Challenging Coaching Conversations

When you are coaching an average or a top performer, the coaching conversation is relatively easy to have because, typically, the person is open to your suggestions, guidance, and feedback. However, having a coaching conversation with a poor performer can be challenging. A poor performer can be in denial, resistant to the feedback, or even argumentative. Coaching someone who isn’t receptive to feedback or guidance for improvement can be intimidating. This can lead to avoiding the coaching conversation altogether, which will usually result in unrealized potential, a tolerance for subpar performance, and underperformance.

The Power of Positive Intent

When approaching a challenging coaching conversation, you first need to consider your own mindset. Are you approaching the conversation with the attitude that you really want to help this person? Having a genuine desire to help someone is where all good coaching begins. If you are only going through the motions because you want to replace a direct report, or because your manager is telling you that you need to improve the person’s performance, then you will fail! Your coaching will be a waste of the direct report’s time and your time. Having a positive intention in coaching means you really want the direct report to improve because you genuinely care about his or her performance and want the person to succeed. Don’t even attempt coaching if you don’t have this mindset.

Conducting a Challenging Coaching Conversation

Once you have a positive intention mindset about a challenging coaching conversation:

Plan and practice the conversation.

Prepare for a difficult coaching conversation by making an outline or script of what you want to tell the direct report. The words you use matter! Focusing on your observations of the direct report’s behavior and its impact on the job are a good place to start your conversation.

Once you have a plan, practice your delivery. Just as words matter, so, too, does your manner of delivery. If your communication in the coaching session appears genuine and sincere, then the direct report is more likely to accept the feedback and work on making changes in his or her performance. Role-playing with another person is effective if you are delivering particularly challenging coaching.

Focus on evidence.

The first goal of coaching is for the direct report to understand the impact of what he or she is currently doing as it relates to the job. If the direct report takes ownership of his or her current performance, then you have already overcome half the challenge!

The best way to get a direct report to understand the impact of his or her current performance and take ownership of it is to use observations of the direct report’s behavior, or share with him or her data that clearly illustrate what he or she is doing and the impact. This is called evidence-based feedback, and you must deliver it objectively. If the direct report feels that the feedback is highly subjective, he or she will push back and refuse to accept it or take ownership of it.

Provide objective and candid feedback.

Too often we feel that even constructive (not negative) feedback is going to hurt a direct report’s feelings. First, making a direct report feel good, while it would be nice, is not the objective in coaching. The objective in coaching is to help the person develop to a higher level of performance. Second, while people don’t always like candid feedback, they do respect it. If you are providing your feedback from a perspective of positive intent, then the direct report will likely respect the candid feedback as genuine and useful and act on it.

Implement an action plan.

Coaching conversations should not get stuck in the past. Once you have given your feedback and provided good, objective evidence to support it, then focus on how to change the direct report’s future behavior. Coaching involves making good changes in the future, so ensure that the difficult conversation doesn’t stall in discussing what the direct report has done in the past.

One way to effectively create an action plan is to gain the direct report’s input on the change that he or she needs to make and how to implement that change. All good coaches are open to suggestions and recognize that if the direct report comes up with the idea, he or she is more likely to take ownership of its execution. Asking good coaching questions and listening with an open mind lead to good action planning.


Conducting a challenging coaching conversation can be intimidating. However, if you first approach it with the proper mindset—that you genuinely want to help the direct report improve his or her performance—then the conversation focuses on the help you are offering. Prepare for the conversation with lots of good supportive evidence, making that the focus of your feedback. Feedback should always be candid, illustrate the impact the direct report’s performance is having, and outline changes that will have a positive result. Finally, stay focused on the future by providing good guidance and action planning that will improve or correct the direct report’s performance.

Coaching is one of the most valuable tools you have for achieving results, so don’t be intimidated by challenging situations. Embrace them as opportunities!

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