Grow Faster: Why & How to Hire an Executive Coach

Leadership is about getting others to do what they can’t do by themselves. The minimum set of traits for a good leader include: vision, optimism, grit, humility, vulnerability, curiosity, and empathy. But that only gets you to “good.” Great leaders need coaching to bring out the best version of themselves.

I recently stepped down as the CEO of LeadCrunch -- a company I co-founded with my partners Sanjit Singh and Brent Payne way back in 2013. The company spent three years bouncing around in the dark as we struggled to find traction. Those were the early years. Things got hard once we gained traction. Brent stepped out after eighteen months as he was having a family and needed a steadier source of income. A brilliant data scientist, he’s now running a machine learning team at Amazon. Sanjit and I built the company up until our Series B financing -- in less than 3 years we took the company from near zero revenue to reach #35 on the Inc 5000 list of the fastest growing privately held companies in America (I hope the company will make specific number public). Sanjit stepped away from the business when he sold his shares after our Series B in early 2019. I lasted another 2 years… wow… Those were the most fun and hardest years. 

Our success can be measured in many ways. I think the most important measure is how well we developed people. A business is the product of people and systems. If you grow people and develop systems for them to create value, you will get robust financial metrics. And we crushed those metrics as we grew faster than almost any other marketing technology company in history. 

It takes a diversity of talent and team grow a company. Customers, employees, suppliers, distributors, investors, and many more. The role of an executive, especially the CEO, is to orchestrate all the stakeholders to focus on a singular goal. Guess what? This is really hard. Especially if you are trying to do something big, like creating and bringing to market an entirely new category of product.

The greatest limitation we all face is knowing what we don’t know. Read Adam Grant's "Think Again" if you don't believe me. The understanding of our ignorance and weaknesses is probably one of the most important skills for a leader to master. When we know we don’t know something, we know it’s time to partner with someone who does. Humans have cognitive limits. It’s called bounded rationality. We can only keep track of about 7 things in working memory at any time. Our brains become hardwired to find shortcuts so that we only pay attention to the things we think matter. Unfortunately, when running a business there are many more than 7 things that matter at any given time. This is why we must be aware of how our mental shortcuts influence our decisions (these are commonly called cognitive biases). 

I’ve spent more than a decade studying cognitive biases in my quest to bring artificial intelligence (A.I.) technologies to market. The greatest value of A.I. is to augment human intelligence, not replace it. As such, we must first understand what makes human intelligence so human. Answer: Our emotions combined with very limited processing power (as evidenced by bounded rationality and cognitive biases). 

To run a great company (or become the best versions of ourselves), I think it is critical for every leader to have a coach. During the course of a career, we will need multiple coaches -- each specific to the challenges we are facing. 

For CEOs of early-stage companies, good coaching is often the difference between the survival and failure of a business. A startup will typically have many dozen stakeholders -- all of which naturally have different agendas and objectives. Few will align with the best interests of the company. 

LeadCrunch benefited from two coaches. Scott Carter coached me and the team for about 6 months between our series A and B financings. During this time, we were growing revenues by more than 300% per year. It was frantic. I needed help learning how to think differently about the day-to-day problems of keeping our team aligned as I managed hundreds of relationships with investors, customers, and suppliers. Scott and I met when we were raising our seed round of funding. After initially declining to invest, Scott approached me several years later offering his coaching services. I hired Scott because he was formerly CEO of a company I greatly admired and had gone through similar challenges himself. He’s now a professional board member helping private equity owned companies grow. 

Most recently, I hired Glenn Gow to coach me on how to grow to the next level. I hired Glenn because he grew his company to about 2X the size of LeadCrunch without any outside investment. I am a huge fan of capital efficient businesses and find inspiration in those that manage to grow while maintaining healthy balance sheets. Glenn cold called me with his coaching services. Here’s the pitch he sent me on LinkedIn:

Olin,

My job is to help CEOs become even better CEOs.

I start by working with select CEOs for a few sessions at no charge.

If you'd like to explore a coaching relationship, please look at my website to learn more about me at www.glenngow.com.

When you’re ready, I’ll be here for you.

His opening sentence was relevant to me. That said, his message sat in my inbox for about 2 months before I responded. Turns out Glenn really only wants to work with CEOs that have made it to the Inc 5000 list. He wants to work with the best so that he continuously gets better himself. Once I did respond, Glenn proved his value in every coaching session. 

