You don't get an executive title until you've proved you're a competent leader.

And proving it starts at the manager and director level, if not even before.

Whether you're at a fortune 500 or a Series A Startup, leadership is the most valuable skill you can invest in. Raising your salary almost always comes from demonstrating your leadership skills.

And if you want to enhance your leadership skills, you can do it in 3 ways:

1. Reading books.

2. Taking classes.

3. Getting 1:1 coaching.

All of them will teach you one main thing: Leadership is psychology. If you want to be a leader, you need to know how humans function socially.

"The best way to predict the future is to create it."

— Peter Drucker

A great coach helps you create the future you want. They show you how to be a leader in every interaction at work.

But with so many executive coaches available, how do you choose the right one?

This guide breaks down the key factors in selecting the best coach. It also has some practical strategies that can immediately enhance your leadership skills.

1. Define Your Goals Before Finding a Coach

"If you don't know where you're going, you'll probably end up somewhere else."

— John C. Maxwell

Before searching for a coach, get clear on what you want to achieve. Are you looking to:

✔ Improve strategic communication?

✔ Develop emotional intelligence?

✔ Enhance executive presence?

✔ Master negotiation skills?

A client Sarah (not her real name) was a technology director at a scaling startup. She struggled to get executive buy-in for a major infrastructure upgrade that her company desperately needed.

Problem was, she was the only one who knew they needed it.

Her technical expertise was top-tier, but she overwhelmed leaders with too much details. They'd stop paying attention and think of her as more exhausting than helpful.

The crucial move for her was to simplify her messaging:

🔹 Speak in terms of risk and ROI.

🔹 Focus on business impact, not technical specs.

🔹 Make meetings conversational, not monological.

The result?

She won her full C-suite support. The way she did it positioned her as a smart decision-maker.

Your turn. Think about the challenges specific to your role.

• Are you managing hybrid teams?

• Navigating complex stakeholder dynamics?

• Leading through uncertainty?

Defining your specific challenges will help you find the right coach.

2. Look for Expertise That Matches Your Needs

"The function of leadership is to produce more leaders, not more followers."

— Ralph Nader

Some executive coaches are former CEOs. They have their strengths, but some have limited perspectives.

They may approach your career the way they approached theirs. Great coaches don't have biases about what your career and leadership style should be.

They're most concerned with helping you discover your unique winning formula.

Here are three game-changing frameworks that strong executive coaches use:

🔹 Story Loops – This technique engages your audience. Instead of telling a story from start to finish, you iterate on it with increasing depth. Start simple with the headline. Then include more details as they ask questions. This is how you nail executive presentations and high-stakes conversations.

🔹 Value Proposals – This is a structured way to argue for a raise and promotion. You showcase your contributions and outline future value. At the end of the day, raises and promotions are investments. You get them when you've shown a clear ROI.

🔹 4-Bullet Updates – This concise framework helps you communicate with stakeholders. It's how you show up as transparent, while avoiding boring and unnecessary details.

A coach who teaches strategies like these isn’t just offering vague advice. They’re equipping you with tools to show off your leadership skills with everyone you work with.

3. Evaluate Coaching Style and Compatibility

"A good coach helps you see what you can be rather than what you are."

— Ara Parasheghian

The right coach helps you discover your own best path forward.

A strong coach:

✔ Listens deeply and asks insightful questions.

✔ Provides personalized, practical strategies.

✔ Adapts their approach to fit your learning style.

✔ Creates a safe space for learning and growth.

✔ Challenges your thinking without dismissing your perspective.

Great coaches also help you reframe your weaknesses as strengths. For example:

🔹 Simplified Data Analysis: Imagine this. Due to time constraints, you deliver an analysis without certain variables. Some people would feel ashamed of their "incomplete" work. Instead, you can explain why the tradeoff was worth it. In this case, a faster report is more important than a comprehensive one. It's focused and actionable, providing enough clarity to prevent decision paralysis.

🔹 Long Emails: If your email is lengthy, acknowledge it. "There’s a lot of info here, but I’ve summarized key points up top to save you time. You can read more details below" This turns a perceived flaw into a sign of thoughtfulness.

Nuances like these help you turn everyday challenges into leadership moves. And the best coaches teach you how to do it consistently.

4. Assess Results and Testimonials

"The price of greatness is responsibility."

— Winston Churchill

The best way to gauge a coach’s effectiveness is to look at their track record.

Ask for case studies or client testimonials that include specific, measurable results.

Some coaches calculate and report their average ROI.

What kind of results should you look for? A strong coach will have a history of helping clients:

✔ Secure promotions or raises

✔ Improve executive presence and influence

✔ Strengthen decision-making under pressure

5. Test Compatibility

"Ego is the enemy of good leadership."

— Ryan Holiday

Even the most qualified coach may not be the right fit for you. Be wary of red flags. If a coach:

⚠ Pushes you aggressively to sign up.

⚠ Constantly brags about their results.

⚠ Doesn’t listen to your specific concerns.

They may be insecure and more focused on selling than coaching.

The best coaches prioritize your growth, not their own ego. And you can feel it quickly.

6. Understand the Investment

Executive coaching is an investment, and costs can vary widely.

Some coaches charge per session, typically $200–$1,000 per hour.

Others offer structured programs, ranging from $4,000 to $20,000 for 3 - 12 month engagements.

When evaluating cost, consider potential ROI:

✔ Can this coach help you secure a raise or promotion?

✔ Will they improve your leadership effectiveness?

✔ Could their guidance prevent career mistakes?

A great coach pays for themselves with the career opportunities they unlock for you.

The Final Checklist for Choosing the Right Executive Coach

Before making your decision, ask yourself:

✅ Does this coach provide proven frameworks and strategies?

✅ Do they have a track record of delivering measurable results?

✅ Do they listen, challenge, and adapt to my context?

✅ Do they focus on long-term skill development?

The right coach will push you, support you, and help you reach new heights in your career.

Conclusion: The Right Coach Transforms Your Leadership

"You cannot swim for new horizons until you have courage to lose sight of the shore."

— William Faulkner

The best leaders don’t go it alone.

• They seek out mentors..

• They invest in their growth.

• They surround themselves with people who challenge them to be better.

A great executive coach won’t just help you succeed. They’ll help you become the kind of leader everyone wants to follow.