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5 ways to get ready for a tough conversation


Editor's note: This popular story from the Daily Briefing's archives was republished on June 29, 2021.

Sooner or later, every manager must have an awkward, uncomfortable, or even painful conversation.

Maybe someone on your team is underperforming. Maybe you need to share news of resourcing cuts amid the Covid-19 epidemic. Or maybe you simply need to talk frankly about the difficult issues roiling today's workplaces, from racial inequity to the challenges posed by telecommuting.

If you're like most managers, you'll feel tempted to put the problem off to another day—but you also know that delaying a necessary conversation will only make matters worse. So the next time you feel yourself dreading an upcoming conversation, try these tactics to help you recognize your discomfort, push through it, and plan your conversation productively and empathetically.

1. Sit with the discomfort

The rest of the tips below are things you might do to alleviate your discomfort. But before you can do that, you must sit with the discomfort long enough to notice it and analyze it. Having the courage to sit through the discomfort you feel serves as an enabler to have productive conversations.

2. Find your values-driven reason to have the conversation

Go deeper than "it's my job" or "senior leadership told me to." To find your reason to engage in tough conversations:

  • Orient towards purpose, rather than self. When we keep silent, it is often for selfish reasons—we're afraid that saying something is going to result in awkwardness, or that they'll be backlash, or that our relationships will get damaged. It's natural to feel these things. Key to overcoming them is to try to attune to purpose: how will having the conversation contribute to larger, shared goals?

  • Ask yourself: If not me, then who else? The "bystander effect" often explains leader inaction. Leaders think to themselves, "There's lot of people around here who could talk about this," and they defer the conversation sideways or upwardly. When you actively consider "who else?" you often realize it should be you (do not deprive yourself of the opportunity to lead!).

  • Ask: What do values demand? Consider the corporate values to which you have subscribed via your employment, as well as your personal values. Then, take the tough conversation you need to have and project it through those values. If you avoid it, what message does that send about what really matters?

3. Reverse the "invisible benefits problem"

Leaders sometimes stay on the curb because they anticipate the pain or loss associated with a tough conversation, and this pain or loss is relatively tangible (such as awkwardness or strained relationships). Simultaneously, leaders often have trouble envisioning the benefits of tough conversations because these are relatively invisible. (After all, you'll never be able to prove that you reduced turnover by choosing to have a conversation at this time.)

To combat this "invisible benefits problem:"

  • Specify the conversation. Often, what you conceive the conversation to be is bigger than it actually is. Make the conversation specific by thinking through the actual two to three things you need to talk about. Then, name the factors or emotions driving your fear; this puts your logical, rational brain back in in charge, rather than your emotional, irrational brain.

  • Make the benefits visible. Write down the potential benefits of engaging in the conversation—for you, your people, and the positive culture you want to build. For example, you might write, "This benefits me because it contributes to my growth and ultimately allows my team to accomplish more, which reflects positively on me."

4. Make the risks of not having the conversation clearer

Often, we easily conceptualize the pain of action while minimizing the pain of inaction. To combat this, outline what would happen if you don't engage in the conversation. What are the consequences for you, your leadership reputation, and your team? For example, people might feel undervalued or unseen, or they might get the impression that you don't care. Often, these risks of inaction compare favorably to the costs of action.

5. Accept the challenge

Stanford University psychologist Carol Dweck pioneered the idea that a growth (as opposed to a fixed) mindset is key to success. Tough conversations benefit from a growth mindset: Persist in the face of setbacks, learn from criticism, and see effort as a path to mastery.

What happens next?

Once you've identified your discomfort, pinned down your values-based reason to act, clarified the benefits and risks of moving forward, and accepted the challenge, your next step is to actually have the tough conversation. Stay tuned for the next article in this series, where we'll dive into specific tools and tactics to make the conversation more open, honest, and productive.


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