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  • Writer's pictureBella Trenkova

"I am uncoachable" - How to Work With Difficult Clients

A few years ago, I was brought in as a Coach by a client with a budget and a team for a modernization project. They wanted to re-platform an app, rebuild it for the cloud, and refresh the business processes. It was a holistic overhaul, and the client wanted to future-proof their investment by using modern tools and practices for Agile, DevSecOps, Lean Product Development, and Human-centered Design.

It sounded like a perfect setup! Until… we had the pre-kick-off meet and greet with the client’s line manager. One of the very first things he said was, “Glad to have you on board as a coach. The team will benefit greatly. As for me - I am uncoachable!”

That immediately raised a flag for me. What he was saying was not that he was uncoachable, but rather that he didn’t think coaching was for him, and he was above and beyond whatever I could have coached. I could tell he was smart, well-read, and familiar with many concepts I was about to bring to the team. We clicked in many ways, but that “I am uncoachable” line stuck with me. I knew it was a boundary that I had to tread carefully.

I am bringing this isolated, personal experience only because it succinctly summarizes a pattern that I have observed with many other clients before and after – the people who make the crucial decision to bring a coach for their team don’t take the benefit of their own investment. They quickly build that invisible fence of “Go coach the team. I don’t need coaching [because I am already perfect].” Sadly, that is one of the early signs of Fixed Mindset and a strong predictor for the success (or the lack thereafter) of the coaching effort:

How can teams become and behave as Agilists when their immediate management doesn’t demonstrate the very essence of Agility – continuous (personal) improvement and Growth Mindset?

Don’t answer that! It was a rhetorical question. However, here are a few of my Do-s and Don’t-s when engaging with difficult (or any) clients:


Establish your coaching agreement early.

Write it on a piece of paper and walk through it with the people you will coach and those who will sponsor your effort, and do it as early as possible in your engagement. There is so much ambiguity and misunderstanding in what coaching means and what a Coach should do. Writing it on a page (no more than 2!) will clear the air and prevent many anti-patterns and dysfunctions.<placholder for a future article>.

Employ your empathy to understand the origins of actions and cultural norms.

Sometimes, it is too easy for us to step into an organization as outsiders and immediately see what’s wrong with it. And the very first reaction is to tell them what exactly is wrong and how they should fix it. ... And that is the quickest way to trigger their defense mechanism and have them shut down and not hear a word of what you say. A better approach is employing your empathy and curiosity. Find out what the historical pain points lead to the present-day culture and behaviors. Take them on a journey where they can (re)discover the roots of their problems, re-examine their thought and behavior patterns, and internalize the not-so-desired but inevitable outcomes.

A case study from the field:

One of my early clients had a very well-formulated and strictly enforced SDLC governance process.  It was fully buttoned up to show that every action, decision, and deliverable along the way was thoroughly documented, tested, reviewed, and approved.  The problem was that with such a heavy-handed governance framework, release cycles were extremely long.  The IT teams couldn’t keep up with the demands from Business.  

A few weeks into the engagement, we experienced a moment of enlightenment.  We were told about a major security breach that occurred a few years ago.  It was heavily publicized in the press and some heads rolled too.  That had triggered a response of extreme risk reduction and avoidance in the organization and hence the heavy SDLC processes.  At that moment, we knew that whatever new and cool Agile practices we suggest, we should always underpin them with how they will not jeopardize, but likely improve the security posture of the organization.  

We had to put ourselves in the shoes of the present-day decision makers and address their historical pain points, before we could invite them to look into a better future.

Actively listen and observe more than you ask. Ask more than you say.

The art of active listening is taught in every leadership and interpersonal skills class. However, too often, it is overlooked by many coaches who feel the pressure to start adding value right away by providing sage advice. Often, we are pressured by our clients with expectations for contractual deliverables and measurable change. However, no quick fixes don’t have a lasting impact. It’s just like fast food – it makes us feel full in the moment, but it doesn’t nurture longevity. The most impactful coaches I have worked with are those who provide a few suggested solutions but only after asking many open-ended questions and listening attentively to their clients' spoken words and unspoken behaviors.

Teach them how to fish; don’t feed them fish.

This is the main difference between Consultants and Coaches. Consultants are brought in to catch the fish, fry the fish, and serve it on a plate for immediate consumption. And sometimes, that may be exactly what the client needs. If the client is smart, and there are plenty of the same fish around – they may observe, learn, and replicate what the consultant just did to catch their own fish. However, how often do clients stumble into the same problem twice? More often than not, the context changes, and the problem space evolves faster than the client can hire the next consultant. The same one-time tricks may no longer work in the future.

A good coach will take the client through the entire process of learning various techniques and practices – the patterns and antipatterns, the rules, knowing when to break the rules, and how to land safely still. A great Coach will teach their clients how to fish under different conditions, going after different catches. Unlike the consultants that solve a discrete problem, coaches will give their clients the tools to be independently successful in the future under any scenario.

Use analogies to break down abstract concepts.

