Bill Campbell was one of the most influential people in Silicon Valley that you’ve probably never heard about.
The former Head Coach of the Columbia Lions, Bill built up an incredible roster of legendary founders who came to him for advice on critical business problems.
Steve Jobs famously scheduled weekly walks with him, and even added him to Apple’s Board of Directors. The Google founders, Larry Page and Sergey Brin, said they couldn’t have made it without him. He also coached Jeff Bezos at Amazon, Jack Dorsey at Twitter, and Sheryl Sandberg at Facebook.
What did all these incredibly talented visionaries and business leaders have in common? Why did they all go to Bill when they needed help? Why do they all credit working with a coach as key to their business success?
As a two-time startup founder and lifelong entrepreneur, I’ve learned a lot from personally working with executive coaches, and I’m going to try to demystify the whole process for other startup founders who are considering working with a coach.
I started my first startup, One Month (an online coding school), in my early twenties and experienced a rollercoaster of successes and failures. I didn’t know what the hell I was doing.
Though we got accepted into Y Combinator, raised $3 million in venture funding, grew the team to 30 people, and helped a lot of people change their lives, it was not a success from a traditional startup perspective.
I was in way over my head managing a large team without any real management and leadership experience (I was only 25 years old after all). After a few years, I got pretty burnt out and had to step back from the company.
I took some time off, wrote a book, did a bit of consulting, and eventually started another company, Ophelia (an online treatment program for opioid addiction).
This one was more successful — we got accepted into Y Combinator (again), raised $68 million in total funding, grew the team to almost 200 people, helped thousands of people recover from opioid addiction, and the company is still going strong.
I applied a lot of my learnings from One Month to Ophelia, and didn’t feel so in over my head — at least until the team grew to about 100 people. Then it was uncharted territory for me again
This time when when I decided to step back from Ophelia after a few years, it was because the company was doing so well that it wasn’t an early-stage startup anymore (and that’s the stage I really enjoy).
One of the biggest assets along the way in my career as an entrepreneur has been hiring and working with executive coaches — just to name a few: Rich Hagberg (of Hagberg Consulting), David Lee (formerly of SV Angel and Refactor Capital), Jason Gore and Robert MacNaughton (of Neuberg Gore), Sabrina Wang (formerly of Mochary Method).
Why I started working with a coach
I was a few years into One Month when my cofounder and I started having some challenges. We both found each other to be difficult to work with, and we regularly disagreed about business decisions and the direction of the company.
The whole company was on the line, and we didn’t really see a way to move forward.
Then I remembered that one of the Y Combinator partners, Jessica Livingston, said that if we ever experienced any co-founder conflict, we should come to her. So I reached out and we got on a call.
“Have you considered working with an executive coach?” she asked me.
“Honestly, not really,” I said. Generally, it felt like a waste of time and money to pay someone else who didn’t really know my business to tell me what to do.
As an entrepreneur, I always felt like I could figure things out myself and that if I did enough research I could find a business book, a blog post, or some framework that would help me solve the issue.
“I haven’t seen a single successful startup founder at Y Combinator who hasn’t worked with a coach at some point,” Jessica said bluntly. “Honestly, if you’re not working with an executive coach then you’re actively doing your startup a disservice.”
This last point stunned me. By not working with a coach, was I hurting my startup? So I resolved to explore and learn more.
Should you work with an executive coach?
Let’s skip forward for a moment. Having now worked with executive coaches for nearly my entire career, I think for most founders and leaders at organizations, the answer to whether they should work with a coach is probably yes.
The only major questions are: i) whether you can whether you can find the right coach, and ii) whether you can convince your company to cover the cost (we’ll talk about cost in a second).
Working with a good executive coach is like designing your own personal MBA, with real tangible benefits for your career, your personal life, and your company.
In a world where we’ve settled on a more industrialized model of education (i.e. 20–50 students in a classroom, mostly learning through lectures), it’s remarkable how much more effective the one-on-one / apprenticeship-based model can be.
Of course we’ve known this for a while. Education researcher Benjamin Bloom found that the average tutored student performed two standard deviations better than students educated in a traditional classroom. Meaning the average tutored student did better than 98% of students without tutors.
