How to Choose the Right Startup Leadership Coach
As a startup leader, you are fighting for the survival of your company while building your exec team, figuring out your role, and driving your initiatives forward. It's impossible for you to do it all well.
It's a practice of extraordinary prioritization–choosing which fires to let burn and which to urgently address.
If you’re like most founders, you want every possible advantage to help you and your company succeed. One key go-to resource many have come to count on is leadership coaching.
In this current funding environment, many leaders are in “wartime” mode, and the right coach can help you make tough decisions to control burn, extend runway and ensure the long term survivability & scalability of your company.
The wrong coach can be a waste of time and money, but more importantly, they can be a liability if they point your attention towards the wrong things.
So how do you help you find the right coach?
Below is a guide to choose a coach that will truly improve your effectiveness and the likelihood of company success.
First, I’ll familiarize you with three different types of leadership coaches we see in the startup world. Then, I’ll share with you a tool you can use to help your leader identify the key focus areas they most need support in.
Three Types of Coaches
The “Business Therapy”/ ”Reactive” Coach
This is the person who is usually an excellent listener, empathetic, able to reflect back and ask probing questions to help you get to the best answer for yourself.
They usually can quickly establish rapport and trust, and often are former therapists.
They 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 burning 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 key 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 the growth of your fast-scaling company.
As a result, you risk having the company “outgrow you”, and if this happens either the company fails, or you end up being replaced by the board.
The “Former Operator” Exec Coach
These former CEOs are initially very valuable because they have wisdom & 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, and help leaders take action sooner
However, we've found that many former CEO-now-coaches tend to think that strategies that worked for them will work for you, and prescribe these “best practices” to you.
They tend to think if they’ve been a successful leader, they can coach others without deeply training in the art of coaching. More like a mentor, they default to their own pattern matching and background of experience, versus truly probing to deeply listen, inquire, and develop your capabilities through effective coaching methodologies.
While they might seem like a fit at first, eventually when your circumstances don’t quite fit the ones they thrived in, this coach’s “best practices” can be a square peg in a round hole for the your situation – and areas that don’t fit that former operator’s background of expertise tend to be blind spots for them.
Some former operators are good coaches if they trained deeply in this capability, but most of the ones I see are actually better off in the role of a mentor who can be consulted for situation-specific guidance periodically as needed.“Structured and Flexible” Startup Coach
These types of coaches are nimble, adroit and skillful at dynamically responding to the week-to-week needs of a leader, while holding the work inside a context of a deeper 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.
They keep a library of tools and startup best practices to support you to level up your exec team and their meetings, have difficult conversations, track commitments, hire effectively, hold 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 this leader needs to acquire to help you stay 6-9 months ahead of the growth of your rapidly scaling and changing company.
A tight leadership plan also includes a board management strategy, a team development strategy, and the coach holds you accountable to executing this strategy through time.
While they will dive with you to address the day-to-day challenges that inevitably come up, your work transcends “flavor of the week” crises, to 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.
These “structured yet flexible” startup coaches actively refresh and regenerate the leadership plan, and many can step in to facilitate high performance teamwork offsites for your exec team as well.
So, which coach is best for my portfolio leader?
There are times when you are burning out or just need to find your own center, and a “business therapy” coach can support your mental health.
Or, you are navigating a particularly tricky situation a “former operator” coach has just the right expertise for.
Typically 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.
We like to match you up with an industry-specific mentor (often a former operator) who, together with your coach, can be the brain trust that you need to navigate through most any challenging situation.
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?
Make sure to meet with 2-3 of the right type of 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.
Finally, here’s a diagnostic tool you can use to identify the key focus areas where you most need support.
We maintain active relationships with various types of top startup leadership resources, and are always looking to match leaders with the right coach, mentor, facilitator, therapist or other resource you might need. Feel free to reach out.
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.