10 Things to Look for in an Executive Business Coach | TAB Boards

In the early stages of building a business, hindsight is often uncomfortably clear.

When The Alternative Board surveyed business owners years ago about what they wished they had done differently at the beginning of their journey, several themes emerged. Many regretted not spending enough time on strategic planning. Others wished they had invested earlier and more consistently in marketing and brand development.

But one insight stood out above the rest:
a large number of business owners wished they had sought better guidance sooner.

That regret is not uncommon, and it’s not limited to early-stage entrepreneurs.

How To Choose The Right Business Coach For Your Business

A widely cited study from Stanford University found that nearly two-thirds of CEOs do not receive outside leadership advice, yet almost all say they want it. The desire for guidance is there. The hesitation usually comes from one place: choosing the right coach.

Executive coaching requires a meaningful investment of time, trust, and money. Choosing poorly can stall progress or create frustration. Choosing well can fundamentally change how a business operates and grows.

To help simplify that decision, here are ten essential factors to consider when choosing an executive business coach.

1. A Proven Track Record of Success

A credible executive business coach should be able to point to outcomes, not just philosophies. Coaching is about helping leaders make better decisions that produce tangible results. Look for evidence that a coach’s work has led to measurable improvements such as revenue growth, clearer strategic direction, stronger leadership performance, improved team alignment, or more disciplined execution.

Proof can take several forms. Long-term client relationships often signal sustained value, while testimonials from business owners facing challenges similar to yours provide important context. Case examples, references, or documented success stories help demonstrate how the coach approaches real problems and adapts to different situations.

Just as important as success is how that success was achieved. Ask coaches to explain their role in the outcome. Coaches who are confident in their impact are typically eager to discuss results openly and specifically. A proven track record doesn’t guarantee success in every scenario, but it does indicate that the coach’s methods have been tested, refined, and validated in real-world conditions rather than theoretical ones.

Diagnostic questions:

• Can this coach point to specific outcomes achieved with past clients?

• Have they worked with businesses similar in size, complexity, or growth stage to mine?

• Are they willing to share references or examples of long-term client success?

2. Real-World Business Experience

The most effective executive coaches understand pressure because they’ve lived it firsthand. Experience as a business owner or senior leader matters because it grounds advice in reality, not theory. Coaches who have navigated hiring mistakes, cash flow stress and strategic missteps understand the emotional and financial weight behind decisions.

This kind of experience builds empathy and credibility. A coach who has personally faced tough tradeoffs knows that leadership decisions are rarely clean, binary, or risk-free. They understand that timing matters, that information is often incomplete, and that the “right” choice is sometimes simply the least damaging one. That perspective allows them to help you think through consequences, prioritize effectively, and act with confidence rather than perfectionism.

When evaluating a coach, ask about the businesses they’ve led, the challenges they’ve faced, and what they learned when things didn’t go as planned. Coaches who can speak openly about failure often offer the most valuable guidance.

Diagnostic questions:

• Has this coach personally led or owned a business?

• Can they speak candidly about failures as well as successes?

• Do their examples reflect real-world complexity rather than textbook solutions?

3. Relevant, Focused Expertise

While a coach doesn’t need to come from your exact industry, relevance is critical. Coaches who concentrate on a defined range of business sizes, leadership challenges, or growth stages tend to develop deeper insight than those who position themselves as experts in everything.

Focused expertise allows a coach to recognize patterns quickly. They’ve seen similar challenges before, and can help you avoid common pitfalls. In contrast, coaches who advertise dozens of unrelated services or work across vastly different contexts may struggle to offer depth where it matters most.

Look for a coach who can clearly articulate who they work best with and why. Specificity is a strength. It often translates into sharper questions, clearer frameworks, and guidance that feels tailored rather than generic.

Diagnostic questions:

• Can this coach clearly describe who they work best with?

• Do their areas of focus align with my business’s current challenges?

• Are their frameworks and examples relevant, or overly generic?

4. Accessibility and Availability

Executive coaching only works when it’s consistent, responsive, and relationship-driven. Early interactions are often the best indicator of what the engagement will feel like long term. If scheduling an initial conversation is difficult, follow-ups are delayed, or communication feels rushed, that pattern rarely improves after a contract is signed.

A strong coach is transparent about their availability. They can explain how many clients they work with, how often you’ll meet, and what level of access you’ll have between sessions. Coaching should feel intentional and customized, not squeezed between other commitments.

You should also consider how the coach shows up during conversations. Executive coaching is not a volume business; it’s a trust-based partnership. You want to feel like a priority, not one name among many.

Diagnostic questions:

• How easy is it to schedule time with this coach?

• How many clients do they work with at once?

• Do I feel heard and given adequate attention during conversations?

5. A Willingness to Challenge You

A strong coach knows when to support and when to push. They are willing to challenge assumptions, question long-standing habits, and surface blind spots that may be holding the business back.

This kind of challenge should feel constructive, not combative. The goal isn’t to undermine confidence, but to expand thinking and force clarity where ambiguity has been comfortable. Many business owners benefit most from coaches who are strong in areas where they themselves are weaker, creating a healthy counterbalance in decision-making.

Growth often comes from conversations that are slightly uncomfortable. A good coach knows how to guide those moments productively.

Diagnostic questions:

• Does this coach ask questions that make me pause and rethink, not just nod along?

