[difficult people] - 20. Aligning Visions: Setting Mutual Expectations
Dealing with Difficult People
The Expectations Talk: A Story of Finding Common Ground
Wei sat in her car, rehearsing the conversation one last time. In an hour, she'd be meeting with Diane, her project counterpart from Marketing, to discuss their working relationship. After months of missed deadlines, conflicting messages to clients, and growing frustration on both sides, Wei had finally scheduled what she mentally called "The Expectations Talk."
She remembered how things had started - small misunderstandings that grew into assumptions, then resentment. Wei thought Marketing was ignoring Engineering's timelines; Diane probably thought Engineering was being inflexible. Neither of them had ever sat down to really discuss how they could work better together.
Taking a deep breath, Wei reviewed her notes one last time. Not to complain about past issues, but to focus on moving forward. She'd prepared specific examples of what good collaboration could look like, and she was ready to listen to Diane's perspective.
The conversation started awkwardly. "I appreciate you meeting with me," Wei began. "I think we both want our projects to succeed, and I'd like to talk about how we can best work together." She noticed Diane's shoulders relax slightly at these words.
To Wei's surprise, Diane had come prepared too. "I've been wanting to have this conversation," she admitted. "Sometimes I feel like our teams are speaking different languages."
What unfolded was a revelation. Wei learned that Diane's team needed more context about technical constraints to plan their marketing campaigns effectively. Diane discovered that giving Engineering's team earlier visibility into marketing initiatives would help them plan resources better. They weren't dealing with a difficult person – they were dealing with misaligned expectations.
What Made the Difference:
Preparation
Specific examples ready
Clear objectives identified
Open mindset maintained
The Conversation Framework
Started with shared goals
Used "we" language
Focused on future solutions
Creating Clear Agreements
Specific actions defined
Timelines established
Responsibilities clarified
The Agreement They Reached:
Communication Protocols
Weekly brief check-ins
48-hour email response time
Shared project timeline visibility
Project Planning
Marketing initiatives shared quarterly
Technical reviews before client promises
Buffer time built into deadlines
Feedback Mechanism
Monthly review of process
Open door for concerns
Regular team cross-training
Moving Forward:
After their meeting, Wei sent a brief email summarising their agreements. It wasn't about creating a binding contract – it was about having a shared reference point for their commitments to each other.
Three months later, their teams were collaborating more smoothly than ever. Not because either Wei or Diane had fundamentally changed who they were, but because they had created clear, mutual expectations about how they would work together.
Try This Approach:
Before the Conversation
List specific challenges
Identify possible solutions
Consider the other's perspective
During the Discussion
Start with shared goals
Listen more than you speak
Focus on specific, actionable items
After Agreement
Document understanding
Schedule check-ins
Celebrate small wins
Remember: The most difficult work relationships often suffer not from bad intentions, but from mismatched expectations. Having "The Expectations Talk" isn't about confrontation – it's about creating clarity that benefits everyone.
What conversation about expectations have you been putting off?
N.B. In the spirit of the theme of this newsletter, someone who is deliberately being difficult could still leverage this kind of conversation against you; it would be wise to keep up any process of documentation that you have started.