In our 2026 Real-Time Business Conversation Index, one respondent shared this insight:
“Colleagues have difficulty with tough conversations. I often see my colleagues take things too personally rather than focus on the facts and possible outcomes. As professionals and senior leaders, we need to lead by example and ensure we take an objective approach to problem solving and addressing issues.”
Difficult conversations arise for everyone. In this series, I’m sharing insights about these conversations and offering ideas for improving them. Your input and experience are always appreciated. We welcome your comments and feedback.
During a recent visit to Toronto, I had lunch with a young woman I met through my volunteer work when she was 8 years old. She’s now approaching 40 and is working towards her Bachelor of Social Work. She shared her disappointment about a recent school assignment. It was a team project, worth lots of marks but, unfortunately, as is often the case, communication completely broke down. While my friend did her best to create and deliver the necessary presentation to the professor, it was an utter failure and no excuses were accepted.
Similar situations also happen in the workplace. The levels of stress they cause, as well as the resentment and delays they create, can be avoided.
Communication often breaks down because team members wait too long to speak up about missed deadlines, lack of input, etc. When this happens, the ensuing conversation moves away from the desired outcome and becomes laced with emotion, assumptions and accusations. Frustration, anger, and finger-pointing lead to a dead end in terms of moving the team forward.
Here’s how to keep a team project on track.
- At the very beginning, agree on the final outcome you wish to achieve. Describe it in words and phrases that are clear and simple. Leave no room for assumptions.
- Also agree on deadlines and, should there be delays, how they will be communicated. Will team members provide a heads-up as soon as possible, or will a last-minute notice be acceptable?
- Talk about what happens if, for some reason, communication breaks down. How quickly will this be addressed and how?
An Example
Let’s say a team is put together to create three learning experiences for the newest members of the company. The final outcome might be:
“By June 1st, we will have three 30-minute learning experiences ready to present to our 10 new employees. The first will focus on our company’s core values and why they are important. The second will focus on our current clients, their projects and their expectations. And the third will present our growth plan, including the new employees’ contributions, and leave time for discussion.”
“Everyone will share the initial outlines of their chosen learning experience by the end of this week. The first learning experience will be delivered as a draft for everyone’s review by May 8th. If there is any possibility of a delay in meeting this deadline, notice must be sent to everyone by May 1st. This will give us time to offer assistance or adjust our schedule.”
Of course, the human element means that even with these best intentions, things can still go sideways. When that happens, someone on the team can get a valuable conversation started by saying, “Let’s talk about something that’s impacting our project.” This opens a door to discussion without creating emotional tension.
Anchor the conversation to the shared goal. “We all agreed to welcome our new employees with these learning experiences by June 1st.”
State the issue or observation that’s jeopardizing the project: “The delays in completing the outlines for each learning experience are setting us up to miss our deadlines.”
Offer a clear, forward-focused ask: “Can we set aside time this week for a one-hour meeting where we’ll work together to complete all the outlines?”
Finally, move towards agreement: “Does this work for everyone? What about a working lunch this Thursday? I’ll book the small boardroom.”
The goal of this conversation is not to ‘address an issue’, which would allow the discussion to lean into emotion and possibly accusations. The goal of this conversation is to adjust how the project will be completed going forward.
Focusing on the necessary changes versus what’s gone wrong, and why, avoids the communication breakdown and re-energizes the team.
Try this this week:
When a team project is in trouble, don’t confront the person; correct the process. The moment a conversation feels personal, the walls of defensiveness are built and valuable communication is difficult to establish. When conversations are about improving the workflow, people engage.
