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Remember when you were a kid? When something didn’t look or smell right, you just came out and stated the obvious. Fortunately, you never got into any real trouble. It was excusable behavior because kids are so honest, they say.

As adults, it’s no longer that easy. Difficult conversations are an inevitable part of being a grown-up and a frequent occurrence if you work in management. In as much as we’d prefer to avoid them entirely, we need to address these scenarios promptly before what started out as a potentially painful conversation may escalate into a heated one.

Here are 6 tips for dealing with difficult conversations:

Think positive

You’re more likely to be anxious if you approach the conversation negatively and fearing the worst. Instead, imagine what the positive outcome of the discussion will be once it’s over.

Once the conversation has taken place, you can both now work on how to avoid the situation in the future. Look at it as the opportunity to move forward.

And if you’re about to painfully admit to your superior that there will be further delays in the submission of a project, it is your opportunity to offer alternative solutions. Or if you’re about to deliver a negative performance review, think of it as helping a colleague better themselves through constructive criticism.

Calm yourself

Difficult conversations can take over us emotionally and physically. We find ourselves unable to focus, breathing heavily, and hearts racing.

In leadership training you will learn that if you know you’re about to engage in a challenging conversation, center yourself. Take a deep breath or even go for a short walk. The important thing is to clear your mind as you prepare to engage.

Be authentic

Some people are so stressed out by tough conversations that they go to the extent of drafting a script in preparation. While you may not be on the defensive end, memorizing the lines you intend to deliver will only come out fake and unnatural. And because the person you are speaking with doesn’t know there is a script, they are likely to ask a question that will throw you off making an already difficult conversation even worse.

Instead, be mindful of the key points. Get straight to the point. Explain each thoughtfully and honestly.

By sympathetic

Remember, this is a hard conversation for the both of you. Just as difficult as it is for you to deliver; it is tough for them to hear.

Take the time to understand how they feel. Have compassion. Are you about to give bad news to a subordinate whose future in the company is looking grim? Or are you about to ask your boss for yet another extension on your deliverables? Whatever the case, consider the feelings of the person on the receiving end.


Allow yourself to find the right words by slowing down and listening. You’ll find that it is in those moments that you are silent that you’ll be able to find the appropriate thing to say.

Make sure that you are genuinely listening and not distracted.


Replay the conversation in your head. What went well and what needed improvement. Is there something you could have done differently? Should you have reacted better? Could you have delivered it

Organizations are strengthened when problems are dealt with swiftly and honestly. Difficult conversations may be hard but something good is always bound to come from having them.

If you found value in this blog and If you have time, let’s jump on a call to brainstorm some strategic leadership concepts you may be unfamiliar with…I think you might be pleasantly surprised! Then, without obligation, we can consider if working together would be beneficial.

If that sounds good, you can use this link to schedule a time convenient to you for us to chat: I look forward to furthering our connection and learning more about you and your business.

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Inscape Consulting Group
Greg Nichvalodoff, BSc. BM (Honors), MBA, PCC, CMC
Office: 604.943.0800
Mobile: 604.831.4734

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