Harnessing Your Leadership Potential: Why Staircase Ventures Invests in Executive Coaching for Founders

It’s no secret that the best athletes in the world work with a coach. At all levels of sport, from recreation to the Olympics, coaches help athletes reach new heights and perform at their best. So why are there so few startup founders who have a coach?

At Staircase Ventures, we believe that professional, results-focused, one-on-one coaching can dramatically improve a CEO’s leadership abilities and their company’s business results. We have observed that regardless of a CEO’s background and experience, an effective coach can lead to improved performance in critical areas such as objective setting, having difficult conversations, effective listening, and team motivation.

That’s why, as part of our Founder Growth Platform, Staircase Ventures pays for six months of executive coaching for all CEOs in our portfolio. The CEO and coach work together to develop a confidential, structured, and targeted approach with clear goals through regular one-on-one meetings.

Our CEO Coaching program was designed in partnership with Mike James Ross. Mike is the former Senior Vice President and Chief Human Resources Officer at Simons, an ex-McKinsey consultant, the co-author of “Intention: The Surprising Psychology of High Performers”, the founder of a successful edtech startup, and a leading executive coach.

Our Senior Associate, Robbie Marks, sat down with Mike to learn more about his perspective on coaching and the benefits of coaching for founders. Here is a summary of the conversation:

Benefits of Coaching

There are two key benefits of executive coaching for founders:

1. Building a foundation of self-understanding; and
2. Leveraging that self-understanding to develop the necessary skills and mindset to become a better leader.

Coaching helps founders discover a deeper sense of self, a crucial ingredient to thriving as a founder over the long term. “When things are going well, it can be easy to be a founder. Customers are knocking at your door; VCs are eager to fund you. But when things are hard, it can be very lonely”, Mike explains. “Coaching can help provide founders with a self-understanding and bedrock foundation so that even in those difficult moments, they can say, I know why I’m doing this, I know who I am, I know my purpose.” Founders start their businesses because they’re driven to solve a problem. “Coaches can help founders articulate that purpose, giving them a solid base to push against when times are tough.”

With a foundation of self-understanding, founders can begin honing the skills necessary to become strong leaders. Founders are often highly skilled at something, whether it be coding, designing products, or closing sales. Their innate skills and experiences led them to where they are today. Yet, as the popular saying goes, “What got you here won’t get you there”. A coach can help a founder close that gap.  

Common Skills Founders Work on in Coaching

Some of the more common things founders work on in executive coaching include:

Time management

When we talk about time management, we don’t mean how to use calendars and to-do apps. In coaching, time management is discussed at a deeper level; what are you spending your time on and why are you spending your time on those things? Mike explains, “Often, I find that when I work with founders, they’re buried under tasks that could either be delegated, should just not be done at all, or things that should be deferred. The decision-making around where a founder spends their time is ineffective. Why are you doing this and not letting somebody else do it? These are the questions where you might get into an interesting conversation of what it is that’s important for a founder and how they can become more effective as leaders.”

Communication styles

“We do a lot of work with founders with communication styles. As a founder, you have this really interesting complex web of stakeholders that you communicate with. You have to communicate with co-founders, employees, customers, and investors. Each of them requires different communication styles and different tools. Successful founders often have strong communication skills but have not yet necessarily honed this kind of multivariate approach.”

Motivating others

“Founders often come to coaching sessions looking to improve their ability to convey a vision and motivate others.” Motivating and inspiring others is a complex skill, and while communication is an important component, founders will also work on empathy, accountability, integrity, decision-making, and goal setting with their coach.

Common Barriers to Working with a Coach

Often, people can be apprehensive about working with an executive coach. Some of the most common reasons (or barriers) are:

1. A negative perception of coaching;
2. Fear of discovering the truth; and
3. Thinking that coaching is a waste of time.

Historically, coaching has been viewed as a remedial solution. Many have the (incorrect) notion that coaching is only needed when something isn’t working. With this perception in mind, founders may believe themselves to be inadequate or not good enough if they feel the desire to start working with a coach. In reality, coaching should be approached with a proactive, positive mindset, viewing coaching as an opportunity to improve, not a means to fix a problem.

Founders might be afraid to face the truth. “They likely don’t want to open the Pandora’s box,” Mike discusses. “For example, I used to be a finance lawyer, living the “high life”, working in Boston, London and New York. If you approached me during that time and told me to engage with an executive coach, I might have said “No” because I knew that the answer to the question “What’s important to you?” would tell me to stop this career trajectory, even though I was enjoying it at the time.” The fear of self-discovery is common, but engaging with coaching and finding your purpose will enable founders to become the best versions of themselves.

Lastly, building a startup is demanding. Founders have negative time and the thought of setting aside a few hours every couple of weeks may seem like an impossible ask. Understandably, founders might say “I don’t need coaching right now. What I need is another developer or another 100 customers.” Pushing coaching to the back burner to focus on tactical problems likely makes a lot of sense for founders who are in the thick of things. However, as Mike explains, “Spending time on the broader skill development and self-discovery process that is afforded by coaching will help founders be more effective at all the rest of the tactical things they need to do.”

For these reasons, Staircase Ventures believes that all CEOs should engage with an executive coach, not because they “need” it, but because it helps them continuously strive for greatness.

How to Prepare for Your First Coaching Session

Preparing for executive coaching is key. Mike suggests asking yourself two questions: “Why do I do what I do?” and “If I could get better at anything (in the context of work/ being a founder) what are the things I would try to get better at?” Having starter answers to these two questions helps founders come to sessions with an understanding of what they’re looking to gain from coaching. This will change over time and a coach will help you figure out your path. “But if you sit down at the first session and say to your coach, “What can you do for me?” it’s likely not going to be a productive relationship.” Be prepared and focused and you’ll get the most value out of your coaching experience.

How the Staircase Ventures Coaching Program Operates

When a company joins the Staircase Ventures portfolio, Mike and the founder have a conversation to get an understanding based on that initial question: “What is it that they’re hoping to gain from executive coaching?” They will also discuss what the founder thinks might work well for them, how they like to work, how they learn, and how they grow.  With a solid understanding of the founder’s goals for coaching, Mike will pair them with 2-3 coaches to have initial conversations. Based on a combination of (i) the needs of the founder, (ii) the skills and experience of the coach, and (iii) the sense of connection that both have with each other, a match is made, and founders begin their six months of coaching provided for under the Staircase Ventures Founder Growth Platform.