Insights
Three Questions to Ask Before Joining Any Company
When I am looking for the next opportunity, I have identified specific areas that help me determine if an organization will be a good fit for me.
Much of it comes from years of experience in building up design orgs at multiple companies. To set qualifications here, I've either led or been heavily involved in building up and managing seven different teams. Each one has had a significant impact on improving OSAT (NPS/CSAT) scoring, reducing release cycle times, and decreasing overall cost by millions of dollars.
From all of this, I've also learned that success isn't just about what my teams and I bring to the table. It's about whether the company itself is actually set up to let design work for them.
So before I look to join anywhere now, I evaluate three things. I'm not waiting for the offer stage; I'm thinking through these throughout the entire interview process. I listen to that little voice in the back of my head that is trying to tell me, "Are you sure this is what you want?" These aren't gotchas or tests to catch people lying. They are research-style questions that are designed to surface the reality (or not) of whether design leadership will be able to thrive.
Question 1: “How does Design participate in product decisions?”
This is an essential question for all designers to ask, whether in a product design role or a creative design aspect. I'm not asking if they "value design," as in any interview process, they will say they do. I'm observing behaviors and reactions. I'm looking for the place where design has actual influence, and not where we are just making other people's ideas look presentable.
Questions I ask them:
"Walk me through how a recent product decision got made, from idea to shipped feature. Who was involved at each stage?"
"When was the last time design or research findings changed the direction of a project? What happened?"
"How does the roadmap get prioritized? Who's in those conversations?"
"If design and engineering disagree on an approach, how does that typically resolve?"
What I am observing during interviews:
Do they reference design or research when explaining strategy, or only when talking about execution?
When describing their product, do they lead with user problems or technical capabilities?
Is there a design leader at the exec level? How long have they been there?
Do they show me their design system unprompted and talk about how teams actually use it?
Do Your Research:
Look at LinkedIn to see if senior designers have been there 2+ years or if there's constant churn. Check Glassdoor for how design is mentioned and scan their blog to see if they actually write about design thinking.
Red Flags | Green Flags |
|---|---|
Design is the last thing mentioned in their process description | Designer and researcher names come up naturally when they describe how features got built |
"We just hired our first designer" at a Series C company with 50+ engineers | Design participated in defining the problem, not just solving it |
All designers report to engineering with no design leadership | Show research artifacts unprompted, such as journey maps, personas, and talk about how teams use them |
They describe design as "making it intuitive" or "cleaning up the UI” | Recent examples where they didn't build something because research showed it wouldn't work |
Can't name a specific example of research changing a decision | Design presents to the C-Suite or participates in quarterly planning |
Roadmap is locked before design ever sees it | They can articulate tradeoffs made because of design input |
Why This Question Matters:
If research and design aren't factoring into their decisions with their products, you'll spend much of your time making other people's bad ideas (with a good one mixed in from time to time) look pretty. You'll be fighting uphill battles, and the team will get burnt out before too long. That's not to say you won't deliver on your end, but you could be delivering on flawed strategies and then taking the blame for why users aren't happy.
I've been there and it's exhausting. No amount of personal effort can overcome a structure that treats design as the team that "makes things pretty."
Question 2: "What has leadership change looked like over the past two years?”
This question is usually either answered quickly and confidently or it's met with some reservations and possibly excuses. It's the most predictive question I ask. Leadership stability is more important than most people realize. It determines whether you can build a team that lasts, or if you'll be rebuilding the foundation over and over. With each new leader, you are always going to have to prove yourself and your team to them.
Questions I ask them:
"What has leadership change looked like over the past two years?” (I use exactly this wording, then stay quiet and let them fill the silence)
"Why is this role open?" (Whether it's new growth or backfill tells you everything)
"Who would I report to, and how long have they been in their role?"
"Walk me through a recent conflict between product and engineering. How did leadership handle it?"
What I am observing during interviews:
Do they answer the leadership question quickly and confidently, or do they hedge?
When discussing challenges, do they blame individuals or describe systems problems?
Do different interviewers tell consistent stories about priorities and direction?
