Executive Leadership

Executive coaches can help you operate at the highest level while balancing work and personal life.

Startups are inherently stressful environments; founders, in particular, face extreme pressures turning their vision into a sustainable business. The most successful founders navigate these challenges through a support network of peers, mentors, advisors, therapists, and coaches.

Executive coaching is a relatively new industry focused on helping founders maintain a healthy and balanced life throughout their entrepreneurial journey. Coaches work with clients on a wide range of topics including:

• Developing leadership capabilities
• Enhancing self-awareness and identifying strengths/weaknesses
• Addressing impostor syndrome
• Handling co-founder dynamics
• Managing stress and burnout
• Improving focus
• Discovering core values and life mission
• and more.

Coach vs. Mentor: Which is the Best Fit?

Understanding the difference between a coach and a mentor is crucial to choosing the right support. In many cases, we find founders are asking for a coach but are actually seeking a mentor. We recommend having both.

Mentors are subject matter experts who have experience solving similar challenges to the ones you are facing. For example, a CEO mentor can share their roadmap for managing a board, building an executive team, or raising a round of funding. They tell you their path to success. While this can be beneficial, it’s also rare that following someone else's roadmap will fully solve your unique challenges.

Coaches rarely offer prescriptive advice. Instead, they use questioning techniques to help clients uncover and address critical challenges. A coach will help uncover your underlying motivations and create your own path to success. The skillsets you build with a coach can apply across many problems and areas of your life.

If you are looking for advice derived from an expert's personal experience, that’s a mentor. If you want someone to help you find your own answers, that’s a coach.

*For the purposes of this post, we will only discuss the process for selecting a coach and our coaching network.

How to Select a Coach

There is no one size fits all in the coaching world. Successful coaching is as much about chemistry as a particular skill-set. While trusted referrals are essential, beware of choosing a coach solely based on their list of notable clients - the "celebrity coach trap."

Coaching styles vary greatly. Some coaches are more Socratic; they employ a purely exploratory question-based approach. Others are more framework-driven and may use assessments (like 360s, DISC, or Hogan). One coach may focus on mindfulness while another optimizes for business outcomes. There is no right or wrong approach, but there will be a best fit for your particular situation.

Below is our recommended process for identifying the right coach:

1. Ask your peers: Gather recommendations from trusted sources.
2. Compare & contrast: Speak to ~3 coaches, ideally with different styles. The key questions to ask yourself are “would I be comfortable sharing more with this person than anyone else” and “does this person understand me better than others”?
3. Come prepared: In the first introductory conversation, often 30-minutes, bring a coaching topic (see example topics above). The best way to understand a coach's style is to experience it. Use ~15 minutes for a mini-coaching session around that topic.
4. Ensure alignment: During your first conversation, define expectations and goals for a coaching relationship. If these align, create a formal agreement and start coaching.

Cost & Time Commitment

Most executive coaches target 6-month engagements to provide sufficient time for progress.

Costs can vary based on coach, executive level, and company stage. Expect $2,000+/month, but some experienced and highly sought after CEO coaches charge $5,000+/month.

Typical time commitments are a 1.5 to 2-hour first session, then bi-weekly 45-60 minute sessions. These may be in person, but can also happen successfully through Zoom or a phone call. Depending on the coach, you may also start the engagement with a 360 review from your executive team or a personality assessment like DISC or Hogan.

Individual vs. Team Coach: Pros & Cons

Given the high cost of an executive coach, some companies decide to use one person for the entire executive team. The CEO chooses the coach, and other team members will have access less frequently.

While this arrangement can work well, it also has potential challenges. Unless there is total confidentiality between the coach and each executive, real issues won't be raised and the team may use it to gain signals on other executives.

If you go the team route, ask the executive coach about their experience coaching a team and how they deal with confidentiality and disclosure.

Facilitated Off-sites: Leadership & Executive Team Effectiveness

Every executive team should have at least one coach-facilitated offsite a year focused on executive team effectiveness (e.g., creating shared values and operating principles, building trust, cultivating team culture, etc). Coaches can design and lead sessions tailored to the unique challenges of an executive team.

Some of the most successful companies (e.g., Slack, Airbnb, and Coinbase), held facilitated off-sites from the initial forming of the executive team. Individual coaching paired with facilitated team sessions can build personal and organizational resilience.

Lightspeed's Executive Coaching Network

Below is a directory of Lightspeed's experienced coaching network. For introductions, please reach out to our Lighthouse team here.

In addition to the list below, Any Dunn, founder of Bonobos and Pumpkin Pie, has also put together an extensive list of coaches worth checking out here.