Putting this list together was more of a struggle than I had anticipated. Before writing a book on being the first design hire at a startup (aka the First Designer In, or FDI for short), I hadn’t given much thought to how one would determine if they are a good fit for the job. It was more of a gut feeling. It’s sort of a layered conversation, starting with some obvious questions like:

If your answers aren’t ”yes, yes, no, no” then you’d likely suffer trying to do this job.

That’s an easy first screen. As an FDI, you won't get much design support so you need to be ok practicing your craft without direct mentorship or guidance. Simultaneously, you’ll be standing up an entire design function, which means lots of pressure. And you certainly won’t withstand that pressure if you have no desire to lead to begin with. These are the absolute basics.

The next layer of the conversation contains lots more nuance, though. Let’s take a look below, just keep in mind that there’s no single factor that would qualify (or disqualify) you from succeeding in the role of FDI—it’s more like a hand-wavy attempt at uncovering if you have the general orientation and desire needed to thrive.

According to Merriam-Webster, having wherewithal means having the necessary resources to achieve a certain outcome. As and FDI, the ultimate outcome you’re trying to achieve is a thriving design function. Here are three examples of internal resources you’ll need to tap in order to get there:

Real talk: doing a self assessment is really hard, but as long as you approach it with honesty then you should be in good shape. The book contains a link to a skills matrix that I find helpful, as well as pep talk about imposter syndrome.

It’s possible you've been called a powerhouse, inspiring, or an overachieving freight train at some point in your life. It’s also likely words like “authority” and “obedience” make you bristle. You’ve always been a self-learner and when you encounter a problem, you research it ad infinitum - books, forums, ask for help - until you feel capable of tackling it.

Careful though: being fiercely independent can sometimes come with a large-ish ego. To ever item mentioned above, there’s a counterpoint:

Everything is a puzzle. Solving puzzles requires a combination of a thrill for challenges, a desire to solve problems, and the ability to see patterns. If you experience sheer joy when these three things come together, then you could truly thrive as an FDI.

Here, try it on for size. How many of these statements sounds like you?

Sure, there will be plenty of mundane tasks that you’ll have to plod through (every job has them) but if you truly love puzzles, there will be plenty of those as well to keep you charged up.

Let me be pretty honest here: the more crazytime you’ve experienced before becoming and FDI, the better. If you’ve grown a few callouses, it’ll be easier to handle the insanity that comes with startup life. You should at least be able to agree with the following statements:

Or maybe that last one was just me?

We’ve only just scratched the surface here, but if you’re honestly considering the job and need a fuller picture of all that it entails, I suggest you read the book. After all, that is why I wrote it.