Here’s my recommendations for hiring a great coach for early-stage companies:

1. Chemistry. Coaching is not psychotherapy… but it’s close. Good coaching will be painful at times. Executives need to find a coach who can dig into the ugly parts of ourselves that need to be addressed. Confidentiality is one of the great hallmarks of good coaches precisely because they are digging into the very things that make CEOs vulnerable. So hire a coach you trust and respect. 
2. Experience. Good coaches have done what you are trying to do. They’ve played the game and spent years studying how to get better. Think of the best coaches in professional sports -- all of whom were players themselves. It is exceedingly rare to find a great coach who never played the game. Think: College players who went on to become students of the fame such as John Wooden, Pat Summitt, and Bill Belichick. Or pros that won championships before turning to coaching like Phil Jackson, Vince Lombardi, and Don Shula. 
3. Focus. Pick a vexing problem to solve together. For most companies, this involves the alignment and focus of teams. Having a clear problem to solve will make coaching far more effective. 

Here’s a list of 11 questions (and the right answers) to use to pick the right coach:

1. Tell me about your experience as a CEO and/or starting a business from scratch? or How many years did you solve problems like mine? (whatever you are facing). (Right answer: Make sure they have solved problems similar to yours. You need someone who has “been there and done that” at least once before. Nothing can replace experience.) 
2. Have you raised money from institutional investors? If so, how much? (Right answer: Yes and at least 2 rounds where each was greater than $5 million). 
3. Have you sold a business? (Right answer: Yes.)
4. Have you had a business fail? (Right answer: Yes. Beware of anyone who claims a perfect track record. They are either lying or likely too confident in themselves.)
5. What is your superpower? (Right answer: Bringing the best out of others by helping them amplify their strengths and mitigate their weaknesses). 
6. What motivates you? (Right answer: The satisfaction of seeing others grow.)
7. What is your weakness? (Right answer: They know they have a weakness and are happy to discuss it.)
8. Do you have direct experience solving the problem I am facing? (Right answer: Yes. Repeat this question in different ways during the conversation. Experience trumps almost everything.)
9. How often do we meet? (Right answer: At least every 2 weeks. Weekly is better. Coaches should also be available on an as-needed basis for things that come up suddenly.)
10. How much does your coaching cost? (Right answer: At least as much as a lawyer. Never “hire” a free coach. You will get what you pay for.)
11. Have a conversation to determine if the person is more curious or more judgemental. Pick a subject that you know a lot about and ask open-ended questions to see how they think. You want someone with a lot of curiosity and little judgement. For example, I know a lot about predictive analytics. So I would ask things like: Tell me how you think about predictive analytics software? Do you have any packages that you love or hate? (Right answer: They will ask for more context before giving any answer.)

Here’s what you MUST avoid. These 3 things are often confused as proxies or alternatives to coaching. They are not. These are toxic:

1. Listening to everyone. You have limited time and attention. Most people don’t know how to start or grow a company. Yet, almost everything thinks they do. Listening to them will create chaos. Especially listening to “investors” who have not invested. Keep focused and beware of your biases and blind spots. Think like a scientist: Use evidence to make decisions. Not other people’s opinions. 
2. Participating in “startup groups.” Almost without exception, these are clown shows that amplify the dumbest ideas in any room. Most of these groups are filled with people who have never founded a business, never hired or fired employees, never invested into early-stage companies, yet spend a fantastic amount of time talking about startups as an exciting life adventure. I thought these groups were bad in San Diego (and they are) only to learn they exist in almost every market. Before listening to an "expert" make sure to verify their startup experience on LinkedIn, Crunchbase, Angel List, etc. Believe me: Startups are much easier to talk about than build.
3. Trying to copy the success of others. Research by Gallup on more than 100,000 managers shows the best executives all have their unique styles. Read “First, Break All the Rules” before you start trying to do what worked for Bill Gates, Elon Musk, and Jeff Bezos. Chances are good that what worked for them will doom your own enterprise.

If you've made it this far, then you might be interested in knowing that I am also a coach. Albeit selectively. I'm not for everyone. After our time together, Glenn encouraged me to also offer coaching services to augment my Go-to-Market advisory services. If you want to know more, please visit OlinHyde.com or contact me on LinkedIn.