Good Game, Coach: Top Tips for Executive Coaching

How to Find a Good Executive Coach (Without Wasting Time or Money)

A coaching relationship in practice.

Hiring the right executive coach for your leadership team can be a great way to maximize their impact and help the organization 10x its results.

At some point, most successful leaders hit a ceiling.

• Maybe they were promoted faster than expected.

• Maybe their company doubled in size.

• Maybe private equity ownership changed expectations overnight.

• Or maybe the skills that made them successful earlier in their career are no longer enough for the next stage, like a college quarterback suddenly facing NFL-caliber competition.

That’s usually when the conversation about executive coaching begins. The problem?

The executive coaching industry is crowded, inconsistent, and filled with vague promises. Some coaches are transformational. Others are glorified motivational speakers with a LinkedIn account and a Canva subscription.

While there are coaching certifications (more on that below), there is no requirement that you obtain one before you call yourself a coach.  I’ve seen “coaches” with little evidence that they know what they are talking about.  I’ve even seen one whose sole success in business led to fraud charges and bankruptcy. But he had a podcast that talked a good game.

So how do you find a good executive coach?

Here are the key factors leaders and organizations should evaluate before making the investment.

1. Begin with the end in mind: Start with the problem you’re trying to solve.

The biggest mistake companies make is hiring a coach before defining the objective.

• Executive coaching is not therapy.

• It’s not generic encouragement.

• And it’s not a “perk” for senior leaders.

The best coaching engagements are tied to specific business outcomes.

Examples might include:

• Transitioning from functional leader to enterprise leader

• Leading through rapid growth or organizational change

• Improving executive presence and communication

• Managing conflict at the senior leadership level

• Becoming more strategic and less tactical

• Building leadership succession capability

• Navigating board or investor relationships

• Improving delegation and accountability

Before hiring a coach, define:

• What success looks like

• What behaviors need to change

• What measurable outcomes matter

A vague goal usually produces vague results, or a friend-for-hire relationship.

2. Look for Real Business Experience

Many executive coaches have impressive certifications. Far fewer have led teams, managed P&Ls, survived layoffs and black swan events, scaled organizations, handled difficult boards, or carried operational accountability.

That matters.

The best coaches often combine:

• Coaching expertise

• Leadership psychology

• Actual executive operating experience

A former CHRO, CEO, division president, military officer, or operational leader may understand the real-world pressures executives face far better than someone who has only worked as a coach.

This becomes especially important in manufacturing, distribution, logistics, private equity portfolio companies, and founder-led businesses, where leadership challenges tend to be practical and high-stakes.

Keep in mind that, just like sports, great athletes don’t always make great coaches. If they have achieved a certification, make sure it's from the International Coaching Federation (ICF), the gold standard for certifications. Keep in mind that a great coach might not have a certification, and a certified one might not be a great fit for your executive.

Ask:

• Do they have direct experience operating in business environments similar to yours?

• Have they led organizations through growth, crisis, or transformation?  (There are plenty of coaches out there who rode the rocket on the way up, bailed out, and now coach.)

• Will they admit to and share that they have made mistakes?

• Do they understand your industry dynamics?

Context matters.

Two professionals are having a discussion.

3. Chemistry Matters More Than Credentials

Executive coaching is built on trust.

If the leader being coached isn’t comfortable being candid, the engagement will fail, no matter how impressive the coach’s resume appears.

The relationship needs enough trust for difficult conversations:

• Blind spots

• Leadership weaknesses

• Team conflict

• Communication failures

• Ego issues

• Burnout

• Strategic uncertainty

That level of honesty only happens when there’s strong interpersonal chemistry.  That might not happen until after a few coaching sessions. 

A good coach should:

• Challenge constructively

• Listen actively

• Ask sharp questions

• Provide accountability

• Create psychological safety without becoming passive

If the coach feels overly scripted, overly theoretical, or constantly “selling,” keep looking.

