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How to have difficult conversations

Strategies for speaking up.
August 25, 2021

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Technology is inherently a people-oriented industry, and doing our jobs well requires constant communication. We communicate all the time in big and little ways, and these collaborative conversations help us to be more successful in our work.

But what happens when those conversations aren’t as collaborative? The conversations where your heart beats faster and your face gets red? Where you’re speaking up instead of speaking with?

I’ve spoken up throughout my career. I’ve voiced my concerns to executive leadership when their actions negatively impacted employees’ safety. I’ve had talks with toxic coworkers (after practicing my approach for days). And I’ve had moments where I thought, ‘Enough!’ and chose to speak up. Each of these conversations was different, but one thing was always the same – that feeling of anxiety as I did my best to navigate a hard conversation.

A couple of years ago, I got together with a group of friends to create a workshop for ourselves. We wanted to support each other in getting better at speaking up – understanding our goals, practicing approaches, and making room for self-care amidst the stress of these interactions.

Difficult conversations are still difficult, but there are ways to make them more productive, for you to have a better chance of being heard, and walk away feeling as good as you can about choosing to have a hard conversation.

Give yourself space for difficult conversations

We often choose to speak up later, rather than in the immediate moment. It’s good to give yourself space to feel vulnerable or check in with your emotions, to avoid a reactive, visceral response.

Grounding exercises can be good for this. You might try deep breathing or focusing on points of contact (feet on the ground, arms on the table, back against the chair). When I’ve been in a situation where I can’t just leave, I look around the room and mentally name the colors I see; a friend of mine used to run through all of the golfing terms she knew.

You can also try soothing exercises, like compassionate touch and self-talk. Compassionate touch might be hugging yourself, or putting a hand on your chest while you take deep breaths. For self-talk, you can say something supportive like, “This feels really hard, but you’ll get through this”. It also might feel good just to acknowledge your emotions and how they’re affecting you.

If you’re able to get physical space, going on a walk is a great way to get through an adrenaline spike. If you have a trusted friend or coworker, ask them for a venting or support session. Whatever your method, giving yourself space allows you to consider all of your feelings and work through the rush of emotions, before figuring out whether you want to speak up and what you want to say.

Why people want to speak up, and why they often don’t

People have different motivations for wanting to speak up. When you’re considering whether or not to have a difficult conversation, thinking about your goals and intentions can help you frame your approach.

Do you want to educate the person you’re speaking with? Are you feeling defensive or angry, and want to share your side of things? Maybe you just want to feel heard, or to re-establish a level of respect. Sometimes, it’s just knowing that staying silent sets a bad precedent, and speaking up for yourself can show others that it’s okay for them to speak up too.

But it is really hard to speak up, and it’s okay if you choose not to. The physical and emotional implications, not knowing how someone might react or even whether they’ll listen – sometimes it’s just easier to take the silent road. To keep your head down and hope it blows over or doesn’t happen again. In the workshop, we talked about some of the things that prevented us from speaking up.

Lack of confidence and fear of retaliation were the two big ones, especially when there’s a power imbalance. In some cases, people felt like it would be a wasted effort – that the other person just wouldn’t listen or participate in a meaningful conversation. There’s also the worry of being dismissed as too emotional or labeled as aggressive or unprofessional.

Strategies for speaking up

Understanding your hesitations can help you figure out the right strategy for when you are ready to have that hard conversation. The ideal outcome is often changed behavior, and that’s easier to achieve if the other person feels like you’re talking with them instead of over them. You can’t predict someone’s reaction, but you can be mindful about your approach and aim for a productive, two-way conversation.

Think about your environment. One-on-one settings usually make people feel less defensive, which means they can be more open to discussion. If you’re able to meet in person, sometimes going on a walk can feel more relaxing and less ‘official’. If you’re meeting in the office, try to grab a room that feels less exposed. If the conversation is happening over a video call, turn on your camera so they can see you – talking to a static photo or a blank square feels impersonal, and it’s harder to find the right cadence of conversation because you’re missing visual cues.

Your language matters a lot. Lara Hogan’s feedback equation is a great framework – start by observing their behavior, describe the impact of their actions, and follow up with a question or a request for changed behavior. This approach allows you to come from a place of curiosity instead of judgment, which makes it easier for the other person to feel at ease as an active participant in the conversation.

Practice what you want to convey. Say these things out loud and see how it feels, or run through the conversation with a friend. If you have a good relationship with your manager, ask them for feedback or coaching. It can also be helpful to let your manager know that you’re having a conversation with someone and to let them know how it went afterwards so they can support you.

Final thoughts

Speaking up is a hard thing to do. I still get anxious, my heart beats too fast, my face gets red. But like any learned skill, having a difficult conversation gets a little easier each time I do it. When I take the time to understand how I’m feeling and what I want to get out of the conversation, it’s more likely that it will be collaborative and productive.

I hope your hard conversations are few and far between – but when you do need to have them, I hope learning from my experiences will help you feel more comfortable and in turn, your discussions will be successful!