The Coach You Didn't Know You Needed
What growth looks like from both sides of the table
The more senior you get, the more responsible you are for developing other people and the less anyone is responsible for developing you. That inversion doesn’t get discussed much, partly because there’s an implicit assumption behind it: by the time you’re here, you’ve built the network and found the mentors you need to keep growing on your own.
That’s sometimes true. If you’ve come up at a steady pace, you’ve had time to build those relationships organically: a mentor from one role or a trusted peer from another. But if you’ve moved fast, that infrastructure often didn’t form when it was supposed to. You were executing, not investing, and then when the formal scaffolding stops the informal version isn’t there either.
Most senior leaders don’t talk about this openly. Admitting that you want development, that you’re not sure you’re getting what you need to keep growing, feels like it contradicts the reason you’re in the role. So the conversation doesn’t happen, and the gap widens without anyone acknowledging it. The problems get harder as you move up and the feedback loops get longer, while the people around you have real incentives to tell you what you want to hear rather than what you need to hear.
The data backs this up in ways that should make organizations uncomfortable. DDI’s 2024 Global Leadership Forecast, drawing on responses from nearly 14,000 leaders worldwide, found that close to 40% of leaders report inadequate coaching from their managers. High-potential employees are twice as likely to say they intend to leave when they don’t have an effective coaching manager. The organizations that take this seriously, building real coaching cultures rather than checking boxes, are 2.9 times more likely to retain top talent. That’s not a rounding error. That’s a structural advantage.
The Standard Offering
What exists for senior leaders is a particular variety of development: an executive coach certified in a framework, asking reflective questions, helping you discover patterns in yourself. It’s not without value. But it tends to surface insights you already half-suspected rather than telling you things you genuinely didn’t know. You leave the sessions feeling understood, but not necessarily different.
There’s a worse version that’s more common than organizations admit. The coaching engagement that gets initiated because your boss is worried about something, but nobody says that directly. You’re told it’s an investment in your growth, but it doesn’t feel genuine and you figure out fairly quickly what it’s actually about. Everyone goes through the motions. The coach asks the questions, you give the answers, but the real conversation never happens. You leave feeling like you dodged a bullet rather than like you grew.
Good versions of formal coaching exist. The distinction is usually less about the framework the coach uses and more about whether they’re willing to say the uncomfortable thing rather than the validating one. That’s surprisingly rare, and harder to assess in advance than it should be.
Honest Friction
What actually moved things for me had nothing to do with formal programs.
Instead, I found I had to surround myself with blunt, sometimes painful, honesty: a peer who would say the uncomfortable thing rather than the diplomatic version, and a few leaders further along who pushed back on my framing rather than helping me rationalize what I’d already decided. Conversations outside my context mattered too – people with no stake in validating my current direction.
None of that was structured or showed up in a development plan. It was almost all accidental, which is a fragile system for something that matters this much.
The thing they had in common was honest friction: someone who saw clearly enough to notice what I wasn’t seeing, and cared enough to say it rather than let it pass. That’s rare at senior levels because most of the people around you have relationships to protect or hierarchies to navigate (in spite of any amount of ‘Radical Candor’ training).
The people who offer honest friction are worth seeking out and keeping close.
Seeking It Out
If you’re in a role where the formal development infrastructure has thinned out and the informal version isn’t in place, the work of finding development becomes intentional rather than incidental. A quick map of where the leverage is, then the reasoning behind each:
The hard part about being specific isn’t knowing what to ask, but admitting to someone what you actually can’t see in yourself. A request like “tell me when I’m rationalizing” forces you to name the blind spot before you’ve resolved it, which is uncomfortable in a way that “give me more feedback” isn’t. Vague development goals are partly about ego protection, and they produce exactly the vague development conversations you’d expect.
