Disappointed man with many moving boxes sitting outside of a tent that’s too small.
You’re probably bringing more to the table than can fit in the…pup tent.

Ready to bring your UX expertise to a startup?

Ten tips from a startup-UX veteran.

Startup job searches are special. You’re going to find a lot of job descriptions that seem boilerplate, many that are looking for purple squirrels (“you must have 15 years of UX experience AND be an ace front-end coder!”). In your interviews, you’ll talk to some founders who spend the whole hour selling you on how cool their product is, and others who come on strong with all the answers about how UX should be done in their company.

Play your “I bring significant UX expertise and you need to listen to me” card early, even during the interview process. This means balancing your own hopeful, please-pick-me emotions (natural in any job search) with your more powerful, I-know-what-I’m-doing confidence.

Before you interview:

1. Assemble a Squad

A squad is a set of personal advisors who are willing to talk about sensitive topics (like specific dollar amounts, titles, etc.) in detail. Make sure at least one member of your squad has significant startup experience, because startups are unique beasts with their own patterns and languages.

Your squad will also help keep you even-keeled and sane. Every aspect of career-related work stirs up mud in your personal pond. It triggers imposter syndrome, fears you’ll never work again, fears you’ll get a position even more uncomfortable than the one you are leaving, that you are getting too old to be taken seriously, and the list goes on. Like a diver in low-visibility conditions, you might start to panic. This happens to everyone. Your squad can help you keep your breathing calm, and remember your own value, as you move forward in the process.

2. Do a Dream Job Spreadsheet.

It’s free, it’s easy, and it will change your perspective on your own skills.

When you interview:

3. Assume the founder is a great salesperson.

Successful startup founders (the ones who are able to raise money from investors) are great at communicating the value and potential of their companies. They have honed their messages over months. They are passionate and exciting to talk to. They make people believe in themselves and their companies.

Often, you will leave initial interviews feeling excited, intrigued, fascinated by the founder, and feeling like you just fell into a million-dollar opportunity. If the founder likes you, you will feel like this was a lightning-strike connection, and that you and this job are perfect for each other. That’s normal, but this excitement is not necessarily an indicator of anything other than the sales talents of the founder.

Bask in the excitement, sure, but then calm yourself down and put the rest of these tips into play.

4. Assume all UX job descriptions are wrong.

Job descriptions are usually ‘thrown together,’ and yet we tend to treat every work as sacred. At least half of any conversation about a UX role at a startup should be you teaching them what they need.

When you meet with the team, present the way you would structure the job description, role, team, and budget. This is also your first chance to speak truth to their power. You’re the expert. If the founder isn’t interested in your ideas, that’s a red flag indicating this might not be a good fit.

5. Know that you won’t be able to build a team for a while.

If you want to get into a startup so that you can build and manage a team as the organization grows, that’s great, but understand that you’ll have to wait for a while to hire additional people and that you will have to fight for the budget. Set expectations: yes, you are going to roll up your sleeves and do the wireframes yourself, but only if you have the right title and position in the hierarchy of the company, and only if you’ve first documented a tactical plan for changes to your role and your team in six months, a year, etc.

Keep this in mind: senior level positions tend to come with direct reports and budgets. Ask about both — because the required money and headcount have to be built into long-term fundraising plans, and those are already drafted.

6. Approach interviews like a consultant

Use all your UX inquiry skills to ferret out what the real problems are and take some time to think about how you’d want to solve these problems. Know that the ‘real problems’ in startups are inevitably combinations of organizational politics, lack of clarity, immense time pressure, haphazard existing designs that no one is willing to ditch in order to start over, and ignorance about what it takes to do excellent UX work.

Treat the interview process as the first UX puzzle you need to solve if you are interested in the company:

  • Who are the users of UX processes and deliverables at the startup? Who should they be?
  • What’s the existing process? What should it be?
  • Is “UX” a checkbox they think they need to tick, or do they understand the value of user-centered design in product success?
  • How willing are the players to actually make changes?
  • What could and should your role be in the early days of your involvement vs in six months, a year, etc.?

You can even say something like “If you hired me as a consultant to help you create the right role and hiring criteria to solve the things you want to solve, here’s what I would say….”

7. Decide whether or not you (or anyone) can ‘fix it.’

Startup founders will talk a lot about wanting to create user-centered processes and products, but almost none of them know what that really means. Don’t assume that you’ll have magical persuasive powers once you are hired. Pick an element of the product or idea you think needs rethinking, and possibly some serious redesign. Suggest a brainstorm session as part of your interview process. Listen for resistance like “that will take too long / cost too much to change” or “we want to move on to new ideas / features.” One ‘design pushback’ session will tell you all you need to know about their actual openness to change.

Startup founders also tend to get excited about new things. One of those new things might be you and the idea bringing a senior UX person onto the team. Once this excitement fades, will you be in a good position to do the work that you know needs to be done?

When you negotiate:

8. Fight for the right title (maybe even more than you fight for salary).

This “fight” isn’t about your need for a great title: it’s about the critical balance and tension there needs to be between UX, technology, and business to create a great product. Hiring a UX leader is a critical moment where a startup’s leadership team establishes the value and positioning of user-centered design in their company and products, but they may not realize that.

Most early-stage startups will tell you that ‘titles don’t matter here.’ What that really means is that they are still thinking of themselves as a small team of equals and that they don’t want to start becoming an organization with tons of process and politics. Just because they don’t want to doesn’t mean they won’t. “Titles don’t matter here” is just another way of saying “we found a seemingly-cool way to say ”we’ve never built an org before we’re pretty sure we can make it up as we go along.”

Try drawing the ‘org chart one year from now’ with your interviewer (if possible, the CEO). If they don’t have a hierarchy now, they will in a year. Show them that having a UX team reporting up through several levels to a CTO or CMO isn’t a good idea if they really want great products. Redraw the chart showing where you must be in order to advocate effectively for the user. This should be a position that is on-par with senior-level engineering and marketing roles.

9. Never accept any offer within 24 hours of receiving it.

This is a good rule for any job negotiation. Getting an offer is exciting, and it will usually come with some time-pressure for accepting. If you have an offer, it means the company really wants you. An extra day or two isn’t going to change that, and typically there’s not a long line of perfect candidates waiting for you to say no. Take the time to re-read these tips, talk to your personal advisors, and let a cooler head make the right decision.

When you join:

10. Don’t let your great initial work ruin your future work.

When you join a startup, you’ll have to dive in and ‘fix’ the existing design as much as you can. And this is the tricky part: you’re going to do it. To the rest of the team, it’s going to look like you’ve all-of-a-sudden fixed process problems, even though you are simply tackling low-hanging fruit. You’re trapped: the better the initial work you do, the harder you’re going to have to fight to do things ‘the right way’ in the future. Tell them this before you start.

The job is out there.

As UX’ers, we try to be user-friendly and user-aware in everything we do. As such we tend to assume that the user is ‘right.’ In this case though, your users are the people offering the job. They are not necessarily ‘right’ when it comes to defining the job or how it should be done.

A little discomfort in the job-search and interview process is much easier to endure than the consequences of taking the wrong job for you, with the wrong title, and not being able to do the work you know how to do. None of this is easy, but you already have all the knowledge and skills it will take to make a good decision.

Coming soon: what you need to know if you want to bring your UX expertise to a blockchain startup.

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