5 Difficult Conversations During Difficult Times [And How to Handle Them]

The Covid-19 pandemic makes the skill of intelligent listening, and pragmatic problem-solving ever more crucial. On the one hand, the global nature of the pandemic can unite us in learning from each other as an international community but can, on the other hand, polarise us with topics such as politics and vaccine mandates.

It can be challenging to have conversations with people who don’t share our own views or who see the world differently from us. However, it’s important to facilitate open conversations about the things we disagree on where both parties feel respected and understood.

Here are some general guidelines for having difficult conversations as well as a few scenarios to consider.

  1. Be Proactive. Take steps to help prevent problems from occurring in the first place. Use an employee handbook and regular staff meetings to clearly communicate workplace rules and procedures so that employees know exactly what is expected of them.
  2. Speak Up Early. When we anticipate stress or pressure, most of us decide whether or not to speak up by considering the risks of doing so. Those who are best at dialogue don’t think first about the risks of speaking up. They think first about the risks of not speaking up. They realize if they don’t speak up early and often, they are choosing to perpetuate and often worsen the situation—and their reaction to the situation—as they begin to work around the problem.
  3. Challenge Your Story. When we feel threatened or stressed, we amplify our negative emotions by telling villain, victim, and helpless stories. Villain stories exaggerate others’ negative attributes. Victim stories make us out to be innocent sufferers who have no role in the problem. And helpless stories rationalize our over- or under-reactions because “there was nothing else I could have done!” Instead, take control of your emotions by challenging your story.
  4. Create Safety. When communicating while under pressure, your emotions likely hijack your positive intent. As a result, others get defensive to, or retreat from, your tirade. As it turns out, people don’t get defensive because of the content of your message, but because of the intent they perceive behind it. So, when stressed, first share your positive intent. If others feel safe with you, they are far more open to work with you.
  5. Start With Facts. When the stakes are high, our brains often serve us poorly. To maximize cognitive efficiency, we tend to store feelings and conclusions, but not the facts that created them. Before reacting to stress, gather facts. Think through the basic information that helped you think or feel as you do—and use that information to realign your own feelings and help others understand the intensity of your reaction.


Below are several scenarios that may necessitate difficult conversations during the pandemic.

Scenario #1 – My friends think differently about coronavirus safety. How do I kindly and respectfully help my friends reframe their perception of COVID-19 compliance.

Last week I was talking to a friend of mine about wearing a face mask. She decided not to. Because Why? She didn’t want to live in fear. She said, Emily, I choose hope, not fear. Wow, that’s a pretty strong value statement. So how could I help this friend think about it differently?

Well, I wanted to help her reframe her behaviour. So, I chose a frame that she was already comfortable with. She’s one to always wear her seatbelt. And all I did was ask her.

Well, why do you wear your seatbelt then? Isn’t that a choice based on fear?

And she said, No, it’s not a choice of fear. You’re not wearing your seatbelt because your afraid you’ll get in an accident?

No, I’m just, just in case.

And then I said, “Maybe you should think about a face mask as just in case.” She looked at me and she thought about it and said, “I’ll think about that”.

Now, sometimes that’s the best you can do in a conversation.

But here’s the thing, if I had come at her and said, you need to wear a face mask because of these eight reasons, she probably would’ve shut down.

As you think about how to help people change their behaviour, start from where they are and reframe their behaviour in the context of things they already do.

Scenario #2 – Delivering tough news to employees in a virtual work environment.

Having a crucial conversation is tough. Having one over email is even harder.

We often get asked, “Which is better? Should I have a crucial conversation face-to-face or on the phone? Or is email okay?”

The answer is, it depends. And it depends on this.

What is going to be better for the other person? When you think about how you should have that conversation, whether on a video call or in an email, I encourage you to think about what is going to be best for that other person.

Let me give you an example.

Last week I had a tough message I had to share with a colleague I deeply care about. We had a call scheduled for Friday and I debated whether I should send an email before that. I finally decided I would.

Thursday afternoon I sent an email, and in that email, I said, “I know this is tough and I wasn’t sure if it would be better or not to send it beforehand or wait for our call, but I wanted to give you a chance to think about it and process it before we come together.”

A few hours later she emailed back and said, “Thank you so much for this email. I did need time to think about this before we talk about it.”

Just think about that statement.

When you send someone an email, if you can do it well, you will give them time to think about it, before you pressure them to talk about it.

And that can truly be a gift.

Scenario #3 – Using video calls to build trust with co-workers and managers

Every conversation is an opportunity to either build  or damage a relationship. How you have that conversation determines what the outcome will be.

So here’s the truth.

It’s not you hearing someone that builds a relationship, it’s them seeing you listen. The other person has to know that you’re listening, know that you’re hearing them in order for that relationship to be built and strengthened.

Now that seems pretty easy in a face-to-face conversation. But how do we do that in a more virtual world?

Well, here’s an idea for how to do it on video conferencing. Obviously, you still get to see a person, but there’s a lot of things you’re not seeing, like what they’re doing with their hands or where they’re multi-tasking.

So here’s what I like to do in virtual video conversations to help the other person know that I am deeply engaged with what they’re saying.

Two ideas: one, share your screen and take notes. That does a couple of things. One, it allows them to see how you’re processing what they’re saying. And two, it assures them, without you even having to explain, that you are paying attention. You aren’t multi-tasking during the call.

The second idea is similar. Sit back from your webcam just a little bit so that they can see your hands. Maybe hold them to the side. Pause, think about it. Put your hands in a place where they can see them. Where they know, consciously or not, that you’re not typing away or multi-tasking on another screen.

Before having a difficult conversation with an employee, make sure you have carefully planned not only what information you need to convey but also how you will deliver it.

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