My Top 10 Tips For Having THAT Difficult Conversation With Your Team Member (that you are probably trying to avoid)

April 1, 2020


A common challenge we all face is how to have a difficult conversation with a team member.

You know “that” conversation you’re dreading?

It may be over something that has been brewing for a while, or it may simply be that you don’t know how to address something that recently came up… or perhaps you don’t want to appear mean.

They’re awkward, uncomfortable and sometimes unpleasant and I know you’ve been there!

If you are feeling that uncomfortableness in your gut and you know you have some ‘stuff’ you need to address then it’s time to get on and do it. It’s time to get your expectations out in the open and clear the air.

And if you follow my tips below, you’ll both feel better on the back of it. Sounds good right? Let’s get going.

Here are my tips to handle it with grace ☺️

1. Always prepare and write down notes relating to what you want to say.

Doing this helps you to remember exactly what you want to say and ensure you eloquently phrase things.  If you think about this in advance you are likely to sound calm and in control, rather than emotional and in a flap. 

2. When the opportunity comes up – take it. Be brave.

If you are having an every-day conversation with the person and they say something like ‘I’m a bit over this’ or ‘I’m struggling here’ or any sort of statement that you can link to your ‘difficult’ conversation, grab the opportunity and get talking! Positive connection terms include “I have noticed that”, “I’d like to talk to you about it a bit more” that will help you lead into and set the tone for your conversation.

You can then decide if it’s appropriate to have the chat right then and there (ideally) or later would be better for both of you. Consider the timing and the environment, and if it’s right for a deep and possibly challenging conversation. 

3. Scheduling weekly or monthly catch-ups automatically creates the opportunity to dive deeper into issues and discussions so this is always a good idea to plan from the beginning. 

Regular meetings remove the potential buildup or suspense of a ‘can we please arrange a time to catch up as I need to speak to you about something important’ 

4. Emotions can escalate quickly when having difficult conversations, so try and de-personalise your language to avoid this as much as possible. 

Using de-personalised language ensures the discussion is now received as an attack, so talk about how you are feeling, what the business needs or what the role requires. Not what the person is or isn’t doing. 
Some positive lead in phrases include: “I feel…”, “What I need from ‘this role”, “What the business needs” and “What I’m looking for here”.

5. Stay calm. LISTEN. Probe. LISTEN. Ask open-ended questions. LISTEN.

By active listening and allowing the team member to do the majority of the talking (and you doing the majority of the listening – at least 70/30) will allow you to get to the heart of the problem in a positive way. 

If you talk too much the person will just tailor their answers or their side of the conversation to what they think you want to hear. Plus, if you talk too much you are probably likely to be reacting in a reactive manner. 
Listen, and try to only talk when the team member is finished. They are more likely to listen to you then because they’ve been listened to.  

6. Speak slowly and calmly.

If you are unsure how you want to respond or you are not confident you have the right phrase or language, use a pre-prepared phrase that gives you the time and space to think, calm down and work out what the business needs.

“I’ll need to think about / process that”, “I’ll need to think about what the business needs”, 

“Thanks for sharing all of that with me”, “I want to digest it and respond properly after some time to think” are all positive, confident terms to revert to in times you need to create space to think prior to responding.

7. When it comes to requests or statements about money, never answer in the moment. 

Always give yourself space to consider the request. “We can have a look at that in the context of what the business needs, the return on investment to the business or change in your responsibility”. 

You ever never want to just give someone more money because they’ve asked. It always has to be in exchange for something. Essentially, any request regarding pay needs to be backed by a business case, involve more responsibility or relate to updates with industry rates. And you are unlikely to have all that information to hand right then.  

If you agree to a pay rise simply because one is requested (and if you agree straight away) you are setting a challenging pattern for your future relationship. 

8. Say Thank You clearly and gratefully to create a safe conversation.

Ensure your team member has heard you say thank you, and I suggest you say it multiple times in a few different ways until you are sure they have heard you.

It makes a significant difference in a difficult conversation when someone feels heard and respected. And the simple gesture of saying thank you communicates this clearly and authentically.

9. Agree to the next steps.

“OK, So you are going to have a think about XYZ and I am going to think about XYZ and we will chat again tomorrow/next week to decide what is right for us both. Is there anything else I’ve missed that we need to do from here?”

By confirming the other person has clearly heard and digested what you have discussed, and agrees to the next steps, it gives both parties reassurance that a resolution will hopefully follow.

10. Follow up the next day to check-in and make sure those next steps you’ve agreed to are implemented and start to happen. 

DO NOT let it just ‘go away’ because ‘everything seems OK’. It’s not and it won’t be. Whatever led you to that point will lead you back there again so ensure there is an actioned resolution.

I’d love to know what you think! Comment below or send me an email to see if these have helped!

And make sure you download my “Top 10 Resources Every Biz Needs to be Running a Remote Team Like a Boss’ – it’s a game changer!.


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