The inside-org feedback problem is structural, not personal. The people around you aren’t dishonest; they’re constrained by relationships they need to protect and hierarchies they need to navigate. Peer groups exist specifically to route around this: they give you people with relevant experience who have no stake in validating your current direction. That combination is genuinely rare, which is why it’s worth building deliberately rather than waiting for it to happen.
Most coaches are trained to validate and reflect, which is the professional default. The ones who push back on your framing rather than return it to you are harder to find, and you can’t assess the difference from a credentials page or an intro call. Bringing something genuinely unresolved to the first session is the fastest diagnostic you have.
The structural problem with quarterly challenge conversations is that they feel unnecessary when things are going well. You skip one, then another, and by the time you actually need that kind of external challenge you’ve lost both the habit and the relationship context that makes it useful. The scheduling is the commitment: the conversation can’t happen if it was never on the calendar.
The Advice-Coaching Distinction
Having been through both the good and ugly side of a coaching experience, I try to think differently about developing others than I would have otherwise. It’s shaped both what I invest in and what I’ve learned to get wrong.
Most of what passes for coaching in organizations is advice-giving. The manager knows the answer and the employee is struggling, so the manager tells them what to do. It feels like development because it involves a 1:1 and a difficult conversation, yet the person leaves with a solution rather than a capability, and the next time they hit a similar problem, they come back for another answer.
Real development is slower and less satisfying in the moment. You’re asking questions you already know the answer to, letting people work through things they need to work through themselves rather than shortcutting to the resolution. I’ve gotten this wrong in both directions. Earlier in my career I gave too much advice and called it coaching, which was efficient and mostly useless. I’ve also overcorrected into asking Socratic questions for things that just needed a direct answer, which was frustrating for everyone. The distinction that seems to matter is whether the person is developing a mental model or just executing a task. The first benefits from working through it. The second doesn’t.
The ICF/PwC research on coaching outcomes reports an average ROI of 7x the investment, with 80% of coached leaders reporting improved self-confidence and 70% improved work performance. That’s the ceiling. Most managers never approach it because they’re running advice sessions and calling them coaching conversations.
Making It Real
Most coaching quality problems aren’t about skill or framework; they’re about awareness of what you’re actually doing in the moment. A few places to look in your own practice:
The first is whether you’re naming what kind of conversation you’re about to have. Most coaching conversations fail not from poor technique but because the person across from you is spending their energy trying to figure out what you want rather than actually working through the problem. Something as simple as “I’m going to ask you questions rather than give you the answer — I think you’ll get somewhere more useful if you work through it” changes the dynamic of the whole room.
Before you offer any perspective: what do they actually think? Not as a warm-up, but as real information. If they’ve already got a reasonable read, they need help stress-testing it, not someone to tell them what to conclude. If they’re genuinely lost, working through it Socratically may waste both your time. The answer determines the appropriate response, and most managers skip the question.
In the last month, how often did you give someone an answer versus help them reach their own? Most of us find the ratio is heavily weighted toward answers. That’s not a failure — advice is faster and often what people are asking for, though it builds dependency rather than capability, and the person who keeps coming back for answers isn’t developing; they’re just staying current.
The evidence of real coaching is slow to appear, which makes it easy to abandon before it pays off. The people who’ve had it somewhere in their career are visibly different to work with. They ask better questions and sit more comfortably with uncertainty rather than waiting for an answer. That’s a learned pattern, not personality. It develops on a timeline longer than a quarterly review cycle, which means the return on what you’re currently investing won’t be visible for a while.
Both sides of this are still things I’m figuring out. Receiving development well at senior levels is genuinely hard, partly because the infrastructure for it disappears and partly because the ego investment in having it together makes it difficult to acknowledge needing it. Giving it well is also hard, for different reasons. The honest friction that actually moves people is a social risk that most organizational cultures don’t reward.
Over the years I’ve had enough people tell me “that stretch working with you was where I actually figured out how to do this” that I know the investment goes somewhere, even when I can’t see where in the moment. That’s enough.
