Coaching | What We Actually Work On
People come to coaching with a stated agenda. The stated agenda is rarely the whole agenda.
That's not a criticism. It's just how it tends to go - and my role is to help figure that out, make the conversation useful, and ensure that you walk away better than when you walked in.
How does this look in practice? It could be a conversation you keep not having, a team that isn't quite gelling, a performance review arriving faster than you'd like. You describe it in reasonable professional terms. And then, somewhere in the session, the real thing surfaces.
That's where the work starts.
After 15 years of these conversations, a handful of themes come up again and again across very different leaders in very different organizations. Not because leaders are all the same, but because certain challenges come with the role.
Delegation, or rather, the version people are actually stuck on
Almost everyone has a delegation problem. And it's rarely the one they describe.
Some people genuinely need to hand more off. But the more interesting version is subtler: the habit of quietly fixing things before they go out the door. Answering a question when passing it back would build more capability. Delegating only to a trusted few rather than empowering (and developing) the whole team. In essence, carrying the cognitive weight of work that belongs, structurally and developmentally, to someone else.
Most leaders who are good at their jobs got there by being the person with the answers. At a certain point, that instinct starts working against them. The shift from "I know how to solve this" to "I know who should solve this, and how to set them up to do it" is not automatic. It takes practice, discipline, and some tolerance for the occasional small miss landing while you hold your nerve.
Communication, and the gap between what people think they're saying and what actually lands
Most senior leaders are competent communicators. The gaps tend to be specific. Burying the ask. Over-hedging. Leading with so many qualifications that the point arrives exhausted. Or the reverse: someone so direct they skip the context entirely and then wonder why nobody is following.
A lot of this work comes down to the first sixty seconds. What you establish before you've said anything substantive sets the frame for everything that follows. How should I take this? Are we exploring or deciding? Do you want my input or my agreement? Those questions get answered implicitly, and faster than most people realize.
There's also a specific version that comes up constantly: the confusion of confidence with certainty. They are not the same thing. Confidence is clarity on what you believe and why. Certainty is having complete information. You rarely need the second to have the first, but people conflate them and stay quiet in rooms where they should be speaking.
The team, which almost always has at least one more complicated layer than the initial description suggests
Leaders often arrive with what sounds like a team problem, which turns out to be a relationship problem, which turns out to be a feedback problem, which turns out to be an avoidance problem. These things layer.
What I've noticed is that the leaders with the most functional teams aren't necessarily the most charismatic or technically brilliant. They're usually the most curious. They ask better questions. They listen to the answers. Their 1:1s feel like conversations rather than status updates. Trust compounds from that, and then motivation follows, and then you have something that actually works.
The ones who struggle tend to be doing the thing they were rewarded for on the way up: solving problems, having answers, moving fast. It served them well until it didn't.
Managing upward, which is underrated and often underdiscussed
Leaders who are skilled at managing their teams often have a blind spot when it comes to managing up. When to push back. When to stay in your lane. When to raise a concern without being filed away as difficult. The tension between being direct and being politically intelligent is real, and it doesn't resolve cleanly.
What tends to help is getting specific: which concerns are worth raising, to whom, and in what register. "I need to flag this" and "here's how I flag this without it backfiring" are different skills, and both matter.
The internal narrative, which tends to surface when nobody's planning on it
This is the one people don't usually arrive intending to discuss. It comes up during transitions, stretch roles, new environments, or the specific moment when a default approach has quietly stopped working and nobody has said it out loud yet.
The coaching I find most interesting happens here. Not because the external circumstances aren't real, but because how someone narrates what's happening to them shapes every decision that follows. The leader who reads a difficult colleague as evidence that the organisation doesn't value them is working with very different material than the one who reads it as a political challenge to navigate. Same facts. Very different room to move.
None of these are tidy problems with tidy solutions, which is probably why people are still working on them ten years into otherwise successful careers. The work is in the noticing, the naming, and then doing something slightly differently once and seeing what happens.
Most of the leaders I work with are already good. They're trying to get better at specific things, for specific reasons, at a specific point in their careers. My job is to pay close attention, ask questions that aren't entirely comfortable, and tell them the truth.
Most people have never had quite that combination. When they need it again - and there's usually a next time - they tend to come back.
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Ellie Hearne is the founder of Pencil or Ink. She coaches leaders and leadership teams, runs workshops and offsites, and teaches on the Oxford AI-Driven Business Transformation Executive Programme. She's been in this work long enough to have seen most things twice