What can someone learn from working with an executive coach? (with Andy Sparks)
Should you have a coach? What are the types of things you can learn?
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Every professional athlete works closely with a coach - someone there to push them to become highest-performing version of themselves. Most people do not have this type of resource in their professional life. Scaling in your career feels more like a single player game; you have to set your own goals, figure out your own plan, and hold yourself accountable. You have to just “figure it all out.” While it is not very common, some high-performing people in startups end up working with a coach. An executive coach. Someone to help them (and their companies) achieve their most ambitious goals.
So what is it actually like to work with an executive coach? What can you get out of it? When does it make sense? What are some of the things people learn (and perhaps what can you implement today just from reading this essay)? We cover all that and more in this essay with Andy Sparks.
Before we dive into the details, tell us a bit about your background.
I was born in Denver, Colorado and in the suburbs there until the middle of sixth grade (11) when my family moved to the suburbs of Philadelphia. I grew up a competitive swimmer and loved computer games and legos.
I went to The Ohio State University from 2007-2011. I started college as a rule-following evangelical Christian majoring in history and graduated as an agnostic startup junkie. I changed my major several times and ended up making my own degree in a combination of history, economics, and business. A huge part of my college experience was joining a club of startup nerds called The Business Builders Club. Just about everybody from that club has gone on to become a VC, found a startup, or bootstrap a business. Our most notable alumn is definitely Ben Gilbert, host of Acquired.
When at Ohio State, I joined a small web development company and started designing apps and bringing in new clients. The CEO gave me a front-row seat to the process of building a company, from product to sales and hiring. So in 2012 when I told him I wanted to fly to San Francisco for a YC interview, he fired me. While my two friends and I didn’t get into YC, we did get into 500 Startups. Our company, LaunchGram, was a sort of proto-ProductHunt where you could follow products and things like video games that had yet-to-release but you wanted to keep tabs on. While I still miss LaunchGram, we were in over our heads and ran out of money quickly.
When I got to California, Danielle Morrill had been a huge help in getting me plugged into the startup ecosystem. So when we ran out of money at LaunchGram, Danielle “acqui-hired” me (basically paying a signing bonus in an asset sale as a soft landing) into her startup, Referly. Referly had raised a seed round after they finished YC, but it wasn’t really working either. So we decided to try and pivot the company.
While fumbling around with a vague idea to start a data-driven media company, we discovered an opportunity to sell investors insights into which startups had momentum using aggregated publicly available information and machine learning. We went from $0 - $5M in ARR in 3.5 years, and we also built a daily newsletter with over 100,000 subscribers. Despite our momentum, we mistook what First Round Capital would now call “developing” product-market fit for “strong” PMF, over-invested in a sales motion we couldn’t afford, and ultimately sold the company. Harvard Business School still teaches a case study about Mattermark.
After Mattermark, I started what eventually became a digital book publishing company, Holloway, in 2016. At Holloway we wondered, “What if you could ask a book a question?” Today, by uploading a PDF to Perplexity or Chat, you can do exactly that. But in 2016 we weren’t there yet. We were on to something early, but if I’m being honest we were unfocused and weren’t clear enough on who our customer was. Holloway ended up as a boutique digital book publishing company with a beautiful front-end reading experience, but a far too complicated publishing system without enough payoff to make the friction worth it for authors. I’m proud of our work there, but this one taught me a lot. My co-founder, Josh, still runs Holloway today.
In 2020 I left Holloway and began coaching other startup CEOs. Today I work with 15-20 CEOs at any given time, ranging in size from companies with 5-100s of employees. Almost all of my clients are building B2B software companies and are usually venture-backed.
What led you to becoming a coach? What has been the biggest surprise in transitioning from being a founder to someone who supports other founders (as a coach)?
When I was at Mattermark, our lead investor, Brad Feld, encouraged each of us founders to work with a coach. I was twenty-four at the time, and I knew there was a lot I didn’t know. I began working with a coach and it was an eye-opening experience. A lot of my friends were founders, and I’d tell them what I’d learned from her over dinner or drinks. Unintentionally, I found myself using what she’d taught me to help my friends informally.
