Dumb Sales Questions
Your reps are losing deals over stuff the rest of your team already knows. Here's how you fix that.
If you’re trying to raise win rates or shorten sales cycles (who isn’t?), here’s a sneaky-effective thing you should try:
Start a #dumbsalesquestions channel in Slack.
What’s a #dumbsalesquestions channel? And why do you need one?
Let’s answer the second question first, with a bit of a hypothetical: Has something like this ever happened inside your company?
An AE is on a call when the prospect asks whether your product integrates with some obscure-but-business-critical system they can’t live without.
The rep isn’t sure, so they say they’ll follow up after the call. Then the call ends, and they realize they don’t know who to ask.
They’re a little embarrassed that they don’t know the answer. They’re also reluctant to bother the one person they know on the already-busy product team with a somewhat intimidating technical question.
So they ask around. They misfire with a few people. Those people refer them to a few other people. Eventually, after working up the courage to message someone in a different office and a different time zone, they find the person who knows.
By the time the answer gets back to the prospect, a week has passed.
What just happened here? Well, you just burned seven days answering a question someone else inside your company could have answered in 30 seconds.
The obvious problem here is speed. You added a week to your sales cycle for no good reason.
But the bigger problem is that the answer was sitting somewhere inside your company the entire time. Your AE just didn’t know who to ask (and didn’t want to look dumb asking the wrong person).
Look, there is always going to be a gap between what your company knows in aggregate and what any individual salesperson knows in isolation. You’re never going to eliminate the gap. But you do need to think about how you’re going to minimize it.
The way you minimize it is not to train every salesperson to know everything there is to know about what you sell and how it works and how to sell it. (That is impossible, especially if you sell multiple complicated products.)
The way you minimize the gap is to make the company’s collective knowledge easier to tap into.
That is what a #dumbsalesquestions channel does.
It gives your sellers (and everyone else) a dedicated place to ask the slightly-vulnerable-but-commercially-important questions that come up during winnable deals.
Questions about pricing. Integrations. Technical details. Partner relationships. Product terminology. Lead follow-up. Competitors. Roadmap items. Process. How things actually work.
All those questions now go in #dumbsalesquestions.
It is a low-tech way to reduce the two kinds of friction dragging your win-rates below where they should be.
The first friction is practical:
I don’t know who has the answer.
The second friction is social:
I don’t want to look dumb for asking.
Putting the right people in a dedicated channel helps you solve the first problem. How you introduce, frame, and operate the channel determines whether you solve the second.
Keep reading for the complete how-to guide.
How To Implement Your Own #dumbsalesquestions Channel
1. Create the channel
#dumbsalesquestions is a dedicated channel where anyone (sales, marketing, product, customer success, support, etc.) posts the stuff they do not know or cannot answer with confidence.
No question is too small. No one is going to make fun of you or judge you for not already knowing the answer.
That is the whole point.
Note: Do not change the name. The name is already perfect. Calling it #dumbsalesquestions sends an important signal and gives people permission to ask before they hesitate and before they wonder whether their question is going to make them look dumb.
The questions are supposed to be dumb. That’s the whole point.
2. Invite the right people.
The knowledge you need to advance and close complex deals is spread unevenly across your company. The person who knows the honest answer on the integration question your customer just asked probably sits in product. The person who knows why you lost the last three deals to a competitor sits in marketing. Your engineering leader knows what’s on the roadmap, what isn’t, and what feature they’re considering adding next. Invite all those people into the channel. You’re doing two things at once here. You’re making that valuable-but-scattered knowledge reachable, and you’re giving your most helpful people on your team a place to be helpful.
A few more worth pulling in: customer success knows how people actually use what you sold them, implementation and support know where things tend to break, and finance knows which pricing structures you can really stand behind. You don’t need the whole company, just enough coverage that almost any question reaches someone who can answer it or point the asker to whoever can.
3. Frame things in a launch post.
This might be the most important step. It’s how you set the tone.
