Coaching

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how to Choose a Coach

Understand Your Objectives

What do you want to get out of the relationship? Put thought into what you’re trying to achieve.

Find Someone with Relevant Experience

It can be helpful to work with a coach who has traveled the path you’re navigating (i.e. a seasoned CEO who has built to scale). In the absence of direct experience, make sure your coach has experience working with people like you, and understands the unique challenges of building an early-stage startup. 

Coaches who don’t have this experience can still be helpful in providing basic leadership guidance - mission & vision, communication, etc. - but may not have enough context to help you navigate some of the specific situations you face as a CEO.  

Don’t Take a “One-Size-Fits-All” Approach to Coaching 

Reaching out to other successful CEOs can be a great place to start when you’re in search of a coach; just don’t assume that someone else’s endorsement will hold true for you. Coaching is highly personal, and it’s important to find a coach who suites your objectives and personal style.

Take a Test Drive

Coaching requires a high degree of trust; it’s important that you find a coach with whom you have a strong rapport with your coach. Don’t rush into it - take the time to get to know each other. Set up a 30 - 60 min. call with each potential coach on your list. Make sure they listen, ask questions, are able to connect the dots and share useful insight. Make sure you vibe with your coach; you’re looking for someone who can hold you accountable and help lead you to positive change, event when it’s somewhat uncomfortable. 

Methodology

As part of your call, ask the coach about their methodology. How frequently will you engage? How will they structure your sessions? Use this as a way to get a feel for what the relationship will look like, but also to make sure you understand how to get the most out of working with your coach. 

Talk to References

Just like any other interview, make sure to follow up by checking references. Talk to people who have worked with the coach you’re considering before to understand their style and how they engaged.