A Supervision Perspective on the Main Challenges Coaches Experience

This piece is written in response to a poll on LinkedIn asking for votes on the main challenges coaching practitioners face in their practice as executive coaches. Thanks to those who voted on the poll for sharing your challenges!

The question was “For those coaches with a significant or primary focus on executive coaching, what are the main challenges to experience in your practice?”

I promised to share some thoughts from a supervision perspective and offer useful frameworks.

The full scope of these topics is almost certainly unique to the individual and their circumstances, and so it is impossible to cover all of them. The ones I have decided to speak to are generalized, and I selected them as I believe they are most likely to play a role for most practitioners.

Issues experienced in sustaining a coaching practice:


Traditional goods and services businesses aim to maintain continuous relationships with existing clients. From a supervision perspective however, in coaching one of the implicit outcomes from work with clients is their autonomy. This means that the coaching around a particular objective for a client, will take place for a definite period after which the client would at least be able to resolve the matter in question, and hopefully apply their new thinking to novel challenges. This increases the likelihood of coaching clients not returning for continued work. Should a coach notice that they have an ongoing and unshifting relationship with a coaching client, a theme to potentially explore in supervision is whether there is a dependent, or symbiotic relationship in play. Another element of this theme is that of letting go.

I approached ChatGPT to fill in any gaps I may have missed in this question, and it suggested “Continuously finding and attracting new clients”. The theme of finding new clients as a coach is complex, nuanced and requires serious consideration of ethics. At face value the suggestion to find and attract new clients may seem reasonable and well meaning. Finding and attracting clients is a phrase borrowed from the marketing of traditional goods and services, which inherently relies on various levels and forms of manipulation. A more appropriate phrasing for the coaching domain would be “Appropriately making oneself visible to clients as a coach”. This means accurately and truthfully displaying one’s services, approach, and personality to clients in a way that is free from any form of manipulation. Some subtle forms of marketing persuasion that are commonly used:

  • Implying that without the service, potential clients would experience some form of deficit.
  • Stimulating emotions like fear or worry, with the suggestion that coaching is a solution.
  • Implying or asserting that successful cases are representative.


Again, I approached ChatGPT out of interest for what it might add to this question, and it suggested “Staying updated with the latest trends and advancements in the field to provide high-quality services”. I could not disagree more with this statement. There are forces at play, probably mostly economic in nature, stimulating coaches to train in the latest coaching modality. These are often on display at regular coaching “summits”. From a supervision perspective I would encourage coaches to maintain a healthy balance between the depth and breadth of their coaching modalities to be able to provide high-quality services. From a systemic perspective chasing the latest trends results in quality service to clients, and an overall negative impact on the domain of coaching. Dr Jonathan Shedler gives a wonderful synopsis of this happening in the therapeutic domain, and I believe that this translates well into others, like coaching. You can check this out at the start of this interview with him https://youtu.be/An52UobuQ8w

And often ignored element of ongoing development is personal development. Diana Shmukler wrote “How we work is who we are… and who we are is how we work”. Coaches are intrinsically part of their clients’ experience of the work and therefore have a professional and ethical responsibility to tend to this aspect.


A person’s personality traits, approach to problem-solving, risk management, complexity and (likely for many) the boring tasks have a major impact on the effectiveness of their behind-the-scenes logistical setup. Discovering in supervision how these elements of self play out in administering one’s practice, lays the foundation for how to proceed best.

For example, a person who is high in trait conscientiousness may find it easier to organise their practice’s administration. A person who has a problem-solving style oriented towards saving time, may not want to be bothered with the seemingly unimportant administrative aspects of their practice (until they need to submit practice logs for certifications, or financial records to their country’s tax agency).

Personal issues emerging from work:

General approach to practice

The point directly above apart personal psychological styles and preferences is pertinent to one’s general approach to practice as well. One’s confidence, comfort, capacity, and skill in managing risks, strategy and challenges, scaling, and complexity are but a few elements to consider in running a practice.

