Executive Coaching

A Business Owner’s Guide to Executive Coaching & Leadership Development

Many business owners get stuck when they reach a plateau of business success.  They struggle to grow their business past this point. The essential challenge boils down to – they’ve done all they know how to do, and what they know has taken them as far as it is going to take them.  

Don’t settle for less- you can enjoy greater growth and profitability for your company with the help of professional coaching and structured expertise to keep your company and team on a path of continued growth. Let executive coaching spark your next round of business growth, and the next, and the next.  

Learn how you can leverage a CEO coach to help you avoid the process of trial and error most business owners endure when learning how to scale their businesses, plus tips on how to grow your key managers and leaders to successfully drive business growth under your guidance. In effect, you’ll learn how you can outsource a part of your leadership development program to help move your business forward.

What is an Executive Coach?

First, let’s start with understanding what an executive coach does.

Executive coaching is a subset of business coaching where you work with an outside expert (your “executive coach”) one-to-one and in small group settings with your most important and promising internal leaders in your company.  

Specifically, a CEO coach is a business coach that works directly with the owner or CEO of a company.

Generally, executive coaches offer extensive career experience running departments or divisions of other companies and will utilize this experience to help your key managers and leaders succeed in their role with your company. The right executive coach will both develop your leaders and focus them on the highest leverage path to drive positive results for your company.

A strong CEO coach, however, will help you grow as a leader and generate stronger results from the company as a whole.

What Do Executive Coaches Do?

Think about how busy your schedule gets on any given day. From an overfull to-do list, a packed schedule of meetings, you barely get a moment to close your office door and just think. And yet you’re also expected to give your top management the guidance they need to continue growing and developing as effective managers and leaders.

This is where an executive coach comes in – to relieve you of the leadership burden of developing and managing your key people.  In essence, your executive coach becomes your partner in developing your best senior executives.

Here are four things that the right coach will deliver to your key staff and your business.

  1. Focus and Prioritization: An experienced coach will help your key staff focus on their highest value activities, projects, and strategies so that they generate enhanced results.  Your staff are most likely struggling to manage a crammed list of projects, fires, and demands just like you are.  Their executive coach will help them prioritize action items based on what will contribute the most value to your company.
  2. Active Accountability: Your executive coach will give your key team the structured support and accountability to make sure they are staying on track. If they lose focus or get distracted, your executive coach will be right there to pull them right back to their highest value activities.
  3. Experienced Sounding Board: When your key team hits a tough challenge that they’re unsure of how to handle, the right executive coach has dealt with exactly that challenge before and can provide them with the right tools to find a solution. Not only does this help them put out fires, but this leadership coaching will help their personal development as they replicate the coaching model with their direct reports.
  4. Leadership Development: The richest results for your staff and your company come over time as your executive coach gets to know the key players in your company and helps them develop the leadership skills to support organizational success.

What Do CEO Coaches Do?

In short, CEO coaches provide all the value an executive coach does, in addition to giving you a strategic organizational framework to manage and lead your business.
Your CEO coach has successfully scaled a company, and in most cases, multiple companies. They have been in your seat and have faced what you’re facing, making them uniquely positioned to coach you through this process.

What to Look For in an Executive or CEO Coach

The executive coach or CEO coach you’re looking for needs to have the knowledge, ability, and industry experience to share their expertise with you and your staff.
Here are some of the most important criteria to look for when searching for an executive coach:

1. Proven Track Record: Your coach needs to have scaled a company, run a division or key department, so that they have the direct, relevant experience to shorten your learning curve and lead you directly to the winning answers.

2. Strong Communicator: Your coach needs to be able to effectively share their insights to you and your staff in a potent and compelling way.

3. Proven Program: Having a great coach is one thing, but that coach having a proven framework and process to help you and your company reach your desired goals is another. For this reason, you should look for not just the right coach, but rather the right business coaching company. Individual coaches may have worked with dozens of companies, but the right business coaching company has successfully helped thousands of businesses thrive and scale.

Business coaching companies with 10+ years of experience will have developed a clear process to proactively guide, develop, and grow your key people and your company. Over the past 20 years, at Maui Mastermind we’ve refined a proven system to help profitable businesses successfully scale and become owner independent. We’ve got the systems, team, and culture to offer proven results every time.

What does the Typical Executive Coaching Process Look Like?

Initial Audit Process

The first step in the coaching process for your business coach is to do a deep dive into your company and understand your business.  What do you do? Who do you ideally serve?  What are your business goals?  What are your major challenges that stand in the way of those goals?  What are the real root causes of those challenges?  What staff, systems, other resources do you have to work with?

Based on what we collectively discover, your business coach will help create a custom plan of action to both help you progress the business and strengthen your leaders so that they are more prepared to handle the next round of challenges.

Initial Implementation Phase 

Now that you have your written plan of action with your executive coach or CEO coach, it’s time to get to work implementing your plan.

In our experience, bi-weekly coaching sessions (either by phone or video conference) work best: they’re frequent enough to keep you on track with the structured accountability and support to create results, but not so frequent that all you’re doing is “talking” and not enough “doing”.

