In most hiring processes, you’re lucky to get 45 minutes to chat with a candidate before having to make a thumbs-up or thumbs-down decision.
How do you use that precious time to get the most important information about the candidate?
For over a year now, I’ve been asking my illustrious podcast guests to share their favorite interview questions (nearly 150 guests now!), and the collection of questions that’s emerged is like nothing I’ve seen elsewhere. These are not just great questions—they are exceptionally good at pulling out the essential insights about the candidate in the least amount of time.
Below, I'll share some of my favorite high-signal-to-noise interview questions, including what to look for in a great answer, grouped by theme. To see the full list, don't miss today's newsletter post (link below).
How to learn the most about a candidate from a single interview question—High-signal-to-noise interview questions inspired by my 150+ podcast guests
Question 1: Talk me through your biggest product flop. What happened and what did you do about it?
“I look for people being brutally honest about how bad it was and why it failed. The rest of the interview, they’re trying to tell you all the wonderful things they did and all the accomplishments they had. And so I think the rawer the answer in terms of how bad it was and why, the better.”
—Annie Pearl, corporate vice president at @Microsoft, ex-CPO at @Calendly
Every startup can be distilled into a simple equation.
And until you can express yours as one, you don’t fully understand your business.
Having this equation gives you a map for understanding your biggest growth drivers, your key inputs and output, and once your teams are aligned behind it, and the equations operationalized, you’ll experience a huge force multiplier—because every team will be focusing their energy on the same (high-leverage) levers.
I teamed up with @danhockenmaier to collect the detailed equations for the eight most common tech business models:
Some of my biggest surprises when researching paths to PMF for top B2B companies:
1. If you build it, they *will* come—if you have strong product-market fit.
Though it often takes years to find initial PMF, once you do, a common pattern across top startups is strong (and explosive) organic growth—primarily seen as cold inbound and word-of-mouth growth.
This was true for Segment, Loom, Dropbox, Canva, Sprig, Stytch, and most others.
2. Stop thinking of product-market fit as a single moment.
It can be, but it almost always isn't.
Instead, think of finding PMF as an ongoing process of finding stronger fit with more and more segments of the market.
Though there will never be a foolproof formula for finding product-market fit, here’s my best attempt at creating a guide for B2B startups that'll save you much time and pain.
It's based on interviews and research into the PMF journeys of 25 top B2B startups.
Here's a peek:
Here's the full post: A guide for finding product-market fit in B2B
Inside: 1. A framework for finding PMF 2. Signs that you’re approaching PMF 3. What to do if you aren’t
A few of my favorite stories of how founders validated their startup ideas:
1. After 6 ideas that didn't work out, Rujul Zaparde (@rujulz) and Lu Cheng created a 16-point checklist for what a great startup idea needs to hit.
"We were very honest with ourselves. We worked on a bunch of terrible ideas before, and if there’s anything we had learned, it’s that today will be the easiest day to kill the idea and do something better. It’ll always be harder tomorrow. ...
"We did 75+ interviews with CFOs, heads of procurement, and heads of finance. It really helped refine the idea. We had 110 pages of notes from 3 weeks of chats. Turns out the response rate is pretty good on LinkedIn when you just want advice."
@christinacaci manually created compliance reports for a few companies and noticed (surprisingly) that they all found them very valuable. She then built @TrustVanta (last valued at $1.6B):
2. The listening path: Talk to tons of potential users first, looking for signs of pull and pain—then start building
The founders of @TheZipHQ (last valued at over $1.5B) spoke with 75 potential users before committing to their idea: