An Entrepreneur's Guide to Finding a Coach

An Entrepreneur's Guide
to Finding a Coach
Steve Schlafman
HighOutput.co
March 2020

One who builds a complex
human system while riding
an emotional roller coaster.
en·tre·pre·neur | ˌän-trə-p(r)ə-ˈnər
Entrepreneur

"Every famous athlete, every famous
performer has somebody who’s a coach.
A coach really, really helps."
Eric Schmidt, Former CEO of Google

DISCLAIMERS
• This guide is far from de nitive
• Its contents are curated from a variety of sources
• This was designed with startup leaders in mind
• There are many perspectives, this is just one
• I couldn't include every coach and organization
• I hope to evolve this guide over time
BEFORE WE GET STARTED, PLEASE KEEP IN MIND

I designed this guide to
help you navigate the
opaque world of
coaching and nd a
great coach.
PURPOSE

Contents
1. About
2. Coaching: An Overview
3. The Coaches Toolbox
4. Process & Fit
5. Coaches & Organizations
6. Pricing & ROI
7. Other Resources
8. Contact Info
07
11
23
32
55
76
84
92

Steve Schlafman
FOUNDER COACH AT HIGH OUTPUT & ANGEL INVESTOR
"My mission is to help founders bring their wildest
visions to life and evolve into extraordinary leaders."
OPERATOR INVESTOR COACH

A BOUTIQUE LEADERSHIP DEVELOPMENT COMPANY BASED IN NYC
1:1 Coaching Workshops 360 Reviews
• Vision & Roadmap
• Bi-Weekly Sessions
• Ad Hoc Calls & Texts
• Exercises & Content
• Mission & Values
• Team O sites
• Post Mortems
• Leadership Salons
• 360 Assessment
• Results & Report
• Development Plan
• Accountability
High Output

BALANCING THE INNER AND OUTER GAME OF ENTREPRENEURSHIP
Emotional Regulation
Energy Management
Self-Awareness
Parts & Shadow
Needs & Values
Vision
Interpersonal Dynamics
Managing & Motivating
Habits & Productivity
Systems & Process
Planning & OKRs
Decision Making
Inner Game Outer Game
The Approach

COACHING
DEFINED
A thought-provoking and
creative process that
inspires leaders to
maximize their personal
and professional potential.
Source: Adapted from the International Coaching Federation

• Help leader become self aware, widen perspective and
nd motivation to:
• Make their own choices
• Change behavior
• Take actions to achieve goals and improve results
• Focus on the now and leader's preparation for a new
future; it does not dwell in the past
• Help the leader learn rather than teach them
WHAT IS
COACHING?
Source: International Coaching Federation
THE ESSENTIALS

• Coach facilitates development by helping leader:
• De ne and focus on desired goals
• Investigate current situation - consider
opportunities and implications
• Brainstorm alternatives and courses of action
• Decide and develop an action plan
• Create accountability and support
HOW IT WORKS
Source: Beacon Executive Search & Coaching (2015)
THE COACHING RELATIONSHIP

• Resourceful: Believe leaders are inherently wise and
resourceful
• Wholeness: View leaders as whole and complete
• Diversity: Honor the full diversity of experience
• Freedom: Believe leaders have freedom to choose
their response to any given situation
• Integrity: Create a psychologically safe space
• Possibility: Believe more is possible than on surface
CREATING A CONTAINER FOR POWERFUL COACHING
PRINCIPLES OF
COACHING
Source: Coaching For Transformation (2011)

• Business Focus: Understand key business initiatives
and situations directly relevant to the leader
• Partnership: Support leader and key stakeholders
• Systems Perspective: Aware of larger organizational
structures and objectives
• Results Orientation: Focus on desired outcomes
• Skills Acquisition: Support leader in growing
professionally
CREATING A SPACE FOR BUSINESS LEADERS TO GROW
Source: Adapted from the Executive Coaching Handbook, Sixth Edition (2015)
PRINCIPLES OF
EXEC COACHING

