I work on design projects with startups all the time. And while most projects go smoothly, sometimes working with a team is more challenging than I thought. Over the years, I’ve learned to spot teams that are easy or hard for designers to work with. I was inspired by Phineas’ great blog post on this topic and wanted to continue the conversation.

I recently wrote an article to help founders hire designers. So this will be the flip side: What questions should designers ask before joining a startup?

The first thing I’ve learned is to be extremely concrete with questions. If you ask people to describe their product development process, they’ll often reply with something straight out of a textbook. If you try to get at job responsibilities, they’ll often tell you what you want to hear. At this point in an interview the company is in selling mode, so you have to drill down deep.

Here’s how I do it.

What does this startup expect from a designer?

Startups rarely have the language to describe the design skills they need. Sometimes all a team knows is that they need a designer, and quick! So it can be up to the designer to uncover the expectations that a team has, and compare those expectations with the type of design work he or she enjoys most.

Ask: Imagine I’ve already been working here for a month and I’ve been doing a great job. What problem would you want me to tackle next?

Listen for:

  • Scope of the project — Is it an icon redesign or a new product line?
  • Type of design work — Visual, interaction, or product level design?
  • Inclusion of business goals — Does the design project flow from business needs? Will design success be critical for the business or a nice-to-have?

Ask: Who is the last designer you’ve worked with? What did you ask them to do? How did the project turn out? What could have been better?

Listen for:

  • Hands vs. brains — Do they expect designers to be “hands” and to implement the vision already in someone’s head? Or do they give designers important challenges and space to find solutions?
  • Past expectations — Do the responsibilities they gave previous designers match the type of work you want to do?
  • Reference check — Get in touch with any designers they mention. They’ll call your references; you should call theirs.

If a startup doesn’t have the right expectations in mind, that’s OK, But you need to have a frank discussion about the work you want to do, and whether there’s room for that role at the company. It’s way easier to do this before you’re hired than after you start.

Is the right team in place to support great design?

You can’t build a great product alone, so you’ll need figure out if the startup already has the right people you want to work with. If they don’t, you’ll need to gauge their willingness to hire these types of people. Sean McBride wrote a great article about roles necessary for great design and it makes a perfect checklist for what to look for in a startup. The two most frequent gaps I see are what Sean calls “detailed design implementer” and “qualitative data advocate.”

Ask: Who on the team does front-end development? Is there anyone who just loves to work with HTML, CSS, and JS? (or Android/iOS for mobile)

Listen for:

  • Who writes code — Are designers expected to do implementation? Are there front-end specialists or does every engineer write a little front-end code when they have to?
  • A partner — Is there a front-end developer you can partner with? Does this person care about design? What have they built before?
  • Quality — Comb through the existing product and look for UI bugs. Ask about them. See if they get fixed quickly.

Ask: What was the last big thing you learned about your customers? How did you learn this lesson? Does anyone talk with customers each week?

Listen for:

  • Sculptors vs sleuths — Are they building a vision that’s inside a founder’s head or are they actively discovering what customers want?
  • Research rhythm — Is anyone talking to customers and watching them use the product on a regular basis? Or is there a data vacuum?

If either of the above roles seem to be missing, it’s a good idea to ask about the next few hires the team wants to make. If the team isn’t looking for people to fill these roles, you can dig in and ask why.

Can design thinking influence product decisions?

Understanding existing habits can shed light on whether a new designer can make an impact. I try to judge the maturity of the product development process, and I try to gauge how much the team is open or resistant to change.

Ask: What’s the last large feature you shipped? Can you tell me the story of how that happened, from the forming of the idea to where we are today?

This question requires some really deep digging. You can follow up with these:

  • How did you come up with the idea?
  • How did you decide to build that idea over other ones?
  • How did you design the interface?
  • How did you know when it was good enough to launch?
  • How did the launch go? What did you learn?

When in doubt, just ask “How did you do that?” a few more times.

Listen for:

  • Closed loop — Are they learning what people want, and measuring whether new features work? Or are they judging success by how fast they can ship new features?
  • Analytical approach — Are they making decisions based on data and reason? Are they honest about what they don’t know?
  • Speed — How fast are they able to move through this loop? Too fast and you won’t be able to get any design done. Too slow and it’s hard to learn from customer behavior and then iterate.

Spot test: Suggest a small change to the product — something you think would make it better. Repeat several times with more ambitious changes each time.

Listen for:

  • Analytical approach — Same as above. Also, have they thought of this idea before?
  • Flexibility — Do they consider new ideas and discuss how to prove or disprove them quickly? Or are they stuck on previous decisions? (See commitment bias)
  • They ship your idea — Do they change the product as a result of the conversation? This has happened to me a few times and it’s always been a great sign.

Decision time

After getting through all the interviews and discussions, you’ll have a tough choice about whether this startup is right for you.

Here’s my biggest tip: Be patient. There are plenty of companies that need design right now — so don’t get stuck into thinking, “this startup will be huge, I have to join now.” The reality is that no one knows whether a given startup is going to be successful. Even the best VCs often get it wrong, and it’s their full time job to evaluate startups! So trust your gut. It’s worth waiting for a product you’re passionate about and a team you want to work with.

There are plenty of other great articles that cover the non-design aspects of joining a startup. Here are some of my favorites:

If you’re a designer and recently joined a startup, what advice would you give other designers who are considering joining a startup? Please feel free to share what you’ve learned in the comments below.