One of the hardest things to deal with at work is the tough conversation that you know you need to have. Whether it’s an employee who is performing poorly, a colleague who is creating a toxic environment, or a peer who consistently undermines you, for most of us, it is uncomfortable to confront the situation and address it directly. You might hope that by some miracle things get better or something changes that gets you out of dealing with the person. But of course, that rarely happens – and the longer you leave an issue unaddressed, the worst and more uncomfortable it gets.

I have found that there are three traps that we can fall into when we neglect having a difficult conversation that must be had. The first trap is beating around the bush – having a conversation with the person but conducting it in a way that the real issues do not get addressed or are glossed over. The second trap is letting things boil over – not addressing the situation until the last straw sends you over the edge and there is a confrontation. The third trap is resorting to passive-aggressive behavior – avoiding or ignoring the person, talking about the person to other people, making snide remarks, or keeping the person out of the loop. All of these traps are damaging and can create negative ripple effects within your team or the organization overall. To avoid these traps, here are a few tips:

  • Remember that feedback is a gift – it’s impossible to change behavior, if no one is willing to give you feedback about that behavior. I have given feedback to hundreds of people over my career and, while there have been many times when the feedback was difficult for them to hear, in the end, they have always been grateful to hear an honest and objective assessment of their actions.
  • Put yourself in their shoes – sometimes the best way to move forward is to get on the same side of the problem. To have a fuller view of the situation and see things from the other person’s perspective, question your assumptions, focus on what they may be feeling and thinking, and get curious about what is going on for them.
  • Get time on the calendar – make the first move and schedule time for the conversation. Once you commit to sitting down with the other person and beginning the dialogue, then progress can be made. And remember that you mostly likely won’t fix and address everything in one conversation. This first meeting is the start of what will likely be several conversations to share viewpoints, gain mutual understanding, and map out a plan of action.

In this great article on, Peter Bregman shares other actions you can take, specifically to address the trap of passive-aggressiveness. Bregman gives a personal account of an encounter he had that led him to face his own passive aggressive behavior and understand what it stems from.

What gets in the way of having your tough conversations?
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