A content marketer sits down on Monday with a keyword tool open and a calendar to fill. The tool suggests "best invoicing software" for the fifth time, with a difficulty score that says don't bother. Meanwhile, on r/freelance, someone is asking how to bill a client who keeps changing the scope halfway through a project. Forty people have replied, and none of the answers link to a single article.
That thread is a better brief than anything in the keyword tool. It has the exact wording a real person used, the context around the problem, and a pile of replies showing what people already know and what they're still confused about.
I'm Julien, and I work on KWatch.io, a keyword monitoring tool for Reddit, Hacker News, X, Linkedin, Facebook, and Youtube. This post shows how to set up alerts that catch questions about your category as they're asked, and how to turn a week of those threads into a short list of posts worth writing.
Keyword tools are good at telling you what lots of people searched for last year. They're much weaker on the long, specific questions that only a few hundred people search for each month, because those phrases are too thin to show up with reliable volume.
Those long questions are often the ones that convert. Someone asking "how do I stop a client from adding work after we agreed on a price" has a real problem today, and an article that answers it well can rank for dozens of variations nobody bothered to put in a spreadsheet.
Reddit and Hacker News are where a lot of those questions get asked out loud. People write them the way they'd say them to a colleague, which is close to how they'd type them into Google or ask ChatGPT. The replies add something keyword tools never give you, which is the list of answers people have already tried and found lacking.
So the goal is to see those questions without scrolling subreddits every morning.
A question has two parts you can match on: a question phrase and a topic. KWatch lets you combine both in one alert. A comma between terms means all of them must appear, so how do you, invoice only matches content that contains both "how do you" and "invoice".
I'd start with three or four question phrases that people use when they're stuck:
how do you and how do i, for process questions.any recommendations and what do you use, for tool questions.is there a way to, for workaround questions, which often hint at a missing feature or a gap in the docs.Then pair each phrase with one or two topic words from your category. If you sell invoicing software for freelancers, that might be how do you, invoice, what do you use, invoicing, and is there a way to, late payment. Each pair is its own alert, so start with the two or three pairs closest to what your product does.
A few filters make these alerts much cleaner. Excluded keywords drop a post as soon as any one of them appears, so adding words like hiring, job, or [for hire] removes a lot of noise on freelance subreddits. Whole Words Only stops invoice from matching words that merely contain it. On Reddit, Included Subreddits limits an alert to a short list such as freelance, smallbusiness, Entrepreneur, which is useful when your topic word is common in unrelated places. These filters come with the Essential plan and above, and our post on reducing noise in keyword alerts covers them in more detail.
The two sites ask different kinds of questions, and they move at different speeds.
| Platform | Typical questions | How fast KWatch checks it | Free plan |
|---|---|---|---|
| Practical "how do I" and "what do you use" questions from operators, freelancers, and small teams | 10 minutes to 1 hour | 2 keyword alerts | |
| Hacker News | Technical "Ask HN" threads, architecture questions, and debates about tools | 1 second to 1 minute | 2 keyword alerts |
For most B2B products, Reddit gives you more questions and Hacker News gives you deeper ones. If your readers are developers, Hacker News comments are often where the best follow-up questions sit, three replies down from the original post. If they're marketers, founders, or freelancers, Reddit will carry most of the volume.
For content ideas, the slower Reddit refresh doesn't hurt. You're not trying to reply in the first five minutes. You're trying to make sure the question lands in your list before you plan next week.
The same setup works on X with posts and replies, but X alerts start on the Essential plan. In my experience, X questions tend to be shorter and get fewer detailed replies, so I'd add it once Reddit and Hacker News are working.
Once alerts are running, you need somewhere to keep them, because a good question is easy to lose in an inbox. On the free plan, each match arrives by email, and a simple email filter into a "content ideas" folder is enough for the first week.
When you want a proper backlog, send each match to a spreadsheet. API webhooks are on the Business plan, and each alert can post a small JSON payload to Zapier or n8n, which then adds a row. A match looks like this (example data):
{
"platform": "reddit",
"query": "Keywords: how do you, invoice",
"datetime": "12 Nov 26 14:05 UTC",
"link": "https://www.reddit.com/r/freelance/comments/...",
"author": "some_freelancer",
"content": "How do you invoice a client who keeps adding small requests after the project is signed off? I don't want to nickel and dime them but it's adding up.",
"sentiment": "negative"
}
I'd keep four columns from the payload (date, platform, link, and content) and add two of your own: a short topic label and a status. Our Zapier and n8n guide walks through the webhook setup.
The AI sentiment tag is a useful hint for sorting. A negative question usually means someone's frustrated with the current way of doing things, and frustrated readers are the ones who'll read a long guide to the end.
After a week or two, the sheet will have more questions than you can write about. The interesting part is grouping them.
Read through and give each question a short topic label. You'll usually find that a handful of labels hold most of the rows. When the same problem shows up five times in different words, across different subreddits, that's a post. When it shows up once, it's probably one person's odd situation.
Then open the best two or three threads for each group and read the replies. The top answers tell you what your article needs to cover at minimum. The replies that say "that doesn't work for me because..." tell you where you can add something new. I'd copy the original question wording into your brief, because it's often a better H2 than anything you'd write from scratch.
This also feeds AI search. Tools like ChatGPT and Perplexity pull a lot from Reddit threads, and an article that answers the exact question people ask there has a better chance of being cited. Our post on getting your product mentioned by ChatGPT, Claude, and Gemini goes into that side.
One caveat before you plan a quarter around this. Alerts tell you what people are asking. They don't tell you how many people search for it, so it's still worth running your best ideas through a keyword tool before you commit. A question that shows up ten times on Reddit and has some search volume is a strong pick. One with zero volume can still be worth writing if it's close to your product, but treat it as a bet.
You'll also only see platforms we monitor. Quora, Stack Overflow, Discord, and private communities aren't covered, so if your audience asks most of its questions in one of those places, you'll need to check them another way.
The quickest test takes five minutes. Create one Reddit alert with how do you plus your main topic word, and a Hacker News alert with the same pair. Let them run for a week and count how many questions you'd have written about.
KWatch's free plan includes 2 Reddit and 2 Hacker News keyword alerts with email notifications, which is enough for that first week. Create your free account and set up your first question alert.
Julien, Product Manager at KWatch.io