• Creating a safe, supportive environment
• Asking empowering questions vs giving advice
• Respecting client’s perceptions and learning styles
• Facilitating goal setting
• O ering support for new behaviors and learning
• Challenging limiting beliefs
• Creating accountability structures
• Sending notes and action items post session
THE COACH IS RESPONSIBLE FOR
ROLE OF THE
COACH
Source: Coaching for Transformation (2011)

• Preparing well for each session
• Taking responsibility for the outcomes
• Expressing what’s working and not working
• Examine own behavior, perceptions and decisions
• Making requests to redesign the relationship
• Showing up as whole self
• Stepping fully into the coaching process
• Committing time to complete action items
THE CLIENT IS RESPONSIBLE FOR
ROLE OF THE
CLIENT

COACHING VS
THERAPY
Source: Daniel Weil, DNW Associates (2018)
CoachingTherapy
Past
An approach that examines your past,
with a focus toward healing, to make you
whole and bring you to the present.
Healing
Trauma
Addictions
Mental Illness
Focus on Healing
Present
This approach works right now and moving forward. There is
nothing to x. You already carry inside you, everything you
need to accomplish your goals.
Potential
Possibilities
Deeper Learning
Transformation
Clients Co-Create Their Own Learnings, Solutions & Actions
Future
Decision Making
Accountability
Action
Leadership

TELLING ASKING
FUTURE
PAST
Therapy
Consulting
Counseling
Coaching
Mentoring

Source: Executive Coaching Survey, Stanford University and The Miles Group (2013)
WHY CEOS HIRE
A COACH

$15B
BUSINESS COACHING MARKET SIZE
IN THE UNITED STATES
Demand for coaching is at an all time
high. A variety of tailwinds will propel
its growth in the next decade.
ANNUAL GROWTH RATE FROM
2014-2019
5.6%
AVERAGE HOURLY RATE
UP 11% SINCE 2017
$398
Source: Ibis World, Business Coaching Industry in the US (2019)

Every coach is unique
with diverse skills,
training, lived
experiences and
cultural backgrounds.
KEEP IN MIND

4 DIMENSIONS
OF EXPERIENCE
A COACH IS THE SUM TOTAL OF THEIR LIVED EXPERIENCE
Professional Personal Cultural Educational

CORE SKILLS
SKILLED COACHES HAVE A VARIETY OF TOOLS (1/2)
• Sharing qualities that we see, hear and sense
• Asking open-ended questions to create insight
• Brainstorming and expanding new possibilities
• Encouraging resourcefulness and action
• Trusting and expressing gut reactions
• Clarifying by articulating needs and values
• Creating structures to verify the plan is on track

CORE SKILLS
SKILLED COACHES HAVE A VARIETY OF TOOLS (2/2)
• Supporting leaders to live in line with values
• Helping leaders move towards vision and goals
• Describing what is happening in the moment
• Mirroring words, energy and feelings
• Sharing new perspectives to open up possibilities
• Requesting for a speci c action to be taken
• Noticing our own internal experience or agenda

CERTIFICATION
THE INTERNATIONAL COACHING FEDERATION CERTIFIES COACHES GLOBALLY
The main accrediting and credentialing body for the coaching
profession. It campaigns for professional standards and
provides independent certi cation for professional coaches
and coach training programs.
To become certi ed, a coach must complete an ICF accredited
program and log at least a hundred hours of coaching.
There are three levels of certi cation:
Associate, Professional and Master.
Nearly 30,000 coaches hold an ICF credential.

