Finding an Executive Coach: Why Algorithms (and Apps like Strawberry.me) Can’t Replace Real Connection
Updated January 26, 2026
The Quick Answer:
Core Question: Are coaching platforms and matching algorithms the best way to find a career or executive coach?
Direct Answer: Platforms like Strawberry.me or BetterUp are excellent for accessibility and initial discovery, but they often treat coaching as a transactional commodity. Because successful coaching is 80% reliant on personal chemistry and trust, an algorithm based on keywords rarely outperforms a genuine, human conversation to determine the right fit.
Key Takeaways:
Chemistry Over Credentials: A coach might look perfect on paper (or an app), but if the personal vibe is off, the coaching will fail. Algorithms cannot predict rapport.
The "Uber-fication" Risk: Purely virtual platforms often standardize the process, whereas executive coaching requires a bespoke, non-standardized approach to your specific context.
The "Fit" Test: Always prioritize coaches who offer a free, no-obligation chemistry call. If you can't talk to them before paying, it's a red flag.
We live in the age of the algorithm. We trust Spotify to pick our music, Netflix to pick our movies, and Hinge to pick our dates.
Naturally, this trend has come for the coaching industry. Platforms like Strawberry.me, BetterUp, and endless others are popping up, promising to use smart data to match you with your "perfect" coach in seconds.
Don’t get me wrong—these platforms are helpful. They democratize access to career coaching and make it easier to find a list of qualified professionals without scouring Google for hours. They are a great starting point.
But here is the limitation that tech startups don't like to admit: Coaching is not a transaction. It is a relationship.
You can use an algorithm to find a driver or a dog walker, because the task is standardized. But you cannot standardize the vulnerable, messy, and deeply human work of leadership growth.
The Limits of Coaching Platforms: Why Algorithms Fail at "Fit"
I have seen clients who were "perfectly matched" with a coach based on industry experience, certifications, and price point—and the engagement was a disaster. Why? Because there was no psychological safety. There was no spark.
Executive coaching requires you to admit your fears, own your failures, and push past your comfort zone. You cannot do that with someone just because a computer said they were a "98% Match."
You need chemistry. You need to hear their voice and feel understood. You need to know if they are the type of coach who will hug you or the type who will kick your butt (and which one you actually need right now).
No algorithm can read that.
Virtual Coaching vs. Private Executive Coaching: What’s the Difference?
The other risk with purely virtual, app-based coaching is that it tends to commoditize the experience. It turns coaching into a "session" you consume, rather than a journey you embark on.
When you are just a user on a platform, the incentive is often volume and retention. When you are a private client, the incentive is impact and transformation.
| Feature | Coaching Apps (e.g., Strawberry.me, BetterUp) | Private Executive Coaching (e.g., Corby Fine) |
|---|---|---|
| Matching Method | Algorithmic: Based on keywords and availability. | Human: Based on chemistry, intuition, and conversation. |
| Flexibility | Standardized: Often follows a set platform curriculum. | Bespoke: Tailored entirely to your specific context. |
| Relationship Depth | Transactional: Focus on session volume. | Relational: Focus on long-term transformation. |
| Best For... | Mid-level management needing general skill-building. | Senior leaders needing deep strategic or behavioral change. |
5 Signs an App-Based Coach Won't Work for You
If you are facing these specific challenges, an algorithm-matched coach will likely fail:
[ ] High-Stakes Politics: You are navigating a complex C-suite power struggle that requires nuance, not generic advice.
[ ] Crisis Mode: You are handling a PR disaster or restructuring where "standard operating procedure" doesn't apply.
[ ] Deep Behavioral Patterns: You need someone to challenge your personality flaws, not just cheerlead your goals.
[ ] Niche Industry Context: You need a coach who understands the specific jargon and pressure of your sector (e.g., Agency life, Tech).
[ ] The "Vibe" Factor: You’ve tried standard advice before, and it didn't stick because you didn't trust the source.
How to Choose the Right Coach (The Chemistry Test)
I believe in the old-school method. Real connections.
I don't rely on a matching engine to tell me if I can help you. I rely on a conversation. That is why I always start with a free, no-pressure chat.
It’s a simple "fit check." We talk for 15 minutes. You tell me what you're struggling with. I tell you how I work.
If we click? Great, we get to work.
If we don't? No hard feelings. I’ll even try to refer you to a human who is a better fit.
Your career is too important to be outsourced to a sorting hat. Use the apps to look around, sure. But when you're ready to choose, put down the phone and have a real conversation.
Frequently Asked Questions
Do coaching apps like Strawberry.me or BetterUp work for executives? They can be effective for skill maintenance, but for senior executives, they often lack the depth and customization required. Executives typically need a private partner who operates outside a standardized app ecosystem to navigate high-stakes ambiguity.
Why is "chemistry" so important in executive coaching? Research shows that the quality of the client-coach relationship (the "alliance") is the single biggest predictor of coaching success—more important than the coach's specific methodology or tools. Algorithms cannot accurately predict this human connection.
How do I know if a coach is a good fit? Never hire a coach based on a profile alone. Always request a "Chemistry Call." If a platform does not allow you to speak to the coach before paying, it is treating coaching as a commodity rather than a relationship.