The Conversation Compass: Your Guide Through Uncomfortable Conversations.
I spend my days chatting with all sorts of people – from CEOs to new grads, across every industry you can imagine. And here's what I've noticed: no matter how impressive your title or how many letters follow your name, everyone struggles with certain conversations.
It's almost comforting, right? We all get that knot in our stomach before a difficult discussion, and we all tend to either clam up, run away, or go in guns blazing – none of which really works out well.
For those moments when you must initiate that courageous conversation—addressing missed deadlines, discussing inappropriate behaviour, or broaching any topic that generates discomfort—the following strategies will help transform potential conflict into productive dialogue and meaningful connection.
React to the outcome, not the event.
When confronted with a situation that leaves you feeling angry, frustrated, or disappointed, your first impulse might be to respond with criticism—to let the other person know exactly how their actions affected you. However, this approach typically creates tension that evolves into passive-aggressive behaviour, leaving essential issues unresolved while breeding animosity and resentment.
Instead, pause and ask yourself: "What result do I want from this conversation?" Perhaps you need to understand what went wrong and identify barriers to prevent similar situations in the future. Most importantly, consider whether preserving the relationship outweighs the momentary satisfaction of expressing your frustration. How do you want to be able to work with this person going forward? That's what it means to react to the outcome and not the event.
This concept of reacting to the outcome, not the event, is equally important in personal relationships and work.
I experienced this firsthand during a family vacation at a resort. My children asked permission to explore a waterpark ride independently, promising to return shortly afterwards. When forty-five minutes passed without their return, I faced a decision about how to handle the conversation.
Had I greeted them with accusations about their irresponsibility, little would have been accomplished. Instead, I chose to remain calm, withhold assumptions, and hear their explanation. When they finally returned, slightly over the agreed time, they explained they had taken a wrong turn and ended up at the far end of the park, requiring a long walk back.
I began by acknowledging what they had done right—staying together and looking after each other—before explaining my perspective: that I had extended trust, and their late return made me question whether that trust was being respected. They immediately understood my concern, offered sincere apologies, and assured me it would not happen again.
We concluded our conversation with hugs before heading to the next slide together—a far better outcome than if I had resorted to guilt or anger. My children appreciated being treated with respect, understood the importance of time boundaries, and recognised the potential consequences of breaking trust.
Not every conversation carries equal weight, but during those crucial exchanges—whether at work or in your personal life—you want to look back and know you responded in a way that reflects your best self rather than your momentary emotions.
Where did I contribute?
The most common frustration leaders express to me involves missed deadlines or communication failures—specifically when team members don't deliver work on time or fail to proactively signal when projects are veering off track. This silence creates a crisis that ultimately lands on the leader's desk, forcing them to scramble for solutions at the eleventh hour while managing expectations with stakeholders. What begins as a simple missed deadline cascades into a high-pressure situation that could have been prevented with timely communication.
I listen attentively to their venting on this specific individual. Then, I pose a critical question: "Knowing what you know now, what would you have done differently?"
Invariably, they recognise their own missed opportunities—they should have established clearer expectations upfront, checked in periodically on progress, and requested status updates when communication lapsed.
This reflection isn't about absolving others of their responsibilities but rather about approaching the conversation from a more productive angle. It acknowledges that while someone else may have faltered, there's a valuable lesson for you as well.
The key to transforming these potentially confrontational discussions into constructive dialogues lies in a fundamental shift: replacing vague expectations with clear agreements.
When both parties explicitly understand their commitments and communication protocols, the foundation for accountability becomes much stronger, and the conversation can focus on solutions rather than blame.
Replace expectations with agreements.
As renowned coach Steve Chandler teaches in his transformative work on leadership, the shift from expectations to agreements represents one of the most powerful changes you can make in professional relationships. When you catch yourself thinking, "They should know what to do" or "I expect them to get it done," recognise this as your signal to implement Chandler's approach.
Instead of simply instructing a team member, "I need this document by Friday to review it," try Chandler's agreement-based alternative: "I need this document on Friday in this format. Can we agree you'll deliver it by midday?" This simple adjustment opens a dialogue where your colleague can either confirm the timeline or propose a workable alternative: "I can't make midday due to another priority, but would end of day or Monday morning work?"