Certi cation is not
required to practice.
There are e ective and
seasoned coaches
without one. Experience
is equally important.
KEEP IN MIND

SKILLS AND
CERTIFICATIONS
ON TOP OF ICF CERTIFICATION, THESE ARE SOME COMMON AREAS OF EXPERTISE
Ennegram
Assessment
Mental Health
First Aid
Non-Violent
Communication
Leadership
Circle Profile
Neurolinguistic
Programming
Internal Family
Systems
Grief &
Loss
Conflict
Resolution
Group
Coaching
Organizational
Development

360
Reviews
Personality
Assessments
Retreats &
Bootcamps
Forums &
Circles
Team
Offsites
Co-Founder
Coaching
Workshops &
Trainings
ADDITIONAL
SERVICES
IN ADDITION TO 1:1 COACHING, COACHES OFTEN PROVIDE A RANGE OF SERVICES
Org Coaching &
Development

Finding a coach requires
patience and a process.
Give yourself 4-8 weeks.
Your goal: to determine
and achieve mutual t.
KEEP IN MIND

STEP 1:
ASSESS NEED
SIGNS YOU ARE READY FOR A COACH
• You want to level up as a leader
• You want to move faster and remove barriers
• You desire accountability
• You want to make tough decisions quicker
• Your team is scaling rapidly and you want help
• You value a neural sounding board
• You are feeling overwhelmed and burnt out
• You have conflicts you would like resolved

STEP 1:
ASSESS NEED
SOME QUESTIONS TO REFLECT AND JOURNAL ON
• What is my current situation?
• What are my challenges and roadblocks?
• What have I tried? What works? What doesn't?
• Who do I want to become as a leader?
• What kind of company do I aspire to build?
• What drives me?
• What activities energize and deplete me?
• What are your desired outcomes with coaching?

Answering those
questions should help
you decide whether to
move forward and meet
with some coaches. Only
you will know.
KEEP IN MIND
tlkj;

SIGNS YOU MIGHT NOT BE READY FOR A COACH
• You blame external factors for your problems
• You don't prioritize the time
• You want to focus too much on tips and tactics
• You delay getting started with a coach
• You want to be given answers
• You don't have specific desired outcomes
STEP 1:
ASSESS NEED

STEP 2:
DISCOVERY
HOW TO FIND POTENTIAL COACHES
• Start with people you trust and respect:
• Founders
• Investors
• Operators
• Advisors / Mentors
• HR Professionals
• Contact coaching organizations (slide 62)
• Search CoachFederation.org

You should meet with
three to ve coaches to
see di erent styles,
philosophies and
approaches. Treat each
like an interview.
KEEP IN MIND

Coaches often specialize.
Some focus on CEOs,
executive teams and/or
co-founders. And some
focus on company stage.
Be sure to ask!
KEEP IN MIND

STEP 3:
INFO SESSION
THE INFO SESSION SERVES AS THE FIRST INTERVIEW
• Introduce yourself and company
• Share your goals and aspirations
• Learn about the coach
• Path to coaching
• Experience
• Philosophy and approach
• Decide if there is a potential t
• Determine next steps (sample coaching session)

STEP 3:
INFO SESSION
SOME QUESTIONS TO ASK THROUGHOUT PROCESS
• What was your path to becoming a coach?
• How and why did you become a coach?
• What experience and certi cations do you have?
• What is your approach and philosophy?
• Who is your ideal client?
• How are your coaching engagements structured?
• What does a typical session look like?
• How do you de ne and measure success?
• How do you invest in your own personal growth?

If you enjoyed the initial
info session, scheduling
a sample session is a
good investment in time
so you can determine if
there's a potential t.
KEEP IN MIND

STEP 4:
SYNTHESIZE
QUESTIONS TO CONSIDER AFTER INITIAL SESSIONS
Source: Ed Batista, How to Find and Choose a Coach (2013)
• Do I feel safe and a sense of trust with this person?
• Have they demonstrated a willingness to be real?
• Do they focus on the practical or the existential?
• Are they warm, supportive, critical and/or direct?
• Are they focused on the big picture and vision, or
more detail orientated and pragmatic?
• Can this person see the world from my perspective,
or at least empathize with it?

STEP 4:
SYNTHESIZE
QUESTIONS TO CONSIDER AFTER INITIAL SESSIONS
Source: Ed Batista, How to Find and Choose a Coach (2013)
• Are they "in my corner" AND willing to challenge me?
• Can they be compassionate AND hold me accountable?
• Why are they a coach? Is their answer compelling?
• Do they have the right level of experience and
knowledge to help me?
• Can they say why they're not a good t for every client?
• Is this person working on their OWN development?
• Can they talk about their growth as a coach?