Fast-forward to 2020, and I was considering what to do next. A friend asked me if I’d ever considered coaching. She worked with a coach, and she said that sometimes our dinners felt just as helpful as her time in sessions. I’d never considered it, but the more I kept pulling on the thread of coaching as a thing to do next, the more “right” it felt.
The biggest surprise from the transition from founder to a supporting role has been discovering a new mindset of ambition and growth. As a founder, you have this clear vision of the mountain you want to climb. As a coach, I haven’t had some big vision of being the best coach (I don’t even know what that means) or to be famous or some big objective. I just want to learn more about the world, how to help my clients, and get better each day. Sometimes it feels disorienting not to have such a big vision like I did when I was a founder, but at the same time it feels great to have the flexibility and freedom to follow my curiosity.
Why should someone get a coach? Who is a good candidate for having a coach? What do you see as the difference between a coach and perhaps a therapist or psychiatrist?
Anyone doing something substantially hard can benefit from the right coach. There are so many reasons a coach can be helpful. If you’re a solo founder, you might need a thought partner. If you have co-founders, sometimes you need to talk to someone about issues you’re having with them. A lot of the time I meet founders in an exploratory call and they tell me, “My spouse told me I can’t keep talking to them about my problems at work.” In short, if you’re doing something hard and find yourself regularly frustrated, stressed, anxious, or generally unpleasant repeatedly, I think it’s a good idea to find someone you can talk things through with regularly.
The “coach vs. therapist” question is a good one, but the answer is hard. There are so many different types of people who call themselves a coach and there are so many different types of therapy. Coaching has its roots in therapy and both use question-asking as a medium for exploring issues. But the variance from coach to coach and therapist to therapist is going to be huge. I think anyone interested in growing as a leader would benefit from exploring both.
One big difference, often, is that a coach is going to have prior operating experience as a founder. That means that they understand your problems (and feeling understood is a huge part of coaching and therapy), identify the root causes of your problems, and help you avoid making the same mistakes.
A lot of coaches will give a canned response about coaching being about the future and therapy being about the past, but I think that’s a load of garbage that frankly isn’t well thought through.
Great therapy will help you identify developmental issues, help you become aware of the ways you defend against discomfort, help you notice and feel your emotions, explore patterns in your relationships, grow your self-esteem, and more. I think I do a lot of that in my work, too, but in a much more subtle way that happens as we work through whatever thing is most salient for the founder in any given session.
How should someone vet a coach? How should they know the coach is a good fit for themselves? What should the interview process be like?
I always point people to two resources on this subject: How to Find (and Choose) a Coach (Ed Batista, 2013) and Homebrew Ventures’ Guide to Executive Coaching (Beth Scheer)
Beyond that, there’s a concept from therapy called the “Therapeutic Alliance” that I think rings true for coaching, too. For the relationship to work, three elements have to be present:
Connection: both people feel a sense of connection, safety, trust, and interest in working together.
Clear Goals: there’s a shared understanding of what the client wants to get out of the work.
Clear Methods: the coach and client are clear about how the coach will help the client achieve their goals.
I recommend founders interview at least three coaches, if not as many as five. Ask your friends or investors if they know of any great coaches. Ed Batista is my coach and I can’t recommend him highly enough.
As you interview coaches, ask them why they became a coach, ask them about their methods. And honestly, ask them to do a trial session, and be willing to pay for it. If one session doesn’t feel like a good fit, ten are unlikely to feel any better. You should leave a call with your coach feeling like you can tell them things you’ve been withholding from others.
Some clients want a coach to help them better manage an emotional issue (e.g., anger, anxiety, etc.), and others want someone to be a bit more practical and problem-solving. Make sure you’re clear about what you want.
