How My Coaching Works

“Life seemed to be an educator’s practical joke in which you spend the first half learning and the second half learning that everything you learned in the first half was wrong.”
—Russel Baker

The field of coaching has a ton of variability. Some folks woke up one day and decided to be a coach, others have a Ph.D. in psychology, others are academics, and so on. So when I meet someone interested in working together, they inevitably have a lot of questions. Below, you’ll find a bit of context on me and how I got here followed by a set of the most frequently asked questions and my answers.

A bit on me

I’ll start with a bit on my career before I became an executive coach to startup founders and follow that with a bit on how I went from entrepreneur to coach. 

Since 2009, I’ve started four companies. The first one makes me laugh because it was an elaborate homebrewing operation I started at 19 that has evolved to become known as “the brewery” amongst friends and family. The second was a sort of proto-ProductHunt. The third was Mattermark, a business analytics and database company where we grew from $0 - $5M in ARR in 3.5 years. And the fourth was Holloway, a digital book publishing company. I’ve been the CEO and the COO. Across my companies, we raised more than $20M in VC money (not necessarily a good thing). And finally, I wrote a book, The Holloway Guide to Raising Venture Capital.

In 2020, I left Holloway to become a coach. Whenever I asked colleagues what my “superpower” was, they’d say, “listening.” I never thought that could be a career, but as I contemplated what to do in the next chapter of my career, friends and colleagues suggested I explore becoming a coach. Since then, I have studied to become a coach at The Hudson Institute of Coaching through a 9-month training program. 

Together, my experience as an entrepreneur and a coach allows me to both coach and advise. My goal as a coach is to help you become more self-aware and use your agency to contribute to the world in a way that aligns with your values. I believe that if you do that, you have a pretty damn good shot at being a successful entrepreneur. 

If this and my answers below leave you feeling interested in working together, you can contact me here.

Who is your ideal client?

I love working with early-stage founders whose companies are growing quickly. This doesn’t necessarily mean they’ve taken venture funding, but in many cases, the founders I coach have raised a seed or series A round of funding. I prefer to work with founders once they’ve found at least some product-market fit. Almost all of my clients are CEOs. If you’re a non-CEO founder, I will not work with you unless your CEO co-founder is either working with a coach now or has worked with a coach for a significant period of time. I also do not work with co-CEOs or CEO/President or any other co-founder arrangement where there is not a clear CEO.

How many clients do you work with?

My maximum is 15 clients at a time, and most of the time I have about ~10 clients. 

How long does a coaching engagement last?

I don’t coach with a fixed timeline in mind. I have some clients I’ve worked with for more than a year and others who I’ve only worked with for three months. Most clients, however, work with me for 6 months or more. 

How are your engagements structured?

I also don’t coach with a fixed structure. I recommend thinking of our coaching engagement in three-month sprints where we will meet every other week (~6 sessions). In the first 1-2 sessions, we’ll set some goals for what you’d like to get out of our work together and then spend the following 4-5 sessions working on those goals. In a 7th session, we’ll do a retrospective, look back on the goals, and see if there’s anything you’d like to change about your goals or how we work together—at this point you should be able to unquestionably see progress. 

Do you have a system?

I do not have a fixed system. Each founder brings unique challenges, relationships, and history and I adapt how I work to each client. In my work, I draw upon research and frameworks on how people change, transitions, interpersonal relationships, conflict management, recruiting, management, and much much more. 

One good metaphor for how to think about our work together is that coaching is a bit like Google Maps. Huh? Like in Google Maps, you have to understand where you are—where your blue dot is—how you got there, what you like about it and what you don’t. Then, you have to pick a destination. Once we’re clear on the here and the there, we can begin to work on picking a route. This metaphor applies to three-month sprints and inside of individual sessions.

If you’re looking for a system for how to become a great CEO, read Matt Mochary’s The Great CEO Within. 

How do we begin?

If both of us feel like there’s a great fit, a few things will happen:

  1. I’ll send a contract that includes a confidentiality clause.
  2. I’ll send an intake form. Expect to spend 30-60 minutes on this.
  3. We’ll schedule our first session.  

What’s an intake form?