Finding a coach is a
highly personal
decision. It's a big
investment in time,
energy and money. Fit is
everything.
KEEP IN MIND

STEP 5
DECISION / FIT
HERE ARE SOME VARIABLES TO ASSESS FIT
• Context: Do they understand my role and industry?
• Experience: Do they have relevant experience?
• Philosophy: Does their philosophy resonate?
• Specialty: Do they specialize in my area of need?
• Connection: Do I feel energetically connected?
• Proximity: Do I prefer IRL or virtual coaching?
• Safety: Is this someone I trust?
• Cost: Does the price t within my budget?
• Gender: Do I prefer to work with a man or woman?

I generally recommend
selecting three to four
' t variables' that you
want to optimize for.
Ask yourself, 'what do I
value most in a coach?
KEEP IN MIND

When evaluating a
coach, think about
whether you want to
index on personal, life,
cultural and/or
educational experience.
KEEP IN MIND

According to HBR, the
ingredients of a
successful relationship
include high motivation
to change and good
chemistry with a coach.
KEEP IN MIND
Source: The Realities of Executive Coaching, Harvard Business Review (2009)

BE AWARE OF THE FOLLOWING RED FLAGS
• Given a deadline to make a decision
• Not o ered a sample coaching session
• Sold a multi-month engagement without an opt out
• Require large upfront payment to get started
• Feel hesitant or uncomfortable to move forward
• Believe the coach lacks training or experience
• Observe the coach talk more than he/she listens
• Deliver more advice than thoughtful questions
STEP 5
DECISION / FIT

Decades of experience or
incredible credentials
don't mean much if the
relationship doesn't
"feel" right.
KEEP IN MIND

1. Contracting
2. Data gathering
3. Goal setting and development of coaching plan
4. Implementation of coaching plan
5. Measuring and reporting results
6. Adjust goals and coaching plan as necessary
7. Transitioning to long-term development
HERE'S THE PROCESS ONCE YOU SELECT A COACH
Source: the Executive Coaching Handbook, Sixth Edition (2015)
STEP 6
THE ENGAGEMENT

A good coach will
customize their
process to your needs
and coaching goals.
KEEP IN MIND

I talked with dozens of
your peers. These
coaches come highly
recommended.
REFERRED
COACHES

Independent
Sunil Arora
Austinfish
Julia Austin
REFERRED
COACHES
Stanford
Ed Batista
Basker & Co.
Jonathan Basker
Founder Coach
Amy Buechler
Conscious Leadership
Diana Chapman
Reboot
Jerry Colonna
Scale.us
Virginia Bauman

Conscious Leadership
Jim Dethmer
Reboot
Chad Dickerson
REFERRED
COACHES
Reboot
Khalid Halim
Rad Reads
Khe Hy
Osprey Leadership
Leigh Kearney
Evolution
Geoff Graber
OnCourse
Jim Kochalka
Priority Coaching
Sharon Daugherty

Reboot
Albert Lee
REFERRED
COACHES
Independent
Ann Mehl
Reboot
Jim Marsden
Evolution
Miriam Meima
The Mochary Group
Matt Mochary
Porthouse Coaching
Tim Porthouse
Rosen & Associates
Jim Rosen
Independent
Tarikh Korula

REFERRED
COACHES
Sulkowicz Group
Kerry Sulkowicz
Coach.me
Tony Stubblebine
Practical Philosopher
Andrew Taggart
Independent
Katia Verresen
Independent
Leo Widrich
Founder Forward
Robyn Ward
The Forcing Function
Chris Sparks
Trium
Jonathan Rosenfeld

The speci c coach you
choose to partner with is
far more important than
the organization he/she
works for. Independents
are equally capable.
KEEP IN MIND

These coaching
organizations and
networks have been
recommended by your
peers.
COACHING
ORGANIZATIONS

