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Executive Coaching

What exactly does a coach do, how do I find a coach and when is the best time to get a coach?
Many startup founders are turning to executive or business coaches for help as they build and scale companies. A good coach is a “performance optimizer” who can help a CEO/Founder perform her best. What exactly does a coach do, how do I find a coach and when is the best time to get a coach?
The Homebrew Guide to Executive Coaching will explore these topics and we look forward to your feedback at

What does a startup coach do?

The role of a startup coach is to help the client's leadership, management performance and development. In a day to day session this can include:
Managing relationships/working styles
Managing stress/work life balance
Prioritizing/managing expectations
Facing fears/imposter syndrome
Delivering difficult feedback
Resolving interpersonal conflict
Creating team alignment
Making tough decisions
Building a strong company culture
In the past, coaches were brought in for executives who showed signs of bad behavior. This is not the case anymore. Some executives are hired with coaching as part of their onboarding process -- it’s seen as a benefit of being part of the management team.

What doesn’t a startup coach do?

A coach doesn’t make business decisions for you. You aren’t hiring this person to tell you what to do. You are hiring this person to help bring out your strengths and address your weaknesses. A coach may help you get to the right decision. You can talk through specific scenarios and how you might handle them but this person is not there to solve your problems. On the other hand, this person isn’t a punching bag either -- someone for you to unleash all your anger, frustrations or complaints on.

How is an executive coach different than a life coach?

An executive coach is meant to focus on business whereas a life coach focuses on the client’s personal agenda. Your executive coach will get to know you personally and there will be things about your personality that will come into play about the way you interact in business settings. However, the coach is not there to talk about your personal issues. If there are major personal events that are happening in your life that are impacting your work, this should be addressed however. A seasoned coach will know the lines between therapy and executive coaching.

What about a mentor or a consultant?

The role of a mentor is to provide words of wisdom whereas a coach actually gets her hands dirty and helps you get to the root of any problems. A consultant can help an executive solve a specific problem. If you are having a sales pipeline issue, then hiring a former sales executive with industry knowledge may be the answer.

A board member told me I should consider working with a coach. Does this mean I’m doing a bad job?

No. This means that the people around you (a board member, an investor, your CEO or colleague) wants to invest in you. Don’t be afraid to ask questions. Do other people at my level have coaches? Are there certain coaches that the company recommends? Is there a list or do I do the research on my own? The suggestion to get you a coach is a sign someone wants to invest in your development which is positive. Welcome the suggestion and ask questions.

Finding a Coach

It feels like an overwhelming process but it doesn’t have to be. Treat the process like hiring a team member. Start by matching your style with someone that will bring out the best in you. , often described as a matchmaker (helping execs finding coaches), details her interview process for finding the right coach in this . If you work for a company where your peers have coaches, get referrals. Talk to founders, CEOs, investors, and anyone you trust who has worked with a coach before.
Find out the following:
What was the catalyst for working with a coach?
Why and how did they choose a certain person?
How long did they work with a coach?
After stopping work with a coach did they go back to work with the same person?
If it was a different person, then why?
If they fired the coach, what was the process like?
If it wasn’t a good match, why?
If they wished they’d done something different, what would that have been?

Red Flags to look for

You should have a gut feeling after you do a phone consultation with a coach. Here are some red flags:
The coach is distracted and you feel she didn’t give you 100% of their attention.
He’s not available in between sessions. Make sure the coach is available via phone and/or email if something important comes up. Crises usually don’t happen on your schedule so make sure this person is accessible when you don’t have something scheduled.
He hasn’t worked with anyone at a company similar to yours (a start up or early stage company). If he can’t relate with the type of environment you are coming from, it’s probably not a good fit.
She tells you something far fetched like “I have a 100% success rate of helping executives achieve their goals.”
He can’t provide credible, recent references.
You detect ego -- he wants to work with you for the wrong reasons (you had a successful exit and she’s more interested in that fact vs. actually helping you).
He wants a lengthy commitment (6 months +) and requires up front payment. You and your coach may not click and you should be able to terminate the relationship after a month or so. A reputable coach will be fine terminating the relationship after a few weeks if the chemistry isn’t there. No one wants to waste time if it isn’t a good match.

So I have a list of 20 coaches, how many should I actually speak with?

No more than 3-4. If you are getting referrals from credible sources, they are all probably good coaches but the secret sauce is really finding someone you click with. Think about whether or not you want someone who is more nurturing or direct. What kind of bedside manner are you looking for? If you don’t have a clear idea, then talk to people with different styles. When you solicit referrals make sure to ask about style and personality so you get a good mix -- especially if you aren’t sure what type of coach is going to be the best fit.

