Questions to Ask Before You Take Your Next Role

Working in a role that makes use of your skills, provides opportunities for growth, has a healthy culture, and where you genuinely enjoy interactions with all your coworkers is a sacred and rare thing. The opposite kind of role can be a nightmare and every effort should be made to evaluate fit BEFORE you accept an offer.

What follows is a list of questions to consider as you evaluate opportunities from the perspective of a design leader (but other functions may get value from it as well).

While the list is long, it is by no means meant to be exhaustive. I plan to keep it evergreen and will add/modify items over time.

Additional note: Strong leaders will not just accept the role as written. You should already have a crisp definition of the kind of role and impact you’d like to have and then use your conversation with the company to stretch the role into that and assess fit from that vantage point.

The Role & Manager

1. What are the core skills and responsibilities for this role?
2. Are there particular hard skills required and to what level of mastery?
3. What does the rest of the org chart look like around this role?
4. Who will report to me? (both solid and dotted-line) How many reports and at what levels of seniority?
5. Is there a need to grow the design team in terms of headcount? If so, which skill gaps have been identified? Is design a bottleneck due to the workload exceeding the number of designers available?
6. Are there people that the company has already identified for termination? Will letting that person(s) go be one of the early expected tasks in the role?
7. What aspects of the design work do you (the manager) want to be closely connected to? Which ones are you handing off to this person?
8. What’s a time when your direct report did not meet your expectations on a core responsibility? How did you get things back on track?
9. How do you ensure that your directs get regular feedback, outside of the perf process?
10. How do you measure success for this role and what is the performance review process like here?
11. What’s an example where you had to provide “cover” to one of your directs or went to bat for them in something they wanted to pursue that may have been slightly outside their regular remit?
12. How do you run your 1–1's and other regular meetings?
13. What would be some wins you would like to see in the first 90 days and first year?

Design Team

1. To what degree is the company customer-focused vs market-focused?
2. What are the main concerns of the design team?
3. What’s working well? What is the team most proud of to date?
4. In what ways does the design team want to change how they’re interacting with their XFPs and more broadly, within the whole company?
5. If their concerns relate to “seat at the table” / influence, are PM and eng leaders open to changing their ways of working to foster this change?
6. Will this design leader be included in strategic leadership meetings, both in off-site and weekly/quarterly planning sessions with the other cross-functional leaders?
7. Is there already a job ladder in place for design and UXRs? Is it harmonized with the other cross-functions? (i.e. titles and leveling match)
8. Is design happening anywhere else in the company (i.e. marketing/branding) and what are expectations around how we’ll collaborate?

Eng

1. What is the current designer-to-engineer ratio?
2. Are there design-minded engineers on the team? Are there examples of those engineers collaborating with their design partners in fruitful or interesting ways?
3. Are there front-end engineers that are involved in design systems work?
4. Are there engineers that can and enjoy building prototypes in code with help from a designer?
5. Is all eng work done in-house, using outside contractors, or a hybrid?
6. Has the head of eng partnered with a design leader in the past? What was their collaboration like?

Product

1. What are the key product usage metrics and how are they tracked?
2. How are smaller/short-term decisions made?
3. How are strategic/longer-term decisions made?
4. Who are the people engaged in key product discussions? Is a design representative one of them?
5. At what cadence is the roadmap revised or is it done in an ad-hoc fashion? What level of formality is involved in this process?
6. Where do insights currently come from, how are they shared throughout the company, and how do they feed into the product decision-making process?
7. Is there an exchange of marketing-led customer insights and product team insights? If so, how do these two orgs collaborate and align efforts?
8. Are the product surfaces instrumented to collect the data that’s most important to the product and business teams? Is the data collected easily queried and/or is there a data analyst in the company that can provide insights to the EPD (eng/prod/design) team?
9. How often do people in the company speak with (and spend time with) customers directly? Are sales and customer support teams empowered to deliver the feedback they receive over to the product team?
10. Do product directives ever come from the founders directly? If so, are there examples where the product team was able to change their minds if there was disagreement?
11. How does product work come into the team and who decides what gets worked on ultimately? What process is used for this?
12. Is there a separate process used for short-term/just-get-it-done work identified by PMs as a “quick win”?
13. How is the success of any project (small/medium/large) evaluated?
14. How are differences of opinion dealt with within an EPD?

Company Culture

1. What are the current largest challenges as a team and overall as an organization?
2. What practices/behaviors does the company employ to allow differing opinions and rough/early work to surface?
3. Are employees generally having fun as they do the work? What are examples of how fun shows up in the company? How do these things roll up into the current employee morale?
4. Is there a budget available for training? Offsites? If so, what’s the process like to get approvals?
5. What programs/practices have been rolled out or are in-plan to improve DEI initiatives?
6. If there have been layoffs, how were they approached? What’s the assessment of how they were handled and what steps are being taken to avoid them in the future?
7. How would you characterize the founders/C-level in terms of how they see the value of design? Do they have any particularly strong personal connections to design?
8. Do the founders provide regular updates to the employees through all-hands meetings or via email updates?
9. Are the founders open to questions from anyone in the company and do they respond with candor?
10. What’s the release cycle clock speed? At what cadence are new features shipped and how difficult is it to make changes to the existing product?
11. Are skip-level meetings utilized in the company?
12. What practices are being used when working with remotely based employees?
13. If the company has verticals, how dynamic and flexible are these teams in terms of product ownership? What are some examples where collaboration and alignment worked well between two teams with different roadmaps? Do ideas get passed between teams and what are some examples?

Business

1. How much runway does the company currently have?
2. What are the key business metrics and how are they tracked?
3. What is the current TAM and is the size fixed or growing?
4. What are the plans for the company internationally?
5. Is the company focused on the current customer for the foreseeable future or are there plans to expand into other customer bases/use cases?
6. (Is the domain of the company something you have strong opinions about?). If so: does the company’s roadmap and vision align with where you think they should be taking things? If not: are you ok with working in a domain where you may have less passion and/or personal experience?
7. How do you see the company changing over the next 1–2 years and how do you see my role growing to enable/drive this change?