The intake form serves a dual purpose. First, it helps me get to know you better and learn more about what you want to get out of coaching. Second, it helps you learn more about yourself. The key is to not rush this. Plan on setting aside at least an hour to think through your responses. The kind of things you can expect to reflect on are what’s going well, what’s not going well, your values, strengths, areas for growth, and your family and work history. Once you complete this form, you’ll be able to review your answers in Notion—we’ll also review this periodically to make sure you’re growing.

How often do we meet?

I meet with most of my clients every other week. Some clients, when going through particularly turbulent moments will meet more often, but it’s totally up to you. You can text or email me anytime as well, and I try to respond within 24 hours. 

Where do we meet?

Right now, due to the pandemic, all of my sessions are virtual. I prefer Zoom or some other format that includes video, as it allows me to pick up on non-verbal cues much better. I’m happy to also hold our sessions over the phone if you have a strong preference to do so.

I do ask that you don’t spend the majority of your sessions walking. Call quality tends to be poor and I find that clients are less focused on our work together. If you need to take a walk every once in a while, that’s fine, but please don’t make it the majority of our sessions.

On the same thread, I ask that clients find a relaxing, private, quiet space with reliable internet for our sessions so we can focus on the work instead of a noisy environment or anything like that.

How long is a session?

Most sessions last 60 minutes. If we’re consistently hitting the 55-minute mark and feeling like there is more work to be done, we may extend it to 90 minutes or more. 

When are you available for coaching?

I coach Monday - Thursday from 10 am - 4 pm PT. I’ve found I feel burnt out if I do more than three sessions a day, so that limits how many I can do. Under special circumstances (e.g. a layoff or something like that), I can meet outside my regular hours.

How do we schedule our sessions?

I prefer to book each client in a recurring (every other week) slot. Once we begin, I’ll introduce you to my assistant, who will coordinate if you need to change your slot or make changes. Most of the time, I’m flexible if you need to move a session around, but if it becomes a regular habit you can expect us to discuss it. 

How does a typical session work?

Most sessions follow the following structure:

  1. The Update: Usually there’s some progress since the last session that’s worth sharing. It can include anything you’ve learned, any changes in priorities or goals, new challenges, or anything like that.
  2. The Work: Pretty soon, you’ll begin to hear my voice asking, “What would you like to get out of today’s session?” After the update, in every session, we’ll declare a clear intention for what you’d like to work on. Sometimes this may be exploring a feeling of discomfort and other times you may want to walk away with concrete steps, but it’s up to you. 
  3. The Wrap Up: When about 5 minutes are remaining, I’ll ask you some form of a question to help you synthesize your insights from our session and come up with a concrete way to apply what you’ve learned. We’ll also periodically set aside time for you to give me feedback at the end of a session.

How should I prepare for a session?

I notice a meaningful difference between the clients who prepare for a session vs. those who show up having just dropped off of another call. I recommend blocking off 15 minutes before each session to reflect on what’s worth updating me on and to pick 1-3 items you’d like to dig into in our sessions. Ask yourself, “What do I want to walk away with at the end of my session with Andy?” That will help focus the work we do together. 

How long does it take to see results?

You should see noticeable growth within the first 1-3 months. Most clients walk away from the first couple of sessions with an intuitive sense of something “working.” At the bare minimum, when we do our first retrospective after 3 months, you should see clear results on your personal work and on your business results. 

How can I provide feedback?

I love feedback. If you have something you’d like to discuss, there are several great outlets for it. First, at the beginning of a session, you can ask to set aside 5-10 minutes for feedback. Second, we’ll regularly look back on our relationship every three months. Third, you can always send me thoughts and feedback in writing via email. Fourth, if it’s something big you can always ask me to hop on the phone to talk something over. 

How much do you charge?

My rate is $2,000 a month. I don’t do per session fees. For the monthly fee, we’ll meet every other week (some months that’s 2 sessions; others it’s 3). If you’re really excited about working together and $2,000 / mo. is getting in the way of working together, let’s talk about it because I can usually work something out for a great fit. I don’t do multi-month contracts or anything like that, as I feel you should be able to opt out at any time. 


Join my mailing list

I send maybe one email a month. Get updates on new projects, personal life updates, new articles, and interesting finds.

Thank you! Your submission has been received!
Yikes. Something went wrong while submitting the form.