I get questions all the time from curious CEOs about what coaching is like, so I wanted to put together an FAQ to help people understand what it’s like to work 1-1 with an Inside-Out coach. 

I’ve attempted to cover all of the most common questions. However, this is intended to be a living document, so please let me know if you want to know more about something or if you have a question that I’ve missed. 

1-1 Executive Coaching

What is it like? How does it work?

A 1-1 relationship with one of our founder-coaches is among the most powerful investments you can make in your own development as a leader and in the growth of your organization. 

Here’s how it works: 

Phase 1: Align on a definition of success

• The first step is to work with your coach to define one or more concrete outcomes for the success of your engagement, as well as the objective criteria that will signal you’ve achieved them.

• Note that the work of coaching spans both your business and your personal life, as relevant mental patterns are almost never contained to a single environment. 

Phase 2: Inquire, Execute, & Iterate

• Next, you partner with your coach on radical self-inquiry in order to bring subconscious, limiting patterns into conscious awareness and to design a more conscious life and business.

• You’ll meet with your coach every two weeks for 60 minutes, and during these sessions, each of you has distinct responsibilities:

  • Your coach will help you dive deep into the specific structures  your mind uses to make meaning, and therefore to drive your behaviors. They will help you overcome subconscious limitations.

  • Your coach will help you design field work that will bring your depth work into your life and will then support you in executing it. Your coach will hold you accountable to becoming who you want to be, doing what you say you will do, and getting what you say you want.

  • You will come prepared with the topic most important to you each session. And you will choose consciously what field work to commit to between sessions. 

  • When you commit to something, you will be unreasonable about completing that action.

• Your coach is available between sessions to support via email, text, or phone as needed.

• Over time, often very quickly and compounding, you will notice changes in many areas of your life including, but not limited to, the one you are focused on changing. Accordingly, your work with your coach will change and evolve as you get closer to the outcome you want.

Phase 3: Finish (or Begin Again)

• At some point, you will either A) achieve your goal, or B) decide you actually want something else. Either option is an opportunity for you and your coach to take a step back and decide what’s next.

• You may decide to end the engagement, happy with the change you’ve made, or you could decide that in addition to the first change, you also want another change, and you realign with your coach accordingly.

What kind of changes do people tend to work toward? 

The types of objectives we work on together in our coaching are as varied as the CEOs we work with. 

Everything from “raise a Series B” and “build a high performing culture” to “find a new type of motivation that doesn’t make me feel miserable” and “transition myself out of company operations and into what’s next.” You can find a brief list of some common objectives or categories of work on our Services page.

There is no limit to what you can work toward with your coach. Oftentimes leaders come to coaching because of a business objective, but the coaching itself spans both business and personal (any divide between the two being made up and unhelpful); often clients must progress in one to attain results in the other. The key to any objective is that it’s important enough to justify the cost – measured in time, money, and effort. 

If your objective is do-whatever-it-takes-to-get-it-done important to you, it is in bounds. If your objective is kinda sorta important, it’s best not to begin. The process of participating in a coaching relationship is challenging enough that, if you’re not committed, you’ll find reasons to turn away. 

What is the cost? Financially and otherwise

Coaching costs along three vectors. Money, time, and effort.

Money:

The cost of 1-1 executive coaching with an Inside-Out coach is a monthly retainer of $3,000 (all inclusive). We also offer a limited number of engagements priced on a sliding scale to high potential, early stage founders, as part of an effort of bringing this work to more leaders. 

All relationships are month-to-month, and you can cancel at any time. Even so, our average length of engagement is about 18 months, and usually involves making a few substantive changes in that time.

Time:

You will engage in two, hour-long sessions per month. Beyond that, you should expect to make your coaching field work a priority in your life. Your work during each two-week cycle might be as simple as a 30min, sweaty conversation, or it could take hours of effort. You choose how much time you spend on your coaching engagement, with the field work you choose to take on after each session.

Effort:

Coaching can be challenging, emotional work. Despite that warning, most clients are still surprised by how deep their current circumstances go, and the depth of emotional effort that is required to change them. This is why we suggest leaving 30 minutes available after each session for processing.

Who pays for it? 

95% of the time the company pays for its employees to receive executive coaching. 

This is true even when the coaching includes both business and personal topics. Coaching works at the level of the client’s mind and how they make meaning in the world. They do that in every context of their life, so a leader is either effective or not, holistically, and any issues in one area bleed into all others.

The highest point of leverage in any company is its senior leadership, and indeed its CEO. Coaching is an abnormally high leverage way to invest in the development of those senior leaders.

How can I ensure I get the most out of coaching? 

We have developed three commitments which support our clients in getting the most value out of their coaching engagement. 

Come prepared:

Before every session, dedicate time to reflecting on what is the most important topic you could bring to the coaching session. This commitment allows you to steer the coaching topics and ensures you’re always working on the most important thing. 

Reveal yourself:

Every human being has what we refer to as their “presentation layer” – the way that they consciously or subconsciously present themselves in non-authentic ways. We do this to steer toward desirable outcomes, to manage people’s perception of us, or for an infinite number of other reasons. When you realize you’re presenting yourself, call yourself out and reveal what you’re withholding. Related: embrace your coach’s role in calling you out on this as well. This commitment amplifies and streamlines your progress.

Be unreasonable:

At the end of every session you’ll have the opportunity to make one or more commitments to your growth, in the form of field work to be completed between sessions. Your coach will never demand that you commit to doing any of this work. However, when you do choose to commit, we ask that you are unreasonable about completing the field work to which you commit. Your coach will support you in this effort as well.

To ensure you get the most from your coaching relationship, we ask all our clients to make each of these three commitments upon entering into a relationship with a coach. Each coach makes the same commitments (although their version of preparedness is distinct). 

Want to learn more? 

Do you also support cofounder coaching, or coaching for an entire executive team?

While we specialize in 1-1 CEO coaching, our coaches also support the healing and strengthening of cofounder relationships, and the systematic development of leadership capacity across entire executive teams. 

Each of these engagements are designed bespoke for each client. Click here to submit an inquiry.

Want to dive deeper?

If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.

Here are a few of my favorites:

• The secret to leadership (why authentic leadership is simply more effective)

• How to fix your cofounder relationship in 3 difficult steps

• The five practices to transform from founder to CEO

• Finding purpose after exiting your company

• How to pitch a big vision to investors without setting yourself up to let people down

Executive Coaching for Entrepreneurs

There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.

I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency that supports entrepreneurs to step fully into their lives, and transform their companies into their masterpieces.

Leveraging 15-years as a founder/CEO, along with deep training in mindfulness, psychology, Neurolinguistic Programming, psychedelic integration and more, I have helped leaders from some of the fastest growing companies and VC funds in the world design a more conscious life and make key changes to improve their performance and satisfaction.

I coach leaders how I want to be coached:

• Focused on the person, not the role.

• Focused on results, without the fluff.

To learn more about working with me, click here.