I am going to say something that most coaches will not say: sometimes, you should fire your coach. Not every coaching relationship works. Not every coach is right for every leader. And staying in a coaching engagement that is not delivering value is not loyalty. It is waste. I have been a coach for over twenty years, I hold an EMCC Senior Professional Coach accreditation, and I have worked with more than thirty senior executives across Southeast Asia. I have seen coaching change lives and businesses. I have also seen coaching engagements that went nowhere, including, if I am honest, a small number of my own early in my career before I fully understood what makes coaching work.
The reason I am writing this post is that I see too many leaders trapped in coaching engagements that are not serving them, either because the match is wrong, the coach is not skilled enough, or the engagement has run its natural course. And I see an equal number of leaders who abandon coaching too early, just as the real work is about to begin, because they confuse discomfort with dysfunction. Knowing the difference between a coaching relationship you should leave and one you should invest in more deeply is one of the most important judgements a leader can make.
So let me be direct. Let me give you the honest framework I wish someone had given every leader who has ever hired a coach. Because the stakes are real. Your time is finite. Your development matters. And getting this right can mean the difference between transformation and stagnation.
The Real Challenge
The coaching industry has a quality problem. The barriers to entry are low. Anyone can call themselves a coach. There is no universal licensing body, no mandatory accreditation, no standardised training requirement. This means that the market includes exceptional, highly trained professionals alongside well-meaning individuals with a weekend certification and a LinkedIn profile. Leaders often do not know how to distinguish between them, and by the time they realise the coach is not up to the task, they have invested months of time and significant money.
But the quality problem is only half the issue. The other half is that leaders often misjudge their own experience of coaching. Coaching, when it is working, is not always comfortable. In fact, the most transformative coaching sessions are frequently the most uncomfortable ones. A good coach will challenge your thinking, question your assumptions, and hold up a mirror you may not want to look into. If you expect coaching to feel like a pleasant conversation over coffee, you will be disappointed, and you may mistakenly conclude that the discomfort means the coaching is not working when it actually means the opposite.
So the challenge is twofold: how do you identify genuinely poor coaching that you should walk away from, and how do you distinguish productive discomfort from unproductive dissatisfaction? Let me give you clear criteria for both.
The Framework: When to Fire, When to Stay
Fire Your Coach If: There Is No Structure or Accountability
Good coaching has structure. Not rigidity, but a clear framework that includes goal-setting, regular review, and accountability. If your coaching sessions feel like aimless conversations, if you leave each session without clear commitments, if your coach never revisits what you said you would do, if there is no sense of progression from one session to the next, something is wrong. I have spoken with leaders who spent twelve months in coaching and could not articulate a single concrete outcome. When I asked what their sessions looked like, the answer was some version of, ‘We just talk about whatever is on my mind.’ That is not coaching. That is an expensive conversation. A professional coach will establish clear objectives at the start of the engagement, create a structure for each session, build in accountability mechanisms, and regularly review progress against goals. If your coach does none of these things, it is time to find one who does. This does not mean coaching should be mechanical or formulaic. The content of sessions should be flexible and responsive to what the leader is navigating in real time. But the process should have rigour. Think of it like jazz: the musicians improvise, but they do so within a harmonic structure. Without the structure, it is just noise.
Fire Your Coach If: You Never Feel Challenged
If every session feels comfortable, affirming, and easy, your coach is not doing their job. This is one of the most insidious problems in coaching because it feels good. You leave each session feeling validated and understood. Your coach agrees with your perspective, sympathises with your frustrations, and tells you that you are on the right track. It is pleasant. It is also useless. A good coach will be supportive, but they will also challenge you. They will ask the questions you are avoiding. They will name the patterns you do not want to see. They will push back on your certainty when that certainty is unfounded. This should not feel aggressive or adversarial. It should feel like someone who genuinely cares about your growth is willing to tell you what nobody else will. I tell my clients early in our engagement: ‘If I am always agreeing with you, I am not adding value. You are paying me to help you see what you cannot see on your own, and sometimes that means hearing things you would rather not hear.’ If your coach never pushes back, never challenges your assumptions, and never makes you uncomfortable, you have a friend, not a coach. And you can get friendship for free.
