An Entrepreneur's Guide to Finding a Coach

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

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

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

4. 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

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

6. 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

7. 1. About

8. 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

9. 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

10. 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

11. 2. Coaching: An Overview

12. 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

13. • 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

14. • 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

15. • 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)

16. • 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

17. • 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)

18. • 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 Source: Coaching for Transformation (2011)

19. 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

20. TELLING ASKING FUTURE PAST Therapy Consulting Counseling Coaching Mentoring

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

22. $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)

23. 3. The Coaches Toolbox

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

25. 4 DIMENSIONS OF EXPERIENCE A COACH IS THE SUM TOTAL OF THEIR LIVED EXPERIENCE Professional Personal Cultural Educational

26. 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 Source: Coaching for Transformation (2011)

27. 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 Source: Coaching for Transformation (2011)

28. 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.

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

30. 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

31. 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

32. 4. Process & Fit

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

34. 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

35. 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?

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

37. 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

38. 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

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

40. 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

41. 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)

42. 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?

43. 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

44. 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?

45. 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?

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

47. 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?

48. 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

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

50. 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)

51. 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

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

53. 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

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

55. 5. Coaches & Organizations

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

57. 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

58. 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

59. 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

60. 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

61. 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

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

63. 10x CEO COACHING ORGANIZATIONS

64. Conscious Leadership Group COACHING ORGANIZATIONS

65. Evolution COACHING ORGANIZATIONS

66. Chief COACHING ORGANIZATIONS

67. Leaders In Tech COACHING ORGANIZATIONS

68. Reboot COACHING ORGANIZATIONS

69. Talentism COACHING ORGANIZATIONS

70. Uplevel COACHING ORGANIZATIONS

71. The Ready COACHING ORGANIZATIONS

72. Trium COACHING ORGANIZATIONS

73. Venwise COACHING ORGANIZATIONS

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

75. 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

76. 6. Pricing & ROI

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

78. 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

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

80. 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

81. 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)

82. 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)

83. 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

84. 7. Other Resources

85. • 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?

86. 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

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

88. ☐ 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

89. 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

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

91. 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

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

93. Make It Happen!