Having what executive coach Alan Cohen calls a “difficult talk” with an employee, business partner or client isn’t easy. I would say for most people, it ranks up there with having a root canal or scheduling a colonoscopy.

Cohen spoke at a PRSA-NCC workshop last week and has written a book called “Those Difficult Talks for PR Pros.” He had a successful career in public relations in New York before becoming a coach and trainer working with executives and business owners to improve their performance and productivity.

When I look back on my management days, there definitely were some conversations I dreaded having. I had to steel myself for the encounter, and I can’t say they went exceedingly well. In his book, Cohen points out what I painfully know from experience—PR people don’t like confrontation. For that matter, who does?

Yet, we all know these kinds of conversations need to take place from time to time in order to maintain a healthy, well-run organization.

So what’s a manager to do in a tough situation? Or what’s an employee to do when he feels the relationship with his boss or a colleague isn’t working?

Cohen provides a number of tips and some helpful checklists in his book. I like his list of 10 things not to do when you need to have a difficult talk. Here are some common pitfalls you should avoid:

1. Not preparing for a talk. Just winging it is never a good idea.
2. Not considering the state of mind of the other person, especially if they are exhausted or depressed.
3. Having the talk in front of other people.
4. Doing it when you are not in a healthy state of mind.
5. Giving too many examples. There is no need to “throw the kitchen sink” at the other person.
6. Not willing to listen to the other person.
7. Focusing more on winning the fight than on the long-term relationship.
8. Being too attached to being right.
9. Having a difficult talk when one or both of you are tired, hungry or irritable.
10. Procrastinating until a situation explodes.

Cohen encourages the initiators of difficult talks to consider solutions that result in a “win-win-win”—a win for them, a win for the other person and a win for the relationship.

Unfortunately, difficult talks—especially when they involve HR or contract issues—often get put off until there aren’t any wins possible for either party. A manager waits until it is too late, and then there really is only one course of action and no viable alternatives.

It’s hard to change human nature, but Cohen makes a good case for why taking on difficult talks earlier, rather than later, makes a lot of sense. He also makes it clear that listening, engaging in dialogue and moving towards a “courageous solution” are the keys to productive workplace communication.

What difficult talks have you had to have, and how have you handled them?