A Beginner's Guide to Untangling Difficult Work Conversations

In today's online meeting environments, and from one mobile conversation to the next, meeting participants often describe how much they miss. They miss friendly greetings at coffee stations, lunchtime meetings in cafes buzzing with chatter, and casual hallway conversations. Yet, many are making progress, advancing work critical client and customer work. Decreasing in-person interactions haven't slowed the need for critical progress conversations. Still, the increase in zooming has only changed a delivery method for the difficult discussions we have at work.

 Most of our meetings that involve difficult topics produce anxiety. We stress, we worry, and we muse through perceptions and conclusions. The ground underneath our feet seems uncertain in these situations, and most wonder if they will ever get the hang of having a difficult conversation at work. We wonder about the consequences of our difficult discussions on the people and groups with whom we have them and the impacts on their families and communities.

 Any how-to guide on handling difficult conversations is incomplete without an appreciation for the context that creates a challenging situation and without personal reflection. Rather than provide a list of steps, this article shares my experiences and observations of others who successfully manage difficult conversations at work. These ideas might provide just the help you need from someone who has met with many in difficult circumstances.

What You Can Do to Plan for The Best Outcomes in Difficult Discussions

Prepare, but not in isolation. Successful outcomes in difficult conversations begin and end with respect. Most difficult conversations involve some reduction or some less. It might be a missed promotion or a performance issue that doesn't seem to be improving. Sometimes, the need for a difficult conversation appears to arise from nowhere, and others follow months of careful planning and consultation with others.

Understand your role and, if you can, your motivations. When rules, standards, or policies are clear, difficult conversations are made easier thanks to rulebooks and manuals. It doesn't mean that they are painless, but they differ from discussions concerning advancement and development. It's known that our dislikes of others mirror our own liabilities and shortcomings. Knowing how you fit into the conversation is critical to not reducing anyone's self-esteem.

 Plan for your discussion; take notes. Conversations are made more difficult when circumstances take control. Someone gets "hot" at a meeting, and tempers flare, and other situations seem incomprehensible from a rational view. If you don't have time to plan, take a deep breath, and focus the conversation on directing energy at the issue, not the person. When you take time to plan, you will benefit from knowing that you'll need to listen more than you speak.

Pause when you meet with people. Sometimes, we're so anxious to get through a plan that discussion is replaced by a practiced and rehearsed conversation. Even if you're nervous and need to get through quickly, don't end the meeting by asking, "Do you have any questions?" People often don't have the presence of mind to consider their questions.

 Let others know that you are there for them. In most cases, people are accommodating and generous. Given the time to reflect on situations, they can adapt and begin a new order. Bill Bridges said it well so many years ago: it's not the fear of letting go or starting something new that causes trouble, but everything that happens in-between an ending and a beginning. It's an excellent reminder to stay focused and be present when you meet with others on difficult topics.

Difficult topic or bad news? Be clear on the types of messages in difficult conversations. Most are beginnings. Introducing and describing a difficult situation is the first step in change and improvement. Be clear of the capacity and capabilities for meaningful progress.

Seek out formulas and don't rely on them. Perhaps someone you know has encountered similar situations. Now is the time to ask your boss, coach, or mentor for advice. You can gain from the experience of others, but there is no substitute for your original involvement. These encounters must begin with an acknowledgment of the inherent worth of the individual. If any of your values include integrity and courage, uncomfortable discussions provide a learning classroom.

Teach someone what you've learned, or at least share it with someone in addition to a family member. Bosses and coworkers fill endless hours of dinnertime conversation in American workers' homes. Stress at work doesn't stop with the last Zoom meeting or customer interaction that you've had. Look for opportunities to share what you've learned and help another person.

Understanding and Unlocking Patterns

Every difficult conversation can be made easier with a few simple practices. First, value straight talk; in other words, be clear and kind in delivery and intent. Above all, avoid jargon because it devalues the first practice, straight talk. 

Remember that a difficult conversation is just that, a conversation that produces outcomes of varying consequences for you and the other person. Because it's a conversation, it means that listening should be at the forefront of most difficult conversations, particularly those where progress is possible. Get in the habit of having "responsible adult" conversations with others at work. 

Most conversations that act our parent, teacher, or other roles of power and influence, cause everyone in a difficult conversation to regress. I am deeply grateful for that lesson about difficult conversations from Charlie and Edie Seashore. They made indelible imprints on my approaches to helping coaches, consultants, and managers creating organizations where people do their best work.