Having “The Talk.” How to Handle Difficult Workplace Conversations

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Jan 8 / Charlotte Barber, BCs, PGC, BABCP®

  • Difficult conversations in the workplace are inevitable, but can be managed effectively through thorough preparation and execution.

  • Successful management of tough discussions entails evaluating their necessity, establishing clear goals, using authority wisely, and identifying agreeable solutions to minimize negative impacts on the team.

  • Mastering difficult workplace conversations is crucial for leaders, and can be achieved by preparing strategically and empathetically, ensuring a constructive and respectful work environment.

Nothing can reduce an experienced leader to a puddle of shattered nerves like having to initiate a difficult conversation with a team member. From disciplinary discussions to difficult project updates and everything in between, there are hundreds of situations in which we might struggle with speaking our minds.

The good news? We can prepare ourselves for even the most intimidating talk by focusing on proper preparation and execution. 

What Makes Certain Conversations So Difficult?

 According to Kerry Patterson, author of Crucial Conversations, the only factors required to make a conversation feel like a bad first date are high stakes, high emotions, and varying opinions. Of course, these factors are all extremely common in the workplace, which – to a certain degree – makes these types of discussions inevitable.

Take high stakes, for instance. Even the most banal companies have to deliver something at the end of the day. So, while not all companies have stakes as high as medical centres or financial services providers, no business is immune to stressful circumstances.

Of course, high emotions are typical of any situation where people must work to accomplish a goal. We all know at least one or two co-workers who thrive on stress, and thus feel the need to inject it into virtually every situation.

Finally, we have varying opinions. This, again, is typical of any situation in which you have multiple people contributing ideas. Even if the goals are the same, the fact that we all have different approaches to reaching them can instantly inject tension into any collaboration.

It only takes one of these factors to send even a competent manager into “panic mode.” However, when you start combining the three, you can end up with a situation that seems so volatile, we often feel compelled to walk on eggshells rather than rush to the heart of the problem.

Preparation is the Key to Conquering Difficult Conversations

Of course, it doesn’t really matter how uncomfortable a conversation makes us. Not only are they necessary, but it’s necessary that we, as managers, perform in a way that minimises the negative effects on our team. There’s a reason why I often compare this to the “birds and the bees” discussion parents have to have with their kids. While nobody relishes the inevitable awkwardness that comes along with it, failing to have “the talk” or executing it poorly can do a lot of damage to someone for whom we’re ultimately responsible.
So, what’s the answer?

In my experience as a coach and leader, the best way to handle an upcoming difficult conversation is to approach it as you would a big test or, if you prefer a sports analogy, a marathon. That is: prepare, prepare, prepare. Difficult conversations aren’t the sort of things we can bluster our way through, as how we act often sets the tone for how those on the other end of the conversation react.

Remember, we’re trying to minimise damage to our team and to the many egos that exist inside of it. Though walking on eggshells isn’t ideal, we don’t want to act like a bull in a China shop either. So, how do we prepare ourselves?

  1. Ask if the Conversation is Truly Necessary. As managers, not every difficult conversation is worth our time and energy. And the best way to determine whether that’s the case is to ask whether the conversation has productive intent. Are we just proving a point? Are we actually acting on behalf of another team member? Will this talk do more harm than good? If the answer to those questions is “yes,” it’s possible that nothing productive will come from this conversation. For that reason, it’s best ignored or delegated.

  2. Determine the Desired Outcome. If you’re going to slog through an uncomfortable conversation with a team member, you should ensure you have a goal in mind. Specifically, you want to establish a reasonable outcome for both parties, lest the discussion seem too one-sided or dictatorial. However, to find that happy medium, you must first have all the facts and evidence at your disposal. This means putting on your detective hat and getting to the bottom of the problem.

  3. Use Your Authority Wisely. Now that you know the conversation is necessary, have all the information, and can envision a suitable solution for all parties, you can finally initiate the conversation. As you do so, it’s crucial that you retain a neutral tone. Stick to the facts you’ve collected, and don’t react emotionally. Most importantly, listen to the feedback you get from your team members.

  4. Identify and Agree on Solutions. Once everyone involved has communicated their views, it’s your job to establish a compromise that suits all parties. While this isn’t always possible, what matters most is that you, as the authority, set objectives, time frames, and some sort of accountability before ending the conversation.

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Preparation is the Key to Conquering Difficult Conversations   

Ultimately, mastering the art of difficult workplace conversations is an essential skill for any effective leader. While these conversations can be daunting due to the high stakes, strong emotions, and differing opinions involved, a little preparation can go a long way. By adopting a strategic and empathetic approach, we can learn to navigate any dialogue while minimising potential harm and fostering a constructive, respectful work environment.

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Difficult Conversations F.A.Q.

What makes certain conversations difficult in the workplace?

Difficult conversations in the workplace often involve high stakes, high emotions, and varying opinions. These elements can create tension and make discussions feel volatile, requiring careful navigation.

Why is preparation important for handling difficult conversations?

Preparation is crucial because it helps minimize the negative impact on the team and ensures the conversation is productive. Approaching these talks with a clear strategy and understanding can lead to better outcomes and reduced discomfort for all parties involved.

How can I determine if a difficult conversation is necessary?

Assess whether the conversation has a productive intent by asking if it's merely to prove a point, on behalf of another team member, or if it could potentially do more harm than good. If it lacks a constructive purpose, it might be best to ignore or delegate the conversation.

What should be the goal of a difficult conversation?

The goal should be to achieve a reasonable and mutually beneficial outcome for both parties involved. This requires gathering all relevant facts and evidence beforehand to understand the issue fully.

How should I use my authority during a difficult conversation?

Use your authority wisely by maintaining a neutral tone, sticking to the facts, and listening to feedback from team members. Avoid reacting emotionally to ensure the conversation remains constructive.

How can I identify and agree on solutions during a difficult conversation?

After all views have been communicated, work towards establishing a compromise that suits all parties. Set clear objectives, time frames, and accountability measures to ensure follow-through and resolution.

What are the key elements to mastering difficult workplace conversations?

Mastering difficult workplace conversations involves strategic preparation, empathetic approach, clear communication of facts, active listening, and a focus on constructive outcomes. This approach minimizes harm and fosters a respectful work environment.

Is it sometimes better not to engage in a difficult conversation?

Yes, if the conversation lacks a productive purpose or if it's assessed that the talk could do more harm than good, it might be preferable to avoid engaging or consider delegating the issue to someone more appropriate.

How can a leader minimize damage during a difficult conversation?

Minimizing damage involves preparing thoroughly, understanding the issue at hand, aiming for a balanced discussion, and seeking solutions that respect all parties' views and needs, thereby protecting team dynamics and individual egos.

What is the role of empathy in difficult conversations?

Empathy plays a crucial role in understanding the emotions and perspectives of the team members involved, which aids in navigating the conversation towards a more positive and productive resolution.

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