How to Have Tough Conversations at Work

I’ve developed a theory that the biggest driver of mindlessness at work comes from lack of communication. Most times, this is connected to the conversations we’re not having about our values, or the boundaries we set (or don’t set) around how we live, honor, and uphold these values at work.

You know the type of non-conversation I am talking about: the really uncomfortable one, where you know what you need to say is going to be awkward and might disappoint another person. Think about it—have you ever edited a response because you felt uncomfortable revealing your thoughts concerning a certain topic?

This might look like:

• Not sharing that you don’t agree that the redesign plan is the best choice.
• Going along with the excitement around a new initiative even though you have serious doubts about its viability.
• Keeping silent about how uncomfortable it makes you that your boss brings her dog to the office every day—and it ends up in your space most of the time even though you really don’t like dogs.

So we halfway share, putting off the conversation we know is coming at some point. And, of course, the longer we avoid having it, the more uncomfortable the conversation can become.

3 Mindful Tips for Tough Conversations

Each day we encounter situations where we halfway communicate what we want to express, request, or need. In many cases, we do this because we fear being judged. Here are three way to navigate awkward conversations:

1. Offer context

It isn’t just about assigning blame. It is about creating dialogue around toxic and disruptive issues, so all involved can feel heard and choose to create a different reality. Offer context as to what the issue is, and, ideally, why it’s actually an issue for you. Done in a nonjudgmental way, this kind of sharing builds compassion and allows everyone to get on the same page. It’s when we don’t offer context that the discomfort grows.

2. Invite options

If someone is making a request that isn’t possible, say so and invite a conversation about what is possible. It’s important to ask how that might work for the person making the request. Explaining, offering another solution, and inviting dialogue increases the sense of sharing and collaboration.

Explaining, offering another solution, and inviting dialogue increases the sense of sharing and collaboration.

3. Be sincere

Say what you mean with grace, respect, and as much authenticity as possible. When you speak from the heart, even if others don’t like or agree with the message, the energy behind the intention comes through. Odds are strong that your honesty will help things to shift.

Transforming Communication

The collective impact from having uncomfortable conversations can be truly transformational. Its effect goes beyond communication in the workplace; it can transform communication in every situation.

The path to navigating this territory with ease starts with awareness. Begin to notice when you are withholding, closing down, or not speaking up. Write about it in a private journal if that’s helpful. Then, with that awareness, begin to experiment with expressing your thoughts, needs, and desires one conversation at a time using the following tips to push through the discomfort.

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