When someone commits to midday Friday but misses the deadline, the accountability conversation becomes straightforward precisely because, as Chandler emphasises, it's now about a mutual agreement rather than an imposed expectation: "We agreed you'd have this to me by midday, and that deadline has passed. I'm now under pressure from the client. What happened?"
The insight that "people support what they help create" forms the foundation of this approach. Including team members in establishing deadlines significantly increases their commitment to follow through.
Conversely, imposing too many unilateral demands often triggers resistance patterns—either direct pushback or the more insidious passive agreement where someone says yes while having no intention of delivering. By adopting an agreement framework, you create both clarity and buy-in that expectations alone can never be achieved.
Help me understand.
If you truly want to transform an accountability conversation into an opportunity for growth and connection, incorporate these three powerful words: "Help me understand."
When someone misses an agreed-upon deadline—like delivering that document at midday—approach the discussion with genuine curiosity rather than confrontation. Begin by acknowledging the agreement: "We discussed that you would deliver this by midday." Then, bridge to understanding: "Help me understand what barriers you encountered. How might I better support you next time? Can we agree that in the future, you'll let me know if you're going to miss a deadline or need assistance?"
This approach fundamentally shifts the conversation's energy from accusation to collaboration. Instead of triggering defensiveness with blame and judgment, you create space for honest reflection and problem-solving. The phrase "help me understand" signals your sincere interest in their experience and challenges, not just the missed deadline.
After witnessing this pattern play out countless times with clients across industries, I've seen how this simple linguistic shift can dramatically change outcomes. When people feel their perspective matters, they become partners in finding solutions rather than opponents defending their actions. The conversation transforms from a confrontation about what went wrong to an exploration of how to make things right going forward.
Use the Rule of Three.
Addressing persistent problematic behaviour—whether missed deadlines or chronic lateness to meetings—presents a common leadership challenge. When left unaddressed, these frustrations typically accumulate silently until an unrelated incident triggers a disproportionate reaction. While your response feels justified after multiple incidents, it appears utterly bewildering to the recipient who hasn't received prior feedback.
Instead, implement the Rule of Three: When someone arrives late once, make a mental note. When it happens a second time, recognise a potential pattern emerging. After the third occurrence, initiate a calm conversation: "I've noticed on these three occasions that you've arrived late for our team meetings. Could we agree that you'll arrive on time going forward? The late arrivals disrupt the group's flow and create pressure on our end time."
This approach typically yields one of two outcomes—either they acknowledge the behaviour and commit to improvement, or they discover an underlying systemic issue, such as a preceding meeting that consistently runs over its allotted time.
The power of this method lies in addressing the situation dispassionately with specific examples rather than emotional reactions. By focusing on observable behaviour instead of character judgments like "irresponsible" or "inconsiderate," you create space for productive dialogue. This factual approach helps the person recognise the impact of their actions without feeling personally attacked, increasing the likelihood they'll modify their behaviour.
Should the pattern continue despite this conversation, you now have a clear foundation for establishing more formal agreements with appropriate consequences.
Final thoughts.
Meaningful conversations challenge everyone—even the most confident among us find themselves unsettled when tackling difficult topics. By integrating a few key principles into your approach, you can transform uncomfortable exchanges into opportunities for genuine connection and growth:
React to the outcome, not the event. Focus on the resolution you seek rather than the emotions triggered by what happened.
Where did I contribute? Acknowledge your role in any breakdown before addressing others' responsibilities.
Replace expectations with agreements. Convert unspoken assumptions into clear, mutual commitments.
Help me understand. Approach differences with genuine curiosity rather than predetermined conclusions.
Use the Rule of Three. Address patterns methodically rather than letting frustration build until it explodes.
And perhaps most importantly, replace judgment with curiosity. When you feel yourself becoming reactive, remember this fundamental truth: the moment you judge someone, you lose your ability to influence or learn from them. Curiosity opens doors that judgment slams shut.
Here’s to better conversations,
Warm wishes,
Lori