How to Lead a Multi-Level Organization: Stop Controlling, Start Coaching

Making the jump to senior leadership sounds like a promotion. But for most technical leaders I coach, it feels more like stepping onto a high-wire with no net. Suddenly, you’re not swimming in the code or cranking on roadmaps. You’re managing managers, and the old tricks stop working. You may be tempted to stick close and micromanage, just to keep the trains running - or worse, to keep yourself feeling useful. But the harder truth? Real momentum happens when you let go of control and actually support your people to think for themselves.

If you keep operating like a super-IC (individual contributor) with a Zoom license, your team will hit a wall. Progress stalls. Leaders underneath you wilt, get frustrated, or leave. The business loses both speed and trust. I see this play out all the time with sharp, driven VPs moving up to C-suite roles. They’re used to being the answer person, and suddenly, being the answer person is the wrong job.

Here’s what I wish every first-time multi-level leader knew: moving from controlling to coaching isn’t about being “nicer.” It’s about changing how you create value and communicate. It’s definitely harder than it sounds. But if you get it right, you’ll unlock more from your team than you ever could alone.

In this post, I’m sharing what happens when you try, where people trip up, and the tactics that work for letting your leaders lead - without going off the rails.

The Old Habits That Won’t Die

When you move up, your instincts might fight you. For years, you were rewarded for detail, hands-on involvement, and quick decisions. At the director or senior manager tier, “helping” looked like giving clear direction and unblocking the team. But at multi-level, that same behavior pokes holes in trust and stalls new leaders’ growth.

This is the trap: You step in “just to help” when a solution isn’t moving fast enough or isn’t what you’d do. Or you give feedback only when something isn’t up to your standards - never early, never as a learning loop.

I work with executives who wander back into status reports land, asking their skip levels to send them weekly updates. If you run detailed status meetings, you’re not scaling leadership. You’re building a bureaucracy around your insecurity.

If you recognize yourself here, don’t beat yourself up. The problem is everywhere. The fix isn’t to swing all the way to detached or hands-off. It’s to coach with intention.

For more on classic mistakes at this stage and how to recognize them, check out “Lessons from Real Performance Management Conversations That Got Tricky.”

From Controlling to Coaching

Here’s what a practical shift looks like:

1. Swap Control for Clarity. The best leaders set expectations up front, then step back. This means spelling out what success looks like, what constraints matter, and why this matters. Then you ask how your managers want to get there.
2. Feedback Loops, Not Pop Quizzes. Coaching isn’t lobbing advice at someone. It’s walking them through their own process so they can articulate their choices - and you can shape thinking when it counts, not after the fact.
3. Leverage Questions, Not Solutions. Tech leaders love solving puzzles. You know what’s harder? Asking hard questions and living with a messy answer. If you do their thinking, you create dependency; if you ask, “What other options did you consider?” you grow independent leaders.
4. Let People Live With Imperfection. Not everything will be 100% your way. Don’t let “perfect” become the enemy of “shipping.” High-functioning teams grow by stretching, failing, and iterating in safe ways.
5. Meet Less, Listen More. Step out of the weeds. If your leadership team knows you’ll swoop in and fix, they’ll escalate everything. Instead, create mechanisms for honest upward feedback and reflection.

Want a deeper dive into how product org design ties into the level of autonomy teams can handle? Here’s a cut-to-the-bone breakdown of product org structures that scale.

Where This Shows Up in My Work

Let’s be clear: none of us is immune. I spent years white-knuckling big launches, writing “helpful” emails at midnight, and “checking in” (a.k.a. second-guessing) new leaders. Every time, it delivered diminishing returns.

Here’s how things flip when coaching takes the lead:

Case 1: Marketplace CEO with a Growing VP Layer
She used to call every shot. The company doubled, and she realized her best VPs were quietly frustrated and sandbagging, running every important decision by her. We rewired her weekly 1:1’s to focus on priorities, roadblocks, and coaching - not reporting. Weekly standup replaced with a monthly deep-dive on how each exec is growing their own people.

Case 2: SaaS CTO Building Out an Engineering Ladder
The CTO felt senior engineers weren’t “ready” for management, so he never let go of release planning. We built an explicit “decision space” for his directors and coached them to draw out tradeoffs. The result? Better velocity, more ownership, and fewer escalations for minor issues.

Case 3: R&D Leader Learning to Debrief Like a Coach
After a major project fumble, instead of dictating fixes, he ran a candid team debrief - asking, “Where did we miss a signal, and how could we catch it sooner next time?” The group got to real insight, not finger-pointing, and the next cycle improved. Honest, open feedback loops matter way more than snappy solutions.

To dig deeper into building authentic trust and candid conversations up and down your stack, read “Building Trust with Your Leadership Team: Candid Debriefs.”

Rethinking How You Communicate

Trust Grows in Loops, Not Lines

The old way: information flows one way, top down, with leaders as the filter. But high-growth companies need multi-directional, open feedback. This means:

• Regular skip-level conversations focused on perspective, not reporting
• Real-time pulse-checks (not lengthy surveys)
• Encouraging leaders below you to disagree with each other (and with you!)
• Making transparent decisions, even if they’re unpopular, so folks understand the “why”

Feedback Is a Practice, Not an Event

Your leaders will mirror your approach. If you drive hard, with zero feedback until there’s a problem, they’ll do that too. Flip it. Build a cadence: brief, frequent coaching moments, not Big Annual Reviews.

Use a “feed-forward” mindset: What should we try next? What’s one thing you might do differently based on what you’re observing now?

Clarity Over Closeness

Don’t just “check in.” Share your thinking openly - what you’re seeing, where the org needs to shift. Let them bring forward solutions. The only way you’ll see high-potential people stretch is if you make space for their ideas (and their mistakes).

Check out how to give real, growth-oriented feedback in “Leadership Skills for Executives.”

The Shift: Control vs. Coaching Table

Here’s a fast punch-list to check yourself:

Why Is This Hard, Really?

Because when you let go, you face all your oldest leadership anxieties.

• “If I don’t step in, will they fail and make me look bad?”
• “If someone else makes the key calls, what’s my value?”
• “If I’m not in the mix, who am I here?”

Everyone hits this wall. Here’s the truth I’ve learned after two decades: your real value going up the ladder is about shaping context, supporting people, and coaching ideas into reality at scale. The great news? It’s more contagious. If you make coaching normal, your whole org will start doing it with each other.

What to Do Next

• Map your meeting time: are you sourcing solutions or rehashing status?
• Pick one direct report and, this week, only ask questions in your 1:1. Hold back solutions.
• Run a debrief on a minor failure. Insist on surfacing three lessons, not three fixes.
• Say “I trust your call - walk me through your thinking” at least once to every manager below you.
• Set up a monthly leader roundtable: what’s one messy decision you’re letting your team own, even if it goes off-script?

And if you need a blueprint for scaling this thinking to the rest of your org, check out my breakdown on how to structure software development teams for growth.

Give Up Control to Go Faster

If you’re leading at more than one level, your job isn’t to know the answer. It’s to build a system where the right people find the answer - faster than you could alone. Coaching over control isn’t softer. It’s just better business. The sooner you step back, the more real momentum you get

If you’re stuck in the “control trap,” pause and ask: what’s one thing I could let go this week, just as an experiment? Your next level of growth depends on it.