Considering an Executive or Leadership Coach? Here’s What to Know.

When to pursue leadership coaching, how to ask your company for sponsorship, and more.

In my role as a leadership coach, I come across many prospective clients curious about coaching, with questions about whether or not they should hire an executive coach, how to set goals for coaching, and other questions about whether or not coaching is right for them at this time. 

Those questions include:

  • Should I hire an executive or leadership coach?

  • When is the right time to hire an executive or leadership coach? 

  • How do I know what I should work on with an executive or leadership coach?

  • How do I find a coach that’s a good fit?

  • How can I get my organization to sponsor an executive coach for me?

  • How do I know when I'm "done" with coaching?

Read on for all the answers. 👇🏽

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Should I hire an executive or leadership coach?

Oftentimes, the topic of executive coaching or leadership coaching comes up when preparing for a big professional change.  For example, maybe you just got promoted to a new role with a larger scope, or you have recently become a first-time people leader or manager of managers.

While you might have a trusted “ personal board of advisors ,” who know you well and have helped you weigh some big decisions, you are now looking for a consistent, objective, trusted thought partner to help you navigate this change. 

When is the right time to hire an executive or leadership coach? 

If the following scenarios resonate with you, now may be a great time to explore leadership coaching as an investment in your professional growth.

Current Employer

  • You just got promoted into a new role or are taking on a bigger scope

  • You are a first time manager (or manager of managers)

  • Your manager or executive sponsor suggested you hire a coach

New Role

  • You are starting a new job with a new company

  • You are evaluating a career pivot

  • You are considering freelancing or starting a side hustle

Internal Opportunities

  • You’ve received feedback that you would like to work on

  • You are battling imposter syndrome

  • Your schedule is jam-packed but you feel like you have no time to get anything done

Big Life Changes

  • You've experienced developments with your partner, such as moving in together or getting married 

  • You are welcoming a baby (or fur baby)

  • You have health issues arise for you or others that you care for 

How do I know what I should work on with an executive or leadership coach?

It’s important to have clearly defined goals for coaching. A good leadership coach can help you decide on these, by asking you questions and questioning your assumptions. To get a kick start on developing these goals, some questions to consider are:

  • What kind of change do you want to see in yourself, as an outcome of this engagement? 

  • What are some feedback areas you have received from your team members or the senior leaders at your organization?

  • Is there a behavior, competency, or leadership skill you feel is holding you back from reaching the next level?

  • At the end of the coaching engagement, how will you know that it was successful?

How do I find a coach that’s a good fit?

Every coach has a different style and approach. Fit is important, as coaching can be a big investment in both time and money. 

Most coaches offer a free introductory session to assess fit and start to learn about your goals. Set up time with anyone you're considering to assess whether the coach is a good fit for you.  

(Note - it’s a two-way street. Self-aware coaches will know if you aren’t a great fit for them and will say so, and may have coaches in their network they can refer you to.)

When you “interview” the coach in these sessions, you can assess:

  • The types of coaching questions they ask. Have they gotten you to think differently or question your assumptions?  

  • How they lead the coaching session. Are they being overly directive with you (i.e. giving you advice), or are they helping you uncover your own answers?

Side note - While advice might feel productive in the moment, this can sometimes lead to over-dependence on your coach.  Effective coaching should be focused on helping you uncover and discover solutions, with a lighter touch on advice.

  • How their own values, mindsets, and beliefs show up in their coaching

Review the coach's website or platforms they’re on such as HireClub or BetterUp . You can read through reviews and testimonials from their experience coaching leaders.  

Questions to consider asking your potential coach include:

  • Can you tell me about your coaching approach or philosophy?

  • What would your clients say about your coaching style?

  • What is your coaching niche or specialty?

  • How long are your typical sessions and how often would we meet?

I suggest you focus less on the specific questions to ask, and instead get a sense of how they coach in that first session to see if it's a fit. Your top priority should be to let the coach run the session to get a feel for their style.

How can I get my organization to sponsor an executive coach for me?

If your company has a professional development budget for things like classes, certifications, or conferences, executive coaching can fall into that category.  If you are not quite at an “executive” level, pitch it as “leadership coaching” or even "performance coaching."  

“Executive Coaching” can sometimes seem like it’s only meant for VPs or C-Suite executives, when in fact leadership coaching can be extremely helpful for high-potential, up-and-coming leaders. 

If you are seeking approval from your manager, highlight how a leadership coach will help you develop in areas identified in performance reviews.  Ask if your manager has other suggestions on your leadership development or what you might work on with a coach.   

For example, you can say:

"Hi Manager, we've discussed [insert opportunity area, such as "leading through influence, or executive communication"] as an opportunity area in my last performance review.  I've done research on leadership coaches and believe working 1:1 with a coach is what I need to get me to the next level. I'd like to use a portion of our professional development budget to invest in my development through a 3-month coaching engagement. What do you need from me to move forward with this approach?"

If you are negotiating a new job offer , ask if your compensation package can include a budget for coaching.

How do I know when I am “done” with coaching?

Coaching yields the best results when there is a specific goal in mind, and a set amount of time to achieve it.  Generally, 3-6 months is enough time to start to uncover meaningful insights and make sustainable changes.

Throughout the engagement, review your original goal with your coach, and assess how you're progressing against it. As you approach success with your goal, it’s a good time to scale back or even press pause on your coaching conversation.

If you keep recurring coaching going after achieving your initial goals and not setting new goals, the sessions may become directionless and lose value.  

After around six months, assuming you’ve made the progress and breakthrough you sought from the beginning, I suggest you go on “maintenance mode'' with your coach - meeting once a month or quarter just to check-in.  If there are new skills that you want to work on, that’s a good time to redefine the next set of goals!

Kelly Ling is a leadership and executive coach with 12 years of corporate experience in various operational and strategy roles, and an MBA from UC Berkeley-Haas.  

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