4. Beware of One-Size-Fits-All Frameworks

Leadership is contextual.

What works for a venture-backed tech startup may fail completely inside a 75-year-old manufacturing company with tenured leadership.

Great executive coaches adapt their approach to:

• Company culture

• Leadership maturity

• Ownership structure

• Industry realities

• Team dynamics

• Individual personality

Be cautious of coaches who:

• Overuse trendy buzzwords

• Force every client into the same methodology or framework

• Speak in abstractions instead of specifics

• Promise a dramatic transformation too quickly

Real leadership growth is usually iterative, practical, and measurable over time.

5. Ask How They Measure Progress

A good coach should be able to explain how progress will be evaluated.

That doesn’t always mean spreadsheets and KPIs, but there should be observable changes that impact real-world results.

Examples:

• Improved communication from peers and direct reports

• Better delegation

• More strategic thinking

• Reduced team turnover

• Improved executive alignment

• Increased confidence in leadership situations

• Greater organizational influence

Strong coaches often incorporate:

• 360 feedback

• Stakeholder interviews

• Behavioral assessments

• Periodic progress reviews

• Clear milestone discussions

If the coaching process feels intentionally vague, that’s a red flag.

No executive should have to go it alone.

6. Understand the Difference Between Coaching, Consulting, and Mentoring

These terms are often conflated, but they are not the same thing.

Executive Coaching

Focused on helping leaders improve performance, self-awareness, communication, and decision-making through guided conversations and accountability.

Consulting

Focused on solving business problems directly.

Mentoring

Usually involves sharing personal experience and advice from someone who has already walked a similar path.

Some of the best leadership advisors blend all three appropriately — but it’s important to understand what you are hiring a coach for.  Startups and growth companies often need a range of support.  A great executive coach cannot fix bad processes, systems, or an outdated tech stack. 

They can help a leader prioritize what to fix and build a plan of action and milestones. 

7. The Best Coaches Tell Leaders What Others Won’t

Senior leaders often operate inside feedback bubbles.

The higher someone rises, the less honest feedback they receive, and the fewer people they can confide in, drop their armor, and be honest with.

A strong executive coach helps break that dynamic.

Sometimes the most valuable thing a coach provides is not motivation — it’s clarity.

The willingness to say:

• “Your team doesn’t trust your communication.”

• “You’re still operating like a functional leader instead of an enterprise leader.”

• “You’re creating bottlenecks.”

• “You avoid conflict.”

• “You’re trying to solve problems your team should own.”

That level of candor is where growth happens. 

8. The Executive Must Want to Be Coached

I’m sure you’d be shocked to find out that some executives lack the self-awareness to realize they could benefit from an executive coach. 

Others see an executive coach as a mole who will report everything they say back to their boss, board, or Operating Partner.

Hiring an executive coach as some kind of executive perk, or adding another sycophant to the circle of yes-men around a leader who has built a cult of personality, is a waste of money, or, as a glorified PIP, can be a waste of money.

If you are a board member or an operating partner insisting on coaching for your company leaders, make sure you frame it as a non-negotiable condition of employment, not a judgment of their ability or a vote of no confidence. After all, the best athletes in the world don’t coach themselves.

You should also have a clear understanding of the level of communication between the coach, the executive, and the board or operating partner. The coach should be able to give progress reports or action items, but not be a snitch - otherwise there won't be the level of candor that is required to be effective.

9. Coaching Cannot Fix a Bad Hire

Sometimes, leaders just are not a good fit.  If they are not performing to the expectations that were established before they were hired, determine:

• Were the expectations realistic, given the hand they were dealt with the organization and current market conditions?

• Are they making progress or making things worse?

•  Is their role a promotion for them, or were they hired for their been-there/done-that resume?

• Can they get better within a reasonable timetable?

• Is their leadership style toxic or in conflict with the organization's culture?

