Spotting Shoals from Shore: How I Learned to Lead Managers

I once heard leadership described as follows:

“Managing projects is like helming a ship with an unruly crew. Managing managers is like standing atop the mast in a storm, shouting orders about a looming reef, unsure if anyone even heard you.”

If that metaphor resonates, I challenge you to rethink your leadership style.

First let’s dissect the obvious: Leading managers is stressful. But why, exactly?

As a project manager, you have visibility into the tasks being completed under your watch. You review the final product before it goes to a customer or client. Bad work products or struggling staff will be immediately apparent—these problems present themselves in the form of sub-par work, and you can mentor or re-direct as necessary.

Overseeing managers is different. In an oversight role, your job is not to drive outcomes. It is to build capacity and empower your managers to achieve their own outcomes. You cannot and should not have full visibility into the steps involved—that’s just project management v2.0. Instead, you must inculcate good judgment among your team. And therein lies the stressor: you rely on your team’s judgment to surface issues to you, and their very judgment may be contributing to the issue in the first place. It’s no surprise that so many people throw up their hands and declare they are done with people management upon reaching a certain level.

But a perspective shift and a few simple tools can shine a light through the fog. I say this not as someone who has this figured out (far from it), but as a careful student of excellent mentors who have helped me grow in this area.

I think there are three habits of successful leaders of managers:

1. They ask probing questions

They don’t fill check-ins with questions like “how’s it going?” Instead, they may ask:

• “What’s the biggest factor blocking you from moving faster with this key client? How can we address it?”
• “If I could find you an additional analyst on this project, how would you deploy them? Would that help free you up to focus more on strategy?”
• “Do you have any team members who are struggling with the quantitative workload?”
• “Who is your happiest client right now and why?”
• “Imagine you’re a happy and productive member of the team five years from now. What can we do today to set up for that future?”

Sometimes, the best thing you can say is “tell me more” and keep saying it until you get to the heart of the issue.

Not only does this approach get you the information you need—it builds perspective on your team and encourages them to ask these questions of themselves.

2. They build and trust their intuition

Your most important people management challenges can’t be solved with a spreadsheet tracker or Monday.com board. These types of tools are critical for keeping the trains on time. But the most important resource on your team is not hours, budgets, or deliverables—it’s good judgment. Everything else flows from that. And it’s simply impossible to keep tabs on every critical judgment call being made by your managers.

The most important resource on your team is not hours, budgets, or deliverables—it’s good judgment.

So how do we lead in a dynamic environment with incomplete information? Intuition is the key. I’m not talking about superstition or wild guesses. I’m talking about a more analytical, practiced form of intuition that helps you target your attention—you might call it “pattern knowledge.”

This might mean keeping a mental list of the top talents and biggest downfalls of your team members and spending your time in areas where high-priority projects and high-risk tendencies intersect. It might mean trusting your gut when you don’t hear from a typically-gregarious client for a while and checking in to make sure they are happy. It may mean trying to know your team better than they know themselves—forming your own opinions about whether they are professionally and emotionally ready for a new level of responsibility, and challenging them if you think they aren’t looking at the full picture.

Building this knowledge takes raw experience and a history of learning from mistakes. Trusting this knowledge takes confidence and a willingness to fall back on prior experience in times of uncertainty. The latter is often more challenging than the former, but it’s a hallmark of successful leaders.

3. They set their sights ahead—especially when it’s hard

Myopia is the first side effect of stress. As the pressure ramps up, we focus on the proximate things that we can control, even if they don’t represent our best chance for solving the problem in the long term. This can become a vicious cycle because myopia is also a source of stress. It’s hard to remember that tomorrow will be a new day if you are obsessing over the tactical problems of today.

Our job as leaders is to cut through this short-term focus and chart a path to a future where the problem is solved, even when the intermediate steps are unknown.

Let’s say you discover that an important project is over-budget a day before meeting with the client. Your natural reaction might be to break out a spreadsheet and start analyzing the problem, or perhaps to get upset with the manager responsible for the overage. But both of these can be delegated. Analysis of the problem can be delegated to the manager (it emphasizes the teaching moment). Attribution of fault can be delegated to a future discussion when everyone is in a calmer state. Your immediate job is to identify what needs to happen to ensure longer-term success—in this case, being transparent with the client and coming with data-driven solutions—and keeping the team focused on that vision.

Our job as leaders is to cut through this short-term focus and chart a path to a future where the problem is solved, even when the intermediate steps are unknown.

A long-time mentor of mine puts it best: Be like a duck. A duck might be paddling furiously under the water, frantically trying to correct for current and wind. But on the surface, the duck appears to be cruising calmly toward its destination. This sets an important example.

So if good leadership of managers isn’t shouting orders from atop the mast, what is it?

It is overseeing your fleet from the shore. It’s pouring over maps and plans for the next voyage. It is watching a storm rage outside while staying focused on your forward-looking work—perhaps a bit guilty of the warm tea and roof over your head, knowing full well that some of your ships may come back battered, but trusting in the captains you’ve trained to weather it. It’s being first in line to congratulate the crew upon a successful voyage, and the last to leave when cleaning up the wreckage of one gone awry.

It's knowing that you can’t spot shoals from the shore—an insight that is essential to both scale and sanity.

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Joe Indvik is Director of Carbon Solutions at RE Tech Advisors, a Legence company. RE Tech is a consulting firm that designs and implements programs to help clients decarbonize and improve sustainability performance.