Why Are Difficult Conversations often so hard to have?

In my latest poll that I ran recently on LinkedIn, I asked for feedback on the above question and the results were very interesting. Over half of the respondents voted for “I don’t like confrontation” and coming in second at 26% was “I struggle with what to say.”

Click here if you’d like to check it out.

Difficult conversations are pretty much part of every leader’s job, because as we know, people don’t always do the right thing. However, in my experience the very high majority of your team want to do a good job, they don’t deliberately mess things up. So, when things go wrong, as they will, most of your team will be open to a constructive conversation to help get them back on track. These conversations are just part of the everyday conversation’s leaders must have with their team members.

In fact, holding these short and concise coaching conversations when they are required (often daily) will eliminate the need to have a bigger more challenging conversation, as the issue is dealt with there and then. It’s when these coaching conversations are missed, bad habits can start to form, which are much harder to change.

When these issues frequently reoccur or are becoming a major problem, it’s time to have the more challenging conversation. As long as you do this in private, deal in facts, remain calm and discuss how the team member can turn this around to a positive outcome, most of these conversations will go well. This should deal with the two main issues over 75% of the respondents raised in this poll.

It’s not dealing with these issues at the time that creates a much bigger problem that often leads to confrontation and that’s something we would all like to avoid I’d suggest.


Roger Simpson – CEO, The Retail Solution and Author of “The Ultimate Retail Sales Experience” With over 35 years’ industry experience, Roger Simpson is recognized as Australia’s #1 Authority on customer ROI in the retail industry and as a global expert on staff coaching, customer service, and selling skills.