Welcome to my first office hours article of six, discussing real life leadership challenges. I’m a leadership coach and want leaders to know they need not be alone in their leadership.

Challenge #1 – A Difficult Conversation


I’m a team leader and people-manager for a team of six software engineers. It’s performance review time again. One of the team is going to receive a bad performance review. This is my second time doing performance reviews, but the first time I’m giving bad news. I am very anxious at the thought of having this conversation. I realise that I prefer to avoid conflict. I’m becoming increasingly tense and stressed as this approaches. It shows up as starting to doubt myself. I go backwards and forwards on whether my direct report’s performance is below what is expected or meets expectations, but I think I know

J.D. (no their real name)

This message immediately grabbed my attention. It resonated strongly with my own past experiences and I felt my own anxiety being triggered! I had to self-manage. And so it seems a natural place to start my office hours series of leadership challenges.

First, I want to thank JD for their openness and vulnerability in sharing this situation. They want something different, and have taken a good step by looking for support and talking openly.

Where to begin?

Where to begin? As a coach my focus is on the person, our manager, JD, (not on the task at hand). What’s going on for them; what is a good outcome for them here; how might they be getting in their own way; how might they play to their strengths?

And there’s a lot to pick through in JD’s situation.

There may be existential doubts: Who am I to judge. How do I know I’m right.

There may be relational doubts: How will this affect my relationship with my report; with my manager, if I don’t attend to this?

There may be instrumental doubts: Is my data reliable, or flawed? What am I missing? What else could I have done to change the current situation?

What would be a good result from this conversation?

Let’s assume this is indeed a low performer feedback session. This is something JD has to deal with. And let’s assume that rather than feel self-doubt, reluctance, fear, JD would prefer to feel confident, calm, helpful, grounded.

Establishing a more positive mindset toward this situation would be a big win for JD, a good outcome, that would likely support more effective performance leadership.

Rather than it being a difficult conversation, this could be a helpful conversation. It could be a pivotal, positive, turning point in the career trajectory of the direct report. This could be the one conversation that turns the direct report around. The report may look back and thank JD for this conversation in years to come, and use it as a shining example of great leadership.

What opportunities might there be in this situation?

There are opportunities here in this first experience of a low performance conversation: What reputation do I want to build for myself as a manager? What can I learn through this process? Where can I grow? What narrative do I want to write about my leadership?

Powerful questions

If I were coaching with JD, I would ask open questions to promote reflection and help JD find a deeper understanding; to evoke some transformation in their thinking and beliefs. (Examples of questions are shown throughout this text in bold italic).

  • What’s your truth in this situation?
  • What vision do you hold for your direct report?
  • What’s being triggered for you in the performance review?
  • What are you uncomfortable being with in this conversation?

JD says they, “think they know”, which I take to mean they already know performance is below what is expected. This is our manager’s truth, and we can build confidence in that by having JD replay the process they’ve been through or, in doing so, identify any gaps and necessary actions.

Tell me about how you got here…

How was the judgement reached and how has it been validated? What resources have been tapped for support? What help have you requested?

JD’s own manager can be a coach, mentor, and role model. They could share their experience and will have broader context.

The HR team will have great experience and guidance, and may have protocols that JD should follow.

JD’s peer managers will have a combined wealth of experience and are a valuable community to build. Leadership can feel lonely and isolated, but there’s already a community of support within JD’s own organisation.

A request for JD – Will you advocate for and schedule a monthly recurring ‘manager’s monthly’ get-together to talk and share people management insights?. (JD gets to say ‘yes’, ‘no’ or make a counter-offer of something else they will do).

There may be process that supports calibration of ratings across the group.

Team mates may have supplied feedback. Productivity data may be available. All these inputs serve as signals. Some of them are weak signals, some are strong. Confidence comes from the interpretation of these signals, and the validation of that.

“Change what you think, change what you feel”

Cognitive psychology holds that feelings are a function of thinking. So if you can change what you think about a situation you will change how you feel about it.

Man is not disturbed by events, but by the view he takes of them.

Let’s challenge what JD may be thinking.

What stories is our manager telling about difficult conversations?

What assumptions are being made here and what evidence is there to support them?

I don’t like criticising people”. (Advocating your point of view, and sharing your values and your data, is a conversation, not a personal criticism).

I don’t like upsetting people”. (You do not control how people react. People are responsible for how they choose to react, not you, so you cannot upset people – they choose to be upset).

I should have given feedback earlier”. (Maybe. So do better next time. Create accountability for yourself. Regardless, your team are responsible for their own performance. The current conversation is still warranted, and in the service of your direct report).

What are you assuming about your direct report? (And if the opposite were true, how would things be different for you?)

My direct report is going to be upset and angry”. (How do you know? You might be doing them a great disservice. How else might they react?)

What’s another way of looking at this?

What different perspectives can we find together around this topic? (I have some cool and fun ways to help generate new perspectives. Do you want to have some fun with this?)

