Why does this happen?
The brief had two reasonable readings and the teammate picked the wrong one. A pronoun pointed at something different in their view of the conversation, or they optimized for the method instead of the goal.
How do I avoid this next time?
Lead with the outcome in plain language ("I want investors to understand and fund this round") before listing a tactic ("write a five-slide deck"). You can revise the outcome or its success criteria with Tycoon Agent at any time, and she will refine the success criteria as reality changes. A comment or new fact that reveals the old target is incomplete is always welcome — Tycoon Agent can safely adjust it when the outcome and authority are preserved.
If the answer itself was wrong rather than off-target, see AI gave a wrong answer; if work stopped partway, see AI stopped mid-task.