Finding the Perfect Match: 10 Questions Designers Should Ask Before Joining a New Company

In an effort to find great talent to join our ever-growing Design team at SalesforceIQ, I interview a lot of candidates. In every conversation with a candidate, I make sure that they have time to ask me any questions they may have about the company or the role. I very frequently receive the same questions over and over again, often those cited in articles about what you should ask during an interview: “what’s the culture like?”, “what is your process?”, and “what does a typical day look like?”. While these are valid questions, they are extremely broad and don’t fully cover the various factors that I believe designers should consider when evaluating their next position.

I often hear from candidates who are looking to leave a position they just recently joined because either the role or the culture didn’t turn out how they expected. While that may be unavoidable in some cases, it’s quite possible that asking the right questions during the interview process may have reduced the chances of accepting a position that wasn’t a good fit.

Not every hiring manager is going to volunteer the information that is important to you without being asked. Your goal as a candidate looking for a new Design position should not just be to evaluate a company the same way one should for any other type of role, but to also dive into factors that will ultimately influence your happiness and growth potential as a designer. Don’t be afraid that you’ll be seen as asking too many questions! By asking questions, you will stand out as being invested in the process and the role, which all hiring managers will appreciate.

5 Questions Everyone Should Ask, Asked in a Better Way

For the standard questions that everyone (including non-designers) should ask, there are ways you can formulate your questions during an interview to get a detailed and helpful response. Aim to be specific and open to avoid “yes or no” responses, and phrase questions in such a way that triggers a broader dialog. Here are five examples:

  1. What factors differentiate your culture from everyone else? This will give you a much better sense of what makes a company special than simply asking for them to describe the culture generically. In SalesforceIQ’s case, I would respond by highlighting our dedication to People, Moments, Ideas, and Results, not just our highly collaborative environment. Other companies may value completely different things, and it’s important for you to find a culture that doesn’t just meet, but ideally exceeds your expectations, as culture is often cited as the number one factor in overall happiness at work.
  2. What impact would I have working at this company? If you simply ask about the typical day, you’ll likely receive a response around responsibilities that you could have received by looking at the job description. Instead, ask about the impact you will have to better understand your overall influence within the organization. In our case, I would talk about how you will be working on a product that so many people use all day every day that directly impacts their performance at their jobs, which is a much more meaningful conversation than a high-level discussion of the day-to-day.
  3. How do you support employees so that they can do their best work? This question touches on a lot of different factors, but by starting here you can help identify what’s actually important to the company as far as career growth and fostering a positive environment. When I’m asked this question, I bring up a wide variety of factors from continuous learning opportunities to our flexible working environment to the support mechanisms we have in place to challenge our designers. When just asked about training, for example, my response is much more limited. Use this question as a springboard to discuss specific things that are important to you doing your best work.
  4. What will I be able to learn from my teammates? Asking “what are the people like?” will result in a generic answer (“they’re friendly!”) that likely won’t help you understand what the company values in its employees. Instead, asking about what skills and experience your teammates have allows you to find out if you can learn something new from them, which is often a key factor in overall job satisfaction. You may end up hearing stories about employees who come from a diverse background, or who have unique skills to share that you might not easily find at another company.
  5. What is the biggest risk to the company? How are you mitigating that risk? While not every company is willing to disclose all of their challenges, this question often prompts a discussion around the health of the company and the team. When candidates only ask about the biggest challenge facing an organization, they often fail to follow-up with what the company is doing to mitigate this risk. This is an important follow-up, as it will help you understand how the company responds to adversity and is protecting itself from problems it may face. This is critical to helping you understand whether or not the company is stable and whether you can trust them to respond to challenges.

5 Questions About Design in an Organization

There are many questions that designers should ask to thoroughly understand how a company views and treats Design as a part of their team. Some companies have negative Design environments that are often extremely challenging to be a part of, and that make your ability to succeed as a designer very difficult. By asking specific questions around Design within the organization, you can better evaluate what your experience would ultimately be like as a designer on the team. For example:

  1. Can you describe how designers are involved throughout the product lifecycle? This question will help you understand whether Design is involved throughout the entire end-t0-end process (as is likely desirable), or whether the company views Design as a specific step in the process that receives requirements from Product and then “hands off” designs to Engineering. Don’t limit yourself to asking only about one aspect of collaboration. Aim to find out whether Design is a key influencer in Product decisions, and whether or not you are given the opportunity to validate ideas both before and after shipping. This will help you understand how strongly the company values Design based on its level of involvement.
  2. How do your designers work together and with the design leadership? Each organization operates a little bit differently, and you should make sure you understand how the Design team(s) functions prior to joining. In our case at SalesforceIQ, we have a relatively small Design team which allows our team members to have a high level of ownership over their own work while still getting the chance to collaborate with other designers and leaders for feedback and mentorship. In other organizations, you may have Creative Directors who are the decision-makers. In others, you may be the sole designer, which gives you a lot of autonomy in defining the Design practice at the cost of not being able to interact with other designers. Find out how you would interact with the rest of the team and how the team thinks about building out the Design function within the organization to ensure that it maps with your expectations.
  3. What’s an example of a recent problem that Design had to solve, and how did they explore creative solutions to that problem? Sometimes it’s not clear whether a company views designers as problems solvers or how much room for creativity really exists within their projects. This question is a proxy for trying to find out whether or not you will be working on projects that involve solving problems in new and creative ways, or whether you will be executing on a pre-determined set of requirements or churning out “cookie cutter” designs. Have you ever felt like a “wireframe monkey” or joined a company that just asks you to “skin” pre-existing sites for different clients? This happens all the time, and makes designers miserable. Make sure to ask the right questions to find companies working projects that will really challenge you and that are solving interesting problems.
  4. How do you resolve disagreements about a proposed design approach? Disagreements are healthy and happen all the time, but how the team handles them is a strong indicator of whether you’ll be entering into a culture that’s truly collaborative and user-centric or whether designers are dictated direction from either Product or Engineering. Understand how the company balances Design and Engineering, who gives feedback on design, how those conversations are facilitated, and who has the final say in the approach. You want to ensure that you aren’t entering into an environment that frequently makes subjective decisions, but rather actively ensures that they’re making decisions in a user-centric manner (or at a minimum, is aware of their challenges and is looking for help in having better conversations around Design).
  5. How do you balance short-term projects and long-term design efforts? Many designers aspire to work on large-scale longer-term design efforts such as redesigns, design systems, or baseline research studies. However, it’s difficult for many organizations to support these efforts and designers often end up trying to stay on top of shorter-term projects rather than being able to contribute to bigger initiatives. By asking how various projects are prioritized, you will get a sense of where the majority of your time will be spent and whether you will be able to work on the types of projects most interesting to you.

There’s no such thing as a perfect design job, and every job will have tradeoffs that have to be carefully considered. However, given the high level of demand for designers, it’s worth your while to find a position that will truly make you happy and excited to go to work every day. Make an effort to really probe during the interview process to find out if a company is able to offer you the type of role and environment that is best for you. In some cases, you may be looking for a strong pre-existing Design culture, in others, you may be excited about building out a new Design practice within an organization. Asking detailed questions related to what you’re looking for and what’s important to you will help you evaluate potential positions against each other more effectively, rather than resorting to picking a position based off of limited information.


Are you in the San Francisco Bay Area and looking for a new position? SalesforceIQ is hiring a Visual Product Designer to join our team. Reach out to me to learn more! I’d be happy to answer any of the above questions, or any others you may have. I’d love to help you find your dream job at SalesforceIQ.

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