Questions You Should Consider Asking

6 minutes


Updated February 27, 2023
Land Your Dream Design Job

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.

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

Here are some good questions to ask your design manager.

  • What are your expectations for me in the first month on the job?

  • How quickly do we ship new features?

  • How involved is user research in the design process?

  • Have you had a designer before who made a mistake or was underperforming? How did you handle their performance issues?

The Product

By now you should also have a good understanding of the company’s offering. However if it’s an enterprise company or a specialized niche, you may not get a complete sense of the product (unlike a publicly available consumer app for instance). In that case, it helps to request a product demo. Think of this as an app critique, now you’re assessing the product to better understand the types of problems and opportunities available to you.

  • How is the product sold?

  • How much tech debt (and/or design debt) does the product have?

  • What are the biggest opportunities for improving the product?

Work-Life Balance

Working in a company that’s a good fit can make a difference between coming to work miserable versus happy. Some organizations pride themselves in going above and beyond, pushing employees to work nights and weekends to achieve a greater mission. Other companies do the bare minimum and everyone leaves the office by six p.m. In the end, it’s a personal preference.

  • What is it like to work here?

  • How many projects does a designer usually work on in parallel?

  • What does a usual day look like for a designer working here?

  • What was the last intense project that you worked on? What made it intense?

Design Team

To understand your growth opportunity, it helps to understand the types of folks you’ll be working with and how the design team is situated in the company.

  • How is the design team organized within the company?

  • Is there a head of design and who do they report to? If they’re under product or engineering then design will always be in the backseat.

  • How big is the design team? Are there plans to grow it? What roles are next to hire?

  • What do you think is a current strength of the design team?

  • What is a growth opportunity for the design team as a whole?

  • How is the design team staffed? You’ll want to learn if there are dedicated researchers, brand designers, content designers and so on. In smaller companies people will wear multiple hats, in larger companies you’re likely to find more specialists.

  • When does the design team come together (for critiques, team outings, and so on)?

Some of the questions that you’ll ask will inevitably overlap with design maturity. Usually, in a company’s early days everyone is a generalist and designers scramble to meet the changing needs of the company. As the org matures, processes become more established and the quality bar rises.

Design Maturity

Design is still a nascent discipline in many orgs. There are many different design maturity models out there, but suffice it to say companies with low maturity offer a different challenge compared to high design maturity companies. In the former you shape the process, in the latter you optimize and get better at your craft.

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Both options may be a good fit for your career. It helps to learn more about the level of design maturity at this company.

  • How are roadmaps or quarterly goals set at the company?

  • When it comes to building features, who determines what to build?

  • How much budget does the UX/design team get?

  • What was the last project driven by UX research?

  • What’s the design to engineering ratio?

  • Is there a design system in place?

  • Is there a design ops team?

One thing to note—in smaller companies with little to no design resources, you may be the only designer. However, you can mature the design practice there quickly if their appetite for it is high. For larger companies, design maturity will be slower—given the layers and various stakeholders, it will take longer even if the impact might be more significant.

Startup-Specific Questions

If you have an offer from a startup, you should also ask about the company’s burn rate and growth ambitions. Every startup carries risk, but that risk can be mitigated with a strong team, strong execution, and decent funding.

  • How does the company make money or how do we plan on making money?

  • Is the company currently profitable?

  • What is our current burn rate—given the current size and funding, how long do we have before we have to raise another round?

Most startups fail. Yes, it may be glamorous to work at one to make a dent in the universe, but remember, not every company will succeed. And that’s OK. It’s nice to see one’s equity amount to something, but see it as a bonus. The most important factor that will contribute to your well-being is the people you’ll interact and work with daily.

Making the Decision

When you get an offer, take the time to zoom out before you zoom in. If you were to take this role, how will it help you achieve your current and future goals? Ultimately, we’re all captains of our own ships. A good job is one that pays well, grows your skills, and advances your career. Of course, choosing a job isn’t all about career aspirations either. Work-life balance is also key. In the end, you should weigh factors based on how important they are to you.

Remember the mapping your futures exercise exercise that we did earlier on? Now’s a good time to reflect, since you’ve been through the process and a few weeks have passed by since then. Are your fundamental goals still the same? Have they changed with new information?

important There will never be a sure thing or an ideal workplace. Companies reorg, teams change, projects shift. The best you can do is to look at core factors (such as culture) and the key people who influence the process so that even in the times of reorg, you’ll still end up in a good place because the culture of the company is one that resonates with your values.

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