How to Have Difficult Conversations [VIDEO]

Let’s face it. We humans can be terrible communicators. But having tough conversations is part of being a grown-ass woman …not to mention it’s essential for getting what you want out of work and life.

Here are a few best practices to remember the next time you’re dealing with a tough conversation:

1. Get clear on your ideal outcomes

Know your goals. What are the outcomes you’re looking for? What is having this tough conversation worth to you? Once you consider what the ideal outcomes of the conversation are, you can make a clearer choice about the potential costs and benefits of engaging in it.

If and when you deem it worthwhile, be focused on the future and the goals you hope to achieve through this conversation. Better yet – lay out the opportunities for mutual benefit or your shared objectives. That focus will help keep the conversation looking forward and not focused on the backward-facing blame game.

2. Understand your audience

Who are you dealing with here? Who has power and authority in this setting? Which relationships are the most important for you to cultivate? Know who your direct and indirect audience(s) are, and consider what concerns, insecurities, and pressures they might be dealing with, too.

3. Express and explore

Before you head into the conversation, consider this final set of factors: what do you need to express and what do you want to explore? What is it that you need to get across in order to achieve your goal? What must you say in order to feel heard and respected?

On the flip side, what remains uncertain? What do you want to explore or gain clarity on? This conversation cannot be one-way to be truly effective, so get curious instead of furious. Ask open-ended questions to better understand where the other party is coming from.

4. Lead with intent, then content

Everyone – women especially – can be seen as less likeable while communicating assertively. But here’s one simple tactic to combat the unconscious biases that are behind such a judgement: open by clarifying your intent before diving into your content.

Behavioral scientists have found that adding a brief statement explaining why you’re about to engage in the conversation before starting right in can help things proceed more smoothly.

Having difficult conversations is never fun, but feeling comfortable doing so is an essential leadership skill.

We dive deeper into owning your voice through assertive communication at Bossed Up Bootcamp, our flagship training for women navigating career transition. Apply now to join us at an upcoming Bootcamp in DC or Boston!

In the meantime, let me know how these practices work for you. Have you recently wrapped up a tough conversation that yielded a positive outcome? I want to hear about it in the comments below!


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  1. Kristen says:

    Thank you for this– I’m having a tough convo with my supervisor this afternoon about her serious lack of communication with our team, so this was SUPER helpful.

  2. plumpdn says:

    Thanks so much, Emily! This video come right on time for me; I have a tough convo with my boss coming up on Wednesday. I am going to write out the intent and what I want to express and explore before hand. – Adria (June ’16 BC NY)


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