Having Difficult but Effective Conversations

There is simply no way to get through life successfully and sanely, without having to sit down with someone to have “the talk.” Whether it’s your spouse, a family member, someone you’re dating, a friend or a work colleague, things just come up that rub us the wrong way, or are actually crises, that must be addressed and resolved. However, we aren’t born with the ability to have a difficult conversation that actually is effective. It’s a learned skill. So here are some steps to get you where you want to go.


The goal of any difficult conversation is to solve a problem while maintaining alignment. In other words, to speak truth about an issue without alienating the person. There is certainly a small percentage of humans that can’t tolerate any confrontation, and you can’t control their reactions. But the great majority of people are ok with hashing out problems. Here are the skills, in order of when to do them.

  • Convey that you are “for” them: Start by letting the person know that, while this is an important conversation, that you want their best. You don’t want to win over them or punish them, you want to solve a problem.

  • State the problem: Clearly and in a few words, state what the problem is, so that it’s understandable. If needed use a few examples, with dates and times, to jog their memory and understand what you’re trying to say.

  • Own your part: Take responsibility for however you have contributed to the issue. It may be 90% or it may be 10%, but the great odds are that you aren’t 100% perfect in this dance. Not only is it the right thing to do, it keeps the person from feeling like you think you’re a perfect parent, pointing your finger at an immature child. If you fail to own your part, you will not take the conversation anywhere near a positive direction.

  • Hear them out/deal with diversion: Everyone needs their day in court, so ask them what their side of it is. There may be info that you need to know, to flesh out how you see the problem. But don’t let the person hijack the conversation with endless diversions to other topics to keep themselves away from responsibility. Warmly, but directly, bring the topic back to the issue you began with.

  • Ask for specific change: People need practical suggestions, not high-concept ones. “I need for you to ask me how I’m doing around half the time we get together, that feels more mutual” is a lot better than “Get your act together.”

  • Consequences if necessary: Sometimes a good conversation is all that’s needed. But sometimes, after a few failed conversations, boundaries are needed.

  • End with “for”: These talks can make the person feel that you don’t care about them. Just reassure them, at the end, that you truly want the best for them and for the relationship.

  • Check in later: After 2-24 hours, reach out to them again and ask how they’re doing with the talk. Sometimes, they will feel hurt or misunderstood. Spend a bit of time clarifying that you really care and want things to work out.

These steps work. If you want more information, check out my book, How to Have That Difficult Conversation That You’ve Been Avoiding. Remember, it’s just a set of skills that you can learn.