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How to Handle Difficult Conversations

Asking three basic questions can strip challenging conversations of emotion, friction

A woman is talking to another woman in a business suit.

Some workplace conversations are just hard to have.

Like telling two of three applicants for a promotion that they won’t be getting one. Or speaking frankly about how unproductive your company’s meetings are.

Andrea Lee, CEO of Thought Partners International and author of We Need to Talk: Your Guide to Challenging Business Conversations (Thought Partners International, 2015), said the first step to having such discussions is to acknowledge that they can be awkward and even painful. She approaches difficult conversations by first asking herself three questions:

  • Where are we now?
  • Where are we going?
  • How would we like to get there?

These questions “can be a game changer,” Lee said. “Without them, there are a lot of assumptions that can be made on both sides, sometimes because of the flavor [workplace] relationships have taken over the years.”

For example, take the tricky task of picking only one of several applicants for a promotion that means more money, more power and more prestige. Lee suggested that the conversation go like this:

Manager: “So why does each of you want to work on the new project, and what is it you hope to get out of it?” This, Lee said, asks the questions “Where are you now?” and “Where do you want to go?”

Team member #1: “I want to do it because I’m already doing similar work, and it will be easy for me to get it done well without additional training. I think it will be a cost-saving if I’m assigned to the project.”

Team member #2: “I want to do it because I have a better relationship with the people involved. They really like me and I think they might bring us more business if I can be the one to wine and dine them.”

Team member #3: “I should be the one to do the project because I’m new and so far I don’t have any projects. I’ll be able to pay the most attention to the project and get it finished.”

Manager: “That’s really clear, thanks for your answers. I want to be clear about my thoughts here, too. We really need to work more efficiently, and bring in more new business this quarter as a priority. Team member #1, I appreciate you would do a great job, but with your experience, my request is that you focus on getting your current priority project done ahead of schedule, and let’s meet separately to talk about your development opportunities. Team member #3 isn’t qualified to go out and bring in new business. Team member #2, it’s true, you might be able to attract more business from this project, so I’d like you to go to the initial project planning meeting and grease the wheels with additional business development in mind.”

Lee noted that the manager has succinctly addressed the three questions.

“When you’re the leader of a team, a good way to use the three questions is to tease out the motivations of all sides, without favoritism,” Lee said. “When people see how fairly you’re using the questions with each group, you will be seen as neutral, and gain credibility. If the above conversation happened in a less structured way, without unbiased questions, the potential for disgruntlement and friction within the team grows.”

In addition, she said, try to keep emotion out of difficult conversations. Perhaps a manager and employee have clashed in the past, and now the discussion is about the worker’s subpar performance.

“Too many challenging conversations happen with emotions being expressed inside the conversations, where they disrupt the outcomes,” Lee said. “Emotions cloud us, we become unclear about what we want, so the conversations become a massive fumbling in the dark. Instead of letting history and baggage gum up the machinery, clear the slate, shake the ‘Etch-a-Sketch’ and start detangling … with the three questions.”

Stop This Meeting

Another hard conversation is telling higher-ups that meetings have become pointless or dull. But isn’t it politically and professionally risky for a manager to question the purpose of a regular meeting that’s arranged by a superior?

“You might think it’s tantamount to career suicide to say, ‘This meeting seems really unproductive,’ and you would be right,” Lee said. “You don’t want to be quite that blunt, but there are ways to stop the meeting anyway.”

Some deft ways to go about questioning a meeting’s purpose by using the questions, she said, include asking:

  • “I’m really curious. We want to get the most out of this meeting, and I’m sure you do, too. What do you want us to listen for and what do you want us to be able to do as a result of this meeting?”
  • “I know this meeting is important, and I want to be sure we’re clear about it. Is there a particular reason you want us to attend the meeting? I don’t want to miss the point, and I’d love your help.”
  • “I know we all have a lot of work to finish, so I’m wondering what your expectations are for this meeting? What do you want to see from us as a result of being in this meeting?”

It’s unlikely anyone will get fired for requesting clarity about goals and expectations, Lee said. “Asking pointedly and genuinely is an excellent path to provoking and revealing the decision that you don’t in fact need to be there,” she said, adding that with any entrenched, unchallenged practice, it may take several tries over time to make your point.

“Stopping a meeting and questioning its purpose is one of the most far-fetched things you can do,” Lee said. But “becoming the person who is able to speak up and tell the truth empowers everyone else in the room to say what needs to be said. Change is possible when people speak up.”


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