How do they talk about people who left? ("Wasn't a culture fit" is a red flag; "moved to a great opportunity" is normal)
Does your potential manager speak about the team with pride or exhaustion?
Do Your Research:
I check LinkedIn for how long leaders have been there (C-suite and my potential manager), look for red flags like too many executives for the company's size, and scan Glassdoor for phrases like "constant reorgs" or "unclear priorities." PE-backed companies get extra scrutiny fro me, I want to know if they respected the people who built the place or just stripped it for parts.
Red Flags | Green Flags |
|---|---|
More than two C-suite changes in 18 months | Leadership team has been stable for 2+ years |
Evasive or defensive answer about why the role is open | Mention departures, that are explainable and normal (retirement, promotion elsewhere, family reasons) |
Your potential manager has been there less than six months (Depends on the person and their background) | Clear, consistent story about company direction from everyone you talk to |
Multiple reorgs mentioned casually, as if that is normal | Transparent about challenges without scapegoating individuals |
Different interviewers contradict each other on company priorities or strategy | Role is new because they're growing and scaling, not because someone burned out |
Blames "the previous leadership" for current problems | Your potential manager has been there long enough to have built trust and knows how things actually work |
Pattern of short tenures across the leadership team | They can name specific improvements leadership has made based on employee feedback |
Why This Question Matters:
I have personally worked at two different companies where leadership changes were constant. I can attest that an unstable leadership means constantly shifting priorities, reorgs that will undo your work and the relationships you've built, and some executives will be out to prove themselves rather than viewing others' competence as an asset.
In these environments, trying to implement a design system, build research and design into the DNA of the company, and create a culture of trust and innovation becomes such a struggle that you can easily lose focus on the work that you were hired to do in the first place.
Having solid leadership that instills a culture of trust and confidence is a place you'll want to work at forever. You and your teams will come to work every day focused on the goals of the users and the business, and you can make a real difference. I've experienced both versions, and I'm only interested in the latter now.
Question 3: "Tell me about a specific user whose life improved because of your product.”
This is a question that any experienced designer or researcher can answer very quickly. We all have those moments where our work has stuck with us and made us think, "This is why I do this work." So when asking a potential employer, you'd expect that same level of excitement and conviction in how they answer.
Questions I ask them:
"Tell me about a specific user whose life improved because of your product."
(Then I shut up and listen to how they answer)"What problem does this product solve that users can't solve another way?"
"How do you know your users? What's a unique thing you learned from talking to them?"
"Walk me through your most meaningful user research finding from the past year."
"If the product disappeared tomorrow, who would actually care and why?"
What I am observing during interviews:
Do they tell you a story about a real person with details, or do they recite features and metrics?
Can they name specific users, or do they speak only in demographics and segments?
Does their energy shift when talking about user impact, or is it flat and rehearsed?
Do they mention users spontaneously throughout the conversation, or only when directly asked?
When pushed, can they connect technical decisions back to user outcomes?
Do Your Research:
For public products, I scan app reviews and social comments, but take them with a grain of salt since we've all dealt with those impossible-to-please users and competitors who are willing to do anything. If you know SEO, check whether their traffic is organic or paid; tells you if people are finding them naturally or if they're spending big to get customers in.
Red Flags | Green Flags |
|---|---|
Can't name a specific user or tell a concrete story with any detail | They light up when telling you about a specific user |
Answer is entirely about business metrics: revenue, retention, engagement, with no human element | Story includes real details, such as a user's name, their situation, what actually changed for them |
"Our users want..." but can't explain how they actually know that | Multiple people across the company tell you versions of the same user stories (means it's real, not just marketing) |
Mission statement uses words like "empower," "transform," "innovate" without specifics | They can connect features to user outcomes without you having to ask |
When pushed for examples, they pivot to technical capabilities instead of outcomes | They share a recent research finding that surprised them and changed the product direction |
Product solves a problem that only exists because of their business model | Clear articulation of whose life improves and how you'd measure that improvement |
They've never actually met a user | Leadership has met users personally and can talk about those conversations |
Why This Question Matters:
How they answer will tell you a lot about how they think about research and design in their organization. Did they get as excited as you do when you get that question? Mission-driven work produces better design. When you know who you are building for and why, you make better decisions. The stakes become real, and when tradeoffs need to be made, you understand what those really mean on both sides.