10x CEO
COACHING ORGANIZATIONS

Conscious Leadership Group

Evolution

Leaders In Tech

Talentism

Uplevel

The Ready

Venwise

These are not the only
organizations and
networks dedicated to
serving leaders. Ask
your peers who they
also recommend.
KEEP IN MIND

Coaching orgs make
sense if you want access
to multiple coaches and
a range of services. They
provide single point of
contact, streamlined
pricing and choice.
KEEP IN MIND

There is virtually no
standardization when
it comes to pricing. The
range varies greatly.
KEEP IN MIND

RETAINER
• $1,000 - $6,000+ per month
• Often sold month to month
PER SESSION
• $300 - $3,000+ per session
• Often sold in packages
PRICING &
PACKAGING*
*Based on conversations with dozens of coaches and founders
MEMBERSHIP (FOR GROUPS)
• $300 - $600+ per month
• Billed monthly or annually

Some coaches will
lower their rate in
exchange for equity or
o er performance
based pricing.
KEEP IN MIND

One day Picasso was sitting at a cafe. He drew a sketch
on a napkin.
A lady recognized him and asked how much she could
pay for the napkin.
Picasso said $20,000.
The lady was shocked, “But it only took you two
minutes to draw.”
Picasso replied, “No, it took me my whole life.”
SUBJECTIVITY
OF PRICING

Created Future
(w Coaching)
Default Future
(w/o Coaching)
What You Pay For
HOW TO THINK
ABOUT ROI
FOCUS ON DESIRED OUTCOMES RATHER THAN COST PER SESSION
Source: The Prosperous Coach (2013)

3.5x
RETURN ON INVESTMENT AS
MEASURED BY PERFORMANCE,
RETENTION AND WELL-BEING
Research suggests a solid ROI on
coaching though outcome data is still
limited.
REPORT IMPROVED WORK
PERFORMANCE, REATIONSHIPS AND
MORE EFFECTIVE COMMUNICATION
70%
REPORT INCREASED SELF
CONFIDENCE
80%
Source: BetterUp (2019); International Coaching Federation (2009)

THE CASE FOR
COACHING
HOW MUCH DO YOU VALUE
• Increased energy, focus and productivity
• Sharper decision making and execution
• Enhanced self awareness
• Fresh perspectives
• More self con dence
• More e ective communication and listening
• Stronger relationships and resolved con icts
• Greater accountability

• Measurable progress on goals and objectives
• Real outcomes in business via key measures
• Increased awareness and energy post session
• Improved interpersonal dynamics and relationships
• E ective internal and external con ict resolution
• Better and faster decision making (e.g. hire/ re)
• More e ective management of energy and health
• Higher employee satisfaction and retention
HERE ARE SOME SIGNS AS THE PARTNERSHIP DEVELOPS
HOW TO KNOW
IF ITS WORKING?

For many the impact of
coaching can be felt in
the rst few sessions
but outcomes can
generally take three to
six months.
KEEP IN MIND

RECOMMENDED
READING
IF YOU WOULD LIKE TO GO DEEPER I RECOMMEND THESE BOOKS

☐ Complete the questions on slide 35
☐ Determine if coaching might be a t for you
☐ Ask your network for references
☐ Schedule initial info sessions with 3-5 coaches
☐ Enjoy the process!
CHECKLIST
HERE ARE SOME NEXT STEPS YOU CAN TAKE

Coaching isn't a
panacea. However, it's
incredibly powerful for
those who nd the right
coach and are deeply
committed to growth.
KEEP IN MIND

The world is lled with
thousands of amazing
coaches. May you nd
the one who helps you
reach new heights.
GOOD LUCK!

THANK YOU
• Sunil Agora
• Julia Austin
• Ed Batista
• Richard Hughes Jones
• Tarikh Korula
• Chris Muscarella
• Jeremy Shure
• Tony Stubblebine
TO THOSE WHO HELPED WITH AND INSPIRED THIS GUIDE

@schlaf
schlaf.me
highoutput.co
superpeer.com/schlaf
SAY HELLO

An Entrepreneur's Guide to Finding a Coach

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