How To Choose a Cofounder Coach: Your Definitive Guide To Finding The Best Fit And Outcome
This guide will help you select the perfect cofounder coach for you and your business partners.
Cofounder coaching is a growing category of services helping cofounders improve communication, teamwork, and execution.
As an emerging category, there is no unitary set of standards defining the practices and competencies of cofounder coaching, meaning there is high variance between providers. The burden of finding a competent coach, then, falls on you the consumer.
If you have experienced difficulties with your cofounder(s) or are looking to protect this most important business relationship before the strain of building a successful company increases, this guide is written to help you identify and select the perfect coach to deliver unparalleled results.
But before we jump in, remember this key point:
The key to attaining the most successful outcome is your relationship with your coach.
Goodness of fit between your goals, preferences, and style with the coach’s presence should be your top priority when considering this service.
You need to trust your coach to have your back in difficult moments and help your team navigate the challenges of operating a successful company while managing complex personal relationships.
To ensure the best fit from the start, read the eight steps to choosing the right cofounder coach below.
1. Learn the three types of cofounder coaches.
There are currently three main schools of cofounder coaches:
Ex-founder turned coach
Coach with psychological expertise
Therapist working with entrepreneurs
Each of these three have particular strengths and weaknesses.
The ex-founder or operator turned coach offers more business expertise than any other type of cofounder coach.
There is no substitute for lived experience, so these coaches have the ability to empathize with what it’s like to be in the trenches.
A common story with these coaches is one of burnout: They started several companies and eventually burned out. Through this process, they may have learned valuable lessons about themselves, the importance of team cohesion, and discovered they want to be the source of support they lacked as founders.
The most common shortcoming of ex-founder turned coaches is they may lack the degree of psychological expertise and training of other coaches. As I have discussed elsewhere, the training of coaches is much less rigorous in content, supervision, and direct hours than most entry level Master’s in Counseling programs.
In contrast, therapists working with entrepreneurs possess counseling skills and other relevant training.
Master’s level clinicians with social work, counseling, and marital and family backgrounds entering the cofounder coaching space are increasing number, as they see the applicability of systems and couple’s therapy theories to business relationships.
While many of these clinicians possess varying degrees of clinical tools, they often lack understanding of business-related dynamics. They may struggle to comprehend business terminology and fail to grasp the stage-specific challenges associated with scaling a successful business.
The coach with expertise in psychology and exposure to business occupies a key middle ground.
They have a foot in each world that allows them to create space for you to discuss the emotional component of business decisions and take a deep dive in the psychological issues preventing your cofounder partnership from thriving.
These coaches are versatile and comprehend the business domain more than therapists working with entrepreneurs.
They often do not provide explicit business advice, as they may not view it as essential to protecting and enhancing the cofounder partnership. Their biggest shortcoming is lacking the lived experience and business expertise of ex-founders, which some cofounders find helpful and comforting.
Keep these three types of coaches in mind as you continue reading: the ex-founder turned coach, the coach with psychological expertise, and the therapist working with entrepreneurs.
2. Determine your specific needs, challenges, and goals.
The next important consideration is a self-audit.
Why do you want cofounder coaching?
What do you hope will change?
Why do you want to start now?
What are your goals?
Answering these questions before talking to a cofounder coach can help determine who you contact and how much value you receive from initial consultations.
Be sure to identify whether your desire for cofounder coaching is proactive or reactive — starting prior to difficulty or after challenges have started. Some coaches prefer helping cofounders build a foundation for long-term success, while others enjoy jumping into difficult circumstances and creating change.
Ask your coach which type of work they prefer and for an example of working with a similar situation in the past.
3. Identify your degree of emotional and business complexity.
Reflect on the state of your partnership.
Think about whether things feel complicated like you are walking on eggshells or dealing with an unresponsive cofounder, or whether your partnership is doing well overall and you are looking for a lighter form of ongoing support.
If you identify complexity in the partnership or if either of you struggle with mental health challenges, searching for a coach with psychological expertise or a therapist working with entrepreneurs may be your best starting point.
In these cases, your relationship and mental health challenges are primary, so you need a provider comfortable navigating these types of issues. Should your need change over time and you may want more operational input consider transitioning to an ex-founder turned coach.
Some founders begin looking for a coach due to performance problems.
Role disputes, transitions to management, hiring disagreements, and not seeing eye-to-eye on long-term strategies are common entry points to cofounder coaching.
If you lack clarity in these areas or have detailed issues related to equity splits, dealing with boards and investors, or logistics around one partner exiting, then working with an ex-founder turned coach may be the best initial starting point.
Often, these coaches have the ability to provide strategic recommendations based on lived experience of what works and does not, in ways the other types of coaches cannot.
4. Determine how much you are willing to invest.
Cofounder coaches have wide ranges of payment structures and rates.
The most affordable option are therapists working with entrepreneurs, who often charge rates similar to their hourly rate with other clients.
To give you a more direct estimate of cost, many high quality therapists in major cities (NY, SF, LA) charge upwards of $200 to $500 per session. Many therapists in smaller cities have lower rates in the $100 to $200 range. And in contrast to coaches, some therapists accept insurance, which would be the most significant budget option available if you are able to find someone with availability and relevant experience.
Cofounder coaches often move away from pricing per session to retainers of varying lengths.
Some charge monthly retainers, others prefer to have clients pay up front for an entire year. These retainers may range from $2k to $8k per month. Some coaches may convert cash to stock options, depending on the situation. In contrast to using private health insurance or paying out of pocket for a therapist working with entrepreneurs, many cofounders working with coaches use their business account to cover the expense.