If you assume that 90% of startups fail, then you should be asking how much it would be worth to you and your investors to increase your company’s chances of success.
One HBS study showed that second time founders are up to 2x more likely to be successful than first time founders, the most likely reason being that they have more skills and past experiences to rely upon.
Having a coach allows you as a founder to tap into the past experiences of others without having to make and learn from the mistakes yourself (you’ll almost certainly still make a lot of mistakes, but hopefully less).
Consider the fact that there’s absolutely no way for a world-class athlete to be successful without a coach. If you want to be a world-class founder and leader, you need a coach as well.
And in my experience, investors tend to be really supportive of their founders working with coaches, because it increases the businesses chance of success.
Finding the right coach
When I set out to find the best coach to work with, I ending up talking with over a dozen coaches, as well as other founders who worked with coaches, and learned a lot about different coaching styles.
I’ve identified five major criteria you’ll want to consider when deciding what kind of coach you want to work with:
- Structured vs. Unstructured
- Individual vs. Organizational-focus
- Strategic vs. Tactical
- Challenging vs. Supportive
- Personal Resonance
Structured vs. Unstructured
The first major difference between coaches I’ve found is how structured versus unstructured they are in their approach.
Some coaches follow frameworks or methodologies that map out a “curriculum,” whereas others take a looser, more relational approach that focuses on the specific issues you’re currently facing. Neither is necessarily good or bad, it just depends what you’re looking for.
To give you an example, the first coach I ended up working with was Rich Hagberg.
I chose Rich because he had come recommended by Y Combinator, had worked with an impressive roster of startup founders (e.g. Twitter, Dropbox, Mixpanel, Reddit), and had the most structured approach of anyone I talked to, which I appreciated.
Rich started with a leadership self-assessment and a 360 feedback evaluation.
The 360 feedback consisted of the 10–12 closest people I worked with (my co-founder, board, and direct reports) completing a long survey about what it’s like to work with me — including my strengths and weaknesses as a founder. This was paired with Rich also doing qualitative interviews with a handful of them.
I’ve learned this is pretty common approach, and a lot of executive coaches will start with a 360 feedback report to get a baseline of where you’re at.
Rich’s leadership framework in particular identified three different core types of leaders — visionary evangelist, relationship builder, and manager of execution.
A visionary evangelist is good at creating a compelling vision of the future (e.g. Steve Jobs, Barack Obama, Martin Luther King Jr.). A relationship builder motivates by building loyalty and investing in relationships (e.g. Richard Branson, Oprah Winfrey, Bill Clinton). A manager of execution is structured, disciplined, and good at setting short-term targets and goals (e.g. Jack Welch, Colin Powell, Martha Stewart).
Founders and leaders are typically stronger in one of these areas (sometimes two), but rarely are they good at all three.
Rich also analyzed my intellectual style (e.g. tolerance for ambiguity, optimism, risk tasking), my personality dynamics (e.g. humility, aggressiveness, anxiety) and my social style (e.g. assertiveness, trust, empathy).
Once the process was finished (it took a few weeks) — I received a report that highlighted my greatest strengths and weaknesses as a leader. I was pretty strong as a visionary evangelist and a relationship builder, but weak on managing execution.
My top strengths included:
- taking initiative
- creativity and innovation
My biggest weaknesses were:
- strategic focus
- planning, prioritizing and maintaining focus
- emphasizing excellence
- developing structures, systems, and processes
(These results are from over 10 years ago, so it’s amazing to see how much as changed. I’ve gotten a lot better at the areas of weakness, but also a lot this still rings true.)
From this report, together Rich and I came up with my 1 year development plan — we decided to focus on conflict management (there were some acute issues I was dealing with at One Month at the time), creating buy-in on the team, and holding people accountable.
For each of these topics, Rich shared with me a set of slides that highlighted different approaches, frameworks, and summaries distilled from books, talks, and thought-leaders in the area. These were usually pretty dense and took me several days to really work through.
Then we set up a 90 minute coaching session every other week to work through the material and, most importantly, apply it to the situations I was encountering at my startup.
