Why Capable Executives Stall, and Where the Real Work Begins

My remedial massage therapist rarely starts working where I say it hurts. She moves around the area for a while, reading how my body responds, and often finds the problem somewhere else entirely, in a place I hadn't thought to mention. Organisations now need leaders who can work with that kind of precision, finding where the pressure sits rather than applying the same general treatment everywhere and wondering why nothing moves.

What is being asked

When I ask CEOs to describe their leadership teams, I hear the same things across very different industries. Their executives perform well independently but struggle to operate as a collective. They drive hard but find it difficult to facilitate. They deliver reliably on this year's numbers, but the next horizon tends to get whatever attention is left over. They reach for a technical fix when the challenge is adaptive. Meanwhile the organisation is being asked to transform while it grows.

Most of these are requests to hold two things that pull against each other, and the larger whole they both belong to. This year's numbers and the next horizon, for instance, both serve an organisation that is still thriving in ten years, and a leader who keeps that in view can weigh one against the other without treating either as the enemy.

Holding polarities is only part of what is now asked. I describe the full ask of leaders as holding more, seeing more and being more. Holding more means carrying complexity, ambiguity, emotion and paradox without rushing to resolve them. Seeing more means sensing the system and its interdependencies, including where leaders themselves sit inside it. Being more means staying coherent and present under pressure while helping others make meaning. Most development effort still goes into adding skills and frameworks, the kind of growth that equips a leader to do more. Holding more and seeing more require something different, and in my experience both rest on being more. What a leader can do depends on what they can see, and what they can see is shaped by how much they can hold while they look.

Capability and capacity

These are rarely weak leaders. Robust recruitment diagnostics usually show genuine strength across what the role requires, from strategic thinking to accountability, so the raw material is often there. What limits them sits somewhere else.

A leader can only hold as much complexity as their current way of making sense of the world allows. Adult development research shows that this capacity can keep developing well into adulthood and is not the same as intelligence or experience. When a situation asks for more than that, a leader tends to filter out what they can't hold, often without realising, and works hard on the smaller version of the problem that remains. The behaviour others notice, such as closing down debate or rushing to a fix, is fed by something deeper, a root that often formed long before the current role. Honing the raw material means meeting that root, because until a leader does, the behaviour tends to return under pressure, however much feedback they receive.

One leader, several layers down

The leader I want to describe is drawn from several I have worked with. She runs a large division whose numbers move in the right direction every quarter, and her CEO counts her among the strongest operators on the executive team.

What the numbers don't show is how others experience her. Her people bring her finished answers rather than early thinking, because half-formed ideas rarely survive their first airing. Bad news reaches her late, often after a small problem has become a large one. Decisions drift upward, and her direct reports, many of them senior leaders with considerable influence of their own, show less of what they are capable of in her presence. She can describe the system she leads in detail, yet cannot see how her own grip produces the late bad news that so frustrates her.

The same pattern colours how she shows up on the executive team. In meetings she reports on her division with precision and defends it well, but she rarely brings a problem she hasn't already solved or offers a view on an issue outside her own area. Asking peers for help would mean admitting something isn't under control. Her CEO has an excellent head of division, but not someone who helps steer the organisation as a whole. Repeat that across an executive team and you have exactly what CEOs describe to me: people who perform well independently but struggle to operate as a collective. None of this shows in the quarterly figures, though all of it is visible in the leading indicators an executive most needs to watch.

The usual response would be to work on these behaviours directly, with feedback, delegation goals and perhaps a coach. My work with leaders like her starts somewhere else, with what is driving them, one layer at a time.

The first layer was a narrowing of focus to outcomes now. Under that sat a mental model she would recognise and defend: my job is to keep everyone accountable. Accountability done well is critical, but in her version it rested entirely on her, and nothing felt held unless she was holding it. Further down, her worth had become tied to her competence and to making sure nothing went wrong. At the bottom lay the root, a conviction formed long before this role, that things would go wrong unless she held them tightly. From inside that conviction, letting her team explore an idea that might fail felt like abandoning her post, and new shoots read as risks to be managed long before they could become anything else.

Finding the point

What helped most with this leader was recognising that her way of operating made sense from where she stood, even though it carried significant downsides. It had grown from assumptions she held about herself and others, and those assumptions had produced rules with a real upside. Her results were genuine, and her control was part of how she had achieved them. Honouring that takes a certain maturity, whether the person doing the work is the leader she reports to or an external coach. Her starting point had its own logic and its own legitimacy, and treating it simply as a fault to be corrected would most likely have deepened the pattern.

Respecting that logic, rather than arguing with it, opened a different kind of space. The fear that had been driving all the activity, which she had long pushed away, could be acknowledged and allowed to breathe. That is where room for new ways of seeing, holding and being began to emerge.

In the months that followed, she learned to hold the tension consciously rather than avoiding it through defensive behaviour or pushing through it. In practice, that meant asking her team what they were seeing before offering her own view, and when the old pattern returned, usually under quarterly pressure, catching it earlier and stepping back before closing a conversation down. Her people started bringing her ideas while they were still forming, and on the executive team she began raising problems before she had solved them, drawing her peers into conversations she would once have handled alone.

Many other challenges can be followed down in the same way. Take the leader who rushes to solve problems because ambiguity is so hard to sit in, or the one who champions a new value proposition in strategy sessions while still steering the business by the identity that made it successful. Each looks quite different from the leader I have described, yet followed far enough, each tends to lead to a root of its own, often formed long before the role.

What precision asks

A common objection is that there isn't time for this kind of developmental work. The assumption is that going beneath behaviour must be slow, months of introspection that a busy executive can't afford. So the effort stays on the surface, or the leader is judged as someone who either can or can't. In my experience the opposite is closer to the truth. Working on the surface is what takes the time, with the same feedback given year after year and behaviour that improves for a few months before returning under pressure. Meanwhile the cost of the pattern accumulates every quarter it continues. Precision is what makes the deeper work efficient. Over nearly thirty years I have frequently seen one or two conversations at the right point open up what has held a pattern in place for a long time.

Living differently under pressure then takes practice. The old grip does return, often at the worst moment, and the difference is that the leader can now recognise it and has a choice about what happens next. As that recognition grows, they can ask for help without experiencing it as a loss of standing, and stay with an experiment without fearing for their survival. The work pairs intensity with compassion, much as my massage therapist does when she finds the sore spot and works it firmly but with care. It also asks something of whoever is doing it. A CEO or coach who avoids their own difficult territory will struggle to stay with someone else while they meet theirs.

Beyond the role

The same grip tends to travel. A leader who must hold things tightly in one role usually brings that pattern to the next, which is why a restructure or a new role rarely resolves it on its own. Organisations often reinforce the pattern as well, rewarding the results it produces and relying on the style that delivers them. The work is most effective when it attends to the leader and the expectations around them together.

For any executive team, the question my massage therapist would ask is worth asking here too: where does the pressure actually sit, and what has it been an intelligent compensation for?

That is where my work with CEOs and their executive teams begins: with the strategic challenge that matters most to you and the point beneath it, so that a group of strong individuals can begin to lead the organisation as one. If you have a capable leader whose development has stalled, or an executive team that performs well apart but not yet together, I would welcome a conversation. I take on a small number of these partnerships each year. Message me here on LinkedIn, or book a time through oisin.com.au, and we can talk through what you're facing.