I have a triangle I sometimes show people that helps to frame the different types of coaches out there. One point of the triangle is the “ex-operator,” another is the “psychologist,” and the third is the “guru.” Some coaches have a PhD in psychology and startup experience, some are ex-founders who wear crystal necklaces and want to take you to South America to do ayahuasca. Think of where you want your coach to sit in the triangle and vet accordingly.
Imagine I sign up to become a client of yours. What happens next? What is the typical engagement like? What are the types of questions that clients come to you with?
When I begin working with a client, I have them complete an intake survey. While this helps me get to know the client, it also forces them to sit down and reflect for a couple hours. My clients regularly remark on how long it’s been since they thought about some of the questions in my intake survey.
Next, we start with sessions. I don’t require any kind of minimum sessions, and I think founders should beware of anyone who does. You should be able to opt-out anytime you want. People should get locked in prison, not coaching relationships.
By the time we have our first session, we will have talked about my methods, which you can also read about here.
In the first few minutes, I’ll ask some variation of the question, “What would you like to get out of today?” Clients usually have a list of 1-5 issues, generally problems that are taking up a lot of space in their mind that they’ve been unable to solve on their own. These range from decisions about underperforming team members, team motivation, disagreements stemming from poor communication, how to increase the sense of urgency on the team, unpacking major crises, how to run a good off-site, and many many more.
While many of the questions clients have are posed as if they want an answer, I rarely give one. “How do I handle this underperforming team member?” is not a question I answer directly with “how-to” right away. My first priority is to diagnose the root cause. If the team member is underperforming, do they know? Did the client set clear expectations? Did they hire the wrong person? We’ll spend a lot of time diagnosing what’s really going on, and we may end up with several action items for the client to effectively solve the root problem(s) and make sure they don’t keep making the same mistakes.
What advice do you have for someone who is eager to work with their coach in a productive manner? How could someone set up their relationship for success? How should a client measure the success of their coaching relationship?
First of all, don’t get a coach because this article told you to or your friends are doing it. Work with a coach because there are tangible challenges you’re facing that you feel stuck on. Work with a coach because you’re interested in having someone in your life who is a professional at helping people change and grow.
Show up on time. Prepare for your sessions, even if that means thinking about it for ten minutes in the shower or over your morning coffee.
I recommend meeting every-other week for a while, maybe even every week if you feel you can afford it. The more often you meet, the more likely the coach is going to get to see “the real you” vs. “the polished you.” After a while, you can meet less often, but let the coach into your world and hit the ground running.
Be honest. A lot of difficulty in our lives comes from a feeling of shame. If you’re yelling at people at work, tell your coach. If you’re scared of fundraising, tell your coach. Sometimes people can sugar coat things because they want their coach to like them or respect them, especially if the coach is a famous founder or something like that. Don’t sugar coat it. Open up.
As for evaluating coaching, Donald Kirckpatrick developed five levels to evaluate a coaching engagement in his book, Evaluating Training Programs:
One: Did you like it? Simply, do you enjoy the time with your coach and the growth you experience between sessions?
Two: Did you learn it? Are you learning new things? Are you developing new skills?
Three: Did you use it? Are you actually using the stuff you’re learning? When your coach gives you a framework, do you put it into practice? Or do you just archive the email all the time?
Four: did it impact the way you show up? So you’re learning stuff, you’re using it, but is it helping? Are people in your life noticing you’re growing?
Five: what was the return on investment? Calculate the ROI. What are the tangible and intangible benefits? Did you increase sales? Add accounts? Decrease costs? Decrease turnover? Reduce complaints? Is the team working better together? Is morale better? Try and do some napkin math on the benefits, then do benefits-costs/costs*100.
What mistakes do you see as people transition from being mainly an individual contributor to a people manager to a manager of people managers? What does it mean to become a good manager? How can I do that?