I loved the structure to it, as it felt like I was making concrete, tangible, and measurable progress among a number of important areas. It also felt like a “personalized MBA” — a curriculum designed specifically for me that was immediately useful.
A lot of coaches take a less structured, looser approach. They may start sessions without a specific plan, just by asking questions like, “What’s going on for you right now?” or “What sorts of issues or challenges are coming up for you?”
This approach is more reactive and can feel more relevant to the specific issues you’re actually facing. In other words, you’re in the driver seat.
Again, neither of these approaches is necessarily better or worse, it just depends on what resonates with you most and what your current circumstances are.
Personally, I tend to find that without structure, longer-term goals and the ability to quantify improvement, I start to feel like there’s a lack of progress from session to session.
Anyway, most good coaches will be able to do both, depending on what you need. It’s just that they tend to be slightly stronger in or more oriented towards one approach than the other
Some questions to assess a coach’s orientation around structure vs. lack of structure:
- What methodologies or frameworks do you follow with your clients?
- Is there a particular school of thought that you’re trained in?
- Do you start with some sort of formal evaluation or 360 feedback process?
- How do you think about quantifying results for your clients?
Individual vs. Organizational-focus
Coaches also tend to either focus on working with you as an individual, or working on your organization through you.
The individual approach emphasizes identifying your personal strengths and weaknesses as a leader and working on those (Rich’s approach above is a great example).
Whereas the organizational approach will evaluate what kind of strengths and weaknesses your organization has (sometimes or often as manifestations of your own personal leadership style), and work with you to help fix those.
There are a number of different approaches I’ve seen here. Patrick Lencioni’s The Five Dysfunctions of a Team for example focuses on a concept called Organizational Health that can be boiled down to:
- Absence of trust
- Fear of conflict
- Lack of commitment
- Avoidance of team accountability
- Inattention to team objectives
Whereas Matt Mochary’s The Great CEO Within focuses a lot on elements of team productivity, such as effective meetings, decision-making, 1–1s, and other organizational basics. (His entire curriculum is available online here)
I’ve been fortunate to work both with Patrick Lencioni’s Table Group for an 2-day executive offsite that helped us diagnose a number of team issues, and gave us a lot of good frameworks and practices to focus and improve on.
I’ve also worked with Sabrina Wang at Mochary Method, who helped me implement frameworks and best practices to improve my 1–1s, make our meetings more productive, come up with better OKRs, make better and faster decisions using RAPID, and many other things.
The one thing I’ll say here is that most executive coaches will have an individual-focus, but some will also be able to help you think about and diagnose issues at the organizational-level.
This can be really helpful as your organization grows quickly and the systems and processes that you use to run your business need to constantly change to meet the need of the stage of business you’re in.
The downside of an organizationally-focused coach can be that they’re sometimes quite opinionated about the best practices to follow and processes to implement, so if that doesn’t align with you and how you want to run your business, it may creation some tension.
For example, they may emphasize a focus on transparency across the company that you just don’t feel comfortable with. Or they may want you to spend a lot of time implementing a really specific meeting structure across your organization but you just don’t want to have to be so authoritative and in the weeds around how every team at your company operates.
One perspective is that a coach that can help you implement organizational best-practices may be better suited for first-time founders or founders that don’t have a good supporting COO (in theory, a good COO should be familiar with and able to implement a lot of the organizational best-practices mentioned above).
The counterargument there is that startups can sometimes grow so quickly that unless you already have the very specific experience dealing with the kinds of problems that come up at different stages of growth (e.g. people becoming territorial, lack of clarity around how decisions are made, information-sharing issues), having someone who can quickly help you diagnose problems and implement fixes will save you a ton of time and headaches.
Some questions to see how individually or organizationally-focused a coach is:
- Do you have a philosophy around how an organization should be implementing processes and best practices?
- How in the weeds do you like to get on organizational processes with your clients?
- How much time do you like to spend on working on individual vs organizational-level issues?
- Do you have first-hand operating experience running a startup? If so, what stage?
Strategic vs. Tactical
Some coaches are going to be much better at helping you with high-level business strategy — you can talk to them about things like fundraising, product pricing, new product development, and market positioning.
