Why Coaching Sucks: A Candid Take for CXOs and Entrepreneurs

Let’s get real: coaching isn’t always the magical, life-changing experience it’s made out to be. For CXOs and entrepreneurs, the hype around coaching often meets the cold, hard reality of busy schedules, conflicting priorities, and, let’s face it, questionable ROI. While coaching has the potential to transform leaders and businesses, it often falls short because of the way it’s approached.

So, why does coaching suck sometimes? Let’s break it down—brutally and honestly.

1. Generic Advice That Could Be Googled:

Too often, coaching sessions regurgitate generic wisdom that you could easily find in a TED Talk or a motivational book. You don’t need a coach to tell you to "delegate more" or "communicate better." What you need is tailored, actionable insights—not vague platitudes that leave you wondering why you’re paying a premium for common sense.

The Fix: Great coaching digs deep. If your coach isn’t asking tough, uncomfortable questions that challenge your worldview, you’re wasting your time.

2. It’s Too Focused on Reflection, Not Action:

Coaches often spend a lot of time helping you "reflect" and "gain clarity." But here’s the thing: CXOs and entrepreneurs don’t need another reflective exercise—you’re already dealing with enough ambiguity. What you need is a coach who helps you move from reflection to action, delivering tangible outcomes that align with your business goals.

The Fix: Look for a coach who emphasizes execution as much as introspection. Coaching should help you get unstuck, not leave you spinning your wheels in endless self-reflection.

3. Misaligned Expectations:

Coaching can fail simply because it’s sold as a cure-all. Some coaches promise to "unlock your full potential" without clarifying what that means or how it will be measured. As a result, you walk away feeling like you’ve gained nothing—even if the sessions were well-intentioned.

The Fix: Set clear goals and metrics upfront. What does success look like for you? Whether it’s better decision-making, improved team dynamics, or faster scaling, make sure your coach aligns with your specific outcomes.

4. It’s Too "Fluffy":

Let’s be honest: some coaching feels more like therapy-lite than a leadership tool. While emotional intelligence and self-awareness are critical, overly "soft" coaching often neglects the hard realities of running a business—like managing cash flow, scaling teams, or dealing with difficult stakeholders.

The Fix: Find a coach who understands the demands of leadership and entrepreneurship. They should bring a balance of emotional insight and strategic rigor to the table.

5. Coaches Who Don’t Get Your World:

Here’s a harsh truth: not all coaches are qualified to work with CXOs and entrepreneurs. If your coach has never led a team, managed a P&L, or navigated the pressures of running a business, how can they truly understand your challenges? It’s like taking parenting advice from someone who’s never had kids.

The Fix: Vet your coach carefully. Look for someone with relevant experience who speaks your language and understands your unique context.

6. The "One-Size-Fits-All" Approach:

Every leader is different, but some coaches apply the same cookie-cutter frameworks to everyone. Whether it’s forcing you into a rigid goal-setting template or pushing a one-size-fits-all leadership style, this lack of customization undermines the value of coaching.

The Fix: Great coaching is tailored. Your coach should adapt their approach to your specific needs, personality, and business challenges.

7. It’s Expensive—and ROI Is Hard to Measure:

Let’s talk money. Coaching isn’t cheap, and its benefits can feel intangible. While leadership growth and personal development are valuable, they’re notoriously hard to quantify. For result-driven CXOs, this can make coaching feel like a gamble rather than an investment.

The Fix: Insist on measurable outcomes. Whether it’s reduced turnover, higher team engagement, or faster decision-making, ensure there’s a clear ROI tied to your coaching engagement.

The Bottom Line: Coaching Doesn’t Suck—Bad Coaching Does

Coaching itself isn’t the problem. In fact, when done well, it’s one of the most effective tools for personal and professional growth. The issue lies in how coaching is delivered and who delivers it. For CXOs and entrepreneurs, the stakes are too high to settle for mediocre coaching.

So, here’s the challenge: demand more from your coaching experience. Find a coach who gets you, challenges you, and delivers real value. Because when coaching is done right, it doesn’t just work—it transforms.