Awkward. The word itself is… well, awkward. Nobody likes those conversations. Yet from time to time we all have something we need to get off our chest. And we know damn well the chestee (Is that a word? It should be.) isn’t going to like it.

Whether it involves family, friends, work, or people we’re involved with in projects and community organisations, the dynamics are the same. Something is going on that needs to stop, or something isn’t happening that needs to happen.

Whatever it is, these things don’t like to be disturbed. But we’re going to disturb them. Poke them with a stick. Here are some rules of engagement:

It’s awkward for them too

In fact, it’s probably more awkward for them than for you. That’s why it’s you starting the conversation. Remember, too, that the other party may genuinely not be aware of the issue. So be gentle.

Find the right place and time

The corridor outside the lunchroom at noon is not the place to tap them up and say, “Oh, can I talk to you about such and such.” Plan your move. Identify a place and time that they are on their own. Go into that space once or twice beforehand without raising anything awkward.

Start with a positive

If you have something positive to say about this person or situation, start with it. Some people—and I am one of them—can take a lot of criticism as long as you open with a sliver of praise. Wall-to-wall criticism can switch people off and you’ve just shifted your task from awkward to difficult. Own goal.

Focus on solutions

You are, in all probability, dealing with something of a sore point for the other person. Something they don’t feel empowered around. Their conversation may reflect this: “You’re saying I’m not able to…” They may bring all manner of negative thinking to the table. (See 12 Signs of unbalanced thinking, Part I and Part II). Don’t get dragged down. Stay upbeat and focus on positive outcomes.

Let them walk away

When you first raise the issue, accept that you are putting the other person ‘on notice’ that something has to shift. Unless it’s urgent, give them time to digest. They may get back to you. Or not.

Don’t take no answer for an answer

Once you’ve opened the can of worms, it’s your responsibility to clean all the worms out. Don’t dig yourself into the same hole as Morrissey and The Smiths: “I started something that I couldn’t finish.” If the other person has had a reasonable amount of time and hasn’t taken any action, get back to them. Let them know, softly but firmly, that the issue needs resolving. If you fail to follow through you place yourself in a weak position. The other party knows that if they ignore you, you will go away. So commit to following through before you begin.

There. Wasn’t so awkward after all, was it?

Image: Max the Brown Tabby and Burt the Grey Kitten: Cat Argument 4 by Found Animals Foundation on Flickr. Cropped to 16:9.

This article was originally posted on LinkedIn.