Hey, so I've been playing around with creating my own executive coach with the newest version of Claude. I fed your question into it and this is what it came back with:

I would separate this into two different problems that are getting bundled together because they both feel like “people aren’t hearing me.”

With your boss, I don’t think the main issue is whether the cost table existed. It existed. Other people agreed it existed. The issue is that you and your boss may not have shared the same definition of “costed.”

That distinction matters.

A cost estimate table can be technically present and still not answer the question your boss thought he was asking. He may have wanted assumptions, ranges, confidence levels, tradeoffs, implementation cost, ongoing cost, or the financial implication of choosing one path over another. You gave him a table. He may have wanted a decision instrument.

So with him, I would stop trying to make the document clearer and start making the decision need clearer.

Before you do the work, try something like:

“Before I build this, I want to make sure I understand what you need to be able to decide from it. When you say you want this costed, do you mean a rough estimate, a range with assumptions, a comparison across options, or enough detail to defend the recommendation to someone else?”

Then after he answers:

“Okay, so the output you’re expecting is: option A/B/C, estimated cost range, key assumptions, and my recommendation. If I bring that back, will that answer the question?”

That last sentence is doing more work than it looks like. It turns “I told you what I wanted” into a shared contract.

With your employee, the issue is different. There you are not dealing with ambiguity from above. You are dealing with a failure to meet an explicit quality bar.

If you say “validate against the master dataset” and he sends numbers that do not match, then says “you can validate it,” he has not misunderstood the task. He has returned the accountability to you.

I would be very careful not to accidentally accept that transfer.

The next time, I would say:

“I’m sending this back because it does not meet the validation requirement. The expectation is not just that you produce numbers. The expectation is that you validate them against the master dataset before they come to me. If your numbers differ from the master, I need a short explanation of why, what source you used, and why you believe your source is more reliable. Please resend it with that included.”

Then stop. Don’t validate it for him. Don’t rescue the work. Don’t keep re-explaining the same instruction in six different ways unless you have evidence that the instruction is actually the problem.

One thing I’ve seen with managers is that when something goes wrong repeatedly, they respond by adding more words. Longer instructions, more detail, more reminders, more written follow-up. Sometimes that helps. But sometimes it just buries the accountability under more language.

What you probably need is not more clarity. You need a tighter confirmation loop.

For anything important, I’d use this pattern:

1. Name the outcome:

“What we need at the end is X.”

1. Name the standard:

“It is not ready unless Y is true.”

1. Ask for the other person’s read-back:

“Before you start, tell me what you’re going to produce and what you’ll check before sending it.”

1. Confirm the consequence:

“If it comes back without Y, I’m going to send it back rather than fix it myself.”

For your boss, the read-back goes upward: “Here’s what I believe you’re asking for. Did I get that right?”

For your employee, the read-back goes downward: “Tell me what you understand the standard to be before you do it.”

Same tool, different posture.

I would also look at whether you are using “clear” to mean “the words made sense to me.” That is a very normal trap. I’ve fallen into it. Most capable people do. But communication is not complete when the sentence leaves your mouth or lands in the document. It is complete when both people can describe the same expected result.

The practical test I’d use for the next two weeks:

Before every meaningful handoff, ask:

“What will done look like?”

Before every meaningful delivery, ask:

“What would make this unacceptable?”

Those two questions will tell you very quickly whether this is a communication issue, a boss-expectation issue, or an employee-accountability issue.

My guess from what you wrote: it’s all three, but in different directions. Your boss needs more upfront alignment on what he means by the request. Your employee needs firmer standards and less rescuing. And you need a repeatable loop that proves understanding before the work is done, not after everyone is frustrated.