I've built product flows that have made people cry tears of joy, and had them asking, "How soon can I have this?” I've also had people look confused and unsure. I have enjoyed every reaction because it has made my work better, my teams stronger, and pushed me further. A company that listens and understands its user base will have the same if they are dedicated to being user-centric.
What This Framework Actually Does
These three questions aren't about finding the perfect company. Mainly because that doesn't exist. They're about setting yourself up for success and laying all the cards out on the table for you to make the best decision for yourself and your career.
I know that everyone has different circumstances, and some may have to take the first offer that comes along. You should always do your homework anyway, so that you have some idea of what you are walking into. I've worked for companies that have passed all these questions, at least in my eyes, and I've also worked for ones where they have passed none of them. The difference is in the outcomes I (and my teams) were able to produce for the business and the users. It's also about how I view my time there and how I talk about it years later.
The companies that have passed these questions? Those are the places where I have built things that have lasted. My teams were able to thrive, the products genuinely helped people, and I left those roles because I had accomplished my goals and not because I felt the foundation falling out from under me.
These may not be your three questions, but if you don't already have your values and your "must-haves" in place for your career progression, now is the time to start.
More to Discover
Insights
Three Questions to Ask Before Joining Any Company
When I am looking for the next opportunity, I have identified specific areas that help me determine if an organization will be a good fit for me.
Much of it comes from years of experience in building up design orgs at multiple companies. To set qualifications here, I've either led or been heavily involved in building up and managing seven different teams. Each one has had a significant impact on improving OSAT (NPS/CSAT) scoring, reducing release cycle times, and decreasing overall cost by millions of dollars.
From all of this, I've also learned that success isn't just about what my teams and I bring to the table. It's about whether the company itself is actually set up to let design work for them.
So before I look to join anywhere now, I evaluate three things. I'm not waiting for the offer stage; I'm thinking through these throughout the entire interview process. I listen to that little voice in the back of my head that is trying to tell me, "Are you sure this is what you want?" These aren't gotchas or tests to catch people lying. They are research-style questions that are designed to surface the reality (or not) of whether design leadership will be able to thrive.
Question 1: “How does Design participate in product decisions?”
This is an essential question for all designers to ask, whether in a product design role or a creative design aspect. I'm not asking if they "value design," as in any interview process, they will say they do. I'm observing behaviors and reactions. I'm looking for the place where design has actual influence, and not where we are just making other people's ideas look presentable.
Questions I ask them:
"Walk me through how a recent product decision got made, from idea to shipped feature. Who was involved at each stage?"
"When was the last time design or research findings changed the direction of a project? What happened?"
"How does the roadmap get prioritized? Who's in those conversations?"
"If design and engineering disagree on an approach, how does that typically resolve?"
What I am observing during interviews:
Do they reference design or research when explaining strategy, or only when talking about execution?
When describing their product, do they lead with user problems or technical capabilities?
Is there a design leader at the exec level? How long have they been there?
Do they show me their design system unprompted and talk about how teams actually use it?
Do Your Research:
Look at LinkedIn to see if senior designers have been there 2+ years or if there's constant churn. Check Glassdoor for how design is mentioned and scan their blog to see if they actually write about design thinking.
Red Flags | Green Flags |
|---|---|
Design is the last thing mentioned in their process description | Designer and researcher names come up naturally when they describe how features got built |
"We just hired our first designer" at a Series C company with 50+ engineers | Design participated in defining the problem, not just solving it |
All designers report to engineering with no design leadership | Show research artifacts unprompted, such as journey maps, personas, and talk about how teams use them |
They describe design as "making it intuitive" or "cleaning up the UI” | Recent examples where they didn't build something because research showed it wouldn't work |
Can't name a specific example of research changing a decision | Design presents to the C-Suite or participates in quarterly planning |
Roadmap is locked before design ever sees it | They can articulate tradeoffs made because of design input |
Why This Question Matters:
If research and design aren't factoring into their decisions with their products, you'll spend much of your time making other people's bad ideas (with a good one mixed in from time to time) look pretty. You'll be fighting uphill battles, and the team will get burnt out before too long. That's not to say you won't deliver on your end, but you could be delivering on flawed strategies and then taking the blame for why users aren't happy.
