How To Make Sure Your Company Gets The Most Out of Executive Coaching

Olga Skipper
11 min readSep 20, 2021


Photo by Tobias Mrzyk on Unsplash

Imagine this: Anna, the founder of a Series A startup, bounces out of her coaching session feeling great. It seem to have given her the support and insight she needed to move into the next stage of her founder’s journey. Surely, she thinks, I should be offering this sort of instrument to my execs to help them grow faster?

The next morning, Anna calls her coach to discuss offering coaching to her executive team. This, she believes, could be the start of something beautiful; a carefree phase filled with inspiring hopes and desires.

In the movie version of this story, this is the point where you might get an upbeat montage set to rousing music. Yet, as with any romantic story, there comes a time when reality kicks in.

In eight out of ten cases, founders lose interest in coaching for their executive team within around six months, as my coaching experience — and that of many of my colleagues — suggests.

They get overwhelmed by their additional role of coaching process owner, communicating with the coaches and the executive team members, and see little positive impact on the organization. As if that weren’t enough, the process often leaves a bookkeeping and payroll mess. The founder, frustrated and disappointed, shifts their attention back towards “more important tasks” such as overall company management and fundraising.

What was supposed to be a boost for the team has turned into a burden.

How Did We Get Here?

At the beginning of your own coaching journey, you’ll likely find it easy to commit and integrate. Let’s say you’re a founder, typically in the pre-Series-A/series A stage. All you need to do is find a coach you’d like to work with, come to an agreement, and pay your fees accordingly. Nothing complicated.

Complexity arises when the coaching is no longer about the founders themselves but begins to involve the company as a system. At this point, the coaching process is no longer a question of one agreement and one invoice. Like everything in a startup, coaching is a process that needs to scale to ensure the smoothest and most effective collaboration between the coaches and the clients while taking the company’s objectives into account.

At the same time, certain important steps are ignored due to lack of experience: choosing one of the two coaching paths; appointing a process owner; creating a clear coaching process within the organization and more.

In this article, I’ll map out what it takes to establish a scalable coaching process, help you easily integrate coaching inside your organization at the executive and C-suite level, and highlight common mistakes you can avoid right from the beginning. I want to help you, as a founder, to experience the real magic of executive coaching, without the pain of figuring the processes out and getting lost in the bookkeeping.

Please note that this article does not address such instruments as leadership training, which are more applicable to first-time leaders. I won’t go into those: just keep in mind that executive coaching is not for everyone. By the end of this article, you will understand why.

The Two Coaching Paths

Let us start with the vital question you should ask yourself before launching your executive team on their coaching trajectory: who owns and influences the coaching agenda?

That is to say, do you (A) want your executive team to choose their own coaching path and topics, or (B), do you want the company to influence the coaching direction?

When I ask founders this question they usually choose option A. This is to be expected since the founder’s initial coaching experience was self-led.

Later in the process, though, founders tend to realize that they need coaching outcomes that move the company forward — especially when the company is sponsoring the coaching process. At this point, the founders might make the mistake of changing the rules in the middle of the coaching process: this can create mistrust between the company and the executive team members, confuse the coach, and make the coaching process and experience less effective.

To avoid this, make sure you establish which path you’d prefer from the very beginning.

Option A: The executive chooses their own path. This lowers the barrier to entry into the coaching process, especially for first-time coaching clients, and usually feels more “supportive.” The downside is that team members might choose a topic or a direction that doesn’t fit with the company’s objectives.

Option B: The company influences the coaching direction. This route can give your executives additional motivation to grow and in certain cases highlights potential conflicts between team members’ aspirations and the company plan.

Entering a company-centric coaching agreement also entails additional steps, such as 3-way conversations, and requires additional roles such as coaching sponsor (usually someone the team member reports to).

There are pros and cons to both paths: nevertheless, you should consciously choose one at the start — and stick to it.

The Process Owner

So now you’ve chosen your path. The answer to this most critical question offers clues about how to integrate coaching into your organization.

Before discussing the two options, you’ll need to select the team member who will be responsible for building and maintaining the coaching process inside your organization.

