Executive Coaching

There is no one-size-fits-all in the coaching world. Successful coaching is as much about chemistry as a particular skill set. We recommend a thorough process when evaluating coaches and conducting ample research to ensure you have the right fit.

Our Recommended Process for Selecting a Coach

1. Assess experience and expertise: Start by reviewing their bio to assess their experience and background. Confirm they have a track record working with startup founders or similar industries. Initiate an introductory conversation with the coach to understand their style, approach, and compatibility with your needs.
2. Ensure style and approach alignment: During the introductory conversation, discuss their past experiences with clients facing challenges similar to yours. Inquire about the results they achieved in those cases. Clearly communicate your expectations and desired outcomes from the coaching engagement. Also, determine if you are looking for a blend of mentorship and coaching (“mentor-coaching”) or pure coaching and discuss your preferences with them.
3. Confirm qualifications and credentials: Verify that the coach has the necessary qualifications and credentials. At a minimum, they should have an accredited coaching certification (you can ask if they’re ICF-accredited) as well as additional specialty certifications, Master’s degrees, etc. 
4. Compare & contrast coaches: Speak to 2-3 coaches, ideally with different coaching styles. Ask yourself questions like, "Would I feel comfortable sharing more with this person than anyone else?" and "Does this coach seem to understand me better than others?". Comparing various options will help you identify the coach who resonates with you the most. Conduct brief (~15-minute) mini-coaching sessions with each around a particular topic to compare and contrast coaching styles.
5. Ask for references: Request references or anonymized case studies from the coach to gain insights into their track record and the impact they've had on their clients.
6. Ask your peers: Leverage your professional network to gather feedback from peers who may have worked with the coach before.
7. Cost and availability: Ensure the coach's fees are within your budget and confirm their availability to meet your scheduling needs.
8. Send agreement: If everything aligns well, create a formal agreement to solidify the coaching engagement.

Lightspeed has a network of preferred coaches to get you started. 

Common Pitfalls

Some key factors to avoid when evaluating coaches include:  

• Not doing your research: It's important to do your research and find a coach who is qualified and experienced in the area you need help with.
• Not being clear about your goals: Clearly defining your goals and setting clear expectations from the coaching relationship is vital for your coaching experience.
• Not being a good fit: Assess if the coach’s personality and teaching style aligns with you.  
• Not being committed to the process: Coaching is a process that takes time and effort. A strong commitment to the process is key to achieving meaningful and lasting results.
• Not being honest with your coach: It's important to be honest with your coach about your goals, challenges, and progress.  Provide them with feedback if you aren’t satisfied with how the coaching is going.
• Not being open to feedback: Embrace feedback from your coach and constructive criticism. ‍

Cultural and Ethical Considerations

Ensuring a successful coaching partnership involves addressing cultural fit, confidentiality, and ethics from the outset. A coach who understands the influence of culture, whether explicitly discussed or not, creates a supportive environment. 

Coaches certified by the International Coaching Federation (ICF) are bound to adhere to a specific Code of Ethics. This standard includes responsibilities to clients (e.g., confidentiality), the coach’s practice and performance, and the professionalism of the coaching industry as a whole.

ICF coaches are required to re-certify their credentials and the Code of Ethics every 3 years. Non-ICF coaches are not bound to a specific ethical standard, but if they completed a coaching program, they likely learned ethical standards for coaching. In most 1:1 engagements, the coach will commit to strict confidentiality with the exception of specific, rare legal obligations and risks.

At any time, you can ask a coach about their certifications and their approach to ethics in their coaching practice.

Cost & Time Commitment

At the executive level, coaches typically provide a coaching package vs. an hourly rate.

A common package is a 6-month engagement involving bi-weekly sessions, totaling 2 sessions a month. The coaching process often begins with a 360 assessment or personality assessment (e.g., Hogan or Enneagram) to focus on key areas for development and establish success measures.

A six-month coaching package, including assessments, ranges from $20,000 to $50,000. For hourly packages, the typical range is $300-600/hr, though we’ve seen coaches with a +$1k/hr rate.

Cost Factors

When considering the appropriate rate for an executive coach, several factors come into play, depending on your specific goals and desired coaching experience: 

• Experience and qualifications: How long have they been coaching? Are they certified? Be cautious of some coaches who charge a premium but lack certifications; be mindful of their expertise and background. 
• Executive level: Do they have a track record of successfully helping executives meet their goals?
• Company stage: Mature companies will likely want coaches who have worked with other companies in their “tier” or the tier they want to get to. Those coaches typically have 10+ years of experience and a set of complementary skills that inform the rate. These coaches can also offer founders valuable insights into the journey ahead, potentially expediting their learning curve.