I've been there and it's exhausting. No amount of personal effort can overcome a structure that treats design as the team that "makes things pretty."
Question 2: "What has leadership change looked like over the past two years?”
This question is usually either answered quickly and confidently or it's met with some reservations and possibly excuses. It's the most predictive question I ask. Leadership stability is more important than most people realize. It determines whether you can build a team that lasts, or if you'll be rebuilding the foundation over and over. With each new leader, you are always going to have to prove yourself and your team to them.
Questions I ask them:
"What has leadership change looked like over the past two years?” (I use exactly this wording, then stay quiet and let them fill the silence)
"Why is this role open?" (Whether it's new growth or backfill tells you everything)
"Who would I report to, and how long have they been in their role?"
"Walk me through a recent conflict between product and engineering. How did leadership handle it?"
What I am observing during interviews:
Do they answer the leadership question quickly and confidently, or do they hedge?
When discussing challenges, do they blame individuals or describe systems problems?
Do different interviewers tell consistent stories about priorities and direction?
How do they talk about people who left? ("Wasn't a culture fit" is a red flag; "moved to a great opportunity" is normal)
Does your potential manager speak about the team with pride or exhaustion?
Do Your Research:
I check LinkedIn for how long leaders have been there (C-suite and my potential manager), look for red flags like too many executives for the company's size, and scan Glassdoor for phrases like "constant reorgs" or "unclear priorities." PE-backed companies get extra scrutiny fro me, I want to know if they respected the people who built the place or just stripped it for parts.
Red Flags | Green Flags |
|---|---|
More than two C-suite changes in 18 months | Leadership team has been stable for 2+ years |
Evasive or defensive answer about why the role is open | Mention departures, that are explainable and normal (retirement, promotion elsewhere, family reasons) |
Your potential manager has been there less than six months (Depends on the person and their background) | Clear, consistent story about company direction from everyone you talk to |
Multiple reorgs mentioned casually, as if that is normal | Transparent about challenges without scapegoating individuals |
Different interviewers contradict each other on company priorities or strategy | Role is new because they're growing and scaling, not because someone burned out |
Blames "the previous leadership" for current problems | Your potential manager has been there long enough to have built trust and knows how things actually work |
Pattern of short tenures across the leadership team | They can name specific improvements leadership has made based on employee feedback |
Why This Question Matters:
I have personally worked at two different companies where leadership changes were constant. I can attest that an unstable leadership means constantly shifting priorities, reorgs that will undo your work and the relationships you've built, and some executives will be out to prove themselves rather than viewing others' competence as an asset.
In these environments, trying to implement a design system, build research and design into the DNA of the company, and create a culture of trust and innovation becomes such a struggle that you can easily lose focus on the work that you were hired to do in the first place.
Having solid leadership that instills a culture of trust and confidence is a place you'll want to work at forever. You and your teams will come to work every day focused on the goals of the users and the business, and you can make a real difference. I've experienced both versions, and I'm only interested in the latter now.
Question 3: "Tell me about a specific user whose life improved because of your product.”
This is a question that any experienced designer or researcher can answer very quickly. We all have those moments where our work has stuck with us and made us think, "This is why I do this work." So when asking a potential employer, you'd expect that same level of excitement and conviction in how they answer.
Questions I ask them:
"Tell me about a specific user whose life improved because of your product."
(Then I shut up and listen to how they answer)"What problem does this product solve that users can't solve another way?"
"How do you know your users? What's a unique thing you learned from talking to them?"
"Walk me through your most meaningful user research finding from the past year."
"If the product disappeared tomorrow, who would actually care and why?"
What I am observing during interviews:
Do they tell you a story about a real person with details, or do they recite features and metrics?
Can they name specific users, or do they speak only in demographics and segments?