This will depend on the company’s size, but by the Series A stage, this person should not be the company CEO and/or founder, who almost certainly has (or will have) too much on their plate to divert sufficient time and attention to this relatively involved task. The process of offering coaching to the team should be the CEO’s/founder’s area of strong influence, not their direct responsibility.

Depending on your company culture and their areas of responsibility, the process owner could be the COO/VP of People/Chief of Staff/Head of Ops or People and their teams. Someone who oversees people processes has a solid connection to bookkeeping and payroll and ideally doesn’t manage the future coaching clients. They will need all these attributes to create a scalable solution.

The process of entering, remunerating, and evaluating the coaching needs to be clear for:

  1. The coaching client (executive team member)
  2. The coaching sponsor (usually CEO/founder)
  3. The coaches you work with
  4. Your payroll and accounts department

The coaching client — your executive team member — needs to know how to choose and engage a coach, the length of the coaching engagement, what topics they are allowed to pick, and how to go about extending or ending their coaching.

The coaching sponsor (the founder or a direct manager) needs to know whether and when their input and feedback is required, whether there are confidentiality boundaries and how to initiate a coaching agreement for one of their direct reports.

The coaches need to know the company policy on the coaching topics, budget, and time budget allocated to the coaching sessions. They need to know who in the company is to be engaged in the coaching process, and to whom they should submit their invoices. Ideally, they should also be made aware of the company’s vision and values.

Your payroll and accounts department needs to be first consulted on which payment model to choose (is coaching a company benefit, a service, or an expense that an employee can claim back from the company?), which payment schedule to propose to coaches, and then to be involved in the budgeting and the payment process.

Steps Along The Path

By this point in time, you’ve answered your main question; you’ve chosen the process owner and consulted your payroll. Now let’s look at the actual process of integrating coaching into your organization.

Here you will see the example of the two processes behind the two options. You might end up with a combination of these.

Option A: You’ve decided to let the coaching client choose their topic and manage the coaching relationship:

  • Define the budget (in dollars, euros or the currency of your choice) that the company is giving for coaching per executive per year, cross-departmentally.
  • Preferably, give the coaching client a stake in the coaching budget (make that budget their “learning budget,” or part of their “department budget,” something that they have a decision over). Define the reimbursement process/schedule or provide the coaching client with the clear payment schedule.
  • Ensure that confidentiality boundaries are clear to the management and everyone is OK with NOT influencing the coaching topic.
  • If needed, create a pool of preselected coaches to cover different demographics, each with a slightly different focus, with a startup coaching background: first-time leaders, C-level, leadership level, founder level.

Option B: You’ve decided to influence the topic and manage the team’s relationship with their coaches:

  • Create a pool of preselected coaches to cover different demographics, each with a slightly different focus, all with a startup coaching background and coaching certification.
  • Appoint one point of contact for the coaches to handle ops questions and communications with the company.
  • Define the coaching budget according to a typical coaching package per coaching client. Typically, this might be the standard length of the coaching engagement (for example 3 or 6 months per coaching client or the number of coaching hours — 10 coaching hours package within the 6 months of engagement ).
  • Make sure the coaching client has a stake in the coaching budget (make that budget their “learning budget,” or part of their “department budget”).
  • Define a payment schedule that minimizes overhead for your payroll, process owner, and the coaching client and communicate it to the coaches.
  • Play around with the different scenarios and create a FAQ: What happens if the coaching needs to be prolonged? What if the client drops coaching? What if the coaching budget needs to be increased?
  • Ensure that confidentiality boundaries are discussed with the coaching client and the coach and clear to the coaching sponsor.

This might sound like some heavy lifting — but trust me, by having this setup in place, you will save effort, time, and money later on, as well as avoiding misunderstandings between the team and the company, and heading off legal/bookkeeping mistakes.

While the first path is shorter and might seem the easiest to begin with, it doesn’t guarantee that the company’s investment will be returned in the form of better performance or OKRs.

Common Mistakes

Beyond these “best practice” tips, I’d also like to share some of the common mistakes founders make when integrating coaching into their organization — the better for you to avoid them.

