities, or planning the next steps. Meetings, emails, and Slack messages can wait until the afternoon.

I also limit reactive interruptions. If someone comes to me with a problem, my first question is, “What do you think we should do?” Nine times out of ten, they already have a great solution—they just need the confidence to act.

Setting these boundaries doesn’t make you less accessible—it makes your input more intentional. And it’s the only way to scale your impact as a leader.

One of the biggest shifts in leadership is letting go of how things get done and focusing instead on what gets done. This requires trust—not just in your team, but in your own ability to step back and let them figure out the how.

Remember, the most impactful leaders aren’t the ones who do it all. They’re the ones who create the conditions for their team to excel while keeping an eye on the bigger picture. That’s where the real impact lies.

And if you want some help, let’s connect and discuss how we can collaborate to achieve your company’s success.

Onwards,