Originally written in 2023, never published, see Note below.

I was sitting in a room with about forty people. A large organisation, several hundred developers across multiple teams, running a Scrum of Scrums-style event to surface their biggest impediments. The usual suspects came up — dependencies, unclear requirements, technical debt. But the issue that kept resurfacing, the one that drew the most energy, was leadership behaviour.

One team lead put it more bluntly than anyone expected: “When the sh!t hits the fan, we don’t want or need leadership to roll up their sleeves and get stuck in. It’s unnecessary interference. They slow things down with what used to work for them back in the day. Just let us get on with it. The ask? Just clear the obstacles in our way.”

The room went quiet for a second. Then half of it started nodding.

That moment has stayed with me because it crystallises something I’ve seen in organisation after organisation. The biggest obstacle to Agile delivering real value isn’t process, tooling, or even team capability. It’s what happens above the teams. It’s leadership — not the absence of it, but the wrong kind of it at the wrong time.

The Reflex That Feels Like Leadership

Most leaders rose through the ranks by being good at the work. They were the best developer, the sharpest analyst, the one who could untangle the thorniest problem. So when pressure mounts, they do what worked before: they dive in. They start making decisions that teams should be making. They redirect priorities based on gut feel. They attend stand-ups and start asking questions that reshape what the team focuses on, often without realising it.

It feels like leadership. It looks like commitment. But from the team’s perspective, it’s interference wearing a lanyard.

The tragedy is that these leaders genuinely want to help. They see a team struggling and their instinct is to contribute — to add their experience, their pattern recognition, their seniority to the problem. What they don’t see is the wake they leave behind: the team that quietly abandons its own approach to accommodate the leader’s preferred solution. The initiative that gets deprioritised because someone senior casually asked “have we thought about…?” in a review. The slow erosion of ownership that happens when every difficult decision gets escalated upward — not because the team can’t handle it, but because they’ve learned that leadership will override them anyway.

The Questions That Shape Everything

Here’s what I’ve come to believe: the single most powerful thing a leader does isn’t make decisions. It’s ask questions. And most leaders are asking the wrong ones.

“Are we on track?” is the default. “What’s our velocity?” is common. “When will it be done?” is almost universal. These questions aren’t bad in themselves, but they tell teams exactly what matters: timelines, throughput, predictability. Teams are smart. They optimise for whatever leadership pays attention to. If leadership measures speed, teams deliver speed — regardless of whether that speed is pointed in a useful direction.

Now imagine a leader who walks into a review and asks something different. Not “are we on track?” but “what’s the most important thing we’ve learned?” Not “when will it be done?” but “what will we learn next, and how soon can we learn it?” Not “what did we deliver?” but “what changed for the people using this?”

These aren’t softer questions. They’re harder ones. They require the leader to care about outcomes they can’t easily measure and to trust teams with problems they could theoretically solve themselves. But they reshape what teams pay attention to. They make learning visible. They make value — not velocity — the thing the organisation optimises for.

Clearing the Path vs. Paving It

The team lead in that room wasn’t asking for absent leadership. That’s a crucial distinction. She wasn’t saying “leave us alone.” She was saying “lead differently.” Stop adding your fingerprints to our work. Start removing the things that prevent us from doing it well.

This is a fundamentally different conception of what leadership means in an Agile context. Traditional management is about direction — setting the course, monitoring progress, correcting deviations. What teams actually need from leadership is clearance — removing organisational friction, resolving cross-team dependencies, fighting political battles that teams can’t fight for themselves, and protecting the space for teams to experiment, fail safely, and learn.

The irony is that this kind of leadership is often harder than the hands-on kind. Diving into the detail is comfortable. It produces visible activity. You can point to your contribution. Clearing obstacles is frequently invisible work — a conversation with another department head, a budget reallocation, a decision to kill a pet project that’s consuming resources. Nobody writes a case study about the leader who quietly unblocked three teams by having an awkward conversation with a stakeholder. But that’s often where the most value is created.

Five Questions Worth Asking

If I could replace every status update meeting with five questions from leadership to their teams, they’d be these:

What is the outcome we’re pursuing? Not the feature. Not the deliverable. The change we’re trying to create for the people who use what we build.

What have we learned? What did the last iteration teach us about our users, our assumptions, or the problem we’re solving?

What will we learn next? What’s the riskiest assumption we’re carrying, and how do we test it?

How soon can we learn it? Not “how soon can we ship it?” — how soon can we get evidence that we’re heading in the right direction?

How can I help? Not “let me get involved.” Not “let me see the details.” What’s in your way that you can’t move by yourselves?

That last question is the hardest one for most leaders. It requires sitting with the discomfort of not contributing directly — of trusting the team’s expertise over your own instincts and accepting that your highest-value contribution might be an uncomfortable phone call rather than a clever solution.

The Leadership Agile Actually Needs

Agile was never supposed to be a framework for building things faster. It was supposed to be a system for staying close to reality — for learning continuously and adapting based on evidence. But that system breaks down when leadership behaviour pulls teams away from learning and toward performing.

The conversation worth having isn’t the one we’ve been having for twenty years about whether teams are doing Agile right. It’s about whether leadership is creating the conditions for Agile to work at all. Whether leaders are asking questions that drive learning or questions that drive compliance. Whether they’re clearing the path or — with the best of intentions — standing in it.

That room full of forty people didn’t need better processes. They had processes. They didn’t need more frameworks. They’d tried those. What they needed was for the people above them to lead differently — to stop helping in the way that felt natural and start helping in the way that was actually useful.

Sometimes the most valuable thing a leader can do is put down the spanner and pick up the phone.

NOTE: This is a version of a blog post I originally wrote in 2023 (for a large consulting firm I worked for). Despite fabulous feedback, it was never published.