Think of these kinds of coaches as external board members. They often have real-world experience to draw on, can provide unique insights, and can be tremendously valuable at helping you think through problems that only you are in a position to decide at your organization.
The thing is, most people are not simultaneously good at or interested in both strategy and tactics. Strategy requires high-level thinking, lots of questioning, and the ability to do deep pattern matching.
Tactical thinking, on the other hand, takes for granted that a particular strategy or goal is the right one, and is more concerned with the most effective way to get it done.
You don’t typically want the same person who’s responsible for executing something to also be constantly be thinking about whether it’s the right strategic approach to take — that’s a recipe for going in circles.
You may or may not want a coach who likes to spend a lot of time discussing business strategy. If you find yourself spending a lot of time thinking about strategy, and want someone to bounce ideas off of, then it can be great.
If, on the other hand, you feel quite confident in the direction your business is going in, then it can be annoying to have someone be constantly questioning your fundamental assumptions and approach.
Some questions to see how strategically versus tactically-minded a coach is:
- What is your approach to problem-solving with your clients?
- In what areas do you typically find yourself being most helpful to your clients?
- How do you define success in your coaching relationships?
- How do you handle situations in which a client’s business is struggling?
Challenging vs. Supportive
To put in bluntly — do you want a boss or a therapist?
You may be looking for a coach who will challenge you. They may hold you accountable and ask you direct questions about why you didn’t do what you said you’d do, or why you didn’t get something done. This can be quite uncomfortable, but it can also be really helpful depending on your style and what you’re looking for.
Most startup founders don’t really have a lot of people around them that challenge them, and you may be the kind of person who likes a good challenge.
On the other hand, you may not want someone who is so confrontational. If you’re going through a rough time personally, suffering from burnout, or already feeling a lot of pressure, then piling on more isn’t necessarily going to help. You may want someone who has a softer, more understanding, and gentler approach.
Most coaches will tell you that they have high standards and hold their clients accountable, but when push comes to shove, there are a lot of different approaches to how that’s actually accomplished.
Some questions to determine how challenging or supportive a coach is:
- How do you handle a client who isn’t meeting their goals?
- Can you share an example of a time when a client was facing a significant obstacle or setback?
- What do you believe is the key to motivating your clients?
- How do you provide feedback to your clients? What’s an example of some feedback you’ve given?
There are so many different styles and personalities out there, on top of what I’ve mentioned above, that at the end of the day the most important aspect of any coaching relationship is whether you resonate with and trust your coach.
Someone I spoke to recently who helps connect startup founders with coaches told me, “I’d pick a good coach who I resonate with a lot over an amazing coach who I don’t resonate with any day.”
If you don’t trust your coach, respect them, feel like they get you, or like you can really get vulnerable with them, then you’re wasting everyone’s time. One of the keys to a good coaching relationship is the ability to share things that you wouldn’t share with anyone else.
It may take some time to figure out if you really resonate with a coach, and may require some trial and error and a few false starts. You may decide on the first call that you really like someone, or you may be intrigued but not really sure.
I encourage you to give it a shot, especially if you haven’t worked with a coach before and are generally skeptical.
At the end of the day, it’s not that high-risk to try it out. Most coaches will do a trial session or two with you before committing, and even then the typical up-front commitment is only three to six months.
Other things to consider
Connections to valuable resources
Depending on who you work with, a coach can be really helpful for introductions to people and sharing other resources that you may need but not know about.
For example, at One Month we needed help with pricing strategy and Rich introduced us to a consultant who was able to work through this with us over a number of working sessions. It was incredibly valuable and we never would have found him otherwise.
Coaches can make introductions to other startup founders who have gone through similar situations, investors, other consultants, potential partners, and more. Be sure to ask.
Of course, any good coach should ask you for feedback on their style and approach, and should be able to adjust based on what you need.
In fact, it’s a red flag to me if they don’t incorporate feedback (in both directions) early and often in your coaching relationship. Like, every session.
And don’t be afraid to give real and honest feedback!
If it’s uncomfortable for you, you should probably force yourself to — most founders and people in general are bad at giving concrete and tangible feedback, but it’s important, so it’s good to practice. Good coaches are trained at being able to take direct or difficult feedback (e.g. “This isn’t really working for me”), not take it personally, and adjust.
