Looking Underneath: "Why Don't My Leadership Team Challenge More?"

A founder arrives at a coaching session frustrated that his leadership team don't challenge more. His team was bright and capable, though most were in their first leadership roles. In meetings, he observed the same pattern. He'd share a view. They'd nod. Nothing. "I keep waiting for them to challenge me," he said. "And they don't."

We started with the team. They were likely navigating one of the most challenging shifts when stepping into a leadership role: the transition from other-authorship to self-authorship. From a place where your sense of what's true, what's right, and what's worth saying is constructed largely by the expectations of those in authority around you, to a place where you can hold your own perspective, even when it differs from someone whose approval matters.

This can be particularly difficult in founder-led cultures, where the founder's preferences quickly become policy, and people calibrate to them. In an environment where loyalty is valued, even the most experienced leader can find it hard to challenge the founder.

The shift from other-authored to self-authored doesn't happen because someone invites it. It happens through repeated experience of risking your own view and discovering that you're still safe, still valued, still in the room.

So, we looked at what his team would be risking. For someone starting out as a leader, disagreeing with the person who founded the company and has been right often enough to build something real isn't a small thing. It's the kind of moment you replay for weeks afterwards.

What helps someone move through that isn't more encouragement to speak up. It's being invited to help design the conditions themselves. A simple question could start to open this up: "If I asked you to play devil's advocate, what would you suggest?" It offers something most people have never been given: a say in how disagreements happen, not just permission for them.

And then, we explored what happens to him when a challenge lands that doesn't align with his perspective. He hadn't thought about it. But when he looked closely, something interesting emerged.

In moments of challenge, he often did the same thing he was asking his team not to do. Rather than sitting with the discomfort of disagreement and responding from his own judgment, he'd read the energy of whoever was challenging him and adjust his position accordingly, not because he'd been persuaded, but because holding the tension felt too high a price.

In that moment, he was possibly not operating from self-authorship either. He'd slipped into other-authorship, managing the team's approval of him, just as they were managing his approval of them.

We stayed with that for a while. Because it didn't stop there.

He reflected on his own feedback conversations. The times he'd softened a message until it lost its edge. Delayed a difficult conversation because the relationship felt too important to risk. Let a performance issue drift, telling himself the person would figure it out. Each of those moments had felt like care. Looking at them now, they were also avoiding his own discomfort with disapproval shaping what his team received, or didn't.

And then there was something harder still. If he wanted his team to develop the capacity to hold a view under pressure, to risk their perspective in the room, he was one of the most powerful conditions for that. Not through what he said about the challenge, but through what he modelled when it landed on him. A founder who visibly sits with disagreement, who responds from their own judgment rather than the room's energy, who gives honest feedback even when it's uncomfortable, that founder is teaching their team something that no invitation to speak up ever could.

This is the threshold that matters. Self-authorship isn't a fixed state you arrive at and keep. It's a capacity you can lose access to under pressure, at any level of seniority, including the top.

What moves someone toward self-authorship isn't being right. It's discovering that holding a view under pressure, even an imperfect one, doesn't cost them what they feared it would. That discovery must happen more than once before it becomes safe.

For his team, the path runs through being challenged and surviving it. For him, it runs through noticing when he's reaching for an external authority instead of his own judgment, especially when that authority is the very thing being questioned.

Where do you notice yourself reaching outward?