  1. Trying to “fix” your executives through coaching.

Coaching doesn’t fix people, and it can’t turn one type of person into another type of person. It also can’t mold a human into a shape (or role) that the CEO might find more desirable. Rather, coaching creates conscious awareness and helps to integrate the clients’ and the company’s agenda into the decision-making and change process. This awareness creates a more sustainable and transparent company-executive relationship.

2. Mixing up coaching and therapy

During the early stages of the company, coaching support might just mean, well, support. First-time leaders especially are at risk of suffering from burn-out, anxiety and self-doubt. Though coaching can help ease this situation, there are certain limitations to what it can do in “healing.” At the same time, such terms as change and movement towards a particular goal are at the core of coaching, and it might be counterproductive when someone is experiencing a lack of mental health support.

Ask yourself a question, what your executive needs, and if not sure, consult with an executive coach, who would recommend a path to choose based on the symptoms and the situation your executive is experiencing.

3. Separating the money from the coaching process

You won’t believe how often I have had to turn down a coaching client simply because they came for “free coaching.” Free, in this case, means lack of commitment, lack of intrinsic motivation, and lack of belief that coaching will shift anything in their life.

To overcome this common mistake, make sure the coaching client knows the price of coaching and that payments come out of their budget — whether it is the personal education budget, the department budget, or another source. It needs to be apparent to team members what the lack of commitment to growth costs them and the company. Money in this case plays the role of a filter and creates a conscious commitment.

To really establish your team’s investment in the process, offer just a portion (for example, 50%) of the budget required: this might seem like a sneaky move, yet it gives you an excellent filter to identify who is committed and wants to move to the next level.

4. Assign a coach to a client without giving both an opportunity to choose

Both of the engagement processes I’ve described mention a pool of coaches, rather than just one coach. As a happy coaching client, you might want to recommend your coach to everyone in the organization, not realizing that what made your experience so successful was the unique bond between you and your coach. Such a bond requires chemistry between both participants in the coaching process, and it will be different for everyone.

In short: allow both a client and a coach to choose who they work with.

5. Choosing a process owner who is too low in the hierarchy or has no access to the founders

If you follow a coaching engagement path that involves a coaching sponsor, you need to make sure your process owner has access to the sponsor and influences bookkeeping and payroll. Just like every other process in a Series A startup, the company’s first experience with integrating coaching is an experiment, and it will need to evolve and find its place in the organization. So only someone sufficiently high up can make this integration happen and ensure that founders are engaged in the coaching process.

6. Involving a coaching provider (that is, a coaching company) too early in the company growth cycle

As a rule, I wouldn’t recommend a Series A startup to engage a coaching provider (a company that has a pool of coaches or multiple independent coaches to draw from) for their executive team. The fact of the matter is that you simply won’t get the same quality of executive coaching that focuses on your company’s growth stage for the same budget when there is a third party involved. At this stage, the executive coaches that you want to engage are typically freelancers, who do not need a provider to ensure their client roster is full, and who can provide the tailored approach you need at this stage.

7. Offering executive coaching to everyone while disregarding other tools and methods

Last but not least, you want your executive coaches to work with your executives — not with everyone in the organization. An executive coach is someone who understands business and life coaching, as well as their role in the executive’s growth path and the systemic perspective of the organization and their departments. These people also have extensive business acumen and experience working with executives in other organizations. They price their services accordingly.

If you want to support your first-time leaders or line managers, you might want to look into other providers, such as business and career coaches, leadership training courses, and books. The offering is broad, and these will be more effective in terms of the price/outcome ratio.


I hope this article has given you key insights into what integrating coaching into your organization can mean for your executive team, and how to go about implementing such a coaching plan. You should also now be more aware of the common mistakes that we coaches observe while working with Series A and above companies.

Investing in the growth of your executives is something you should get started with early on. I encourage you to view these efforts as an investment in your company’s future.

As usual, if you have any questions, don’t hesitate to reach out.



Olga Skipper

Executive coach and Advisor for Tech Founders and Entrepreneurs. Asking uncomfortable questions.