Gini Dietrich

Mastering the Art of Difficult Conversations

By: Gini Dietrich | November 8, 2009 | 

Last week I read an article on Harvard Business Review called “The Martial Art of Difficult Conversations.” While the author related a personal story to reflect on how to have conflict conversations, it very well applies to business.

I hate conflict. I hate hard conversations. I have this innate need to be liked and I used to think that if I had the hard conversations, people would like me less. Turns out, people like me less if I won’t have the hard conversations and the relationship ends, be it business or personal.

Once I realized that, it became easier to have the hard conversations.

But what do hard conversations really mean? They mean honesty. They mean professionalism. They mean no personal attacks. But they most importantly mean listening.

In social media, we talk about all of these things and how important they are as we build relationships online. But what about using the same philosophy offline, as well?

I’m not going to say it’s easy. Especially when you’re dealing with a situation that you just KNOW you’re right. So following is what I do when I need to have a hard conversation, or someone approaches me with a complaint.

1. If the person comes to me, I ask a lot of questions. I ask questions until the person has said everything they have to say. When I feel like they’ve said their peace and they just need a solution, I ask “big brain” questions such as “How would you like this to end?” or “In a perfect situation, how do you see this going?” I never offer advice, I never offer my opinion. I just ask questions.

2. If I have to have the hard conversation with someone, I don’t sugarcoat things nor do I belabor the issue. I start by saying, “We need to have a conversation that is going to be uncomfortable for both of us, but I think we can work through the issue and come to a solution together.” Then I state the issue. Then I ask some questions to understand the other person’s point of view.

There are plenty of times that I have to peek down at a post-it note that says three things:

1. Count to 10

2. Ask questions

3. Don’t get defensive

If I follow these three reminders, I tend to have better, more effective conversations that result in better relationships.

What do you do to master the art of the difficult conversation?

About Gini Dietrich

Gini Dietrich is the founder and CEO of Arment Dietrich, an integrated marketing communications firm. She is the author of Spin Sucks, co-author of Marketing in the Round, and co-host of Inside PR. She also is the lead blogger at Spin Sucks and is the founder of Spin Sucks Pro. Join the Spin Sucks   community!

  • Asking questions is a good call. How about: “Why do you feel that way about it?” Or the classic, “Will this matter five years from now.”
    I think the key is perspective. Sometimes the difficulty arises not because one person is right and the other is wrong, but both want to be right.
    I think we’ve all heard the advice, that sometimes it’s not about just picking battles, but also letting the other person have an “out.”
    The goal to an uncomfortable conversation is to have a comfortable finish (the finish may even be a day later). One must think about how that outcome can be reached before the conversation starts.

  • Good topic to raise, and I echo Jeff…these conversations need to have a win/win outcome where both sides know how they will move forward.

    I find in a lot of cases that the block to a successful outcome of a difficult conversation is a failure by both sides to understand each others viewpoint.

    I don’t think that you can truly resolve conflict, or differences, without fully understanding how and why the two sides differ.

  • And to concur with the previous two comments in deed a win/win situation is the ultimate goal. I like the “post-it” note coaching here Gini. I think most people shoot first, aim second and prepare themselves third when it comes to difficult conversations.

    Letting the other person talk first allows you to determine what really is at issue here but moreover lets them feel that they are actually being heard – from this the conversation can then be led to creating a solution based on what you’ve heard. Great post and even better points to ponder. Cheers,


  • Great post! Great comments, as well. In addition to asking questions, try to test what you’ve heard. It helps to get to that point by restating (not reflecting…please don’t do that) what you believe the other person is feeling or thinking. If you listen with all your might, you’ll get to a spot in the conversation where you can say things like “so that must make you feel…” or “then are you thinking?…” that enables you to gauge whether or not you’re understanding what they mean, or just operating based on your own filters. I find it also helps to remember that understanding isn’t the same thing as agreeing. I think it’s far more difficult and much more important to true conflict resolution.

  • Great post, Gini! Having difficult conversations – we call them fierce conversations – is part of business life and as much as I hate conflict too, learning to have them helps in many ways. The hardest part for me and for the people I’ve training in my company is understanding that leaving a conversation in ‘tension’ is often healthy. I have to count way higher than 10 – often to 30 and if it is a really hard conversation we have a company rule to ‘sleep on it’ and take another pass the next day. The reward for learning to master these hard conversations is much better results and stronger business relationships.

  • Excellent subject and suggestions, Gini. I love that you:
    — Ask what outcome they would like
    — Keep the Post-It note handy.
    — Get right to it AND pave the way for a successful resolution by stating that you believe you can work together to solve this. How perfect!

    Other tips: Remember that no one and no thing is against you. Gary Simmons has an great book on handling conflict: “The I of the Storm.”

    Keep it on cause & effect: “When you do ____, I interpret it as ______”
    (e.g.”When you show up late to our meetings, I interpret it as disrespect.”)

    As a coach, I like to advise setting the intention beforehand. This can be an intention for more harmony, clarity, understanding, cooperation, relief.

  • Hello Gini,
    Responses here are excellent, particularly Jeff’s suggestion to allow people an out.

    I come from a different background, publication production.

    It would be an exageration to say it was always war, but it would be close. We fought over ethics, content, story leads, story play, deadlines and just about anything else you can imagine. When advertising came at me with a request to accommodate a really huge ad placement, I couldn’t say no, but I had to hold my ground if I were to maintain any respect.