Once you set up the channel, you have to explicitly declare why you’re doing this and what this channel is for. This is what HBS professor Amy Edmondson (famous for her research on psychological safety) calls framing. Framing is a leadership technique you use to set up your work so people know what’s expected of them. Amy’s research uncovered that people in work settings speak up more (and perform better) when their work is framed as a learning problem instead of an execution problem.
Frame your work as execution-focused and every question sounds like an admission you can’t do that part of your job. Frame it as learning-focused and the same question turns into an opportunity to surface something that’s holding you back and improve your performance.
The key here is to explicitly frame what the channel is for with a “launch post” right when you set it up.
Say why you’re starting the thread, say explicitly that not knowing something (and needing to ask for help) is normal, and then (the part that matters) ask the first dumb question yourself. If the most senior person in the channel models it, everyone else will follow. If the most senior person only ever answers and never asks, the thread never unlocks its true power (because people are still a little unsure re: whether it’s safe to ask their question or not).
4. Praise people when they use it.
The first couple of weeks in #dumbsalesquestions are always a little slow. People are waiting to see what happens to the first couple people who stick their necks out and ask a real question. So when someone posts, thank them in the open, and mean it. You’re not being nice. You’re showing everyone watching that the person who asked (a) got help and (b) didn’t suffer any consequences. That makes it easier for everyone else to ask about what they don’t know without hesitation.
5. Remind people it’s there.
Like anything else, you have to remind people that the #dumbsalesquestions channel exists. Bring it up in your sales meeting. Drop a question in yourself every week or two. Point new hires at it on day one. A channel nobody remembers might as well not exist.
6. Turn good answers into reusable answers.
Slack is great at getting you a quick answer. It’s terrible at making that answer reference-able later on. A great reply to a common question scrolls out of sight in a day and gets asked again six weeks later. So when you know a question/answer deserves to be memorialized, move it somewhere permanent (e.g., your sales wiki, a battlecard, the integration list, the pricing guide, onboarding docs ) and drop the link back in the thread.
7. Mine the channel for ideas.
Every month or quarter, depending on traffic, pull the whole thread and run it through AI. Ask it to spot patterns and suggest process improvements you can formalize. What comes out: proposal templates, a formalized integration list, sales training topics, and marketing angles you would have never thought of otherwise. The questions your team is asking is the best hint you can get about how to grow faster.
Final Thoughts
Winning teams share a unique quality: their people are quick to admit what they don’t know, and quicker to help each other fill those gaps. You can’t buy that quality, and you can’t order people to have it. But you can help create it—and a #dumbsalesquestions channel is a sneaky-good way to get started.
For that to work, people have to feel safe. That’s the real magic underneath all of this: psychological safety. When Google went looking for what separated its best teams from the rest in Project Aristotle, psychological safety emerged as the strongest predictor, well ahead of who was on the team or even how smart they were. Psychological safety helps teams not only get their work done faster, but improve what they’re doing as they go. It’s the secret ingredient to higher performance.
I’ve written before about how our brains process uncertainty in much the same way they process physical pain. It’s why a buyer who doesn’t feel certain about a purchase will kick the tires for months and then vanish into “no decision.” That same wiring is running inside your team. Asking a dumb question in front of your peers is a status risk, and your brain treats an uncertain risk to your standing a lot like it treats a physical one. “Are you sure you want to do that?” it asks.
That matters because an unanswered question doesn’t stay in Slack. It follows the rep into the next sales call. When that thing they should have asked about comes back their way in the real world, they hedge, avoid the subject, or promise to follow up later because they still aren’t sure. The buyer may not know exactly what’s wrong, but they can feel the uncertainty. It’s contagious. And unless you give that seller a place to ask those kinds of questions, that uncertainty will infect your future pipeline for as long as you let it.
So yes, go start a #dumbsaleschannel. But you can’t just announce that the channel is safe. You have to prove it. Answer questions without judgment. Thank people for asking them. Have leaders ask the questions first.
Do that consistently, and you turn the things people are embarrassed to ask into a running record of where the company needs to get clearer, and a practical way to help everyone get better at their job.
I prefer “#difficultquestions” but we do the same thing. Key is making sure there is a clear customer ready answer that you say verbatim if it came down to it. Another banger.