Just as I did above 😊

Jokes aside, I have found analogies to be a super powerful tool in the coaching toolbox. (Heck, I can write a whole article on this topic!) At its core, coaching is the art of bending minds and hearts and taking them to places they haven’t been before, helping them see and experience things they haven’t seen or experienced.

Our human brains don’t process the unknown too well until we can link it to something familiar that can help us decide if a threat or award is hiding in the unknown. And when we can’t decide this quickly enough, the default brain response is to assume the unknown as a threat. It is a basic survival mechanism that kept our ancestors alive in the darkness and the unknown of the jungle.

Flash forward to the modern day - our brain patterns haven’t changed much. Anyone who has attempted any significant Change effort can tell the stories of resistance and prevalent fear of the new and unknown. On the other hand, if we can connect the new and unknown to something relatable and safe, all of a sudden, the big monster in the closet turns out to be the shadow of a cute teddy bear. (Oops, I did it again! How did it work?)

Allow room for mistakes and “poor decisions” that lead to lessons learned.

To extend my analogy streak, good Coaching is like good parenting – no one wants to see their offspring (e.g., client) fall off a cliff. However, if we don’t let them explore a little, trip up, and even scuff their knees, they will never learn how to scale mountains, protect themselves when they are on their own, and what risks are relatively safe to take vs what leads to a crash and burn. Our job as coaches is to protect them from the latter but not be in the way of the former.

And speaking of making mistakes, here are a few to avoid as Coaches:


Don’t expect your every word or recommendation to be treated as gold.

It takes a great deal of humility to accept that we are not always right. And even if we are, it may not be the right timing or state of mind of the client. Accept that there are many viewpoints and that from some of them, what we consider the absolute truth may look very different. Stay humble!

Please don’t take it personally.

On more than one occasion, I had to swallow my own ego and process why, as a coach, I am super effective with some clients and teams and not so effective or well-accepted by others. It is a big grain of salt to swallow, but then I eventually remember what people say and think about me is, to a lesser extent, a reflection of me but much more a reflection of their own state of mind and being. The teacher appears only when the student is ready. You can do everything right, but if the client is not ready – it will go to waste. It’s not personal!

Don’t say, “I told you so.”

It is bad form, period! At home with your spouse or kids, at work with your co-workers, or as a coach with your clients. It sounds tempting to get a small validation victory of, but ultimately, it doesn’t help anyone. The better approach is asking, “What did we learn?”

Don’t be a passive observer.

This may sound contradictory with the couple of “Do” points above about observing more and allowing them to make mistakes. However, there is a big difference between being a passive observer vs actively listening, attentively observing, and holding up the guardrails. The latter is what great coaches do: the former … just don’t be that “coach” who crosses arms on the chest and waits for the crash & burn so that they can emerge as the “smart” one with an “I told you so!” Don’t!

Don’t preach from the pulpit.

This is a huge pet peeve of mine. In my practice and on my journey, I have encountered many flavors of coaches. The one that I personally can’t stand is the Coach who is so pure and true to the Agile canon that they forget that nothing in nature and life is an absolute truth, 100% white or black, or 100% right or wrong. Just because one has read a few books or has practiced Agile successfully in one (or a few) organization doesn’t make them the next messiah. The world is colorful and messy; there is no one-size-fits-all. Get down from the pulpit and roll up your sleeves to solve real-world problems with your client!

Don’t be afraid to call a spade a spade.

This one and the next one may sound a little contradictory. So let me try to illustrate the difference.

There is that old fairytale about the Emperor Who Had No Clothes. Everyone in the kingdom was so afraid to tell the emperor that his tailors were crooks and he had no clothes, so they all colluded to complement the newly crafted fine threads he was (not) wearing. It took a young and innocent child to point out and ask loudly, “Why is our Emperor naked?”

Such collusion exists in many organizations and work environments. We invented too many words such as “team player,” “collaborative,” or “social safety” and too often use them counter-productively and not in their original spirit, but to hide the ugly truths. Usually, out of fear of repercussion, being singled out, or canceled. It takes great of courage and integrity to say that “our Emperor is naked.” And that’s what a good coach should do.

Don’t call their baby ugly.

However, a great coach would do it with empathy and diplomacy in a way that doesn’t evoke an immediate defensive knee-jerk reaction. In a way that helps their clients see and call out the truth and do it constructively and positively.


I hope at least some of those Do-s and Don’t-s were helpful. I’d love to hear about the lessons YOU learned.

And to finish the story that I opened with. The team did build a new product within just a few months – the client didn’t get everything they hoped for. Still, the product was so much more visually pleasing, user-friendly, business-process-streamlined, and maintainable that it was worth the investment. The “uncoachable” manager thanked me for the many things he had learned in the process. So, it turned out – he did get coached after all. Because I didn’t preach from a pulpit, I never told him what to do or what decision was right or wrong, but I asked the right questions and called out the dysfunctions.

If you make them think twice and try something new once – you are doing a great job as a coach!

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