How to Get Critical Conversations Right

November 25, 2020

Joe Cox

Best practices for leaders to ensure their critical conversations with team members are successful.

animation of two people having a critical conversation at work

How leaders handle critical conversations with their teams has the power to make or break an organization over time. And especially during tough times, getting critical conversations right can make all the difference. Conversations that go well can unite a team and get work done better and faster. However, conversations that go poorly can bring work to a standstill.

The work example below details an upcoming conversation between a leader and a team member. The goal of the meeting is to agree on a plan for dealing with some company-wide changes due to the pandemic. Read on to get leadership development best practices for ensuring your critical conversations like these are successful, and everyone leaves on the same page.

Meet Alex and Emma

Alex's engagement stands on an absolute knife edge. He is a skilled and experienced marketer at a medium-sized manufacturing company. But the marketing department has been hit by wave after wave of layoffs. And it has just been announced there are more changes coming.

Even with this uncertainty, the marketing team was still asked to submit a budget for the new fiscal year. However, no one on the team is sure of upcoming customer behavior. And massive third-party spending restrictions have the team already working with the bare minimum. They all know that just getting through the next quarter is going to be tough.

Not to mention, as the company’s sales continue to plummet, targets for lead generation are higher than ever. But the team is without the necessary resources—human and financial—and the team can see their workload piling up. Everything is starting to get a little too much.

But where is Alex's leader?

The hard truth is that Alex's leader, Emma, is also in a spin. Why? Because before 2020, the company relied heavily on face-to-face interactions to build connections and trust within their teams. But the pandemic has challenged the company’s employees to work together in different ways.

The Pandemic Turned Leadership Upside Down

Working from London, in the midst of a second lockdown and with no clear end in sight, leaders across the company feel their “leadership toolkit” has been significantly reduced.

No longer do they have the luxury of face-to-face interactions or lunchtime table tennis competitions to make genuine connections and check in with what they need. Yes, keeping people connected and having those inevitable critical conversations is even harder now in the “new normal.”

For Emma, the past few months have been dominated by discussions on staff turnover, budget reductions, and shifting strategic and cultural priorities. And this is all happening while work resources are stretched to their limit. But Emma and other leaders take some small comfort in knowing this is the norm for many organizations.

Still, these critical conversations deal with the stark reality of the suffering business. And Emma can see herself drifting further from her team. But these changes are necessary to keep the business afloat. She knows her team "gets it," even though senior management hasn’t really offered up a rationale for a lot of the cutbacks.

If senior management did explain the changes in detail, Emma thinks, then it would just be opening a can of worms, right? I have a one-on-one meeting with Alex this Friday. But I just don't have the bandwidth to get feedback from him on things that can't be helped right now. It's better to focus on what’s next. Keep moving the business forward.

Do you know an Emma? Or an Alex? Or maybe you can empathize with one of them? We've all experienced changes in our roles which we didn't see coming. Likewise, it's easy for a feeling of helplessness to start to bubble up from both the leader and direct report. I wish I could say above is an extreme example. However, I've heard variations of this example many times over the past few months.

Best Practices for Having Critical Conversations at Work

In every Emma and Alex situation, what is lacking is willingness to stare down challenges and address the personal needs of each other. Not focusing only on the practical needs of the business but also on the Key Principles to driving continued engagement: ensuring people feel valued, respected, listened to and understood, and supported. And doing this in every critical conversation.

Today’s pivot to work from home, along with COVID-19 worries, has certainly made workplace communication more difficult, and more tense. Each discussion requires much more careful consideration so that people receive the care and attention they need to be productive.

So, back to our friend Emma. What should she be doing to prepare for her next critical conversation with Alex? It starts with thinking about both the personal AND the practical needs of her daily interactions with Alex. Let's look at some questions Emma should be asking herself at each stage of an upcoming important conversation with Alex.

How to Prepare for Each Stage of the Conversation

Open: How will I open the conversation to make Alex feel comfortable? How can I show him I’m not assuming I know how he is thinking and feeling? How will I share my confidence in the team and our organization’s future?

Clarify: What questions can I ask to understand Alex's situation and any concerns he may have? How will I listen and respond with empathy to defuse any emotions? What will I say to maintain his self-esteem and promote involvement in his upcoming work?

Develop: What questions can I ask to seek ideas for addressing Alex's concerns? What ideas do I want to share? What will I say to stay focused on desired outcomes (Alex's increased engagement and connection with the rest of the team to manage workload)?

Agree: What might I say to guide Alex toward a sense of confidence without providing too much coaching? How might I provide support without removing responsibility to make his workload more manageable?

Close: How can I be sure we both understand the key points of agreement and next steps? What might I say to express confidence in Alex or enhance his self-esteem to create energy?

Turning Common Sense into Common Practice

These interaction guidelines are built on common sense, right? Indeed, they are! But the tricky thing is making empathy, involvement, and sharing rationale common practice throughout the conversation.

DDI developed Interaction EssentialsSM for leaders to learn and use in their day-to-day interactions. Using these can be the difference between a conversation that moves people towards business goals, or away from them. And knowing how to balance the personal and practical needs of interactions is a key part of the core skills of leadership. And these skills work just as well virtually as they do in person.

So when you're looking for ways to support leaders working remotely during a global pandemic, jumping from one virtual call to the next, remember to revert back to the basics of leadership. Giving your leaders the skills to have successful interactions ensures their teams will see results—and in turn, see success within the organization.

Get proven content to help your leaders quickly solve their toughest leadership development challenges. Learn about DDI’s leadership development subscription.

Joe Cox is a consultant based out of DDI's London office. When not working with multinationals to strengthen their leadership pipeline, he can be found watching London theatre, eating delicious food, taking long walks by the Thames, or wrestling with a piste map in the French Alps. During lockdown, however, mostly just food. Reach out to discuss leadership trends and insights, or West End musicals at

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