What is an executive coach?

An executive coach helps you identify and achieve your most important professional and
personal goals faster and easier than you could on your own.

For entrepreneurs, these goals are usually quantifiable.

Great examples:

  • Increase sales by 20% in the next 6 months
  • Create a lead generation system that consistently delivers 10-12 highly qualified leads
    per month
  • Reduce my work-week to three 4-hour days
  • Shed 80% of the “in the weeds” tasks I do so I can focus 80% of my time on the role I
    love most and delivers most to my business.
  • Organize my business such that I can take three 1-month vacations per year.

Why do entrepreneurs hire executive coaches?

These goals are diverse and unique to the client, but they typically break down into two
categories: professional goals (optimizing the role of the client and his team to improve scale,
sales, profits, imposter syndrome, partner/investor relations, valuation, competitive advantage,
market position, etc.) and personal goals (relationships with spouse and family, fulfillment,
anxiety, depression, life-after-business-sale, philanthropy, legacy, etc.)

What makes a good entrepreneur coach?

Experience and a successful track record with your specific situation is essential.

The best coach will have already done what you want to do – for themselves and for their

Entrepreneurs shouldn’t hire a coach who isn’t a successful entrepreneur themself or at a
minimum, who hasn’t created massive transformation for other entrepreneurs.

Assuming the coach you are interviewing has “been there and done that”, the next most
important criteria is chemistry.

There’s either a good “fit” with your coach or there isn’t. That’s why scheduling a real coaching
session with prospective coaches is so important before you make your choice. (see below).

What’s the difference between leadership coaching and executive coaching?

Executive coaching refers to the type of client the coach typically works with. And leadership is
often one of the topics coaches work on.

As an executive coach, I work with founders, CEOs and their teams in high-performance
companies (or companies that aspire to higher performance). Our clients set specific goals in
our deep dive strategic planning session that kicks off coaching.

How can I tell what coach is right for me?

Assuming your coach is a successful entrepreneur her/himself, It all comes down to chemistry.

Again, I strongly recommend asking a prospective coach for a free sample coaching session on a
real topic that is important to you. If the coach listens to you very carefully, if you feel deeply
“gotten” and understood, and the coach offers you new perspectives and opportunities you
hadn’t considered and offers to hold you accountable for taking action, they might be right for
you. I also recommend talking to some of the coach’s past or current clients.

Should I get a coach that specializes in my industry?

Short answer: yes, if a good coach exists in your industry.

This is the trifecta of coach selection:

  1. hiring a fellow entrepreneur who has been successful for his/her own businesses and for their clients’ businesses,
  2. who you feel a strong connection with, who really “gets you”, and
  3. who knows your industry. In that order.

How important are coaching certifications and credentials?

Not important, especially compared with the “trifecta” described above.

Early in my coaching career I worked with Fortune 500 companies that required all the industry
coaching certifications as a way of creating a short list.

I have all of them. I am certified by the International Coaching Federation (ICF) and by the
Coactive Coach Training institute, the “Hogwarts” of executive coaching. I’m even a licensed
mental health therapist (which comes in handy in lots of situations…).

For entrepreneurs in particular, the most important credential is whether your coach has
succeeded as an entrepreneur. No amount of certifications or credentials will compensate for a
coach that has no “at bats” in your field.

How long should executive coaching last?

Most minimum engagements with a coach range from 6 months to a year. I’ve found 6 months
is the right time period to identify needed changes, implement a new action plan, conduct two
90-day sprints, and achieve key goals.

How does entrepreneur coaching work?

Here’s the basic coaching structure:

Step 1: Discovery

Your coach will take you through a discovery process, typically including a series of
assessments and interviews, to help you both get crystal clear about your goals and how
you want to measure success and ROI.

Step 2: Plan

Based on the discovery process, your coach will work with you to create a detailed
strategic plan with specific milestones over the course of the coaching engagement.

At Doubledare, we work in 6-month sessions with two 90-day sprints. Although we
sometimes work with our clients over several years, we have found that this two-sprint
cycle results in the best results.

Step 3: Focus

Most entrepreneurs love new ideas and are easily distracted. One of the most important
roles an executive coach can play is to keep the client laser-focused on taking daily
action that will deliver her/his goals as quickly as possible.

Doubledare provides its clients with a confidential online dashboard that allows them to
record daily/weekly action, access all coaching documents including recorded sessions,
strategic plans, and log progress and new ideas into a shared virtual white-board.

Step 4: Accountability

One of the most valuable parts of hiring an executive coach, especially for
entrepreneurs who sometimes live in solitary echo chambers, is receiving candid
feedback and consistent accountability.

Accountability, and the entrepreneur’s complete willingness to accept it, may be the
single most effective aspect of hiring a coach. It ensures that the value of coaching –
achieving important goals faster and easier than you would on your own – is received.

How often do I work with a coach?

At Doubledare, we are available to all individual coaching clients 24/7 to ensure that challenges
and opportunities that may arise are effectively managed in real time. (My clients have my
personal cell phone and use it as necessary.)

Apart from immediate issues, I meet with my clients at least once a week for 30-60 minutes via
Zoom to review work completed, resolve any outstanding issues, and assign action steps. All
notes, action steps, and recorded Zoom sessions are available in each client’s private online
locker for review at any time. Over time, the frequency of regular coaching sessions may
increase or decrease depending on each client’s specific needs.

How much does coaching cost?

The best executive coaches — those with the deepest specific experience and client success —
charge between $2,000 and $20,000 a month.

My experience with my own coaches is that you get what you pay for.

Coaches that consistently return 10X on their clients’ fees should and do charge more for more
measurable impact.

Is entrepreneur coaching worth it?

It is if you want to move faster and get better results than you are right now. I work with super-
talented, driven, focused
 individuals. But as they say, it can be “lonely at the top”. As gifted as
they are and as much as they have already achieved, new clients typically report feeling “stuck”
or “burned out”.

Clients should expect to 10X their investment in measurable results. The right coach can often
generate results like this in the first phone call if the client will commit to taking action. BTW: I
offer a “Love-It-Or-Leave-It” 30-day guarantee. If you’re not happy for any reason (or no reason)
within the first 30 days, you can opt out of the 6-month commitment. (I’ve never had a client
take me up on it, but it’s there if you need it.)

How can I calculate the ROI of hiring a coach?

Again, your coach should be able to 10X your investment in a quantifiable, monetizable result.

For example, if you pay your coach $20,000 over six months, your ROI should be $200,000 in
measurable value ($200,000 sales increase or run-rate for same, for example). Or, at a
minimum, your coach should deliver a result that is worth $200,000 to you over time.

What would you pay, for instance, to move from a 60-hour work week to < 12-hour work week,
if your business performed better than ever? What would that be worth to you over a five year

Bottom line: coaches should be paid for transformation – a transformation that you whole-
heartedly participate in and commit to – but a true transformation in your life.

A good question to ask yourself before investing in a coach: “If I achieve my goals, will the
investment in a coach feel like a bargain?

Who shouldn’t get a coach?

I have hired and worked with several outstanding coaches over my 30 years in business. (I work
with one now.) In all cases, I was humbled by a problem I couldn’t budge on my own and was
willing to accept direction from someone who had already solved this problem for themselves. I
made the time and put everything I had into the work. And I did what my coach recommended.

While I am coached, it is the most important work I do.

Some reasons not to get a coach:

1) Coaching requires at least enough humility to accept the old adage that ‘If I keep doing
what I’m doing, I’ll keep getting what I’m getting”. Most entrepreneurs are rightfully
sure of themselves. But this can be a major obstacle to important change and will
torpedo a coaching relationship before it gets started. (PS. This is why coaching ordered
by entrepreneurs for their team mates almost always fails, unless the teammate is 100%
committed for their own reasons.)

2) If you don’t have the time or aren’t willing to make the time, you won’t get results. No
matter who your coach is.

3) Entrepreneurs are not famous for their patience. (My wife says I am the most impatient
person she knows.) With the best coaches, you will see some immediate results, if only
in reframing the problem and creating a new approach to solving it. But real
transformation – the kind you would invest tens of thousands of dollars in — takes time.
If you know you can’t be patient enough to let the new approach from your coach take
effect over at least a six-month engagement, do yourself a favor and don’t hire a coach.

Interested in entrepreneur coaching?

For more information about coaching, or to schedule a free sample coaching session, click below.