Does their energy shift when talking about user impact, or is it flat and rehearsed?
Do they mention users spontaneously throughout the conversation, or only when directly asked?
When pushed, can they connect technical decisions back to user outcomes?
Do Your Research:
For public products, I scan app reviews and social comments, but take them with a grain of salt since we've all dealt with those impossible-to-please users and competitors who are willing to do anything. If you know SEO, check whether their traffic is organic or paid; tells you if people are finding them naturally or if they're spending big to get customers in.
Red Flags | Green Flags |
|---|---|
Can't name a specific user or tell a concrete story with any detail | They light up when telling you about a specific user |
Answer is entirely about business metrics: revenue, retention, engagement, with no human element | Story includes real details, such as a user's name, their situation, what actually changed for them |
"Our users want..." but can't explain how they actually know that | Multiple people across the company tell you versions of the same user stories (means it's real, not just marketing) |
Mission statement uses words like "empower," "transform," "innovate" without specifics | They can connect features to user outcomes without you having to ask |
When pushed for examples, they pivot to technical capabilities instead of outcomes | They share a recent research finding that surprised them and changed the product direction |
Product solves a problem that only exists because of their business model | Clear articulation of whose life improves and how you'd measure that improvement |
They've never actually met a user | Leadership has met users personally and can talk about those conversations |
Why This Question Matters:
How they answer will tell you a lot about how they think about research and design in their organization. Did they get as excited as you do when you get that question? Mission-driven work produces better design. When you know who you are building for and why, you make better decisions. The stakes become real, and when tradeoffs need to be made, you understand what those really mean on both sides.
I've built product flows that have made people cry tears of joy, and had them asking, "How soon can I have this?” I've also had people look confused and unsure. I have enjoyed every reaction because it has made my work better, my teams stronger, and pushed me further. A company that listens and understands its user base will have the same if they are dedicated to being user-centric.
What This Framework Actually Does
These three questions aren't about finding the perfect company. Mainly because that doesn't exist. They're about setting yourself up for success and laying all the cards out on the table for you to make the best decision for yourself and your career.
I know that everyone has different circumstances, and some may have to take the first offer that comes along. You should always do your homework anyway, so that you have some idea of what you are walking into. I've worked for companies that have passed all these questions, at least in my eyes, and I've also worked for ones where they have passed none of them. The difference is in the outcomes I (and my teams) were able to produce for the business and the users. It's also about how I view my time there and how I talk about it years later.
The companies that have passed these questions? Those are the places where I have built things that have lasted. My teams were able to thrive, the products genuinely helped people, and I left those roles because I had accomplished my goals and not because I felt the foundation falling out from under me.
These may not be your three questions, but if you don't already have your values and your "must-haves" in place for your career progression, now is the time to start.
More to Discover
Insights
Three Questions to Ask Before Joining Any Company
When I am looking for the next opportunity, I have identified specific areas that help me determine if an organization will be a good fit for me.
Much of it comes from years of experience in building up design orgs at multiple companies. To set qualifications here, I've either led or been heavily involved in building up and managing seven different teams. Each one has had a significant impact on improving OSAT (NPS/CSAT) scoring, reducing release cycle times, and decreasing overall cost by millions of dollars.
From all of this, I've also learned that success isn't just about what my teams and I bring to the table. It's about whether the company itself is actually set up to let design work for them.
So before I look to join anywhere now, I evaluate three things. I'm not waiting for the offer stage; I'm thinking through these throughout the entire interview process. I listen to that little voice in the back of my head that is trying to tell me, "Are you sure this is what you want?" These aren't gotchas or tests to catch people lying. They are research-style questions that are designed to surface the reality (or not) of whether design leadership will be able to thrive.
Question 1: “How does Design participate in product decisions?”
This is an essential question for all designers to ask, whether in a product design role or a creative design aspect. I'm not asking if they "value design," as in any interview process, they will say they do. I'm observing behaviors and reactions. I'm looking for the place where design has actual influence, and not where we are just making other people's ideas look presentable.
Questions I ask them:
"Walk me through how a recent product decision got made, from idea to shipped feature. Who was involved at each stage?"
