How to have difficult conversations

I’ve recently been reading Crucial Conversations (Patterson, Grenny, McMillan, Switzler), because I wanted to know how to have hard conversations with people. It’s something that everyone struggles with.

Designers at my company can’t be successful if they can’t communicate their ideas to stakeholders, ask for resources or deal well with conflicts. Whether at work or at home, if you can’t talk about the things that matter to you, you’ll end up in less-than-ideal situations. 

I wanted to outline some things from Crucial Conversations that stuck out for me. 


Understand how you got into this particular conflict or issue:

  1. Notice your behavior. Ask: Am I in some form of silence or violence (flight or fight)
  2. Get in touch with your feelings. What emotions are encouraging me to act this way?
  3. Analyze your stories. What story is creating these emotions?
  4. Get back to the facts. What evidence do I have to support this story that I’m telling myself about the situation?

Watch for clever stories that we tell ourselves. 

  1. Victim stories: you intentionally ignore the role you have played in the problem. You tell your story in a way that judiciously avoids whatever you had done that might have contributed to the problem
  2. Villain stories: automatically assuming the worst possible motives or grossest incompetence while ignoring any possible good or neutral intentions or skills a person have have. 
  3. Helpless stories: Making ourselves to be powerless to do anything healthy or helpful. 

These  stories get us off the hook and keep us from acknowledging our own sellouts. When we feel the need to push our ideas on others, it’s generally because we believe we’re right and everyone else is wrong. We exaggerate, lace our language with inflammatory terms and appeal to authority (“everyone knows this is the case, even my boss thinks so”). The harder we try, the greater resistance we create, the worse the results and the more battered our relationships. 

Focus on what you really want 

Focus your brain on the end goal when conversing so that you are responding in a way that will get you there rather than continuing to fuel a fire or comments that lean away from it. “…as the conversation unfolds and you find yourself starting to, say, defer to the boss or give your spouse the cold shoulder, pay attention to what’s happening to your objectives. Are you starting to change your goal to save face, avoid embarrassment, win, be right, or punish others?…Our motives usually change without any conscious thought on our part.”

Ask yourself these questions when you find yourself slipping out of dialogue:

  • What do I really want for myself?
  • What do I really want for others?
  • What do I really want for the relationship?
  • How would I behave if I really wanted these results?

Make it safe.

“The worst at dialogue …totally ignore the crying need for more safety. They say whatever is on their minds – with no regard for how it will be received. Or…they conclude the topic is completely unsafe and move to silence. The good realize that safety is at risk, but they fix it in exactly the wrong way. They try to make the subject more palatable by sugarcoating their message…. They try to make things safer by watering down or dressing up their content. This strategy, of course, avoids the real problem, and it never gets fixed.”

The best do this:

“Can we change gears for a minute? I’d like to talk about what happens when <insert problem>. It would be good if we could both share what’s working and what isn’t. My goal isn’t to make you feel guilty, and I certainly don’t want to become defensive. What’ I’d really love is for us to come up with a solution that makes us both satisfied in <scenario>.”

^ The person is being upfront about the issue rather than avoid it. They create contrasting statements that help to make the situation safe for the other person. And they stated a goal that they wanted to achieve. 

Remember the ABCS

  1. Agree: point out areas of agreement.
  2. Build: add elements that were left out of the discussion
  3. Compare: rather than suggesting that he/she is wrong, suggest that you differ. Rather than saying “wrong!”, try “I think I see things differently. Let me describe how.”

Document your outcomes. Write down the conclusions and decisions you’ve made. Make sure that there’s a follow-up and that you’re both held accountable. 

Last step: read Crucial Conversations

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Note to design students.

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Image by Mark Skrobola

Professor Eppinger, one of the instructors of the Product Design and Development course I took at MIT asked us one day during my final semester of college to sketch a new concept that would bring new technologies and existing products together (we were given specific options, which were written on the board). Everyone – engineering, business and design students – took about five minutes to come up with something. He then asked us to show the class what we had just sketched via overhead projector.

Nearly everyone who ran up to the projector was an engineering or business student. The sketches were (from a designer’s point-of-view) poor and the ideas were vague, but they were confident about their concepts.

Very few of the design students went up to the projector. Why?

Most likely, it was because many of them didn’t feel like their ideas were presentable (along with the additional fear of public speaking). Design students spend an awful lot of time perfecting their work. The director of RISD’s Career Center even mentioned to me once that he sees lots of students perfecting their portfolio, but never really finishing it or taking a ridiculous amount of time to finally put it online. Designers prefer to show their work when it’s reached a certain stage, and five minutes isn’t that stage when there are seventy-five other people looking at it.

Therein lies a problem.

If you don’t present your idea because you don’t think it’s presentable enough, your AMAZING idea will be bypassed for someone else’s so-so idea, because they spoke first.

In school, you’re often given an assignment in school where you can thrash out ideas by yourself first before you discuss them with anyone. You then form a way to visualize your idea and you “present” it in the sense that you already know what ideas you’re offering before you speak. You make sure everything looks perfect. Sketches and models, are they stunning? Good.

Real life involves coming up with ideas on the spot and communicating your concepts effectively to people who might not understand exactly what you do. You can’t wait until midnight when everything starts clicking. You don’t have a lot of time to digest everything.

So what do you do? You have to practice thrashing your ideas out around other people, with other people. You have to accept that not everyone is a visual person. Some people are primarily verbal and understand through words alone, which is why they feel that powerful words alone can do the trick. You have to put yourself in situations that you might fear at first but will grow accustomed to with time. You’ve GOT TO SHIP YOUR IDEA, because everyone deserves to see what awesome things you have to offer.

I say this, because it’s true. Show your work. Show it loud. The real world is at your feet.