When Asking is Easy (and Answering Isn't)

14 Jan 2026 in Power Skills

It's 4pm on a Thursday, and I'm patting myself on the back that I've managed to align multiple teams on a tricky project. The requirements document has been reviewed and approved by everyone involved, and I'm excited to see what's been scoped come to life.

I'm about to sign off for the day when someone from our SaaS team pinged me: "Hey, quick question. What would it take to make this multi-tenant?". It's as though the walls come crashing down around me. It's not a quick question at all - it's one that takes deep technical, historical, and organizational knowledge to unpack.

I sigh as I make another cup of tea and settle in to write an essay of a response, trying to balance the need for details without it appearing as though I'm trying to overwhelm them with complex explanations.

Questions like this aren't malicious. They're often great questions, asked in good faith. But they reveal something important about effort - it's much easier to ask questions than to answer them.

Asymmetric Questions

An asymmetric question is one where the effort to ask is trivial compared to the effort to answer.

This asymmetry isn't inherently bad. I'd choose to work with a curious team over a disinterested team every time given a choice. But when left unchecked, these questions can lead to a high emotional load for those receiving them.

I've been the person receiving the questions, and my responses have ranged from "Why are they asking questions that they definitely won't understand the answer to?" (which was an unkind categorization on my behalf) to "This sucks. Weeks of alignment undone by a single question. Maybe I can pretend I didn't see it?" to "This is a good question. I should have covered this in the first place. It's going to take time, but it's worthwhile".

Lack of knowledge is often the driver of asymmetric questions. The person asking is often missing the context required to realize how much effort it will take to answer what appears to be a simple question.

In general, the more senior or cross-functional your audience, the higher the likelihood is of one of them asking an asymmetric question. This isn't malicious - their curiosity spans domains that they're not totally familiar with.

Asymmetric questions can be valuable, but they can also be distracting. If the system that the asker is operating in rewards visibility, you're going to get spontaneous questions that don't add much. They don't care as much about the answer as they do about being seen to contribute. Over time, this erodes focus and encourages reactive rather than strategic work.

Managing the Imbalance

Asymmetric questions aren't malicious. They're born from curiosity, but left unchecked they can command a lot of time. It takes 30 seconds to ask a question, and 30 minutes to answer it.

My rule of thumb for asymmetric questions is to spend twice as long answering a question as it took to ask it. If they spent a minute asking a question, I'll give it two minutes of thought then respond (usually to ask clarifying questions of my own). The asker's response might take 5 minutes to write, and so I'll take 10 minutes to respond.

If a question takes one minute to write and will take twenty minutes to respond to, schedule a call. That's a good sign that there's something missing from either the asker's knowledge, or from your proposal itself.

The goal isn't to stop people asking questions. It's to right-size your response.

The first step to navigating asymmetric questions successfully is to get past the resentment stage as quickly as possible. Even being aware of the knowledge asymmetry, I still have an initial burst of resentment every time someone asks "why don't we do X?".

The impact that their question has on the project, and on me as an individual, is huge. But I need to separate intent from impact. People don't generally ask asymmetric questions without a reason.

Once you're past the initial resentment, you can engage with the asker in good faith. Many people see a question and feel like they have to answer it immediately, and in depth. This usually isn't the case.

Exploring or Deciding

Questions on proposals are either exploring or deciding.

If someone is exploring an idea e.g. "Did we consider internationalizing the docs?" then you can respond with a similar level of depth. You could say "We did, but the return on investment for both time and cost wasn't there. I'm happy to dig in more if you like."

If the same question is phrased slightly differently, they're looking for a decision: "Why aren't we internationalizing the docs?". My personal instinct here is to write a 10 paragraph response in the comments section of a Google doc, but that's the wrong approach. Instead, propose a follow-up with the correct audience: "That's a good question. A full answer will take some time to put together. Can we chat next week with a few others that were involved in the decision?"

Clarify and Redirect

If the question is open-ended, don't try to answer every potential question. Here's one question that I had recently:

Why don't we provide a hosted version of {Dependency X}?

Instead of diving in, I asked a clarifying question to narrow the scope: "There a couple of reasons. Are you asking about technical, cost or market reasons?". The author came back with "market" and I explained that a hosted version would be well received by the market, but the technical implications (single tenant dependency) meant that the cost of providing a service (COGS) was too high for it to be a viable option for us.

Asking questions turns what sounds like a demand into a conversation. Either the asker wants to really dig in and you can have a fruitful conversation, or (as I've experienced many times) they just don't respond at all and you can forget about the question entirely.

Answer with Intention

Asymmetric questions are inevitable in collaborative work, especially as scope and seniority increases. By clarifying the questions and matching your effort to their intent you can keep projects moving without letting "one quick question" derail weeks of progress.