Marcy Swenson
Helping founders grow as fast as their companies

My Writing

Insights to help you thrive.


I'm Thinking of Hiring an Executive Coach. What Should I Know?

We have been coaching and advising CEOs and founders for over twenty years leading to the creation of over $40 billion in current market value (as well as being former founders). We’re often asked -- “What is it that you do, anyway?”  

We (Marcy Swenson & Dale Jasper Stephens) hope to demystify the role a coach might play in your journey as a founder and how to select the right coach for you. We’re also excited to have an article to point people to when they ask us these questions.  :)

Few founders start with all the skills, self-awareness, habits and knowledge needed to grow their companies successfully. Finding an executive coach after raising a round of funding is becoming so commonplace that many venture firms have created rosters of recommended coaches for their portfolio companies. A few decades ago, having a coach meant you were the problem CEO -- the one that needed extra help. Today, startup CEOs are the elite athletes of the business world, and having a great coach is a competitive advantage for high performers.

Hang on. What is coaching?

Executive coaches engage in collaborative, confidential conversation, focusing on an individual’s (or team’s) learning and development. A coach is not a consultant (hired to give advice), or a mentor (focused on sharing their own relevant experiences), or a therapist (licensed mental health professional with experience dealing with mental illness), though they may at times give advice, share experiences, and provide emotional support.

Executive coaches help clients gain self-awareness, communicate more effectively, prioritize more impactful work, become better decision makers, understand their personal values and manage their attention and emotions. Coaches partner with their clients to establish development goals, and sometimes conduct and interpret 360-degree reviews, behavioral assessments or confidential interviews. Data gathered by coaches should be focused solely on your development, and is held in confidence between you and your coach. A founder or senior exec may choose to share learning objectives with key colleagues, at their discretion.

Although coaches are not in the business of giving advice, they need to be skilled at recognizing patterns of behavior, as well as understand the business and team environments their clients are operating in to be successful. A coach’s understanding of systems and patterns helps them to guide the client’s learning, and to ask questions that spark new and helpful ways of thinking. The best coaches are not highly dependent on specific tools or models, but rather adapt their use of tools to the specific needs of each client.

When should I get a coach?

Founders at venture-backed startups are most likely to look for a coach just after they raise Series A financing. They finally have the cash to pay for coaching, and they need to build their team (and themselves) quickly. Getting a coach at this stage can give you an edge over your competitors, and allow you to move and grow as fast as possible.

At earlier stages, founders are generally heads-down doing something they already know how to do, and scrambling to launch their first product. Coaches can be valuable during that process, but the general consensus is that it’s not necessary, and time can be better spent on getting your product out the door, and bringing on initial customers. When we have coached founders prior to product market fit, the sessions are further apart because there is less going on.

A coach is an especially good investment for a founder or leader who is taking on significant additional responsibility or learning a new set of skills. If you’re feeling overwhelmed, ineffective, or are getting feedback from colleagues asking for behavior change, you might want to hire a coach.

Why is coaching important? How will coaching help me build a more successful company?

Founders and CEOs are often the first people at a company to work with a coach, although sometimes it’s a VP on their team that first asks for coaching, the founder notices their increased effectiveness, and decides to give it a try themselves. Occasionally founders are self-conscious about using a coach to help them learn, but generally it’s seen as something that successful people do to get even better at what they do.

At the Director level, VP, and C-level, coaching is used to improve performance, as well as increase retention for key team members. Coaching enables leaders to see blind spots more easily and ask for help earlier, which both translate directly into better company outcomes, especially in a fast-moving startup.

The reason that coaching is less likely to be offered below the Director level is cost -- paying more than 15% of someone’s salary to a coach to make them more effective or retain them usually doesn’t make sense. There is an upsurge of online coaching solutions (some robots/AI, text based coaching, specific behavior change) that can effective, though not suitable for handling complex challenges.

When coaches are first engaged at a startup, coaches are usually hired based on the best fit for the executive who needs coaching. A seasoned VP of People can help with coach recommendation & selection, as well as make coaching a part of the Learning and Development process.

What should I expect?

You will get the most value from coaching if you are willing to be vulnerable about your toughest problems from the start, and if you work on the challenges in coaching that you are less likely to resolve on your own.

Your coach’s goal is to end every session with concrete steps to move you through wherever you’re currently stuck. Practically, that takes many forms -- sometimes it’s very specific goals such as “I’m going to have a difficult conversation with X person.” Other times it’s more broad -- “this week, I need to spend Y hours on recruiting.”

A good coach holds space for you to think through your issues and holds up a mirror. A great coach pushes you try new things, break mental models, and create multiple paths forward. A good coach makes you feel satisfied. A great coach makes you uncomfortable, but you know you’re learning.

What makes a great coach?

Getting a recommendation for a coach from someone you trust, who has successfully helped someone like you achieve the results you are looking for is a great starting point. Although coaches can be certified, that is not necessarily an indication of quality. Trust and chemistry are also important -- you’re going to talk to them for at least a few months, if not longer, and it really helps to look forward to meetings. They need to be within your budget, and available to work with you. Some coaching/clients have a strong preference about meeting in person, others want to meet virtually on phone or video. Both are very effective, unless you want to work on something that requires constant eye contact, like learning to read body language.

A great coach will help you with your initial objective, but also help illuminate your blind spots, and sometimes that will result in a new objective that’s even more meaningful or valuable.

Here are different ways to assess a coach:

  1. Client focus: the coach who works with brand new managers is less likely to also work with the CEO -- they are building different skill sets, and the CEO coach is generally going to be more expensive, so not generally a good investment for a new manager.  A coach might specifically work with sales or engineering leaders, for instance.

  2. Flexibility vs specialization: many master coaches are incredibly flexible -- they have a wide range of tools and skills, and they are choosing the right thing for each client in the moment. Some coaches use a very specific tool or methodology with every client; though it can be useful for learning a specific thing, they are less flexible overall.

  3. Operating experience: it can be incredibly helpful to work with a “been there, done that” coach-- they are not only focused on your learning, but also act as a thought partner on strategy, deeply understand the business environment, and the challenges of your role. It’s important that all coaches avoid just giving advice -- training and certification programs are fastidious about making sure new coaches don’t do this. A good coach will occasionally give you their perspective, but generally is helping you to develop your own. It can be hard to find coaches with hands on experience, as most execs stay in leadership rather than turning to coaching.  A coach who has been working with clients in a particular area for decades will often have the equivalent of operating experience, from having so many conversations with clients.

  4. Aspirational: your coach should feel developmentally ahead of you, especially in the area where you are looking to grow. If you’re looking to be more present and mindful, your coach should feel more present and mindful. If you want to be more assertive, your coach should model directness even in your initial conversation.

Where do I find a coach?

Your best bet is to ask founders and leaders you admire who are a year or two ahead of you for referrals. If you’re at Series A, ask the CEO of a Series B company. Asking a Fortune 500 CEO for a referral if you’re a seed-stage CEO doesn’t make sense, and vice-versa -- the needs and skills of a corporate coach are different than a startup coach. It’s perfectly reasonable to ask a coach to do a short sample session with you, so that you can see how it feels to work with them before signing up for an engagement. Many investors have a roster of recommended coaches, and incubators have message boards where you can find recommendations from other founders.  Other places you can ask for coaching referrals include your friends, and of course, Google.

We know first hand that being a founder is lonely, and we both wish that we’d had coaches when we were building our companies. No matter what stage you’re at, asking for help is a sign of strength, not weakness.  If you’re curious about coaching or are looking for coaching recommendations, please feel free to email either of us. If we’re not a fit for you, we will do our best to refer you to a great coach in our network.