Note: The coach may conduct a 360 assessment to gain a comprehensive understanding of the client's developmental areas and determine the most effective ways to support them. While this assessment is highly valuable for validating coaching goals, it's important to note that it may incur additional costs due to the time commitment required.

When determining if a coach is a good match for you, consider asking about their primary coaching style. For example, some coaches are more Socratic, employing exploratory questions as their primary tool, while others may rely on frameworks and assessments (like 360s, DISC, or Hogan). There is no right or wrong approach, but there will be the best fit for your particular situation. Here are some of the most common approaches: 

• Socratic: Primarily uses questions to explore the client's inner thoughts and experiences, aiming to advance development and goal attainment.
• Framework-Driven: Utilizes various frameworks, tools, and assessments to uncover blind spots and gain insights into behaviors and actions.
• Mindfulness: Encourages moments of reflection and guided experiences to enhance self-awareness and personal growth.
• Developmental: A thought-partnership approach concerning goals and is grounded in tools and frameworks to facilitate progress.
• Transformational: Focuses on meaning and purpose and how these aspects are activated in your life through goals and actions.
• Assertive: Involves challenging the client, playing devil’s advocate, and identifying blind spots.

Many exec coaches, including Maya and Shannon, have expertise in multiple approaches, styles, and frameworks. This versatility allows coaches to adapt dynamically during coaching sessions and employ the most suitable tools to support the client effectively. 

Additionally, while your coach will likely challenge you to find the right solution for yourself, you should always feel respected by your coach for the decisions you make, even if you disagree. You are the ultimate authority in your life, and the coach's role is to provide the best possible support.

Evaluation and Follow-Up 

Many coaches will dedicate time at the mid-way point of the engagement (i.e., 6th session in a 12-session engagement) to seek feedback and discuss progress against goals. Additionally, a final feedback session is common at the end of the coaching engagement. Feedback can be gathered through a structured form sent directly to the client or through a live discussion. In cases where the CEO or CPO is a sponsor or part of the process, there’s also the option to provide feedback directly to another party if that's preferred. 

Some useful questions to consider during these feedback sessions are: Am I making progress toward my goal(s)? Have my goals shifted? Do I leave my coaching sessions ready to engage as a leader of my company in a more powerful, values-aligned way?

Coaching isn’t intended to last forever, and you and your coach should be in good communication about whether or not you are experiencing continued growth and development or if you have met your coaching goals.

Individual vs. Team Coach

Both individual and team coaching can offer valuable benefits, depending on the goals. If you would like to work more on yourself, your leadership style, and how you show up in the world, an individual coach is likely a great fit.

Alternatively or in addition to individual coaching, team coaches can be a real advantage in the following situations:

• You want to bring your leadership team together for the first time.
• There is an interpersonal conflict or lack of alignment between leaders about the direction of the company or product.
• The team is stuck, and you are having a hard time troubleshooting why.

Facilitated Off-sites: Leadership & Executive Team Effectiveness

There are some critical conversations that simply won’t happen in the day-to-day running of a startup. These include: re-committing to the vision of the company, deeply understanding each other’s goals and roles as related to the success of the company, and just genuinely “getting” each other. Having these conversations, however, can speed up the pace of the day-to-day work because you are operating in a more cohesive way.

The key is to ensure you are getting ROI out of the off-site. No one likes committing extensive time talking to each other without interactions and outcomes being meaningfully different on the other side. Off-sites can be either self-facilitated or led by an experienced facilitator, possibly a coach, to maximize their effectiveness.

Self-facilitated Pros and Cons

Pros

• Cost-effective choice.
• Limited to your team (guaranteeing confidentiality).

Cons

• Requires significant effort, as you have to decide on discussion topics, purpose, and duration as well as communicate conclusions and follow-up items.
• Requires time and effort to manage the conversation, taking you away from fully participating in the discussion with your team.

Facilitated Pros and Cons

Pros

• Enhances accountability.
• Helps prevent "rabbit hole" conversations.
• Provides meaningful feedback and next steps.
• You're able to actively participate in the conversation.
• Can ensure a neutral, unbiased environment focused on inclusivity and equality.

Cons

• Additional costs.
• Requires time to ensure the fit of the facilitator with the team.
• Necessitates time with the facilitator to ensure the design meets your needs.