You would spend maybe Monday to Thursday and you would actually go into the building where the customer worked and you would work alongside them. You would literally get a desk there.
Live in your customer's world, not your conference room
Discovery → Customer Interviews
If you truly, truly want to solve a problem, get out of your building, get out of the assumptions, get out of your opinions. Immerse yourself, find someone who has the problem, stick with them until you discover a solution for this problem.
You had to be willing to just jump on a plane that night if that's the best thing to do for this customer and if it's going to get us to where it needs to be to win.
The best way for you to figure out what is the intensity of the problem is not to ask them but to watch them or to watch them solve the thing that they do.
When you take a new role, become best friends with a researcher, and spend time watching customers use the product firsthand because what they maybe report on or are trying to do a study about might be very different from what you observe.
You can't empathize with the summary. You have to be in the room fully immersed, no phones, just actually hearing the words and the intonation. That's how you're going to get the full color.
At Vercel we have one of our internal operating principles as increasing exposure hours. Try to quantify how much time you expose yourself to watching how people use your products, even to watch how people use other products, and you'll develop that muscle.
The main thing is the whole company has to be with the customers or talk to them and then understand where the product might work well or where it might fall short.