The "what did you do last week" interview: 10 questions that find real problems

Ask someone "What's your biggest problem?" and you'll get a shrug, or the thing that annoyed them this morning. People are too close to their own work to see it.

Ask them what they did last week, and you get facts. The problems show up on their own.

How to run it

Sit with one person for 20 to 30 minutes. Do this with the people who do the work, not just the owner. Do it one at a time, so nobody is performing for their coworkers.

Have their calendar, inbox, or phone nearby if they're willing. Looking at last week's actual messages beats remembering. When someone says "I handle the orders," say "Show me last Tuesday's."

Don't offer fixes while you're asking. The moment you say "oh, we could automate that," they start defending the current way. Just ask, and write down what you hear.

And follow every answer with two small questions: "How long does that take?" and "How often?" Those two turn a complaint into a number.

The ten questions

1. Walk me through last Tuesday, from when you got in. Pick any normal day. You'll hear the real order of things, including steps nobody put on a job description.

2. What did you do last week that you did more than twice? Repeated work is what's worth fixing. Once is a task. Three times is a pattern.

3. What did you do that you wish you hadn't had to? This catches the annoying work, such as chasing people for information or fixing mistakes someone else made.

4. Where did you copy something from one place to another? Copy and paste is the most reliable clue in the whole interview. If information is typed into one system, then typed again into a second, there's almost always a fix.

5. What did you have to look up, or go ask someone for? Every time someone interrupts a coworker for an answer, that answer should live somewhere findable.

6. What did a customer ask you more than once? Repeated questions can often be answered ahead of time. See answer the same ten questions faster.

7. What fell through the cracks, or almost did? Missed callbacks, forgotten orders, an invoice sent late. These cost money and are embarrassing, so people only mention them if you ask directly. Ask in a friendly tone. Nobody's in trouble.

8. What does only one person here know how to do? That's a risk. If that person is out sick or quits, the work stops. It's also a good candidate for being written down.

9. What did you put off this week, and why? Things people avoid are usually tedious, confusing, or scary. All three are worth knowing about.

10. If one annoying thing disappeared tomorrow, which would you pick? Save this for last. By now they've named several, and they'll pick the one that matters most to them.

What to do with the answers

Right after each interview, while it's fresh, write the problems as plain sentences. "Rosa retypes every order from the email into the notebook, about 20 a week, 10 minutes each." Keep the person's name and the numbers.

After three or four interviews, you'll see the same things come up. When two people who don't talk to each other name the same problem, that's one to take seriously.

Then rank them. Don't skip ahead to building.

Mistakes to avoid

• Interviewing only managers. They describe how things are supposed to work.
• Asking "what would you automate?" Most people don't know what can be automated, so you get either nothing or a wish for a robot.
• Writing down solutions as you go. Notes should say what's wrong, not how to fix it. You'll have a better idea after you've heard four people.
• Skipping the numbers. "It takes a long time" can't be ranked. "It takes 45 minutes every Friday" can.

You can print the discovery question list and bring it with you.