I recently landed a contract role, so I’m out of the interview cycle for now. Sadly, I know plenty of good people still slogging through the job hunt drudgery. The market is rough right now.

I was fortunate to work with an interview coach a year ago. He suggested two questions to ask the interviewer, and they really improved my interview game.

1. Who should NOT work here?

2. What’s not in the job description, but you secretly hope I have?

Both go after the same thing, which is what nobody puts in writing.

The first question pokes at the Achilles heel. You’re asking them to describe a bad fit, and people are surprisingly candid about it. One hiring manager told me the wrong person was “an introvert who isn’t willing to work with others and only wants to read the documentation for answers.” That told me plenty about how much importance they placed on collaboration and how they work together day to day.

Another company’s answer might have described me exactly. If that ever happens, it’s a sign to walk away.

The second question is the leg up. They just gave you a wish they assumed couldn’t be granted. If you match it, tell that story right then. You’ve answered a requirement your competition doesn’t know exists.

That’s a tie breaker, and you usually need one.

Both questions also changed the room. Interviews run on a script and both sides know it. Ask something off-script and they sit up. They have to actually think. I watched the energy shift in real time. Answers got longer and more honest.

For a few minutes, they’re the ones being interviewed. People remember the conversation that made them think.

If you’re still in the cycle, steal these. They cost nothing and they change how it goes.

In 2008, at the end of a team retro, I handed out 3×5 cards and asked each person for at least one good thing and one bad thing about me. Honestly. Brutally. They looked at me funny. Then they asked for more cards.

34 comments came back. The most common:

Good

• You don’t inflict change.
• You hear our concerns and adapt. You don’t force us to do it by the book.
• You explained the philosophy instead of telling us to just do it.

Bad

• You talk too fast and cram in too much.
• You sometimes try so hard to help that you step on people’s toes.

I wrote it all down and challenged others to try it themselves.

Almost 20 years later and I recently stumbled across my writings when looking for something else. All 5 are still true. The positives held. As do the negatives. I still talk too fast, and I still sometimes step in and act when I should have more patience with the people I’m trying to help.

Those years of experience did not fix them. It taught me to notice them faster, sometimes mid-sentence. That’s progress.

The lesson I took in 2008 was that it takes guts to ask. But the durable part is that a handful of colleagues, in 90 seconds each, gave me something to stay mindful of. Honest feedback from people who work next to you every day has a shelf life you would not believe.

“No matter the circumstances you can always improve. You can always start improving with yourself. You can always start improving today.” – Kent Beck

I’m glad past me wrote it down where present me would trip over it.

Sometimes I find people get really hung up on sprint boundaries and the intense focus to start and end things within a sprint. They want everything committed to at the beginning to be nicely completed at the end.

Academically this makes sense, but reality is different.

What happens when I finish all my work 2 days before the sprint ends? Do I fill the other 2 days with code reviews and tech debt work? Do I just wander off and take paid leave? (the answer is no)

I prefer to describe sprint boundaries as “mile markers along the side of the road.” You don’t stop and get gas at a mile marker, you get gas when you need gas, and when there’s a gas station available. But the mile markers are a scale you can measure progress against, and without measuring distance, there is no concept of pace or progress.

Instead, think about pipeline flow. If you need work, you pull from the backlog. Refinement should be continuously creating ready work, and the team should keep pulling it in.

Sprint boundaries are a moment to measure and reflect. Keep driving past them.