In supervision coaches will discover how are these play out in practice, what their personal defaults are, and how to both develop and operate effectively at the boundaries. While this knowledge and skill set is useful in the day-to-day management of a practice, it is especially valuable during times of hardship, novel and significant challenge, or when luck is just not on one’s side. Supervision plays a supportive function in these circumstances whether it is with your trusted individual supervisor or your community of colleagues in group supervision. As a reflective practice, supervision affords learning after these experiences.

Personal issues impacting professional relationships

As with one’s approach to practice, one’s personal styles, preferences, biases, and other psychological aspects will play out in, and influence the work with clients, both organizational and individual. Reflecting on one’s coaching experiences, sheds light on what transactional analysis calls intra-psychic (inner psychological processes) and inter-psychic (between oneself and others) dynamics. Working with a new awareness of these dynamics affords novel options to be explored and practiced; options based on present reality, not contaminated by the past (one’s subconscious).

When we engage with another person, their expressed thinking, feeling and or behaviours may remind us subtly and subconsciously of someone from our past. We may metaphorically impose the face of this person from our past onto the person in our present and engage with them as if they were the person from the past. This process is called transference, in that the persona of one person is transferred onto another, within one’s mind. When this happens, one is no longer engaging with the reality of the person in the present and the potential outcomes of the engagement, but rather manipulating the present reality and even limiting potential futures with the other.

When a practitioner is being treated by a client as if they are someone from the client’s past, they can be stimulated to reciprocate. This is called countertransference. This is really scratching the surface of this phenomenon and its various forms. A common example of how this might occur in coaching is the presumption by the coaching client that the coach will perform the role of teacher, with the client transferring their own experiences of teachers onto the coach, likely based on their feelings and apprehensions about the coaching work and context. When this occurs, the coach may experience the client as reliant on coach to provide answers, or being ‘naughty’ in the sessions, or expecting homework for example.

Transference and countertransference can play out in many ways. Through reflection with a supervisor on the coach’s unique experiences, the coach can learn how to recognize this for themselves, resolve it appropriately in the moment with their clients, and minimise their own transference and countertransference.

Client and Organisational issues emerging:

Professional relationships impacting you as person

The piece above about transference and countertransference applies here as well.

The Contract

A wonderful starting point for resolving issues emerging from the work with clients is to review the initial contract. Contract in this context means all aspects of the agreement with the client. Elements of the agreement are:

  • Administrative agreement. Who, what, where, when, reporting, costs.
  • The professional agreement. The methodology the practitioner uses and limitations thereof, the intended outcomes, any limitations on the agreement.
  • The psychological relationship. Biases, preferences, personality styles, prejudices, unpredictable dynamics emerging in the relationship.

When a challenge emerges in the work with an individual or organizational client, it is useful to reflect on and discuss the parameters of the contract. Are these still appropriate? Were they appropriate to start with? If not, what hooked the practitioner? What underlying dynamics impacted the initial contract (e.g., organizational culture)? Is client safety insured? Is the practitioner personally and professionally safe? Is the practitioner the best person and/or professional for this particular piece of work? What limitations has the practitioner encountered in their approach and/or methodology?

How each of these questions is resolved will emerge from exploration in supervision through a developmental approach.

Parallel Process

It is almost inevitable that the underlying dynamics which the client experiences in their world will start to play out in their relationship with the coach. The coach may find themselves unconsciously playing along with these dynamics, in the coaching relationship. This is called parallel process. The recognition of parallel process furthermore occurring in the supervision relationship is a valuable way to both label it and resolve it.

Organisational Culture

It is easier to make sense of an organization’s culture when exploring how it is acted out by individuals and groups, its values and beliefs, its operational context, and its character, ‘energy’ and ‘feeling’. In this way an organization’s impact on coaching clients, the coaching relationship, and the coach can be more clearly observed and responded to in a way that not only empowers the individual clients, but also the wider system.

Ethical Matters

Think of ethics as a systemic perspective on the behaviours of its role players (at a minimum coach and client, but intrinsically other affected groups too) and the impact these have both immediately and over time. How are people’s globally recognised human rights impacted by these behaviors? What limitations are created for people and systems by these behaviours? Within the complexity of the coach’s system with their client/s, what considerations are there and what responses are most ethical?

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