Reference Checking

Once you have spoken with a few people, you will likely have a gut feel for who you clicked with. The next step would be to check references. Talk to at least 3 former clients of the coach you may want to hire and be prepared to ask specific questions. If you have specific concerns, don’t be shy. There are the basic, tactical questions such as:
How long did you work with the person?
How many sessions until you developed rapport with the coach?
When did you feel like you started to actually practice what you were learning in the sessions in real time?
Then there’s the more subjective...
Were there things you wanted to work on but had a harder time addressing?
Did you feel you were made a priority?
Were there things you wish you could have communicated differently with your coach about?
Is there anything you didn’t get out of coaching that you feel you could have gotten out of a coach with a different style?
When you look back on your time spent with this coach, do you feel it was a success?

I’m going to meet with a coach I hired. How do I prepare?

Be open. You have to want to be coached and put the time in. If you aren’t willing to commit, it may not be the right time to engage with a coach.
Identify the key challenges and growth areas you'd like to focus on
Set a vision for yourself for (6-12 months out). What would you like to be different as a result of working with the coach? What would a 10 out of 10 look like?
Don’t just listen. Actively listen and participate.
Your coaching session may only last a few hours but it shouldn’t be limited to that time. It should be incorporated into your entire workflow.

I’ve been working with a coach for 6 months and I don’t know if anything is actually changing.

How do you know if coaching is actually helping and how can you measure your results?
Run 360 assessments. For more info on performance management, check out this . What, if anything has changed since you started working with a coach?
Are you retaining your employees?
Are your direct reports being promoted?
Are you achieving your goals?

How long should I expect to work with a coach?

Some founders have coaches they’ve worked with for 10+ years and other founders work with someone for several months. This really comes down to you and your goals. It’s a big time and financial commitment but it’s an investment in yourself. Think of it as “self care.” Some people hire coaches when they really need some discipline, others when they need help on something specific and others when they just need a general accountability partner. It’s also common to take a break from coaching and then revisit. Maybe it’s with the same coach or maybe someone new. There is nothing wrong with exploring a different coach as your business scales and your needs change.

How do I break up with a coach?

If you don’t feel like your coach doesn’t “get you”, doesn’t hear you or doesn’t prioritize you, then it may not be a good fit. You should schedule one session last session with the coach to give them direct and transparent feedback. Tell her what you didn’t get out of coaching that you hoped you would and give her a chance to respond. Some execs work with a coach for many years and actually outgrow their coach. This is fairly common and should be an open dialog between founder and coach.

When is the right time to get a coach?

For some executives, it’s when you start a new job. This is usually in an environment where all your peers have coaches and it is a benefit of the job. If you are new in a role and are curious about getting a coach, speak up. Talk to your peers about the when and the why, and ask for referrals. Ask your boss or someone in HR if coaching is something that is available to you and if the company is willing to cover the cost.

I recommended a coach to a VP on my team, now other members of my team are asking for a coach.

Should I be thinking about coaches for all members of my team? In a perfect world, yes. However; you may not have the budget. As a leader, you should be committed to the development of your entire team. How do I message this to the team? What if I get the question: why don’t I get to work with a coach? Are they in trouble because they got paired up with a coach? The messaging should be kept simple: Our company supports developing leaders and we want to set up each individual for success. If you think you would like to work with a coach, let’s talk about your goals. Remember, each person’s relationship with a coach is private so you don’t need to go into detail why that person is working with someone. If you referred a team member to a doctor or therapist, it wouldn’t be acceptable to ask why.
Coaching is a personal journey and finding the right coach at the right time is more of an art than a science. What works for your colleague in finance may not work for you as you begin to work with a coach. Don’t be afraid to ask trusted peers questions and talk to several coaches to get a good sense of who is out there. There are many different types of coaches with different styles so finding someone that is right for you isn’t going to be an overnight process.


What Can Coaches Do for You?
Reprint: R0901H Today’s business leaders increasingly rely on coaches for help in understanding how to act in a demanding and volatile world. These confidants and advisers can earn up to $3,500 per hour. To understand what they do to merit that money, HBR conducted a survey of 140 leading coaches and invited five experts to comment on the findings. Commentators and coaches agreed that the reasons for engaging coaches have evolved over the past decade. Ten years ago, most companies hired a coach to help fix toxic behavior at the top. Today, most coaching is about developing the capabilities of high-potential performers or acting as a sounding board. As a result of this broader mission, there’s a lot more fuzziness around coaching engagements, whether it be with regard to how coaches define the scope of engagements, how they measure and report on progress, or what credentials a company should look for when selecting a coach. Do companies and executives get value from their coaches? When we asked coaches to explain the healthy growth of their industry, they said that clients keep coming back because “coaching works.” Yet the survey results also suggest that the industry is fraught with conflicts of interest, blurry lines between what is best handled by coaches and what should be left to mental health professionals, and sketchy mechanisms for monitoring the effectiveness of a coaching engagement. The bottom line: Coaching as a business tool continues to gain legitimacy, but the fundamentals of the industry are still very much in flux. In this market, as in so many others today, we have to conclude that the old saw still applies: Buyer beware!

Updated 12.1.23

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