In Brief: Executive coaching platforms match you with whoever is available. Directories let you browse profiles. Matchmaking services do the work of understanding your actual situation and finding someone specific to it. For senior leaders navigating real career complexity, the difference isn’t a feature — it’s the outcome.
Why an Algorithm Can’t Find Your Executive Coach
Jonathan Dunnett is the CEO of Enable Leaders, a curated executive coach matching service. With decades of experience in leadership and leadership development, he’s passionate about helping emerging and senior leaders find the right executive coach for them, all at no cost for the match.
The Problem With How Most Executives Find a Coach
Most senior leaders find a coach the same way they find a restaurant — they search, scan reviews, and pick someone who looks credible enough. Some use a platform their company subscribes to. Some ask a colleague who used someone they liked.
None of these approaches start with your specific situation. They start with availability.
That gap — between what’s available and what you actually need — is where most coaching engagements fail to deliver. Not because the coach isn’t skilled. Because the match was never built around the right problem.
Want to skip the algorithm and embrace human? Enable Leaders matches leaders with vetted coaches — curated, free, and fast.
Three Ways Executives Find Coaches (And What Each One Actually Delivers)
Coaching Platforms
Platforms like BetterUp, Torch, and Bravely and other executive coaching platforms operate at scale. They aggregate large rosters of certified coaches and match them to users through intake questionnaires and algorithms. For companies rolling out coaching to hundreds of mid-level managers, the model works — it’s efficient, measurable, and easy to administer.
For senior executives, it tends to fall short for a specific reason: the match is optimized for availability and credential verification, not for the nuanced fit that makes coaching transformative at the executive level.
When you’re a VP navigating a political landmine with your board, a C-suite leader managing a team you inherited from someone the organization loved, or a founder trying to scale beyond what got you here — credentials matter less than context. You need someone who has actually been in a version of your situation and come out the other side. Platforms struggle to surface that distinction. Their intake process captures what you want to work on. It rarely captures what’s actually going on.
Coach Directories
Directories — including the ICF coach finder and dozens of niche coaching platforms — give you a searchable database of coaches with profiles. The quality varies enormously. Credentials are verified but context is not. You’re essentially browsing and hoping.
For executives who know exactly what they’re looking for and have the time to vet candidates themselves, a directory can work. Most don’t. They spend hours scrolling profiles, book three chemistry calls, feel lukewarm about all of them, and either settle or give up.
The directory model puts the entire burden of finding a fit on the person who is least equipped to assess it objectively — the person who needs the coaching.
Matchmaking Services
A matchmaking service does something different than an executive coaching platform: it starts with your situation before it thinks about coaches.
That means a real intake conversation, not a dropdown menu. Someone who listens for what you’re not saying as much as what you are. Who understands the difference between a leader who needs strategic thinking development and one who needs political navigation skills — and knows which coaches in their network have done that work in the specific contexts that matter.
The output isn’t a list of available coaches. It’s two or three specific people, with a clear reason why each one fits your situation.
Why Executive Coaching Platforms Fall Short for Senior Leaders
An algorithm can match on credentials, availability, industry, and stated goals. It cannot match on:
- Chemistry under pressure. Executive coaching works in the space between what you say out loud and what’s actually driving your decisions. That space only opens with the right person. No intake form captures it.
- Contextual experience. There’s a meaningful difference between a coach who has read about navigating a hostile board and one who has sat across a hostile board themselves. The platform doesn’t know which one you need. A good matchmaker does.
- The problem behind the problem. Most executives describe the symptom, not the cause. A leader who says “I need help with my executive presence” often needs something deeper — help managing the anxiety that’s undermining their presence, or a reframe of what presence actually means in their specific organizational culture. The algorithm takes the stated need at face value. A skilled matcher probes it.
- Trust calibration. Senior leaders are skilled at managing perceptions. They’re often guarded in intake questionnaires in ways they wouldn’t be in a real conversation. The quality of the match depends on the quality of the input, and the quality of the input depends on how safe the process feels.