Quarterly Regrouping

Each quarter, we suggest that you and your coach step back to evaluate your progress and create your next quarter’s action plan.

With our clients, we gather for a quarterly event where we actively guide our coaching clients and their teams to create the focused plan they need to direct their best time, attention, and resources for the next 90 days.  We’ve found that this structured process of rolling quarterly action plans gives you the perfect balance between looking fresh at your business, while also giving you time to dive deep into the execution and make meaningful progress on your clearly prioritized action sequences.

Continuous Implementation Phases

Every 90 days you’ll go back to plan the next quarter, then balance that planning time with another 90-day “execution sprint”.

Remember, you’ll have regular bi-weekly sessions with your coach so that you can troubleshoot challenges that arise, and get back on track if you get pulled away.

What is the ROI of Executive Coaching?

What returns should you expect from coaching? Simple: for every $1 invested (see below for typical executive coaching costs) you should expect a $2 return within 12 months, and a $10 or greater return over 36-60 months.

The right executive coaching program or CEO coach should be willing to guarantee a minimum level of results. At Maui Mastermind, we’ve offered our business coaching clients a minimum 200% return on coaching within the first 12 months or we refund a client’s full coaching fee for the year.

Part of the initial work with your executive coach should also include establishing objective criteria of success, and this should include a bottom line increase in profitability well above the “cost” of coaching.

Here are some of the other key benefits you should expect from the right business coaching relationship beyond immediate increases in profitability:

  • Increased alignment between your leadership team and front-line workers. This will lead to better results and increased staff retention.
  • Faster development of your key managers and leaders. Your executive coach will model the best ways to focus your direct reports, hold them accountable, and spur them to grow.
  • Increased “Owner Independence”. An experienced coach will help you not only solve problems and seize opportunities, but do so in a systematic, sustainable way that increases strategic depth so you are less reliant on yourself as the owner, or any single team member.

Confidentiality in Executive Coaching

Your CEO coach (or your key staff’s executive coach) gives you a confidential space and experienced sounding board to work through your toughest challenges. You will be able to speak candidly knowing that your CEO coach may just be the single person in your business life who will tell it to you straight.

Hiring an Executive Coach

What Should You Look for in an Executive Coach or CEO Coach?

Here are three questions you should ask to find the right executive coach or CEO coach for your business.

  1. Has my coach ever built a thriving, owner-independent company before? 

In our world, there is no shortage of people who label themselves as “business coaches”. It’s important to distinguish those that have successfully scaled one or many businesses, from those that have simply built a self-employed job for themselves.

At Maui Mastermind, all our clients get to the benefit of working directly with successful CEOs and business owners who’ve personally built and sold multi-million dollar businesses.

You deserve a business coach who has done what you want to do, and has direct experience helping other business owners and their key staff do the same.

  1. Are you getting just an executive or CEO coach, or are you also getting a proven structure and methodology to build a thriving business? 

It’s not enough to just work with a great business mentor: you also need a concrete road map that lays out the priorities and sequencing you need so that you know what systems, team, and culture you need to develop, and when you need to develop them, along with a step-by-step plan so that you and your team can actually build out your company’s systems, teams, and controls.

  1. Does the coaching program just focus on individual, one-off business challenges or does it also make sure you’re making consistent progress on a defined road map to reach your desired exit strategy for the business? 

Your CEO coach needs to help you balance your business’s immediate day-to-day operational needs with its longer term development strategy. 

After 20 years helping business owners successfully scale and eventually exit from their businesses, we’ve come to realize the importance of utilizing forward-thinking strategies from the start. The “end stage” thinking needs to be built into your company along the way, not just bolted on top at the very end.  

How Much Does an Executive Coach Cost?

Executing coaching services can range from $1,000 to $3,000 per month, depending on the program, frequency of sessions, and number of in-personal leadership trainings or workshops along the way. 

Most reputable CEO coaching programs will range from $2,000 to $5,000 per month, depending on the caliber of coach and other added benefits within the program.

Remember, because of the ROI you should expect from the right business coach and business coaching program, the program should effectively be free to you.  If it isn’t providing positive ROI over its cost, you’ve chosen the wrong program.

A Proven Path for Scalable Business Success

At Maui Mastermind, over the past 20 years our business advisor and coaching staff have scaled over $62 billion of businesses.  What’s more, we’ve seen the impact of our business coaching programs on the lives of thousands of other business owners and staff members just like you.

Ready to take your business to the next level? Schedule a complimentary 60 minute business coaching session with one of our expert business coaches today.

Learn More About Our Coaching Program!



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Executive Coaching
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Executive Coaching
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Maui Mastermind Business Coaching
Business David is a Wall Street Journal and Business Week bestselling author of 11 business and financial books. A syndicated columnist for Inc.com and HuffingtonPost.com, David’s articles have appeared in over 6,500 publications. As the founder and CEO of Maui Mastermind®, David has worked with 100,000+ business coaching clients and community members to buy, build, and sell over $5 billion of businesses.