• Are they willing to disagree respectfully and explain why?

• Do they challenge my thinking with evidence and experience, not opinion alone?

6. A Strong Professional Network

An experienced executive business coach brings more than advice — they bring context.

Coaches with a strong professional network can expose you to peer perspectives, specialized advisors, and connections that accelerate learning and opportunity. This network effect compounds over time, especially when introductions are thoughtful and relevant rather than transactional.

A broad, active network is often a signal that the coach has earned trust across industries and leadership circles. It also suggests they stay engaged in the business community rather than operating in isolation.

Diagnostic questions:

• Can this coach connect me with peers facing similar challenges?

• Do they have relationships with specialists I may need as my business evolves?

• Does their network feel current, active, and relevant?

7. Built-In Accountability

Accountability is ultimately about momentum. When an external, objective partner is checking in on priorities, it becomes far less likely that important initiatives get buried under daily operational noise or deferred indefinitely.

A high-quality executive business coach helps translate strategy into action by building accountability into the coaching relationship. This includes setting clear goals, defining concrete next steps, tracking progress, and revisiting commitments consistently.

The presence of accountability sharpens focus, encourages follow-through, and creates a rhythm of execution that turns good intentions into measurable results.

Diagnostic questions:

• How does this coach track progress between sessions?

• What happens if I don’t follow through on agreed actions?

• Do they help me prioritize, or simply discuss ideas?

8. Genuine Generosity and Intent

Generous coaches share perspective freely and focus on helping you grow more capable and confident as a leader. Their generosity shows up in consistent, often subtle ways: how attentively they listen, how prepared they are for each conversation, and how deeply invested they seem in your progress.

This intent is rarely performative. It reveals itself through thoughtful follow-ups, a willingness to teach rather than impress, and genuine curiosity about your business, your challenges, and your decision-making process.

By contrast, coaches who lack generosity may still sound polished or authoritative, but the relationship often feels transactional. Conversations can drift toward surface-level advice or self-promotion rather than sustained, engaged partnership. When generosity is present, coaching feels collaborative and energizing, and that difference compounds over time.

Diagnostic questions:

• Does this coach seem genuinely interested in my business, or primarily in selling their services?

• Do they give insight freely, or guard it behind paywalls and buzzwords?

• Do I feel encouraged and energized after conversations — or drained?

9. Trust and Personal Fit

You don’t need to be best friends with your coach. But you do need to feel comfortable being honest about all your doubts, mistakes and blind spots that are difficult to admit internally. Without trust, conversations remain guarded and surface-level, limiting the coach’s ability to help you think clearly and make better decisions.

Fit extends beyond credentials or experience. It shows up in communication style, mutual respect, and how the coach engages during conversations. You should feel listened to, not rushed or talked over, and confident that your perspective is being understood. A coach who creates psychological safety makes it easier to explore uncomfortable topics, challenge assumptions, and work through uncertainty.

When trust and fit are present, coaching becomes a space for clarity rather than performance. That environment allows leaders to think more openly, act more decisively, and make progress that is both meaningful and sustainable.

Diagnostic questions:

• Do I feel comfortable being candid with this coach?

• Do they listen as much as they talk?

• Would I trust this person with sensitive business decisions or concerns?

10. A Clear, Repeatable Process

Perhaps the most important factor in choosing an executive business coach is whether they operate with a clear, structured process.

Effective coaching is not improvisational. There should be a defined methodology for diagnosing challenges, setting priorities, building strategy, and measuring progress. A repeatable process reduces guesswork and makes outcomes more predictable.

Coaches should be able to explain their approach clearly before engagement begins. If the process feels vague or constantly shifting, it’s a warning sign.

Diagnostic questions:

• Can this coach clearly explain how their process works from start to finish?

• How do they measure success over time?

• What makes their approach different from informal advice or peer conversations?

Coaching should not be improvisational. It should be structured, deliberate, and measurable.

This is where organizations like The Alternative Board differentiate themselves. TAB has spent decades refining a proprietary coaching process rooted in peer advisory, strategic planning, and accountability.

As TAB member Rick Maher, CEO of Effective Human Resources, Inc., once explained:

“I wanted a process that had to be followed — a regimen. The Alternative Board has a very deliberate process. The process is the only way I can see success.”

Avoid coaches who are “shooting from the hip.” Seek those who can clearly explain how they help you achieve results — before you commit.

Want additional insight? Download Hiring a Business Coach for Your Small Business now 

Making the Right Choice In A Business Coach

Choosing an executive business coach is not a decision to rush.

Many business owners, like Susanne Meyers of Daily Affiliate Tasks, find that it takes time to identify the right fit — especially when weighing cost, compatibility, and credibility. That hesitation is understandable. The stakes are high.

Don’t be afraid to speak with multiple coaches, ask detailed questions, and evaluate approaches carefully.

For business owners seeking a proven path forward, The Alternative Board’s Business Coaching Sessions combine experienced facilitators, peer insight, and a structured process designed to drive measurable improvement. The Alternative Board’s Business Coaching Sessions simplify the process by providing you with a trusted adviser who can help you work through business challenges and opportunities to increase performance. TAB has perfected its proprietary coaching process over the past twenty-five years and continues to build its track record of satisfied business owners.

When done right, executive coaching is a catalyst for significant, positive growth. And choosing the right coach may be one of the most consequential decisions a business owner ever makes.