Given this significant range in fees, it is important for you and your cofounder to consider how much you are willing to pay for the engagement.
A few suggestions to keep in mind:
If you feel a great fit with a coach you believe will facilitate growth, it’s better to pay a high rate for three to six months than it is to hunt for a bargain rate with someone less competent who may require more time to create change.
If a provider does not assign a proper valuation to their services based on service quality, expertise, and market, it may be an indicator they struggle with understanding basic business principles.
If cost is your primary restriction, tell the coach and see if they are willing to be flexible or ask for less expensive resources.
Please contact coaches directly for more information about their compensation.
5. Think about your preferred meeting structure.
Here are a few questions to ask yourself:
How often would I prefer to meet?
Do I want ongoing sessions on a regular basis?
Would I prefer focused, short-term work?
While most cofounder coaches have experience in long-term client engagements and shorter-term work, it’s important to contemplate which type of approach you want and to ask the coach about their preferences. Similarly, some coaches prefer a 2x/month meeting frequency, while others enjoy meeting on a weekly cadence.
Contemplate your degree of openness to what the coach recommends versus your preference based on comfort, level of urgency, and opportunity cost.
6. Consider your desire for individual growth opportunities.
When considering finding the right cofounder coach, it’s important to identify whether you want the coach to play multiple roles or exclusively focus on the cofounder dynamic.
Some cofounders choose to engage in personal therapy, business coaching, and cofounder coaching at the same time. For those individuals, finding a cofounder coach who specializes in cofounder conflict navigation may generate higher returns than searching for a generalist.
In contrast, cofounders lacking other support systems and may enjoy the opportunity to engage in 1:1 coaching to supplement the cofounder work or may benefit from group coaching options. Think about whether you want a coach with the ability to serve several roles or one, then ask your coach about their experience in this area.
Note: Each coach structures engagements differently. Some start with individual meetings, then transition to joint meetings, and others start with joint, then sprinkle in individual meetings. Other coaches utilize assessments to build language around different communication styles then engage in group sessions.
There is no single right way to do this work, but it is worth asking the coach how they typically proceed.
7. Engage in a consultation call or two.
Armed with knowledge of what you want to get out of a coaching engagement and having thought through some of your preferences, it’s a great time to speak with several cofounder coaches. Most offer free 30 to 60 minute consultations to gather information and assess goodness of fit.
Here are a list of recommendations to guide your intro call:
Going into the session, have a good idea about which type of coach you are speaking with (the ex-founder turned coach, coach with psychological expertise, or therapist working with entrepreneurs).
Share your goals and challenges with the coach in an honest, transparent manner. This will help the coach better assess fit and provide more accurate feedback to you about reasonable expectations for the time required to create change.
Ask about the coach’s experience working with types of situations in the past. Be curious about how the coach helped facilitate change.
Ask the coach what they think of your situation and how they would approach working with you. Even if you choose to go a different direction, understanding more of their thought process may be helpful.
Ask what sessions look like in terms of structure, frequency, and duration. Discuss any preferences, hesitancies or concerns you have about these issues prior to moving forward.
Ask the coach whether they prefer a more directive or non-directive approach. That is, do they come up with topics of conversation or do they expect you initiate? Know your preference and tell them.
Ask if they enjoy preventative work or jumping into difficult situations. To be more direct, see if they like working with cofounders in your situation or know someone else who does.
Ask the coach whether they teach a set curriculum of skills or whether they prefer more organic, free-flowing approach. Regardless of their answer, ask them why they approach the work in the manner they do.
Ask about their background, qualifications, and/or how they started working with cofounders. Reflect on whether they react with defensiveness or openness to share.
Earlier rather than later, ask about the coach’s availability. Sometimes scheduling is a barrier when not identified early in the process.
If you’re still uncertain of fit, ask about whether they would be open to doing another consultation or a trial. It’s okay to take your time making a decision.
Discuss the financial component. If cost is a barrier, ask if they would reduce their fee. If they are not able to, ask for other referrals and resources.
Ask about next steps. It’s important to leave your call knowing what is required to move the engagement forward.
Overall, aim to not just understand the details of how the coach structures their work with cofounders—most of this can be found on their website—but why they use their particular method and approach.
The more you can understand how the coach thinks, the better you can assess fit.
While you do not need to think the same way as the coach to benefit, you must feel out whether their thinking makes sense to you or not. It’s very helpful when you meet a coach and think, “Yes! I think about this situation in the same way.” That’s how you know you have a great fit.
After the call, meet with your cofounder(s) and have a candid discussion. Take decisive action and then proceed to the step below.
8. Provide feedback early and often.
The most important component of a healthy and successful cofounder coaching experience is the relationship with the coach.
Building a meaningful, trusting relationship starts from the beginning of the engagement. Share your honest feedback early in the process to ensure you are getting the most out of sessions.
If you want your coach to facilitate more of the conversation, tell them. If you’d like more tools or want them to talk less or feel they are taking sides, tell them!
Feedback is a crucial component to building a real working partnership and good coaches seek feedback to make sure they are providing top-notch services.
On average, I recommend giving a coach four sessions to assess fit.
If you provide feedback, meet with them four times, and the service feels unhelpful, move on and try a different provider.
I hope you found this guide useful!
If you or your cofounder have more questions, please feel free to contact me or another cofounder coach for support.