This is the blog of Adam Kalsey. Unusual depth and complexity. Rich, full body with a hint of nutty earthiness.

Product Management

Ask One Question To Help You Reach Product-Market Fit

Everyone wants product-market fit, that magical state when the market you’re selling to wants the product you make. But how do you measure it? How do you know that you’re on the right track? How do you know what you should be doing next to advance toward product-market fit?

There’s a single question you can use to identify what your customers want from you.

Peg shape puzzle

"What problems would we need to solve for you to double what you pay us?"

There’s a lot to unpack in that question.

The way to get more of a customer’s money is to bring more value to the customer. This question identifies what form that value might take. You’re also asking for a giant step up in value. You’re not asking how to get a little more money, you’re asking how to double it. You’re asking for moonshots, not incremental improvements.

When asked this, most people won’t have a good answer right away. They’ll draw a mental blank. They might be shocked that you’re trying to charge more. When you encounter resistance, you can overcome this anxiety by prompting them. Are there times where they’ve wanted to use you for something but were blocked in some way? Are there more people in the company that could use your product, and what’s preventing that? Do they buy other products to enhance your product or fill a gap in yours?

Most of the answers you end up with will fall into three buckets. Doubling how much of the product they use. Doubling the price they pay today. Or doubling how many different products they buy from you.

The customer might think about how to double how much of your product they use and pay for. They’ll think about how much they buy measured in licenses, seats, usage, or however you sell your product.

When answered in this way, the customer is telling you what’s missing in your product that would help them increase how much they use it. They could tell you that they’d love to give all their employees access to your product, but it’s too expensive to do that. You might use this information to explore volume discounts or site licenses. They might tell you that you’re being used by one department right now, but there’s a key feature that would make the product attractive to a different department.

Or the customer might think of doubling what they pay you by considering how you could double the price. The same amount of usage, a whole lot more valuable.

Customers that answer this way are thinking about how they could use your product to make more money or save more money. They’re paying you for customer support software that lets them track and answer email and phone inquiries, but they’re also buying social media management software so they can respond to customer requests over Twitter and Facebook. They’re paying for a tool that syncs customer issues with their CRM so account managers can know their customers better. If you could do those things in your product they could consolidate their vendors.

The answer might also reveal extra products you could offer. Customers love how you automate their customer support email; could you offer a product aimed at salespeople?

In all cases, the customer is telling you what adjacent problems you need to solve to become twice as valuable to them. This question gets them thinking about how to expand your solution to cover the additional problems they have. Those problems will almost always be related to the ones you’re already solving for them, or will be the same problems but applied to a different market. Either way, you’ll learn valuable information about how to improve the product or more precisely target the right market.

Recently Written

AI as Your Strategic Thinking Partner
Oct 12: AI becomes a lens on your own logic. It doesn’t replace your judgment—it sharpens it. By asking questions you wouldn’t think to ask yourself, it turns private reasoning into something visible and testable.
Your OKR Cascade is Breaking Your Strategy
Aug 1: Most companies cascade OKRs down their org chart thinking it creates alignment. Instead, it fragments strategy and marginalizes supporting teams. Here's what works better than the waterfall approach.
Your Prioritization Problem Is a Strategy Problem
Jul 23: Most teams struggle with prioritization because they're trying to optimize for everything at once. The real problem isn't having too many options—it's not having a clear strategy to choose between them. Without strategy, every decision feels equally important. With strategy, most decisions become obvious.
Behind schedule
Jul 21: Your team is 6 weeks late and still missing features. The solution isn't working harder—it's accepting that your deadlines were fake all along. Ship what you have. Cut ruthlessly. Stop letting "one more day" turn into one more month.
VC’s Future Lies In Building Winners
Jun 21: AI and megafunds are about to kill the traditional venture model, forcing smaller VCs to stop hunting for hidden gems and start rolling up their sleeves to fix broken companies instead.
Should individual people have OKRs?
May 14: A good OKR describes and measures an outcome, but it can be challenging to create an outcome-focused OKR for an individual.
10 OKR traps and how to avoid them
May 8: I’ve helped lots of teams implement OKRs or fix a broken OKR process. Here are the 10 most common problems I see, and what to do instead.
AI is Smart, But Wisdom Requires Judgement
May 3: AI can process data at lightning speed, but wisdom comes from human judgment—picking the best imperfect option when facts alone don’t point the way.

Older...

What I'm Reading