How good are you with those difficult conversations?

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How good are you with those difficult conversations?


From time to time you feel the need to sit down with one of your team to have one of ‘those’ conversations. You know the type. The tough love conversation that may be a little uncomfortable but is absolutely the right thing to do!

It’s one of those leadership activities that many sales leaders find difficult despite knowing that it is the only way to move someone from stuck to unstuck. Normally it’s because us humans don’t want to upset people, to appear unkind or make people feel uncomfortable.


Let’s take an alternative perspective…

Imagine that you are unconsciously doing something that has a negative effect on the people around you. You have no idea that you are creating this negative impact. Nobody tells you because they don’t want to make you uncomfortable or upset you but they are all feeling it and maybe even talking about you amongst themselves. How kind is that? How would you feel when you eventually find out?

Having that difficult conversation is the kind and right thing to do.


Give your sales person the opportunity to change

If you say nothing and hope the issue goes away by itself you are inadvertently saying that the behaviour you want them to change is acceptable. They will continue to behave in that way when they are triggered to do so. They often have no conscious awareness of the impact they are having.

By bringing it to their attention…in rapport and with compassion, you have a really good chance of shifting their perspective and their behaviour. You can agree on the first steps and a review date.

That way you can both leave the conversation feeling good about yourselves and each other.


Some pointers to keep you on track…


Convey your positive intent

Make it clear you are on their side. Always do this face to face…even if it’s on Skype or similar

Describe only what you have personally observed

Never have a conversation about behaviour that you have not witnessed for yourself. Someone else’s version will always be distorted by their viewpoint and could be wildly inaccurate based on their perspective of the person or behaviour…and how it affects them. Keep it specific and factual and about the behaviour…not them as a person.

State the impact of the behaviour

Increase their awareness of the consequences of their behaviour…for them and others. Use a supportive tone.

Ask your sales person to respond

Give them an opportunity to share their perspective. Do not interrupt. If you’ve done a good job they are unlikely to jump to defence. If they do let them air their thoughts and summarise your understanding back to them.

Focus on solutions

This is the whole point of the conversation. Get your sales person to come up with their own solution, first steps and review date.

Use coaching questions throughout

This is not your opportunity to show how much you know or to share how you would fix it.


You really are supporting and developing your sales people with every one of these conversations. Whilst they are not easy…the more of them you have, the easier they become. The best thing…the results always make it oh so worth it!

Until next time,

Leigh 😊

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