"Keep me in the loop" sounds like a pretty straightforward request. But what comes to mind when you hear it? Do you copy the person on emails, plan to update them at your next meeting, or check in before making a decision? I can see how any of those might make sense. I can also see how two people could leave that conversation feeling clear about what happens next, only to discover later that they had very different things in mind.
There are so many phrases like that at work. "Use your judgment." "Take initiative." "Get back to me as soon as possible." We use them because they feel familiar, and we usually have a pretty clear idea of what we mean. But our understanding comes from somewhere. It may reflect a previous job, a leader we learned from, or an experience that taught us to handle something a particular way. The person we're talking with has their own experiences informing what those same words mean to them.
Some recent research on AI had me considering this again. Researchers writing in The Leadership Quarterly found that supervisors tended to trust employees less when they used AI-generated work. In an experiment looking at company policy, that drop in trust was no longer statistically significant when the company encouraged AI use. It was still there when the company prohibited it or hadn't stated a policy at all. That last part caught my attention. Even without a stated policy, using the tool affected how employees were viewed.
There are plenty of worthwhile conversations to have about AI, including accuracy, confidentiality, and where our own judgment comes in. What interested me here was the possibility that a person could make a choice they understood to be acceptable and have it affect their supervisor's trust. For me, that brings up a question that reaches beyond technology: How often does an expectation feel so familiar to one person that it never occurs to them to explain it to someone else?
I think about something like taking initiative. In one workplace, that might mean recognizing a need and moving forward. In another, it might mean recognizing the same need and bringing a recommendation to your manager. There can be good reasons for either approach. Someone who has learned to be successful with one may need a conversation to understand the other, even when both managers use the same words. Until that conversation happens, what looks like hesitation to a manager may feel like good judgment to the employee.
That distinction matters when we talk about performance. Someone may be capable, thoughtful, and trying to do good work, and still miss an expectation they didn't realize was there. There may also be a real concern that needs attention. I don't think we can know which conversation we're having without making room for both possibilities. "Tell me how you understood what we were asking for" could help us learn something that we wouldn't hear if we began with a conclusion about their effort or ability.
There's also the difference between what the work needs and how a manager prefers to see it done. A report may need accurate information, a useful recommendation, and a Friday deadline. One manager may also prefer to talk through an outline before someone starts. That preference may help the work, or it may simply be how that manager is used to doing things. Either way, the other person needs to know. And if the work meets the need through a different approach, there's room to consider whether that difference matters as much as it first seemed.
Of course, clarity is a conversation, and everyone has a part in it. Questions help, examples help, and talking through what a good outcome looks like can uncover differences neither person knew were there. We won't anticipate every situation, and sometimes we'll discover the gap only after something doesn't go as expected. There can still be a useful place to begin: "I had something different in mind, but I'm realizing we may not have talked about that part." From there, we have an opportunity to understand each other and agree on what happens next.
As you think about the people you work with, consider an expectation that feels obvious to you. Maybe it's when to ask for help, what needs your approval, or how you like to receive updates. Where did your understanding of that expectation come from, and what might someone with a different experience understand instead? That could be a worthwhile conversation to have before either of you has a reason to be disappointed.