I’m not necessarily advocating that as general advice, but it is advice that I hear a lot. It came up yesterday in a conversation about asking a local grocery story to care a certain type of peppers.

Might as well ask, right? The worst that can happen is that they don’t carry the new peppers and everything is exactly as it is right now, which is not bad, just not as great as it would be if the store carried these amazing peppers.

Email is a perfect medium for this kind of advice, since email opens the door for anyone to ask anything.

I could ask Barack Obama to come on my podcast, but I probably won’t hear back or if I do, I’ll get a no. I could ask a Google high-up if they could bring back Google Reader, but I probably won’t heard back or if I do, I’ll get a no. But if I get a yes, wouldn’t that be amazing?

There are more realistic scenarios. I could ask someone in my field to help me with a problem I’m having. I could ask someone with more influence than me to help spread the word about my product. I could ask the bike shop for a discount. I could ask them if they want to go out with me. I could ask to have pizza for dinner.

Those seem more like tossups whether I’m going to get the answer I want, but hey, might as well try, right?

One way to characterize all this is how Andrea Donderi did:

This is a classic case of Ask Culture meets Guess Culture. In some families, you grow up with the expectation that it’s OK to ask for anything at all, but you gotta realize you might get no for an answer. This is Ask Culture.

In Guess Culture, you avoid putting a request into words unless you’re pretty sure the answer will be yes.

That “might as well ask” idea is Ask Culture. The opposite being someone who rarely asks for things (among other characterizations) which is Guess Culture. It feels right to me, similar to the distinction between introversion and extroversion. (I heard about all this from Rachel).

Me, I’m guess culture, apparently. I don’t often ask for anything, or if I do, it’s a result of heavy calculation on my part. Like I really need to ask because there is a lot of pressure on me to do so, or I feel like I’ve built up enough points that asking is just cashing in on those points.

Is that a weakness though? Shouldn’t I just ask more because who cares if they say no?

My brain won’t let me. I think it’s because when I’m the target of Ask Culture, it bugs the hell out of me. Take the classic (pre-pandemic) email: let’s just get together for a coffee and I’ll pick your brain. That’s Ask Culture. They might as well just ask, since the worst that happens is that I’ll just say no. But that’s not the worst that can happen. Chances are, now I think you’re obnoxious, needy, and selfish, and I don’t want to have anything to do with you. There were actual consequences, because you needed something and not only did you not get it right now, you’ll likely not ever get it from me, because it’s a burnt bridge. That culture might work for you sometimes, or might have worked great in your family dynamic, but I feel doesn’t translate particularly well to the business world.

I don’t mean don’t ask anything, I just mean be more empathetic in your asking and be aware of what the consequences might be.