Moving on from a coach
In most coaching relationships, there comes a time when you feel like it’s time to move on.
Often this is because you’re not getting as much out of the sessions as you used to. Or the circumstances that you’re facing has changed and your coach is no longer the best suited person to help you.
This is incredibly common — and also somewhat inevitable.
But before deciding it’s time to move on from your coach, there are two important things to consider:
- Are you fooling yourself? It’s also quite common that once you get through the low-hanging fruit — the areas where you can make meaningful process very quickly — that things start to get tougher and more uncomfortable. That’s ok. Sometimes these can be the areas where the most meaningful change can happen, and it can take a while to get there.
- Have you given feedback? Before assuming your coach is no longer right for you, consider whether you’ve given them direct and honest feedback, and time to adjust their approach and style to what you really need. Don’t assume they can’t do it if you haven’t given them an opportunity to.
That being said, if it really is time to move on, any good coach should be able to handle this conversation and process elegantly. They will understand (it’s an important part of the job after all).
So it’s time to address the big question: How much does it cost?
Executive coaching can be expensive, and many founders who haven’t worked with a coach before can experience sticker shock when they first hear the price:
I’ve worked with coaches that charge anywhere from $3k to $10k per month.
It’s usually stage-dependent, so very early stage founder coaches might be in the $2k to 5k range whereas later-stage founder coaches are probably closer to $5k to $10k.
It’s most common for coaches to charge on a monthly basis, and offer either 60 minute sessions every week or 75–90 minute sessions every other week, with ad-hoc availability in between as important things come up (three sessions a month with two scheduled and one ad-hoc is also somewhat common).
Of course, you can find cheaper coaches and people who charge on an hourly or a per-session basis, but most coaches price based on the value they’re able to provide for a business, and prefer to build a longer-term relationship with fewer clients. Think of it like hiring an employee who makes you more effective.
After a trial session or two, usually you’ll agree to some upfront commitment (often three to six months, but sometimes as much as a year), and then go month to month thereafter with the ability to cancel at any point with 30-days notice.
Some coaches may also agree to lower their fee in exchange for a portion of it to be paid with equity, but that’s not as common and I wouldn’t recommend it unless you know they’re worth it. Equity is expensive and you can always negotiate an equity component of the fee later on, after you’ve already gotten started.
Finding the right coach
So you’re seriously considering working with a coach… how do you find a good one?
A lot of coaches work individually and can be hard to find online. I recommend reaching out to other startup founders you’re friends with and asking them who they have worked with and would recommend.
There are also coaching groups or organizations you can explore, such as:
As well as coaching matching platforms, including:
If you’re really struggling to find the right coach, shoot me an email at firstname.lastname@example.org, and I’d be happy to try to make some specific recommendations based on what you’re looking for.
(I’m also exploring taking on a limited number of coaching clients myself, so if that’s something you’re interested in, let me know.)
Once you have a list of coaches you’re interested in potentially working with (I’d limit this first list to 3–5 so you don’t get overwhelmed), reach out to and set up some short conversations with a few to see whose approach you like best.
Consider the questions I’ve mentioned above as well as:
- What’s your coaching philosophy and methodology?
- Do you have experience coaching people in similar roles, industries, or stages of company?
- What kinds of clients would you not be the ideal coach for?
- What are some challenging situations you’ve helped other founders with? How did they turn out?
- What are some of your favorite coaching resources for founders?
- What tools or assessments do you use in your coaching?
Also you can totally ask to speak to some other founders they’ve worked with as references. That can be time-consuming — and you’re likely to hear glowing reviews from clients they’re currently working with — so if you want a little more transparency you can try to ask for to speak to former clients that they no longer work with as references.
That being said, choosing to work with a coach is relatively low-risk if it doesn’t work out, and there’s nothing as good as just trying it out, so if you’re on the fence I encourage you to jump in and give it a shot.
…And that’s all! If there are any important pieces I missed, or questions still on your mind, please let me know by commenting here and I’ll either add them to this post or write a followup.