You’re reading an excerpt of Land Your Dream Design Job, a book by Dan Shilov. Filled with hard-won, personal insights, it is a comprehensive guide to landing a product design role in a startup, agency, or tech company, and covers the entire design interview process from beginning to end, for experienced and aspriring designers. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, commentary and future updates, and a high-quality PDF download.

Interviewing People Who Left

Now of course, current company employees will be biased in favor of the company. It’s rare that someone will tell you that the org isn’t in good shape or that the work environment is stressful. So it helps to get a second opinion. Talk to a former designer if there was one. Sometimes interviewing the people who just left will give you an unbiased view of the workplace you’re about to join.

story When I was getting background info on one of my managers, I looked at his connections on LinkedIn. One of those connections—let’s call him David—worked with my manager a few jobs ago. Coincidentally, David also worked closely with a CEO of another company that I interviewed with. Small world!

Questions You Should Consider Asking

As you’re reaching out to folks and setting up coffee chats, it helps to have a strong question list ready that gets to the heart of the matter. Just like interviewing users, you don’t want to ask leading questions but instead get at the truth by asking about existing behaviors.

I recommend you get a clear signal on the work, work-life balance, the design team, the company’s design maturity, and—if it’s a startup—how much runway they have left.

The Work

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