The Senior Direct Who Pushes Back on Everything
"Every time I give feedback, it turns into a debate."
Meet Riley, a newly promoted manager leading a mixed-experience team. One team member — ten years older, confident, and vocal — pushed back on almost everything.
Whether it was process updates or project feedback, discussions somehow ended with Riley defending decisions rather than leading them. The team noticed the tension. Riley started dreading 1:1s.
Riley didn't want to micromanage or escalate — just find a way to lead firmly and fairly.
From frustration to framework
The AI Coach helped Riley unpack what was really happening: a mix of unclear boundaries, mismatched expectations, and unspoken status tension.
Rather than offering a one-size-fits-all fix, the coach guided Riley through a simple framework:
- Clarify the goal before the next 1:1: "What outcome do I need from this conversation — alignment, accountability, or buy-in?"
- Reset expectations with structure: Use a boundary script grounded in behavior, not attitude.
"I really value your experience — and I need us to align on how we apply standards so we can deliver consistently as a team."
- Create a follow-up plan: Define one clear metric or behavior to revisit in a week.
🎥 See how it works
Manager
I have a team member who has been with the team for about 4 months now. He transferred in from another department and is about 10 years older than me. I have noticed that he pushes back on every single thing, it's almost like he has to have the last word and has to be right. For example, …
AI Coach
Before offering suggestions, can I ask a few questions to better understand the context and your ideal goal:
a. What's your main goal here? Are you hoping to improve your working relationship with this team member, set clearer boundaries, or address the behavior more formally?
b. How does this team member interact with others on the team? Is the pushback and "bossy" behavior just directed at you, or do others experience it as well?
c. How does he respond to feedback in the moment? Does he get defensive, or is there any openness once …
Clarity today — confidence tomorrow
After a few coaching rounds, Riley didn't just have a single script.
They had:
- A framework for handling future pushback with more structure and less emotion.
- A clearer mental model for when to seek alignment versus when to set direction.
- Saved conversations inside the AI Coach to return to for sparring and fine-tuning before the next real-world discussion.
Work2gether AI didn't replace experience — it helped Riley build it faster, one real situation at a time.
What Riley gained
- A practical structure for tackling difficult dynamics with confidence.
- Reflection prompts and scripts tailored to their real context.
- A safe space to rehearse and refine — before stepping into the next conversation.
Behavior change takes time. But with a clear path, steady practice, and an AI coach that's always on, managers like Riley keep moving forward.
Want your own "sparring partner" for tricky conversations?
Try the AI Coach that helps you think, plan, and communicate like the leader you want to be — one conversation at a time.
👉 Try it yourself, free for 14 days →
👉 Explore more Manager Moments →
Because good teams don't stand still. They grow — one step at a time.