How to Manage Difficult Conversations

Is there someone in your life who is driving you nuts?  A colleague, spouse, friend, boss, staff member, child?  I’m going to share my simple strategy for dealing with any difficult conversation in a way that actually improves the existing relationship.  Coaching is about clarity and authenticity, which is the focus here, rather than strategy. You can use the following questions to prepare for virtually any difficult conversation (except maybe asking someone out—you are on your own for that one).  I strongly recommend writing out your answers and/or discussing them with a friend or coach.  The most challenging aspect of difficult conversations is the preparation.  Once that is complete, it is relatively easy to tailor the structure of the conversation to your specific circumstances. If you were being 100% straightforward and not worried about the other person being upset, liking you or firing you, what would you say? Feel free to use profanity.  Be as rude as you like when sorting this out.  Often, we spend so much energy trying to repress what we really think and feel that we never fully identify it.  I’m not suggesting that you actually say this to the person, but there is value in getting to the core of what you want to say.

Once you know what you want to say, how can you say it in a way that is direct but not abrasive or offensive? This is not nearly as difficult as people usually think.  One very effective method is to tell the person your experience rather than your judgments.  “I have noticed that I feel resentful when you come to work late” goes over a lot better than, “Arriving late for work is irresponsible and unprofessional.”   If you say the later, the other person will likely become defensive, whereas it’s a lot harder to argue with “I feel…” though admittedly, some may try.  Personally, I often say something like, “It may not be reasonable for me to feel this way, but…”  People have told me that they are concerned that it is unprofessional to express feelings at work, or that their office environment is manipulative and cutthroat and they don’t want to show weakness. At this point, I could go in about ten different directions as a coach, but for the moment I will just say this:  It takes courage to try something new, but this approach really does work.  And frankly, the harder this is, the more likely it is that the conversation will create a huge shift in your work environment.  Try it, and call me if it creates a mess.  I’ll help you clean it up.

What do you want from the other person? Do you want a raise?  Do you want him to leave you alone?  Do you want him to admit that you are right?  Do you want a change in behavior?  If you were to form this as a request what would it be?  Requests are most likely to lead to positive change if they include specific actions.  “I want you to improve your writing” may be clear to you, but the odds are it won’t be clear to the other person.  “Improve” is open to interpretation, whereas “I want you to have a colleague edit your work before you give it to me” is more objective and therefore more likely to yield positive results.