"When was the last time design or research findings changed the direction of a project? What happened?"
"How does the roadmap get prioritized? Who's in those conversations?"
"If design and engineering disagree on an approach, how does that typically resolve?"
What I am observing during interviews:
Do they reference design or research when explaining strategy, or only when talking about execution?
When describing their product, do they lead with user problems or technical capabilities?
Is there a design leader at the exec level? How long have they been there?
Do they show me their design system unprompted and talk about how teams actually use it?
Do Your Research:
Look at LinkedIn to see if senior designers have been there 2+ years or if there's constant churn. Check Glassdoor for how design is mentioned and scan their blog to see if they actually write about design thinking.
Red Flags | Green Flags |
|---|---|
Design is the last thing mentioned in their process description | Designer and researcher names come up naturally when they describe how features got built |
"We just hired our first designer" at a Series C company with 50+ engineers | Design participated in defining the problem, not just solving it |
All designers report to engineering with no design leadership | Show research artifacts unprompted, such as journey maps, personas, and talk about how teams use them |
They describe design as "making it intuitive" or "cleaning up the UI” | Recent examples where they didn't build something because research showed it wouldn't work |
Can't name a specific example of research changing a decision | Design presents to the C-Suite or participates in quarterly planning |
Roadmap is locked before design ever sees it | They can articulate tradeoffs made because of design input |
Why This Question Matters:
If research and design aren't factoring into their decisions with their products, you'll spend much of your time making other people's bad ideas (with a good one mixed in from time to time) look pretty. You'll be fighting uphill battles, and the team will get burnt out before too long. That's not to say you won't deliver on your end, but you could be delivering on flawed strategies and then taking the blame for why users aren't happy.
I've been there and it's exhausting. No amount of personal effort can overcome a structure that treats design as the team that "makes things pretty."
Question 2: "What has leadership change looked like over the past two years?”
This question is usually either answered quickly and confidently or it's met with some reservations and possibly excuses. It's the most predictive question I ask. Leadership stability is more important than most people realize. It determines whether you can build a team that lasts, or if you'll be rebuilding the foundation over and over. With each new leader, you are always going to have to prove yourself and your team to them.
Questions I ask them:
"What has leadership change looked like over the past two years?” (I use exactly this wording, then stay quiet and let them fill the silence)
"Why is this role open?" (Whether it's new growth or backfill tells you everything)
"Who would I report to, and how long have they been in their role?"
"Walk me through a recent conflict between product and engineering. How did leadership handle it?"
What I am observing during interviews:
Do they answer the leadership question quickly and confidently, or do they hedge?
When discussing challenges, do they blame individuals or describe systems problems?
Do different interviewers tell consistent stories about priorities and direction?
How do they talk about people who left? ("Wasn't a culture fit" is a red flag; "moved to a great opportunity" is normal)
Does your potential manager speak about the team with pride or exhaustion?
Do Your Research:
I check LinkedIn for how long leaders have been there (C-suite and my potential manager), look for red flags like too many executives for the company's size, and scan Glassdoor for phrases like "constant reorgs" or "unclear priorities." PE-backed companies get extra scrutiny fro me, I want to know if they respected the people who built the place or just stripped it for parts.
Red Flags | Green Flags |
|---|---|
More than two C-suite changes in 18 months | Leadership team has been stable for 2+ years |
Evasive or defensive answer about why the role is open | Mention departures, that are explainable and normal (retirement, promotion elsewhere, family reasons) |
Your potential manager has been there less than six months (Depends on the person and their background) | Clear, consistent story about company direction from everyone you talk to |
Multiple reorgs mentioned casually, as if that is normal | Transparent about challenges without scapegoating individuals |
Different interviewers contradict each other on company priorities or strategy | Role is new because they're growing and scaling, not because someone burned out |
Blames "the previous leadership" for current problems | Your potential manager has been there long enough to have built trust and knows how things actually work |
Pattern of short tenures across the leadership team | They can name specific improvements leadership has made based on employee feedback |
Why This Question Matters:
I have personally worked at two different companies where leadership changes were constant. I can attest that an unstable leadership means constantly shifting priorities, reorgs that will undo your work and the relationships you've built, and some executives will be out to prove themselves rather than viewing others' competence as an asset.
In these environments, trying to implement a design system, build research and design into the DNA of the company, and create a culture of trust and innovation becomes such a struggle that you can easily lose focus on the work that you were hired to do in the first place.
Having solid leadership that instills a culture of trust and confidence is a place you'll want to work at forever. You and your teams will come to work every day focused on the goals of the users and the business, and you can make a real difference. I've experienced both versions, and I'm only interested in the latter now.
Question 3: "Tell me about a specific user whose life improved because of your product.”
This is a question that any experienced designer or researcher can answer very quickly. We all have those moments where our work has stuck with us and made us think, "This is why I do this work." So when asking a potential employer, you'd expect that same level of excitement and conviction in how they answer.
Questions I ask them:
"Tell me about a specific user whose life improved because of your product."
(Then I shut up and listen to how they answer)"What problem does this product solve that users can't solve another way?"
"How do you know your users? What's a unique thing you learned from talking to them?"
"Walk me through your most meaningful user research finding from the past year."
"If the product disappeared tomorrow, who would actually care and why?"
What I am observing during interviews:
Do they tell you a story about a real person with details, or do they recite features and metrics?
Can they name specific users, or do they speak only in demographics and segments?
Does their energy shift when talking about user impact, or is it flat and rehearsed?
Do they mention users spontaneously throughout the conversation, or only when directly asked?
When pushed, can they connect technical decisions back to user outcomes?
Do Your Research:
For public products, I scan app reviews and social comments, but take them with a grain of salt since we've all dealt with those impossible-to-please users and competitors who are willing to do anything. If you know SEO, check whether their traffic is organic or paid; tells you if people are finding them naturally or if they're spending big to get customers in.
Red Flags | Green Flags |
|---|---|
Can't name a specific user or tell a concrete story with any detail | They light up when telling you about a specific user |
Answer is entirely about business metrics: revenue, retention, engagement, with no human element | Story includes real details, such as a user's name, their situation, what actually changed for them |
"Our users want..." but can't explain how they actually know that | Multiple people across the company tell you versions of the same user stories (means it's real, not just marketing) |
Mission statement uses words like "empower," "transform," "innovate" without specifics | They can connect features to user outcomes without you having to ask |
When pushed for examples, they pivot to technical capabilities instead of outcomes | They share a recent research finding that surprised them and changed the product direction |
Product solves a problem that only exists because of their business model | Clear articulation of whose life improves and how you'd measure that improvement |
They've never actually met a user | Leadership has met users personally and can talk about those conversations |
Why This Question Matters:
How they answer will tell you a lot about how they think about research and design in their organization. Did they get as excited as you do when you get that question? Mission-driven work produces better design. When you know who you are building for and why, you make better decisions. The stakes become real, and when tradeoffs need to be made, you understand what those really mean on both sides.
I've built product flows that have made people cry tears of joy, and had them asking, "How soon can I have this?” I've also had people look confused and unsure. I have enjoyed every reaction because it has made my work better, my teams stronger, and pushed me further. A company that listens and understands its user base will have the same if they are dedicated to being user-centric.
What This Framework Actually Does
These three questions aren't about finding the perfect company. Mainly because that doesn't exist. They're about setting yourself up for success and laying all the cards out on the table for you to make the best decision for yourself and your career.
I know that everyone has different circumstances, and some may have to take the first offer that comes along. You should always do your homework anyway, so that you have some idea of what you are walking into. I've worked for companies that have passed all these questions, at least in my eyes, and I've also worked for ones where they have passed none of them. The difference is in the outcomes I (and my teams) were able to produce for the business and the users. It's also about how I view my time there and how I talk about it years later.
The companies that have passed these questions? Those are the places where I have built things that have lasted. My teams were able to thrive, the products genuinely helped people, and I left those roles because I had accomplished my goals and not because I felt the foundation falling out from under me.
These may not be your three questions, but if you don't already have your values and your "must-haves" in place for your career progression, now is the time to start.