am I annoying my coworkers by asking for a ton of context on everything?

A reader writes:

I am three months in at my new company, and I’m the newest member of a team that only came into existence about nine months ago. There are tons of growing pains/opportunities/whatever you want to call them, but I’m really energized by the atmosphere and I’m generally thriving (as is the team).

I’m inquisitive by nature: I always want tons of context and I tend to ask a lot of questions that boil down to “but why is it this way?” Ths is innate in me, but I amplify it at work because at other jobs I’ve seen insufficient, untimely, or incomplete information torpedo a project or client engagement. Further, because we are a growing team making policy and procedural changes on the fly, I view my approach as essential to ensuring we are looking at a situation from all perspectives.

When I do press for additional context from a particular teammate, I’ve noticed that she will appear flustered or defensive, and I worry that she may feel that I’m challenging her in some way. I am decidedly against “power moves” and I’m sensitive to the scourge of mansplaining (or “man-questioning” in this case). More broadly, I don’t want to appear to my team/management like an annoying wrench-thrower standing in the way of progress.

Is there a way I can couch my questions so that my intentions are clear? Do I have a sit-down with the teammate I’m worried about offending?

I wrote back and asked, “Are you only doing this when you’re heavily involved with a project and really need the context, or are you also doing it more casually, when you don’t really need that context and are more just curious?”

It’s fair to say that this is my everyday default setting, but I amplify it in project meetings/communications so nothing slips through the cracks.

Hmmm. It’s possible for this tendency to be really irritating and to come across in ways you don’t intend — like as challenging a system that someone might not have time to fully explain to you, or as thinking you know better than others, or as focusing on the wrong things at the wrong time.

It’s not that there’s not value in understanding why things are a certain way. That can help you do a better job of your own work, and it can help you and others spot areas where things could be improved or problems warded off.

But just because there’s value in it, that doesn’t mean that you should do it whenever and wherever. There are going to be a lot of times when that’s simply not your job, or where it’s not the most important thing to be focused on at that moment. And if you seem oblivious to that — even though you mean well — you risk really alienating colleagues over time.

Now, if doing this is your job — like if you were brought in specifically to do efficiency analyses or something like that, and everyone knows that — that’s different. Even then, though, you wouldn’t just do it willy-nilly at meetings; there would be a time and a place for it, and you’d have a set of priorities that would govern where you’d focus first. (And in your case, it doesn’t sound like this is your specific job; it sounds like this is just your inclination.)

In general, you need to pick and choose. There are times when it does make sense to dig in and really ask questions and ensure you’re getting all the context (generally, with your own projects or projects where you’ll be playing a major role, or where you represent an important perspective that might be getting overlooked). But if you do it all the time, as your default setting, you’re going to exhaust people and come across as if you don’t understand who’s responsible for what (or as if you don’t respect the people who own the areas you’re questioning and questioning), or as if you don’t get what it makes sense to spend time on and when.

If I were in your shoes and questioning how this might be coming across — but not convinced it was a problematic behavior — I’d ask people straight-out. With the coworker who seems to be bristling when you question her, you could say something like, “Hey, I sometimes ask a lot of questions because I do better work if I understand the context for something and I like to look at a situation from all perspectives. But I don’t want to overstep, and I’m worried that I may have. Am I reading you correctly in situations like X and Y recently that it was too much?” You’re not looking for a yes/no here so much as you’re looking for a conversation — it’s giving her an opening to talk about how this is landing with her.

But no matter what she says, you really need to consider whether, in any given situation, it’s your job to look at the situation from all perspectives. For most people, it’s going to be their job sometimes and someone else’s job other times. When it’s someone else’s job, they might welcome input sometimes — but not every time. And they probably won’t welcome feeling like you are stepping in to do their thinking for them, especially when giving you the full context might take significant time that they don’t have.

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