When a Platform Makes Sense (And When It Doesn’t)
An executive coaching platform makes sense when:
- Your company is rolling out coaching to a broad population of managers
- You need standardized delivery and centralized reporting
- The coaching goals are relatively defined and consistent across participants
- Budget is constrained and scale is the priority
A matchmaking service makes sense when:
- You’re a senior leader navigating something specific and high-stakes
- You don’t have time to run your own vetting process
- The situation requires someone with real contextual experience, not just coaching credentials
- Confidentiality matters — you need someone outside your organization’s ecosystem
What “Vetted” Actually Means
Every coach on Enable Leaders’ roster has been through a personal vetting process — not a credential check, a conversation. The criteria isn’t just ICF certification and years of experience. It’s whether this person has navigated the kinds of situations our clients are in, whether they coach in a way that serves the client rather than their own framework, and whether we’d send someone we care about to them.
That process takes longer to build than an algorithm. It produces matches that the algorithm can’t.
The Enable Leaders Process
Enable Leaders is a curated executive coaching matchmaking service. We work with mid-to-senior leaders — Senior Managers, Directors, VPs, and C-Suite executives — navigating career pivots, organizational complexity, and leadership transitions.
The process is simple:
- Tell us what’s actually going on. Not a sanitized intake form — a real two-minute description of your situation. The more honest, the better the match.
- We do the work. We review your needs personally and identify two or three coaches from our vetted network who fit — not just your stated goals, but your actual situation.
- You meet them. You choose. No commitment, no pressure. If none of them feel right, we go back to the roster.
The matching service is free. The coaching engagement is between you and the coach.
Frequently Asked Questions
How is a coaching matchmaking service different from a coaching platform?
A coaching platform uses an algorithm to match users with available coaches based on credentials, stated goals, and availability. A matchmaking service does the intake work personally — understanding your specific situation before identifying which coaches in the network are the right fit. For senior executives navigating complex or high-stakes situations, the quality of the match matters more than the speed of the process.
How do I know if I need an executive coach?
If you’re navigating a significant leadership transition, a political challenge you can’t discuss internally, a promotion that’s changed what’s expected of you, or a pattern you keep running into in your career — those are the situations where executive coaching delivers the most value. A free consultation is the right starting point to assess whether coaching is the right intervention for your specific situation.
Is executive coaching worth it for senior leaders?
Research consistently supports the ROI of executive coaching for senior leaders — both in terms of leadership effectiveness and career outcomes. The caveat is that the ROI depends heavily on the quality of the match. A skilled coach working on the wrong problem, or a good match that the leader isn’t ready for, produces limited results. The intake and matching process matters as much as the coaching itself.
How much does executive coaching cost?
Executive coaching rates vary widely depending on the coach’s experience, the scope of the engagement, and the delivery format. Independent executive coaches typically charge between $300 and $1,000+ per session. Some engagements are structured as multi-month programs. Enable Leaders’ matching service is free — fees are agreed directly between the leader and the coach. A transparent conversation about investment happens before any commitment is made.
What makes Enable Leaders different from BetterUp or other coaching platforms?
BetterUp is an enterprise platform built for scale — it works well for companies deploying coaching across large populations of managers. Enable Leaders is a boutique matchmaking service built for individual senior leaders who need a specific, high-quality match for a specific situation. The difference is human curation versus algorithmic matching, and a roster built for depth rather than volume.
How long does the matching process take?
Most leaders receive their coach matches within 24 hours of completing the intake. Chemistry consultations with matched coaches are typically scheduled within the same week.
The Right Coach Exists. Finding Them Is the Hard Part.
Most executives don’t struggle to commit to coaching. They struggle to find the right person — and once they have a mediocre experience, the skepticism that builds makes the next attempt harder. The good news? You found Enable Leaders.
The match is the magic. Get it right and the coaching works. Get it wrong and the best coach in the world won’t move the needle.