Preparation Is Key for Difficult Conversations in the Workplace

Part 1 of 3 articles that will provide tips for Preparing, Engaging, and Acting to manage difficult conversations in the workplace.

Tough conversations make everyone nervous. We need to address a situation, but we don’t know how to start and we don’t want to hurt feelings. We hope that if we ignore it, the problem will go away. 

But it doesn’t go away! Something that may be a small problem, left untended, can balloon into a big issue. 

Proof in point: A study of more than 1,000 executives and project management professionals across 40 companies, 2,200 projects ($10,000 IT projects to $1 billion-plus restructures) found that project leaders can substantially improve their organization’s ability to execute on high-stakes initiatives. But they could only achieve this by changing their behavior around problems that contribute to almost ALL project failures. (Excerpted from Silence Fails, Vital Smarts and the Concours Group, 2008.)

The needed behavior? 

Engaging in tough conversations about key topics.

Those topics often include unrealistic deadlines or team members who were unwilling to support a project. Many of these issues probably surfaced early, in small details that should have been addressed immediately. Instead, they became major problems.

The ultimate outcome of a tough conversation should be positive change, and the ability to follow the process through to an actionable plan is critical.


Tip #1: Examine Your Intent 

Why do you feel the need for this conversation? If you are angry, desire vindication, or don’t like the other person, you may need to take a long look in the mirror. If you want to shame someone, prove you are right, or are unwilling to believe another point of view, this is a fight, not a tough conversation.

Tough conversations, in their best form, are moments when someone cares deeply about another person. They care so much that they are willing to be honest with that person in the hope they can create a better future. 

If you believe this information could raise awareness, help another person grow, or benefit a larger group, you are on the right path. It’s like having a tough conversation with yourself before approaching the other person. Understand that the best conversations allow for both sides to be heard. You need to be ready to be vulnerable, hear things you may not like, and above all, head into the conversation with positive intent.

Tip #2: Gather Data and Formulate Questions

Once you have positive intent, it’s time to get real data about the situation. Data allows you to remove emotion, which is critical when people may be hurt or angry. The more you can point to actual data, the less you engage in “He said…”/“She said…”

For example, your team is grumbling that a key person is “late all the time and we have to pick up his work.” It’s affecting morale and trust in the team. 

What is the proof of lateness? Can you gather punch-in times? Have you seen the person arriving late with your own eyes, multiple times that you can document? Or did it only happen once and is being blown out of proportion? Most importantly, this may be a time to ask probing questions of the “grumblers.” When pressed, do they have data, or are they just stirring up issues?

The key is that if you accuse a team member of lateness and he or she denies it and asks you to prove it, you need to be ready to do so.

Next, consider what you don’t know. Preparing open-ended questions that allow you to hear the team member’s side of the story will fill in the blanks. And often, you can begin with the most elemental questions. For example:

  • Could you share your understanding of our work hours policy? (Perhaps this person transferred from another division that had more flexible hours and is working late into the evening when other team members have gone home. No one sees that.)
  • How’s work/life balance for you? Are there any current challenges that are making it tough for you to be on time?
  • How can the team and I support you better? (This may be an opportunity to learn any number of things about how this team member is managing workload, pressure, and team relationships.)

By spending as little as 15 minutes preparing for this conversation, you can be confident in your approach, have data to lean on, and know what you need to learn from the other person. Preparation is the great differentiator—your outcome relies on it!

Look for the next 2 installments in this series, Engage (in Marchand Act (in April).

Karen Hough is the founder and CEO of, a company that builds adaptable, flexible, improvisational leaders and is in the top 1 percent of U.S. women-owned businesses. She is an Amazon #1 bestselling author, winner of multiple awards, and a Yale grad. For more information, visit: