Are You Ready to Be the First Designer In?

Are You Ready to Be the First Designer In?

Starting a UX design team from scratch is challenging, exhilarating and, frankly, not for everyone. I've compiled some information that will help you decide if you're ready to take on the challenge.

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:

  • Do you have enough experience to work solo?

  • Do you want to work solo?

  • Are you opposed to someday leading a team?

  • Are you easily pressured into submission?

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:

  • stamina — you've got at least a two-year energy runway so that you don't burn out before completing the job.

  • self awareness — you're able to honestly evaluate your skills, and skill gaps. Careful: being over critical can be as unrealistic as being overindulgent.

  • inner fortitude — you're ok with your mantra being "it's my job to be wrong" and you can make others see the wisdom in that statement.

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.

Fiercely Independent

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:

  • Being a powerhouse doesn’t mean plowing forward at all costs. You need to be a thoughtful powerhouse. The keyword is confidence, not arrogance.

  • Disliking authority doesn’t mean you are the authority. You, and everyone around you, must be inspired to act.

  • Being a self-learner doesn’t mean being a lone wolf. You’ll only succeed by building collaborative relationships.

Puzzles are AMAZING

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?

  • You get a secret high off of figuring out organizational issues.

  • You inwardly grin at the challenge of figuring out who actually owns engineering’s time.

  • You slip into the zone when sorting through loads of data looking for a thread that might just show you a way forward.

  • You nerd out over tasks like figuring out documentation systems.

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.

You’ve Seen Things

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:

  • You’ve experience both good and bad leadership so you know how you want to lead.

  • You're not starstruck by founders or execs, and you’ve got a sense of how to manage them.

  • You're able to spot toxicity, and are willing to get help when dealing with it.

  • You’ve been in a company where the HR department was fired and replaced with a 4 foot inflatable kangaroo wearing a post-it on its chest reading “HR”.

Or maybe that last one was just me?

Need More Help?

For Founders & Investors

Companies getting ready to hire first FDI, or with a designer already on board who could use an assist, I can work with you on getting your company set up for success. You can schedule anything from a single AMA call to recurring monthly help. Check out the options to work with me here.

For Designers

I am available on ADPlist for free mentoring (for designers only). Also, if you haven’t bought the book yet, it’s a great low-cost option to get a ton of info and supplemental swipe files.