The number one challenge people have in transitioning from an IC to a manager is unlearning their tendency to see a problem and do it themselves. Keith Rabois has a great metaphor for this he calls “editing vs. writing” (You can read the full transcript of his lecture here). Think of a newspaper. An IC is a writer at the newspaper and a manager is an editor. If an editor sees an opportunity for a great story, they’ll assign a writer to the story (they won’t write it themselves). But new managers have to unlearn the habit of writing the story themselves. Keith also talks about how this metaphor extends. Editors have to “take out the red pen,” give feedback, and ask for improvements to “drafts” of IC’s work.
To make it practical, imagine you’re a new manager. Someone on your team comes to you and says, Mrs. Boss, “There is a problem.” A common mistake of the new manager is to respond by trying to solve that problem themselves. A more experienced manager will respond by asking the IC what they’ve done to try and solve the problem, and if they haven’t tried anything they will ask them to come up with a few options to solve the problem and make a recommendation.
Another great way to think about management comes from Dee Hock, the founder and CEO of VISA. Dee says that people get management all wrong. They think management is about managing “down” or managing people who report up to you. But the reality is that 50% of your time as a manager needs to be about managing yourself. Are you doing what you say you will? Are you acting with integrity? Are you hiring the right people? If you believe this, you will also hire people who are good at managing themselves, and you will not need to micromanage them.
There’s a giant section of every bookstore on management and how to become a good manager, so while I don’t have a simple answer, I can give you one more way of thinking about the skills of a great manager. Michael Dearing has a great course called General Management, and in that course he talks about Daniel McCallum, and early management pioneer who professionalized the U.S. railroad system and helped the Union win the Civil War. McCallum developed six principles for assessing general management that it would be wise for any new manager to consciously work on (Dearing translated into modern English and they are below):
Ability to get everyone aligned behind the right projects & investments.
Ability to make sure responsibility & authority are allocated appropriately.
Ability to measure how things are going along the way.
Ability to stop and make corrections if things are going badly.
Ability to do 1-4 with humanity and respect for other people.
I recommend taking Dearing’s course, and Dave and Marsden Kline’s MGMT Accelerator is also a terrific course in general management skills.
If you could come up with one piece of advice and plaster it in the sky for every current startup founder to see - what would it say? Why?
The best hiring process in the world will mishire 30% of the time and closer to 50% of the time with executives. Be ready to fix your mistakes. You make two decisions to hire someone: first; the day you make them an offer, and second; on day 89 when you decide to keep them on board. If someone is not blowing you away by day 89, you need to fire them and start over. You may know sooner than day 89. If you do, cut your losses. But do not keep them on past day 89 if it’s not working. Save yourself the recruiting fee. Do not wait and hope for magic that is not coming.
What do you think is the most unexpectedly challenging aspect of starting and running a company? What attributes of company building do you see people get wrong most often?
The amount of conflict the average person can get away with avoiding with relatively minimal consequences is a dramatically higher amount than what an executive at a company can tolerate without putting the company (and their career) at risk.
Conflict can be within oneself: “to be conflicted” about whether to do A or B. A founder or executive has to learn to address this state of being conflicted and decide.
Conflict can be between others: one executive thinks the company should do X, the other thinks Y. A manager sees underperformance where an individual contributor sees unfair expectations. An executive proposes to solve a problem one way and their CEO has this unexplainable gut feeling that’s not right—the CEO cannot avoid the feeling and needs to lean into the discomfort so the executive and the CEO can get to the bottom of it together.
All the different stakeholders—customers, employees, investors, vendors, and the broader industry community—will at some point be upset about something.
On top of the conflict comes the crushing sense of responsibility. You are the CEO. There is no boss to blame. If you’re upset with your staff, who hired them? You did. Every conflict, everything that seems to go wrong stares back at you in the mirror with a sense of cruelty that will undermine your sense of self-worth and confidence if you let it. You must not let it.
You then begin to lose patience for the people around you who are less conflict-tolerant, who act less responsibly. Judgment creeps in where compassion would better serve you. Embracing the scale of conflict and ownership without succumbing to cynicism is the mountain every entrepreneur has to climb.