    The art of diplomacy was never my forte. Any chance of developing this skill was blunted by years of dealing with willful editors who brandished fierce teeth. When I moved to magazines for a time, I struggled in the rough-and-tumble environment, where I had to hold up under withering pressure while dealing with competition for resources and very difficult people. Thankfully, I had a good boss, who was instructive, though lacking in subtlety. His favorite quote: “You need to be a diplomat, who can artfully tell someone to go to hell, and how to enjoy the trip.

    I tried the approach of getting everyone to like me, too. The managers I recall didn’t invest in becoming popular. They demanded respect. I struggled a while before my reputation caught up with the reality I was a hardworking person who held his ground. My upward mobility was held in check until the owner was satisfied I was tough enough for greater responsibility.

    I think you can hold your ground, and be considerate. Holding your ground doesn’t mean you have to blow anyone’s hair back in making your point. Insisting your right only invites more argument.

    I formed a habit of negotiating and defining parameters. “If I have to drop four more pages into the book, that means your the writers are going to deliver their copy four hours earlier next week. How are you going to make that happen?” Or, “I agree with you up to the point where my people work another four hours to accommodate your eleventh hour addition to the magazine pages.” If I didn’t put the problem of a solution back on the person making an unreasonable request, or whatever it was I was about to accommodate, people would walk all over me every week.

    Agreed Gini, listening is an excellent approach. The next step is to establish what you require to do your job.

  • Sometimes, the best conversations to have are the difficult ones. If you don’t have them, nothing gets done. I wish more people would recognize this… On the flip side, confrontation sometimes doesn’t work. Hard conversations get easier when both parties are reasonable and cool headed.

  • First of all it is great to see a CEO take this topic on.

    This excerpt captures the most missed aspect of tough conversations in my opinion: listening. “But what do hard conversations really mean? They mean honesty. They mean professionalism. They mean no personal attacks. But they most importantly mean listening.”

    So much time is spent preparing on what we have to say. I have seen a lot of people prepare for tough conversations (like a difficult performance review) as though they are planning to make their case to a jury. They set up the conversation in a way that results in righteousness and debate rather than creating a relationship that is actually stronger than it was before you had the conversation.

    I believe it is what we cannot hear is usually at the heart of what creates the need for these kinds of conversations to begin with.

    Here is one of the best pieces of advice I have ever received: If you are not being listened to chances are you are not listening. It is one way we can always take personal responsibility and perhaps even avoid getting tangled in a difficult conversation to begin with.

    Great post Gini!

  • As always, the comments are smarter than the post itself. We all agree Jeff makes some great points. And I love what Ray says about commanding respect, not necessarily popularity. It’s a great thing to remember in our every day lives.

    When I work with clients in both offline and online communication, I help them practice listening as the foundation for anything they do. It’s hard to do because, as human beings, we all want to be heard. But if you can master listening, you’ll command respect and be a master communicator and hard conversations won’t be that difficult, after all.

    P.S. Thomas, I typically have to count higher than 10, too. That whole impatience, hot temper thing.

  • I love this post and find it extremely relevant though I, like Raymond, come from a different background as well (psychotherapy). I appreciate your honesty Gini that it is much less enjoyable to be confrontational. I am in complete accord with the other comments on the idea of acting “as a team” and letting the other party know you are aiming for a win/win situation.

    Your 3 tips are simply stated (and thus easier to remember) -which is important in those difficult conversatios when emotions could possibly short circuit our more rational brain functions.

    I find in my therapeutic work with clients, in addition to your strategies its easier for me to have a hard conversation and be confrontational if I say a thing or two about the person’s strenghts first. For example “I really appreciate your desire to have effective communication with me” – or something to that effect – “and this is an area, I need to discuss with you further..”

    I think some of my hardest conversations involve “saying no” – could you do a post about that as well?!?

  • Um Erin? As one of my IRL best friends, YOU know I don’t know how to say no. It’s impossible for me to do. Perhaps someone can guest blog on that topic for Erin and me??

  • Awesome post! Ironically, talking about having hard conversations is just as uncomfortable as having them. Which is probably why hardly anyone has yet touched upon the topic. Great advice on handling these situations, I think that’s 95% of the problem: no one really knows where to start a hard conversation without it going downhill–in a hurry.

  • Gini
    Great blog, this is why I like to listen as I told you the other day I learn from what people have to say and people love to talk about everything. As for saying NO people will go out of there way to not say it and even spend money they don’t have sometimes to keep from saying it. Me on the other hand I say it more than I should and I tell people that if your not interested just tell me NO so I can move on.
    All the comments where great and as informative as the article. Thanks once again.

  • ava diamond

    The post and comments are so wonderful I have little to add. Yet, I would add one thing to your post-it note–breathe (deeply)

    I think it helps keep me relaxed and open if things feel tense.

  • Todd Woods

    Get to the root cause with a little emotion as possible. Deal in facts but maintain empathy for the situation.

  • Pilar Iglesias

    Gini – I loved this post, especially the “Don’t get defensive” rule. I think when anyone is met with a difficult situation the automatic response is to be defensive instead letting that go and taking that feedback as a learning tool.

    I sent your post around my office – thanks!

  • Laurie Riedman

    This is a great post and love all the comments! I’ve often said to clients, friends and even my kids — that our culture – particularly our business culture – trains most of us to avoid conflict rather than deal with it.

    I won’t echo all the great tips / advice given in the post and the comments – but just wanted to celebrate that there are folks who see conflict as the opportunity it is for positive change.