Some notes on hiring

I recently listened to a great interiew with CEO Coach Matt Mochary.

I'm not entirely sure what a CEO Coach is/does, beyond what the title conveys. But if you're involved with recruiting in your company, it's worth your time. It's a very wide-ranging interview, but for the recruiting stuff, I'd start at 42:00 and listen for 20 mins or so.

There's a couple of nice, pragmatic things in there that you could use in your own practice. But there's one key takeaway for me: listen to your gut.

The logistical part of reducing the opening call from 45 mins down to 15 mins is something I may try. Looking back through my review notes, I can't find a single person who I couldn't get a read on almost immediately. Not one! That makes a pretty compelling case for the extendable 15 min introduction interview. Mochary's right, at least for me: you can feel it almost right away.

Beyond logistics, here's some techniques and questions I've found helpful over the years:


Ask candidates to use "I" not "we". The path your previous company was on is basically irrelevant to our conversation. How you achieved product-market fit. How you were solving this set of problems with this set of solutions. Etc. All irrelevant. What you worked on though? That's extremely relevant.

Tell me all about the exact features you worked on. Tell me about how you saved people time and money from the things you implemented. Show me what you did and are passionate about. Send me the links to the pages. Show me the search interface you built, the landing page you sweated over. Show me the animations you built. Show me the thoughtfully crafted api routes. When you ask people to start with "I", it really helps.


Are they up to date? In the frontend world, where stuff changes so, so fast, it's important to see if your candidates keep up. I've found this dead simple to get a handle on. I simply ask: "You're starting a new side project tonight — what stack are you using?"

This is deceptively simple. It tells me so much, really quickly. Are they committed to one framework, or do they like to dabble? It gives me a good sense of what "shape" the person is — ideally, a nice "T" shape with broad general skills and depth in 1-2 areas. Sometimes, you'll reveal an "I" person: someone with a lot of depth (which can be great). Or a flat, "hyphen" person who's just dabbling in lots of areas without focus. This question also gives you a good sense of motivation.


Where are they in the stack? Another question that I get a lot of mileage out of: "Where do you see yourself in the stack". I've met very, very few people over the years who are truly good across the entire stack. All the way from design to the api layer. I can definitely count them on one hand. So I'm always using this question to see where they are. This is the one question I press the hardest on and the one I come back to most often. If I'm not satisfied with how well I think I've placed them on the spectrum, I'll keep asking.

One handy thing I try is to press just beyond where they say they are. For example, if they say they've done some backend, I'll really dig into that and see what they've done. I'll start with something that's almost certainly too far out and work my way back. "Have you built an api from scratch", is a great way to get a sense of how far back someone has gone. Open-ended, leading questions like this tend to tell me a lot.


Don't give up Perhaps the most important thing I've learned from these interviews is to not give up. If you're not getting answers that make you feel 100% confident in your decision, keep asking. I'll circle back a couple of times to key questions and keep poking and re-wording. A couple of times, I've also had moments of additional candour. I feel totally comfortable now saying something like: "I don't feel like I've got a good sense of your skills with x". This tends to snap focus into the conversation in a very useful way. It can be a little awkward, but definitely not as bad as leaving the interview without a strong feeling of giving the candidate a yay or nay.

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