Need to Have a Difficult Conversation? Try This Simple 4-Step Method


In most cases, hearing (or saying) those four words are enough to send shivers down most people’s spine. 

A reader wrote me recently asking for advice on a similar topic. I’ve changed a few things in order to protect this person’s privacy, but here’s the gist of it:

I’ve said something unpleasant to a colleague. Maybe I spoke too soon, but I meant what I said. 

I wasn’t kind. But I was honest.

It doesn’t change the way I feel though–about this person, or the situation. I’m not sure if I should feel bad about it. We don’t have a great relationship. I don’t believe we can.

Would it have been better for me not to say anything?

Please share your thoughts.

And here’s what I wrote back:

Of course, I can’t speak to your specific situation without knowing the details (or without hearing the other person’s side of the story). But apologies can go a long way in building and maintaining relationships–so that’s a start.

Still, if you meant what you said and felt that it needed to be said, then maybe it’s good you said it. 

Just remember that often times much more important than what we say…

For the future, if you find yourself needing to have a difficult conversation, try this four-step process:

1. Follow the 3-question rule.

Before saying something that you think will be difficult for another person to hear, ask yourself:

  • Does this need to be said?
  • Does this need to be said by me?
  • Does this need to be said by me, now?

If the answer to all three questions is yes, skip ahead to step three. 

But if you only make it to the second question, i.e., this needs to be said by you but it can wait, proceed to step two.

2. Consider the time and place. 

While calling someone out in front of others may be needed in certain circumstances (extremely rude behavior that shouldn’t be tolerated, and should be made clear to all that it won’t be), it’s usually more advantageous to speak privately. So, think about a time and place that will allow you to discuss in as relaxed a setting as possible.

This shows respect for the other person, and respect begets respect. Additionally, you make it easier to have an actual conversation about what happened. 

3. Consider how you want to communicate. 

There are a few options here, and you might choose based on various factors, including:

  • your personal relationship with the other party (family, friend, colleague, close relationship or not, etc.)
  • the circumstances (are there many people around, how serious is the offense, what’s the other person like, etc.)
  • your own strengths and weaknesses (can you say it humorously and effectively get the point across, would a stern look for now followed by a conversation later suffice, etc.)

There’s much more to consider, but this is a start.

If possible, frame the discussion in a way that relays helpfulness. Asking for permission to share something you’ve noticed, or sharing how you’ve made a similar mistake in the past, can go a long way in getting the person to listen while minimizing the tendency to get defensive.

Additionally, be sure to give the person the chance to express themselves, and how they saw the situation from their perspective. Sometimes this helps expose the other person’s blind spots…Or, it can help you to communicate with empathy.

4. Continue learning.

Communication is an art, one that takes time and practice to improve–especially this type of communication, where you are offering criticism or counsel.

So, after a conversation like this, take time to analyze and deconstruct. 

  • Did the conversation go well? 
  • Did you accomplish your goal? 
  • What worked? 
  • What would you do differently?

These questions can help you to continue improving as a communicator, and continue strengthening your relationships.

After all, we all need people who tell us what we need to hear, not just what we want to hear.

The key is to master the art of tact. 

And as Sir Isaac Newton so aptly put it:

“Tact is the knack of making a point without making an enemy.”

The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.

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