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A Guide to Finding A Leadership Coach

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Coach vs. Advisor/Mentor vs. etc…
Why and When You Should Get a Coach
Choosing the Right Coach
The Process
  • Mina Benothman's Headshot
    Mina BenothmanGrowth Marketing Manager
8 min

Scaling your early-stage company is both an exciting and overwhelming journey. For many first-time founders, understanding how your responsibilities and org should evolve along with your business can be tricky to navigate.

I sat down with Elle Destree, an executive coach and learning & development consultant, to hear more about the process of finding a leadership coach to help guide you through those transitions. She’s previously worked on initiatives at Facebook and Airbnb, and now works with clients in the software, entertainment, and biotech industries.

Coach vs. Advisor/Mentor vs. etc…

Although these titles get thrown around interchangeably, there is a nuanced, yet significant difference between who they are and what they can do for you. Whereas you might seek out an advisor or mentor who has specific experience in your field, a coach does not need to have experience in your industry — in fact, you might benefit from their outside perspective because the coach can offer you new ways of thinking.

A key difference is in how the coach shows up to the conversation. A coach will ask you questions, reflect your thoughts back to you, and note distinctions. They will usually not tell you what to do or prescribe advice. On the other hand, an advisor or mentor will often share their own experience, give you advice, or tell you what they think you could do in a given situation. Even though coaches and mentors serve different purposes, it doesn’t hurt — if anything, it could be more effective– to have both.

Why and When You Should Get a Coach

Many leaders hire a coach when they are going through a major transition within their company, such as a promotion, job change, or shift in responsibilities. You might also hire a coach when you’re going through a life transition, like moving cities or starting your own business. A coach can also help you make a decision about where to go next in your career, whether you’re trying to figure out which job offer to take or you’re thinking about changing industries entirely.

Regardless of your specific circumstances, having a clear idea of your developmental goals and what you’re hoping to gain from working with a coach is a good idea before starting to meet with coaches.

If you’re thinking about hiring a coach, ask yourself whether you’re willing to put in the work that coaching requires. You’ll want to be ready to meet with a coach for your sessions, but also to try new practices or self-reflection activities in between sessions. Getting a coach when you’re not open-minded, ready, and willing to change could result in a waste of time and energy — you really do get out of it what you put into it.

Choosing the Right Coach

Unlike Advisors and Mentors, it may not matter what industry the coach comes from because they’re not there to give you advice on your specific industry. Look for a coach that has rigorous training from a recognized institute or program. Ask the coach what kind of training they have, how long the program lasted, and whether they had supervision from an experienced coach.

Elle recommends working with a coach who has completed a 9-month to 1-year long certification program or has a credential from the International Coach Federation (ICF). Ask whether their training program included coach supervision, where an experienced faculty coach observes the coach and offers feedback.

The right coach can impact your professional and personal life in positive ways. The opposite can be said for a coach who isn’t a good fit for you. So don’t rush the process. Elle encourages her prospective clients to meet with at least 2 potential coaches before deciding. Without a point of comparison, it’s hard to get a feel for what is and isn’t going to work for you. A coach should offer you a complimentary “chemistry” conversation, where you spend some time getting to know one another. Use this time to ask them all of your questions.

The Process

Once you’ve decided on a coach, depending on the size of your company and who hired the coach (e.g. your manager), your company or the coach may do what’s called a 360-degree review. Essentially, they’ll collect feedback from your coworkers, direct reports, HR, and managers to get a better understanding of how you work, what your strengths are, and some potential opportunities for development. If the coach doesn’t do a 360, they will likely have an “intake” session with you at the beginning of the engagement so they can get to know you and your developmental goals.

A typical coaching engagement is on average about six months, and during that time you meet with the coach for about two 1-1.5 hour sessions a month with practice exercises in between sessions. There are many different approaches to coaching engagements, depending on the coach’s style and the expectations of your company, so ask prospective coaches how they typically structure their engagements before you hire them.


True development takes significant time, so you may not see progress right away. People learn faster when they aren’t given advice but instead, shown how to reframe and rethink how they navigate uncertainty or a problem that may arise, even though this approach can feel slower than simply implementing someone else’s advice.

Lots of first time leaders struggle with delegation as their list of responsibilities grows along with the business. I asked Elle how she would help a potential client approach this problem. To help them develop delegation skills, she would seek to understand what the client is fearful of with regards to delegation. She would then work with them to help them understand the opportunity delegation provides and to mitigate their fears.

By reframing in this way, the client may realize that they can’t do their job as a leader, i.e. create conditions for others to do their best work, if they’re scattered. By the end of the coaching engagement, the client may be able to have more capacity for delegation — by stepping back, providing more growth opportunities to their team, and not taking on more than they can handle.

Your relationship with a coach is different from a relationship with a mentor or a therapist in that you’re not looking to work together for years. An engagement can take more than six months but should take no longer than one year. If it takes longer than that, it’s probably a sign that something isn’t working– either you’re not being open enough to the change or you need a new coach. You might come back to a coach after parting ways with them for a while, but it’s a good idea to try to incorporate what you learned during the coaching engagement on your own for a while before continuing to work with a coach.


In the Bay Area, the cost of a coaching engagement can range from a couple thousand to tens of thousands of dollars total, depending on the experience of the coach and the depth of the work with the client. Regardless of what you can afford, it’s recommended that you budget for one because inevitably, you or your company will go through a transition and you’ll be expected to rise to the occasion as a leader.

You might question the ROI of hiring a coach but companies that have invested in coaching for their leaders have seen increases in employee performance, satisfaction, and retention, among other benefits. Investing in even just one leader can have a positive impact on your whole org and business.

If you’d like to learn more about how you can work more productively, inclusively, and sustainably as a leader, you can check out Elle’s website or reach her at elle@elledestree.com.