Six tips on how to have critical conversations at work

Jane Counsel, front and centre

In my time as a manager, one of the most challenging parts of the role was having those difficult conversations with reports, whether about performance issues, or … well let’s face it, everything in the end is a performance issue! Now that I’m an executive coach, I have critical conversations as part of my day job – and I love it!


First of all, a definition: There are lots of terms for the tricky conversations I’m talking about: difficult; crucial; constructive; courageous; challenging; ‘carefrontational’ and critical. All these adjectives have a different flavour but I think we’re talking about the same essential ice cream here.

In our practice we generally use the term ‘critical conversation’, as these interactions are a critical part of coaching success for our clients. I’ll define critical conversations, in the context of coaching, as ‘a conversation to help the coachee surface and resolve issues preventing progress’.


It’s not really fair to compare the experience of these conversations in a managerial versus a coaching context, because the dynamic is completely different. Between a manager and a reporting employee, there’s a power differential. It’s the manager who by virtue of their position has control, and they generally initiate the conversation, with performance improvement on the agenda.

For a leadership coach it’s a different story. I am engaged by the client to assist them in working through their self-defined issues. My agenda is for them to increasingly take charge of their own learning. It’s a partnership we willingly and mutually create. Ultimately the client is in control; they choose to put themselves in my hands for some of this work.

I think there are things managers can learn from professional coaches in navigating the difficult conversations they must have. Not everything, but some things.


1. Build trust

Build rapport and trust before you even go there with critical conversations. No one opens up in a climate of mistrust. Respect is an important ingredient here, and following steps 2-5 will go a long way to building trust.

2. Set a framework

If you set a framework for giving and receiving feedback there are no surprises. For an employee this should be part of the induction process. For a coachee it’s a part of setting agreements in the first coaching session. It’s about scripting what is to come:

‘You’ll find that I ask a lot of questions . . . My role is to help you dig deeper . . . there might be some times when I challenge you . . .’

3. Time and place

I think face to face is important, because body language and facial expression are eloquent. Having said that, phone conversations can be powerful, if you are highly skilled with listening, asking the right questions, and responding to tone, silence, and what is not said. It’s also vital to have enough time and privacy to move the conversation through to a useful conclusion.

4. Ask don’t tell

Organisational development expert Edgar Schein talks about three sequential levels of critical inquiry:

4.1. Pure inquiry. This is the initial phase of information gathering. He says that the longer you spend here, the more likely that your person will come up with the problem and the solution themselves. So resist the urge to jump ahead!

4.2. Diagnostic inquiry. This is where you start to focus attention on words or affect that might provide points of entry to a deeper conversation. ‘You mentioned some tension with your manager . . . can we explore that a bit?’

4.3. Confrontational inquiry. In this phase you are challenging some aspects of their story. ‘How might you be contributing to that problem?’ This is not so much confrontational as reframing.

The ‘ask don’t tell’ rule is a good general rule for critical conversations. But it’s also important to put on your mentor or advisor hat at times, and give your point of view.

5. Listen deeply

This should be the easiest thing – after all you just have to sit there. However, it requires putting aside your own preconceptions and narratives, and listening to stand in their shoes. This is the basis of empathy.

6. Critical reflection

Sometimes I find it useful to use a specific critical reflection technique such as storytelling, metaphors or conceptual mapping. These can provide a way to question assumptions and open the possibility of an alternative view.


I can think of three great reasons:

  1. This is how your coaching client will grow. That’s why they’ve come to you.
  2. In the process, they develop skills for critical conversations with their reports.
  3. In learning to have critical conversations the coach grows as well.

Contact Glenn to discuss a coaching approach to critical conversations, or for his coaching opportunities.

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