Fire Your Coach If: The Relationship Does Not Feel Safe
This might seem to contradict the previous point, but it does not. A coaching relationship should be challenging and safe simultaneously. You should feel that your coach will push you, but also that they genuinely have your best interests at heart. You should feel that what you share is held in strict confidence. You should feel that your coach respects your autonomy and does not impose their own agenda or values. If you feel judged, manipulated, or unsafe in your coaching relationship, that is a legitimate reason to end it. Trust is the foundation of effective coaching. Without it, the leader will never be honest enough for the coaching to work. I have had leaders come to me after previous coaching engagements where they felt their coach was more interested in demonstrating their own cleverness than in genuinely serving the leader’s development. Or where they suspected the coach was sharing confidential information with the sponsoring organisation. These are serious breaches that justify immediate termination of the engagement.
Now for the other side: when to stay and invest more deeply.
Double Down If: You Are Feeling Uncomfortable in a Productive Way
There is a specific kind of discomfort that signals coaching is working. It feels like having a mirror held up to a part of yourself you have been avoiding. It is the discomfort of seeing a pattern you did not want to acknowledge. It is the tightening in your chest when your coach asks the question you have been hoping nobody would ask. This discomfort is not a problem. It is the mechanism through which growth happens. If you leave a coaching session feeling unsettled, reflective, and slightly challenged, that is usually a sign that you are in exactly the right engagement. Do not run from that. Lean into it. The leaders who get the most from coaching are the ones who learn to sit with this discomfort rather than flee from it. The impulse to quit coaching often peaks just before a breakthrough, when the old way of thinking is being challenged but the new way has not yet fully formed. If you quit at that point, you lose everything you have invested.
Double Down If: You Are Starting to See Patterns You Never Saw Before
One of the clearest indicators that coaching is working is the emergence of pattern recognition. You start noticing things about your own behaviour, your relationships, and your decision-making that you never saw before. You catch yourself mid-reaction and think, ‘There is that pattern my coach and I discussed.’ You start seeing connections between events that previously seemed unrelated. This is a sign that the coaching is rewiring how you think, not just what you think about. It is the most valuable phase of any coaching engagement, and it typically begins three to four months in. If you are in this phase and considering ending the engagement, I would strongly encourage you to continue. The patterns are just becoming visible. The real work, translating that visibility into different behaviour, is what comes next.
The key principle underlying this entire framework is simple: effective coaching should be structured, challenging, safe, and productive. If any of those four elements is missing, the engagement is not working. If all four are present and you are feeling uncomfortable, that discomfort is probably the sound of your leadership growing.
A Story From the Field
I once received a call from a CEO in Kuala Lumpur who had been through two coaching engagements with two different coaches over three years and felt that coaching ‘did not work’ for him. His CHRO had recommended he try once more, with a different coach. He was sceptical, to put it mildly.
In our diagnostic session, I asked him to describe what his previous coaching engagements had looked like. The first coach, he said, was very supportive and affirming but never challenged him. ‘It felt like paying for a friend.’ The second coach was extremely structured and methodology-driven but felt impersonal and formulaic. ‘It felt like a consulting engagement with homework.’ Both descriptions told me what he needed: challenge with warmth, structure with flexibility. We began the engagement with clear, mutually agreed objectives and a commitment to honest feedback in both directions. Within four sessions, he was engaging at a depth he had never reached before. Six months in, he told me it was the most valuable professional development investment he had ever made. The issue had never been that coaching did not work for him. The issue was that the previous matches had been wrong.
He later reflected that the experience had taught him something important about coaching: it is not a commodity. The quality of the coach, and the fit between coach and leader, matters enormously. A poor coaching experience does not mean coaching does not work. It means that particular engagement did not work.
Key Takeaway
Not all coaching is equal, and not all discomfort is dysfunction. Fire your coach if there is no structure, no challenge, or no safety. Double down if the discomfort is productive, if you are seeing new patterns, and if you sense that growth is happening even when it is uncomfortable. The ability to distinguish between a bad coaching engagement and a good one that is doing hard work is itself a leadership skill.
Your Next Step
Whether you have never tried coaching, have had a disappointing experience, or are considering deepening your current engagement, the starting point is the same: an honest diagnostic conversation. I offer a complimentary 60-minute being-specific.com/contact/”>diagnostic session, valued at RM 1,000, where we assess your situation, your goals, and whether coaching, specifically with me, is the right fit. I would rather have an honest conversation that concludes coaching is not what you need than begin an engagement that does not serve you. That is the standard I hold myself to as an EMCC Senior Professional Coach. Visit being-specific.com/contact to book your diagnostic. The leaders who benefit most from coaching are the ones who choose it deliberately, not out of obligation. Make a deliberate choice.
