What You Expected and Never Said

The gap between assumption and agreement — and why it’s where most leadership friction lives.

This is a story for any leader who has found themselves waiting on something they never actually asked for.

Six Months of Work, Three Months of Waiting

Greg had done everything right.

Six months building the business case. Every number stress-tested. Org chart mapped, approval chain documented, presentation polished to a finish line he could see clearly. When his COO told him to bring it forward, he brought it forward — clean, detailed, and ready.

What he got back was a verbal “sounds good” and a handoff.

The handoff went to Carol, his direct supervisor, to secure final sign-off from the executive team. Greg assumed that was the end of his job. Carol would champion it. The approval would come. He would execute.

Three months later, he was still waiting.

The company built commercial aerospace components — Tier 1 supplier to three of the largest aircraft manufacturers in the world. Nothing moved without executive sponsorship. Every structural change required traceability documentation before it was real. Greg managed a significant portion of the operations division, and his reorganization proposal had gone quiet.

He came into his coaching session that morning with the frustration already on his face.

What Carol Should Have Done

“Walk me through it,” the coach said.

Greg laid it out. Carol was supposed to champion this. She was supposed to get in the room with the executive team, put her authority behind the plan, and get the yes. That’s how it works. He’d done his part.

“And did you tell her that?” the coach asked.

“I briefed her thoroughly. She knows the whole picture.”

“That’s not what I asked. Did you tell her — specifically — what you needed her to do?”

Greg paused. “I told her I needed her support.”

“Okay. What does support look like in this situation?”

Greg opened his mouth and then closed it.

“Because I’m hearing you describe what Carol should have done — champion the plan, get in the room, get the yes. And I want to ask: did you ever say those words to her? Not implied them. Said them.”

The silence sat for a moment.

“No,” Greg said. “I assumed she’d know.”

“The expectations that cause the most damage in working relationships aren’t the unreasonable ones. They’re the reasonable ones nobody ever named.”

The Mistake Greg Almost Made

“So I need to pause my expectations of her,” Greg said. “Give her more time. Back off.”

The coach shook his head. “I want to push back on that.”

Greg looked up.

“Pausing your expectations isn’t the answer. You had a clear picture of what you needed — schedule the meeting, walk in with her authority behind the plan, get the yes. That wasn’t an unreasonable ask. It was a completely reasonable one.” The coach paused. “The problem isn’t that you expected too much. The problem is that you expected without ever making the contract explicit.”

Greg sat back. “I should have told her exactly what I needed?”

“What do you think?”

“I mean — yes. Obviously.” He let out a short laugh. “But I guess I thought it was so obvious I didn’t have to.”

Greg was quiet for a moment.

“My expectations were all assumptions I never had any real dialogue with anyone about.”

The coach nodded slowly but said nothing.

What the Contract Actually Was

“So what do I do with this?” Greg asked. “The approval is still stuck. Carol still hasn’t moved it.”

“What would you actually want her to do?” the coach asked. “Name it precisely.”

Greg thought about it.

“Schedule the time with the executive team. Give me the platform to present it. And walk in behind me — not to carry my water, but to make clear she’s aligned.”

“Have you ever said that to her?”

“No.”

“Okay. So now you have the ask. What would it take to go have that conversation?”

Greg drummed his fingers on the table.

“I need to think about how I approach her. Carol’s not wired like me. I come in with the architecture, the details, the whole thing built. She’s more relational. She leads through influence.”

“So if you walked in and handed her the architecture and the details—”

“She’d feel like she was receiving an assignment,” Greg said. “Not a conversation.” He shook his head. “I’ve been packaging this wrong for the type of person she is.”

“What would the right package look like?”

“I’d need to start with her. What she’s carrying. How this fits into what she’s trying to do. Make her a partner in it — not just the delivery mechanism at the end.” He paused. “And then make the ask clearly. This is what I need from you. Can we agree on that?”

“That’s a different conversation than the ones you’ve been having,” the coach said.

“Yeah.” Greg sat with that. “I’ve been waiting on Carol to do something she never actually agreed to do.”

“Two people. Two assumptions. Zero conversation. Full friction.”

The Conversation He Should Have Had Months Ago

Greg had the conversation with Carol the following week.

He didn’t open with the plan. He opened with her.

“I want to make sure I understand where you are on this before I ask anything of you. What do you see? Where do you have reservations?”

Carol was quiet for a moment — surprised, maybe, that he was asking. Then she talked. She walked through her hesitations, the questions she hadn’t voiced, the parts of the plan she wasn’t sure she could defend in the room.

Greg listened. He answered what he could. He sat with what he couldn’t.

By the time the ask came — I need you to schedule the time with the executive team, walk in with me, and make clear you’re behind this — Carol didn’t look like someone receiving an assignment. She looked like someone completing a decision she’d already made alongside him.

“I can do that,” she said.

The executive team met the following Thursday. Greg presented. Carol sat at the table and didn’t hedge.

The reorganization was approved.

The business got the structural capacity it had needed for months. Not because Greg worked harder on the case. Because he finally said the words he should have said months earlier — and made it possible for Carol to say yes.

“He had built the entire contract in his head. Signed it himself. Carol had no idea it existed — until he finally said the words.”

Your Turn

Something to Ask Yourself

What expectation are you currently holding that the other person has never actually agreed to — because you’ve never said it in clear, specific terms? What has carrying that assumption already cost the relationship?

Sit with that before moving to the next question.

If you named the ask precisely — not “I need your support” but the exact action you need — what would change about how you approach the next conversation?

That second question tends to do more work than the first.

The Practice Challenge

Identify one relationship where an unspoken contract is generating friction. Before your next conversation with that person, write one sentence that names the specific ask — not a feeling, not a general need. One concrete, nameable action.

Then say it out loud to them. Not implied. Said.

The ROI

Leaders who name the ask clearly recover the time and energy spent managing friction that had no real source — just a gap between what they expected and what they ever communicated. Organizations move faster when the people doing the work know what success actually requires from each other.

About High Order Group

High Order Group works with senior leaders navigating complex organizations and high-stakes working relationships. We help leaders see what they’re carrying — including the contracts they’ve never made explicit — and build the clarity and relational skills that move people and business forward together. Learn more at highordergroup.com.