390. The Most Annoying Employee I’ve Ever Had (why some people get promoted and others don’t)

Siri transcribes the words you say, while Wispr Flow learns how you think and what you mean, and that difference mirrors the difference between two kinds of employees.
Most employees operate like Siri: they follow your literal instructions, get it wrong, and force you to review and correct their work over and over.
Employees who act like Wispr learn how you think, remember your terms, and fill in the gaps, so you spend less time explaining.
You don’t promote people because they follow instructions well; you promote them because working with them makes your life easier.
The same dynamic applies to you: your boss, board, or biggest client is also giving you instructions, and those instructions are often incomplete.

Stop measuring employees by how precisely they execute your words and start noticing who understands your intent.
When you give an instruction and it comes back wrong, ask whether the employee lacked context or whether you never gave them the context they needed to learn you.
Invest in learning how your people think, what matters to them, and how they make decisions, because that investment is what turns a Siri into a Wispr.
When someone’s instructions to you are vague, try to understand what they mean instead of executing the literal words and then acting surprised.
Recognize that the people who get promoted are usually the ones who reduce your workload over time, not the ones who never need correction.

Think of the person on your team you trust most with complicated work: what do they understand about you that others don’t?
Pick one employee who keeps needing correction and ask yourself what context you could give them so they start learning how you think.