  • Currently, this is a scary task that makes me uncomfortable because I don’t like causing upset.
  • This is a tough conversation involving another human being.
  • I have feedback that I believe is important.
  • Tough feedback is a gift that empowers the report to be more impactful and effective
  • I care about this person and really want them to succeed, and that’s why I’m taking the time to be respectful and honest and show them how they are showing up.
  • The report is resourceful, creative and whole. They are responsible for their own performance and are fully capable of succeeding. My feedback is an important input that allows that to take the necessary action to change this situation.
  • Holding people accountable for their own actions is an important part of growing my leadership capability. It’s also important for growing the leadership capability in others.

What’s going to allow you to sleep well after the conversation?

Regardless of how the conversation plays out, what would allow you to sleep well? Knowing that you did the right thing by your report? What are the core values you can lean into? You were honest; direct; compassionate; hard but fair; were there for them; listened?

Imagine it’s five years from now. How will you look back on this conversation?

The conversation is one moment in time. For a short while it’s in the future. It will be in the present for a few fleeting minutes. Then it will be one of countless past experiences in the mists of time.

Finding perspective can be useful in getting grounded and quieting the mind.

To Action

In work I am detail oriented, and in coaching I work to balance my natural tendency to push toward action. JD’s leadership challenge seems ripe for preparative actions, and action makes for a more natural fit in writing.

What preparations would be helpful for you to make, ahead of the conversation?

There’s a lot that can be covered in planning and preparation here. As a coach, I have to self-manage carefully here since JD has to own their own actions.

How do you want to be with your direct report during the conversation?

Imagine the situation is reversed. How would you want your manager to be with you, if they were giving you tough feedback?

For me the mantra of “Backbone and Heart” comes up. Backbone refers to having a spine, to being strong, to not running away from the conversation or avoiding difficult parts.

Heart refers to seeing your report as human, acknowledging this is tough for them to go through. What does being compassionate look like to you? How can you help your report get to a place optimism and buy-in for a better future?

Leadership is often about holding competing tensions lightly. Backbone and heart is a good example of this.


Practice, preparation and rehearsal will serve JD well in a difficult conversation. Sure, it won’t go exactly to plan, so what’s the minimum necessary plan? What are the table-stakes in this conversation? What are the non-negotiable requirements?

How might you be distracted from off message in this conversation?

What can you anticipate happening that would make the conversation tougher for you?

Derailing; distraction; arguing; being drawn into details; comparisons; strong emotions? You cannot control the report’s reactions. You can anticipate and prepare?

A request for JD – What will you do, and by when, to prepare for some of these distractions?

How can you manage the logistics to best honor your values?

  • Which day, time of day, location? What will the report likely need immediately after the meeting?
  • How might you ensure confidentiality of this conversation?
  • How might you avoid awkward small talk with the report immediately prior to the conversation?
  • What do you expect the direct report to do after the meeting?
  • What state do you want to be in before the meeting and how will you achieve that?

How might you structure the conversation?

  • Tell the report up front what’s going to happen, give them structure
  • Tell them you need for them to listen
  • Tell them they will have time to process what they hear, and then hold that space
  • There’ll be time to talk and agree what happens next
  • Acknowledge there’s a lot of information to take in

What will your report expect next, after leaving the meeting?

What are the concrete outcomes and next steps? Is this conversation part of process? What are JD’s expectations of the direct report over the next performance period?

What is your vision for the direct report?

Share a clear vision of the positive outcome you see for the report; acknowledge and champion them through this period.

How will you know your message has been heard?

Check for understanding; has the report heard and understood the message? Can they repeat the process for what happens next and what is expected?

What follow-up might you expect to have?

Are there any formal steps you are required to take, perhaps from HR? Are you expected to write up the conversation and send it to the direct report or HR?

A request for JD – Will you draft (but not send) a summary email before your conversation? It will work as a rehearsal for you, and help clarify your conversation points


JD has has been courageous and open in sharing this challenge and allowing me to use to walk through how a coaching conversation might look.

And so my final words are for JD.

I know you’ve got this JD. It’s clear how much you care about your direct report, and how uncomfortable you were coming into this coaching. I know you will have a positive and productive conversation with them. I know you can hold the discomfort you feel and be okay with that. And I’m sure in the near future when this is past, that your report will thank you for you too, for supporting them in making an important shift.

What would you offer JD to lighten the load of this leadership challenge? Please add to the comments. And also please share your feedback about this office hours leadership challenge.

Further Reading

If this article isn’t working for you, I do appreciate you trying. There’s plenty straight up ‘how-to’ advice out there. Here are some interesting and informative examples:

Grenny, J. (2019) 4 Things to Do Before a Tough Conversation. Harvard Business Review [article]. 22 January. Available from: https://hbr.org/2019/01/4-things-to-do-before-a-tough-conversation [Accessed 09 September 2019].

Raina, S. (2019) How to Have a Difficult Workplace Conversation With Ease. Forbes [article]. 18 July. Available from: https://www.forbes.com/sites/forbescoachescouncil/2019/07/18/how-to-have-a-difficult-workplace-conversation-with-ease/#5383656f3599 [Accessed 09 September 2019].

Smith Bennett, V. (2018) Navigating Difficult Conversations. Medium [article]. 07 March. Available from: https://medium.com/@vsmith.bennett/navigating-difficult-conversations-c5927b85e7b1 [Accessed 09 September 2019].