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Debugging Difficult Conversations as a Pathway to Happy and Productive Teams

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Any time we talk to someone or to a group when there are high stakes and/or high emotions, difficult conversations can happen. If we ignore difficult conversations they typically don’t resolve themselves, in fact, they often get worse. Handling difficult conversations involves thinking about the logistics, having the proper mindset, and preparing yourselves.

Andrew Murphy gave a talk about tackling difficult conversations at NDC Oslo 2023.

Murphy mentioned that many of our day-to-day conversations are difficult conversations, like performance reviews, interviews (on both sides), or persuading people to use the framework/platform/tool we prefer or built:

When the impact of having (or not having) the conversation is high, the chances are it’s a difficult conversation.

We often get worried about what other people will think of us, or our actions, Murphy said. We fear we will hurt, upset, or anger the other people involved. This makes it troublesome to separate what is truly in the best interests of the people involved, and what is just us shying away from it, he said.

Murphy presented a three-step model for tackling difficult conversations:

  • Logistics: How can you, logistically, make sure the conversation is productive and effective?
  • Mindset: This usually comes down to the courage to have the difficult conversation itself! Impostor syndrome is real, don’t let it stop you from achieving your goals
  • Preparation: What data/observations can you gather to help? How can you plan how the conversation will go? How could it go wrong?

We should ask ourselves why having this difficult conversation is important, Murphy suggested. What do you hope to achieve from it? How does it help you, the other person, and everyone around you? This should help you gain the courage and confidence to follow through with it.

Murphy mentioned that often people have two modes when it comes to difficult conversations: neutral and turbo. They flip between the two, delaying until they have no choice but to go full throttle into it. By taking a step back and thinking about the situation as logically, and objectively, as you can you can prepare yourself for dealing with it, Murphy explained:

If you find yourself cycling and getting angry or frustrated when thinking about the situation, then it’s really important to do this.

When the conversation goes wrong, Murphy suggested staying true to the reason you are having it. Reminding yourself what’s at stake, and for whom, means you can always come back to a place of compassion for the particular situation and person, he concluded.

InfoQ interviewed Andrew Murphy about difficult conversations.

InfoQ: Why do we need to have difficult conversations?

Andrew Murphy: Because we want the world to be a better place. Because we want the people we work with to be happy, effective and productive in what they are doing. When we don’t have difficult conversations the situation doesn’t get better, in fact, it may even get worse!

How many times have you thought to yourself "I don’t want to talk to them about that"? I know I’ve thought about it a lot. But rarely the problem disappears all by itself. Most often, we need to tackle it head on and deal with it before it gets worse.

InfoQ: How can we handle the logistics of conversations?

Murphy: Think about the "who, what, where and when" of the difficult conversation:

  • Who should be involved? As few people as possible to make sure it happens. Difficult Conversations aren’t a forum for airing grievances to the public
  • What should the outcome be? Getting it straight in your own mind what are you going to talk about and why is that an issue.
  • Where should we discuss it? Probably not in the middle of standup
  • When should it happen? As soon as possible, usually!

These allow you to plan for it and ensure you have everyone you need, when you need them, in an environment that is productive and not threatening.

InfoQ: How can we prepare ourselves emotionally for difficult conversations?

Murphy: If the reason you need to have a difficult conversation with someone is that they’ve hurt you, then unless your emotional resilience is excellent, taking a breath will help put you in the right mindset for approaching it. Barelling forward in turbo mode is sure to lead to exactly what you don’t want - and unproductive conversation.

InfoQ: What’s your advice for when we’re uncomfortable about a difficult conversation?

Murphy: Don’t worry about making yourself feel comfortable when you are preparing for a difficult conversation. It’s perfectly fine to feel uncomfortable! These are high stakes and highly emotional situations.

If you’re totally comfortable with them then you might have lost perspective or empathy for those around you. Do try to be confident going into it, though.

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