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May 8, 2023

How to Choose the Right Executive Coach for Startup Leadership

man in a white shirt seated at a glass table leaning forward and gesturing with both hands

If you’re like most founders, you want every possible advantage to help you and your company succeed. One go-to resource many have come to count on is leadership coaching.

In the current funding environment, many leaders are in “wartime” mode, and the right coach can help you make the tough decisions needed to control burn, extend runway, and ensure the long-term survivability and scalability of your company.

Choosing the wrong coach can be a waste of time and money–or worse, a liability–if they point your attention towards the wrong things.

So how do you find the right coach?

In the guide below, I will help you choose a coach that will truly improve your effectiveness and the likelihood of your company’s success. First, I’ll familiarize you with the three types of leadership coach we see in the startup world. Then, I’ll share a tool you can use to identify the key focus areas in which you most need support.

Three Types of Executive Coach

Meet the three types of executive coach you’ll find in your search. Each one has particular strengths and weaknesses in the support they provide. Review their profiles to help choose the type you should hire.

1. Business Therapy / Reactive Coach

This coach is usually an excellent listener. They are empathetic, able to reflect back your insight and ask probing questions to help you get to the best answer yourself.

They usually can establish rapport and trust quickly. Often former therapists, these coaches can help you foster more self-awareness, reflect on your actions, understand your tendencies, strengths, and weaknesses, and be more confident.

Leaders appreciate this type of coaching as a “shock absorber” to soften the ups and downs of a stressful startup leadership ride – and these relationships can last for years. They are also a great coach if you are starting to burn out or just need to find your own center.

However, we’ve found these coaches typically don’t have the pattern recognition to be an effective thought partner in operating the business. Often, session time is spent dealing with “flavor of the week” challenges that fluctuate from week to week, distracting focus from more persistent priorities.

As a result, this coach may not be driving focus and systematically building the long-term development of new skill sets, capabilities, and mindsets that are critical for you to level up and stay ahead of your fast-scaling company’s growth.

If you stay with this type of coach, you risk having the company “outgrow” you, where either the company fails or you end up being replaced by the board.

2. The Former Operator Exec Coach

These former CEOs are initially very valuable because they have the wisdom and experience that come from having successfully scaled a company.

They can also be good guides in a “wartime” context, because they’ve often personally felt the pain of not acting swiftly enough – they have the memory scars and the pattern recognition to know when something’s not working. This first-hand experience lends them the gravitas to help leaders take action sooner.

However, we’ve found that many CEOs-turned-coaches tend to think that strategies that worked for them will work for you, and they will prescribe them as “best practices.” They tend to think they can coach others without in-depth training in the art of coaching because they’ve been successful leaders themselves. More like a mentor, they default to their own pattern matching and background, versus truly probing to deeply understand and develop your capabilities through effective coaching methodologies.

While they might seem like a fit at first, when your circumstances eventually don’t quite fit the ones they thrived in, this coach’s “best practices” can be a square peg in a round hole. Situations that don’t fit that former operator’s expertise tend to be blind spots for them.

Some former operators are good coaches if they trained deeply in this field, but most of the ones I see are actually better off being mentors who can be consulted for situation-specific guidance as needed.

3. Structured and Flexible Startup Coach

These types of coaches are nimble and skillful at dynamically responding to the week-to-week needs of a leader, while holding the work inside the context of a developmental plan.

They specialize in working with startups and have a broad base of startup-specific tools to quickly identify, diagnose, and address challenges facing fast-scaling startup leaders in wartime.

Startup coaches keep a library of tools and startup best practices to help you with key leadership tasks such as leveling up your exec team and their meetings, having difficult conversations, tracking commitments, hiring effectively, holding your team accountable, etc.

These structured and flexible startup coaches will also co-create some form of a leadership plan with you. Derived from a deep inquiry, pattern matching, and 360 feedback (from exec team and board), this leadership plan is a roadmap of the tools and mindsets that a leader needs to acquire to help them stay six to nine months ahead of the growth of their rapidly scaling and changing company.

A tight leadership plan also includes a board management strategy and a team development strategy. The coach holds you accountable to executing these strategies over time.

While they will dive into the day-to-day challenges that inevitably come up, they understand that your work transcends “flavor of the week” crises. They will proactively equip you with the tools and mindsets to help you scale yourself and your team to meet what’s around the corner in your startup journey.

Structured yet flexible startup coaches refresh and regenerate the leadership plan on an ongoing basis. Many can even step in to facilitate high-performance teamwork offsites for your exec team as well.

So, Which Executive Coach Is Best for You?

When you are burning out or just need to find your own center, a business therapy coach can support your mental health.

When you are navigating a particularly tricky situation, a former operator coach has just the right expertise.

However, we have found that the structured yet flexible startup coach is most often the best fit for the dynamic ride most startup leaders face. They are even more effective when they are partnered with an industry-specific mentor (often a former operator) and both act as a brain trust to help you navigate most any challenge.

So, if you have a sense that a coach could be helpful for you, consider what type of coach you need. Business therapy coach? Former operator? Or a startup leadership coach with a structured and flexible approach, complemented by mentors?


Leadership Goal

Executive Coach Match

Mental health support: burning out; need to find center

Business therapy coach

Situational support: navigating a particular business challenge

Former operator coach

Startup leadership support: tools and strategies for leading a team through the volatile ups and downs of a startup ride

Structured yet flexible startup coach


Whichever type you choose, make sure to meet with two or three coaches before you decide. While chemistry is important, if you are on the fence about which coach to choose, index towards the one who delivered the most value in your initial session. It’s often an indicator of the trajectory of the relationship.

If you are on the fence about which coach to choose, index towards the one who delivered the most value in your initial session.

Finally, here’s a diagnostic tool you can use to identify the key focus areas where you most need support. This may help inform your criteria when choosing a coach.

About the Author

Bryan Bayer is senior startup leadership coach and cofounder of Neuberg Gore, a premier executive coaching firm that has helped hundreds of startup CEOs and their leadership teams gain the mindsets and leadership skills to scale their companies.

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