How to Prepare for a Tough Conversation

At some point, we all need to be involved in a difficult conversation at work. 

These are usually unpleasant experiences that feel a little unnatural and uncomfortable. Most of us much prefer the opposite: easy-going and happy relations. 

In my policing career of over 35 years, I had to have many difficult conversations with people with whom I worked in various capacities. I’ll bet you know exactly what I am talking about!

Fortunately, there are things we can do to make difficult conversations meaningful. We can prepare. When we are prepared, we can be direct but not overly emotional. We can consider our goals for the discussion and speak with the end in mind. With proper planning, both parties can experience a better conversation and outcome.

Do Your Homework

Being properly prepared is key. 

So, the more you prepare, the more likely the conversation will go well.

We need to have the facts before we speak. Don’t get caught in the dilemma of a subjective mind and attitude. Instead, through proper fact-finding, you can work from an objective lens that fosters a more meaningful dialogue.

Difficult discussions can often become emotional, and people can get triggered and defensive. 

Aim to present the facts objectively and calmly. You will reduce the possibility of a discussion becoming emotionally charged. This is something to avoid at all costs, and the outcomes are rarely beneficial. Instead, let’s keep in mind to maintain a balanced professional tone. Looking at things from a fact-based standpoint helps to facilitate this.

If you need to prove something, you should have that proof and be prepared to show it. 

Prepare To Be Direct

Being indirect, unclear, vague, or skirting around an issue can land as insincere and unfocused. It’s best to prepare ahead so you can be direct with your communication but not be insensitive.

Remember to be clear, firm, and kind with your words.

Know exactly what you want to say, say it carefully, but keep an open mind. 

Don’t rush to make your point; wait silently for a response. Remember that it’s possible to be direct without seeming rude or calculated, and you can get to your point sensitively without humming and hawing. Be firm and be fair.

Have Concrete Goals In Mind

Engaging in difficult conversations without a planned outcome can potentially backfire and feel like a waste of time for everyone involved. 

A concrete goal is a roadmap that helps you navigate emotions and get where you need to go in the conversation.

This preparation does not need to involve a lengthy script or memorized speech. List the things you would like resolved or start working toward resolving by the end of the discussion.

Your goal with these difficult workplace conversations should be to find a solution that will hopefully work for everyone.

Ideally, all parties should be involved in brainstorming ideas and contributing to the solution. 

If you can all agree on the problem, you’re halfway closer to solving it than if you do not!

By learning to effectively prepare to hold difficult conversations in a manner that produces the best possible outcome for all parties, we are also changing the way we think about these conversations. 

We are shifting the narrative from difficult to beneficial and unpleasant to positive.

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