You might not know the right answer on the surface.  But don’t just hope for the best or that they will figure it out.  Nothing can hurt an organization worse than tolerating a bad leader.  The best talent will leave, and the company will lag behind the market.

A good executive coach might be able to tell you if the executive is "fixable" after a session or two. 

Be honest about the situation.  I’ve seen many executives let go because they were put into an unwinnable situation, whether it’s expecting miracles with no resources or trying to turn around an organization that has been sliding for decades.  Like coaching the Jets.

A constructive, collaborative relationship is key to effective executive coaching.

10. How to Vet an Executive Coach Before You Hire Them

Hiring an executive coach should be treated with the same rigor as hiring a senior executive.

Too often, organizations rely on referrals, polished LinkedIn profiles, or charismatic sales conversations without doing meaningful due diligence. A strong vetting process helps separate credible leadership advisors from people who are simply good at self-promotion.

Here are several smart ways to evaluate an executive coach before committing to an engagement:

Ask for Specific Client Examples

Good coaches should be able to describe:

• The types of leaders they typically work with

• Common leadership challenges they help solve

• The business environments where they are most effective

• Examples of measurable improvement

They do not need to violate confidentiality, but they should be able to speak concretely about outcomes. If every answer sounds abstract or overly generalized, that’s a concern.

Request References

Talk to former clients whenever possible.

Ask:

• What changed as a result of the coaching?

• Was the coach willing to challenge difficult behaviors?

• Did the engagement produce measurable improvements?

• Would they hire the coach again?

• What type of leader benefits most from this coach?

Pay close attention to whether references describe actual transformation versus simply enjoying the conversations.

Evaluate Their Ability to Ask Questions

The best executive coaches are rarely the people doing the most talking.

Strong coaches ask thoughtful, incisive questions that:

• Expose assumptions

• Clarify thinking

• Reveal blind spots

• Force prioritization

• Drive accountability

If the initial conversation feels dominated by canned frameworks, personal branding stories, or motivational speeches, that may indicate a more superficial approach.

Understand Their Process

A professional executive coach should be able to clearly explain:

• How the engagement is structured

• Frequency of meetings

• Expected duration

• Whether assessments or 360-degree feedback are used

• How progress is measured

• How confidentiality is handled

• What happens if the engagement is not working

Structure creates accountability. An unclear process often leads to unclear outcomes.

Watch for Red Flags

Be cautious if a coach:

• Guarantees dramatic results

• Claims expertise in every industry and leadership challenge

• Avoids discussing measurable outcomes

• Cannot articulate a coaching philosophy

• Spends more time selling than listening

• Lacks meaningful executive or organizational experience

• Creates dependency instead of building leadership capability

The goal of coaching is not long-term dependence. It is stronger, more self-aware, and more effective leadership.

Trust Your Instincts

At the executive level, credibility matters.

Leaders should leave the first conversation thinking:

• “This person understands business.”

• “They asked sharp questions.”

• “They challenged my thinking.”

• “They seem capable of telling me what I need to hear, not just what I want to hear.”

That combination of trust, credibility, and constructive challenge is usually a strong signal that the relationship has potential.

Final Thoughts

Executive coaching can be an extraordinary investment when done well.

The right coach can help a leader:

• Scale with the organization

• Improve decision-making

• Build stronger teams

• Increase executive effectiveness

• Navigate major transitions with greater confidence

But coaching only works when:

The leader is coachable

The objectives are clear

The chemistry is right

The coach has both credibility and practical insight

The goal is not to find someone who simply makes leaders feel better. The goal is to find someone who helps them become better leaders.

About The Rivet Group

At The Rivet Group, we work closely with middle-market companies on leadership hiring, succession planning, and organizational growth. Through that process, we often help clients identify executive coaches, leadership advisors, and strategic HR partners who can help leaders scale alongside their organizations.

The right leadership hires matter.

So does helping that leader succeed once they arrive.