Landing Those Awkward And Crucial Conversations

awkward conversations

Clients often tell me things like: “I am nervous about this conversation. I have been putting it off. How do I start? “

 Or, “I am nervous about letting X know he isn’t being appointed. I don’t want to lose him, and I know he will be disappointedThen he will sulk, and those around him won’t want to interact with him, yet he is a key player in the team.” 

And, “one of my team members is causing havoc with our stakeholders. He leaves people feeling that he thinks they are stupidHow do I tell him this?” 

Well handled, these awkward yet crucial conversations can be an opportunity to improve the business and relationships with team members.

Imagine a future when staff and leaders have awkward conversations with one another and are confident they will maintain or improve their relationships and the business in doing so! 

So how do you do it?

Essentially, it’s a matter of knowing what you want to achieve, what you want to say, and having the courage to start the conversation.

What are these awkward conversations about? 

These kinds of conversations tend to fall into four areas:

  • Communicating bad news 
  • Changing culture and behaviours
  • Providing clear direction to teams and groups
  • Clarifying expectations of behaviour or performance

What makes these conversations so awkward?

I ask my clients this – what do they tell me? There is quite a range of responses, but I hear three that come up often. 

You might recognise some of these yourself:

  • Not wanting to hurt the other person’s feelings or upset them. 
  • Feeling nervous they will end up in a fight, or the discussion goes out of control, or the conversation goes off purpose. 
  • Disliking conflict.

 Think about these:

1. Not wanting to hurt the person’s feelings. Frequently the business is being hurt by these behaviours or at the very least the leader, either in work not being done well, or the emotional time reflecting on the person and what they are doing.  

2. The anxiety that the discussion may go out of controlSubstantial emotional time and energy is already being put into unproductive thinking about these situations and the consequences, so the situation is already ‘out of control’.

3. Not liking conflictThen it’s time to learn to have greater ease with conflict and holding your perspective in the face of push back. The role of the leader is to create unity in direction when there are conflicting perspectives

So, how do we have these conversations?

At least three things are required.

 The first is to be brave. Raising these awkward areas requires bravery. Being brave is sticking to your vision. Being brave in raising an area others have avoided, probably for many years. And being brave in diving in and not being sure what the outcome will be.

The second thing is to have a conversation structure: 

  • Identify a clear purpose for the discussion
  • Clearly and simply describe the behaviour you notice
  • Then, ask if the other wants to know how the behaviour affects you, or others
  • If yes, simply let them know, then ask either: “Were you aware of this?”, or, “How do want to make a change?”

Thirdly, work together on a plan. Be prepared to have this conversation over two or three days or two to three weeks.

Be aware that you may be the first manager to let the recipient know this. While the negative behaviour seems blindingly obvious to you and others, it may not be to the individual. 

Starting The Conversation

Many of my clients tell me that the hardest thing is starting the conversation. These kinds of awkward conversations need what I call a “warm up”.

You can read more about warming up to conversations on an earlier post. Warm-up is referred to as metacommunication. 

Obviously, if you are going to discuss poor behaviour, whoever you are working with needs to hear several of the things you think they are doing well BEFORE you introduce anything that isn’t working.

One thing to bear in mind is that many recipients are shocked and embarrassed when they hear critical performance feedback. Mostly this is because you are likely to be the first person to raise this.     

How to begin?

Begin by relating to the context or purpose of the conversation. 

Something like: “This is a chance for you and me to reflect on what’s going well and a few adjustments that are needed. I’ll begin with where you are going well. The things you are doing well with are x, y, and z; you interact well with others, you share information, etc. I appreciate you being dependable in those areas. I can rely on you absolutely for those things. These qualities of yours, really contribute to the team working well.

And, there are one or two things that aren’t working for me.”

Either: Do you want to know from me, or what do you think these might be? 


I want to bring one or two things to your attention. One or two areas of your behaviour that are no longer acceptable to me, or in our team. 

Then, either:

  • What do you think I might be referring to?


  • How about I let you know what these are, and then you respond? 

Be conscious of these crucial conversations, you are building a relationship:

  • Keep it simple. No long explanations.
  • Be generous, rather than unkind.

Then what?

The process from there will be different in each situation, depending on the recipient’s response. By thinking ahead and taking these first steps, you will be improving the performance of your business and your team, and quite likely building better and stronger relationships.

Clients who take the first step tell me that they feel a sense of both relief and control as they move to resolve a situation that has been unproductive and stressful for themselves and the team.  

To ensure crucial conversations are a natural part of your identity, contact me.

© Diana Jones

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