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Navigating the grey: My journey through ethics and complexity in Strategy Coaching


When first learning about ethics in executive coaching, I was introduced to the list of does and don’ts of coaching ethics. Most were obvious, like maintaining confidentiality, informed consent, boundaries, working within my expertise, and not sleeping with your clients. What could go wrong? Follow the list and be an ethical coach.

A few years later, a situation arose that taught me more about ethics and challenged my understanding.

My client, an entrepreneur, was in my office telling me about a new deal he was grappling with because of a few strange things with the person offering the deal. We unpacked it, and he mentioned the person's name late in the session. I knew him. It was a sociopathic ex-colleague I knew could sell ice to Eskimos at a premium price even after it had already melted and disappeared down the drain.

Emotions rose in me as I sat there. I wanted to shout, Run! Don’t do the deal. This guy always sells the world and delivers value only to himself.

I wanted to tell my client that this was his Odysseus moment. He needed to tie himself to the mast of the ship, put earplugs in his men’s ears and get as far away from the Sociopathic Siren and his proposed deal as possible.

This posed an ethical dilemma that wasn’t on the list. What was right and what was wrong? I wanted to help my client. But I couldn’t tell him to run from this deal. His experience might differ greatly from my interpersonal experience with the same person. Maybe it was the best deal in his life, and I talked him out of it. That would be a disaster and not very helpful.

But maybe doing the deal was also completely disastrous, specifically because of the severe lack of good character in our slippery sociopath. If I didn’t warn him and share what I knew about his potential peril, then I was causing harm.

What should I do with this situation? There was no easy answer. No right or wrong. No list of ethics do’s and don’ts.

This situation was my real schooling in the ethics of coaching.

Straightforward decisions are like a single-threaded maze, easy to navigate. In a complex decision, like a real ethical dilemma, spotting a direct route is like finding a straight corridor in a labyrinth - we might feel good while in it but are likely to get lost just around the next corner.

True decision-making acumen doesn't lie in strolling down clear corridors but skilfully navigating the labyrinth's intricate passages. Ethical dilemmas arise specifically in the grey areas with no easy answers. I grappled with my client's issue and had to decide where in grey I wanted to end up. Even having decided I didn’t have the comfort of right or wrong.

In the nearly twenty years since this incident, I have discovered that not having a definitive answer is not only the domain of ethical dilemmas in coaching. Any leader in business lives in a world that is poorly defined. If solutions were easy, everyone would make the right choices repeatedly, yet we know this doesn’t happen.

In any complex situation, we must grapple with ill-defined, often paradoxical decisions where we must wade in and figure out what to do. Some tools can be useful, but none provide a blueprint - they are just crutches to structure our thinking.

The lesson I learned that day, with my slippery sociopath, is that the most valuable thing I could do in a complex situation requiring a decision was to make explicit how I was thinking about the situation and why I was making the decisions I was making.

Some of these decisions will need to be corrected. Nobody gets complex decisions right all the time. By making explicit what I was doing, i.e. writing down all the aspects of the decision:

Doing this gives me a fighting chance to improve my ability to make complex decisions.

Even better is doing this with someone else who can help me see my blind spots and be honest so I don’t bullshit myself. People have won Nobel prizes showing how poor we are at complex decisions. But of course, we all believe it is other people, not ourselves.

So what did I do with my client? I asked him to give us both time to reflect on his deal. When we revisited the topic in the next meeting, I had a clear strategy in mind. Understanding my role as a facilitator and not a decision- maker, I guided him through the decision-making process without imposing my perspective. I used open-ended questions to challenge his thinking and assess the potential risks and benefits from his viewpoint. While remaining careful not to give too much emphasis to my past experiences, I tactfully shared some generic insights gained from similar situations, aiming to broaden his perspective. In this way, I ensured that he owned his decision while also benefiting from my experiences and insights.

Reflecting on the situation with the Deceptive Deal-Maker has been illuminating. It shed light and made explicit my approach to navigating complex decisions and ethical dilemmas in my strategy coaching.

The process of writing has helped me articulate my thoughts, distil my experiences, and structure a methodology for confronting similar challenges in the future.

Professor Malcolm Charles at UWC was a major influence on my thinking about ethics. He ran a workshop for us in our early years of coaching. And Dr Michelle van Rheenen is a colleague whom I met on day one of our Master's journey at Middlesex. She is the best-qualified person I know, and I trust her to discuss my ethical dilemmas.