How I interview people for my design team, peers in other teams and my potential boss

The “Bobs” from “Office Space”

Hiring is the manager’s most important responsibility. The results of the process and the effort put in will make or break our team.

Every great manager I’ve known can proudly recount their best hires and walk you through how they blossomed. Those same managers also have stories where they failed by missing an indicator, breezing through the process, or going against their best judgment. And they can tell you about the resulting sleepless nights, stressful conversations and ruined team dynamics.

So, I’ll say it again — hiring is the manager’s most important responsibility. And it is a skill we should all be constantly working to improve. There is nothing innate about it.

In this piece, I’ll provide a high-level overview of how I interview people at different stages in their careers, taking their current role and the one they’re applying for into account.

I do not claim to be a hiring expert. I’ve hired some amazing people over the years and I’ve made some mistakes. But, I’ve done my best to examine the good and the bad to constantly improve how I interview and who I choose to hire or recommend. Feel free to take and adapt as much of this as is useful for you, and if you have questions or suggestions, please let me know.

Interviewing people who are new to the field

The number one factor that I look for is potential (as I noted in a previous piece about hiring junior designers). No matter the level of the role or the person’s years of experience, I want to know how they’ll grow within the team and what types of responsibilities they’ll likely take on over time. If I bring someone in as an Associate Designer, I want to have a feel for how long it may take until we’ll trust them to own the design for a significant area. If I were to hire a Product Manager, I want to have a feel for their ability to take on multiple products in time. Or if it’s a Dev Manager, I’ll dig into whether I feel this person will be able to build and manage a larger team, eventually managing other managers.

It’s less about where this person has been compared to where I think they can go.

work + attitude + drive = potential

  • Their work — does their experience to date provide a strong foundation for future growth? Does it demonstrate unique skills?
  • Their attitude — are they positive? Not in a happy go lucky way, rather do they view challenges as opportunities?
  • Their drive — Are they motivated to learn and solve challenges? Are they excited about crafting a product that will help people? Did they revisit work that they weren’t happy with after the assignment ended?

The search to understand potential guides my entire process. From the first view of their resume through the in-person interviews, I’m trying to understand if this person is someone that I’ll need to nudge forward or if I’ll be running to keep up.

Six questions I ask people looking to join my team

Of the projects you’ve worked on, which are you most proud of?

This is a great way to kick off the conversation as it leads on a positive note and gives me a view as to how the candidate thinks. It often segues well into the next question as many people are most proud of their hardest projects, which drove them to learn and improve.

Which was the most challenging?

This is one of the most important questions I ask. The candidate’s answer provides insight into where the candidate feels the most challenged and their level of self-awareness. The specific challenge is rarely important. What I’m looking for is how they recognized that they were facing an uphill battle, how they sized it up and how they achieved success.

If you could redo one of your projects, which would it be and what would you change?

We all have examples of projects where there just wasn’t enough time or we weren’t as skilled as we wished. This question provides a view into how they’ve had to handle tradeoffs when reality meets creativity.

Please provide an example that shows where you successfully made the case for your idea. What was the opposing idea?

This strikes to the heart of communication and influence. A lot of our work is subjective, so it’s important that a candidate be able to show why she’s made certain choices clearly to those she works with. The followup question looks to see if she took the time to understand the opposing viewpoints or just pushed ahead.

Can you show me an example where your idea wasn’t used?

Following up from the last question, I want to understand how the candidate handles setbacks and whether she recognizes that good ideas can come from many angles. It also provides a view into collaboration and individual versus team orientation.

What do you want to learn next?

I love to know what people are excited about and the gaps in their skillsets thatchy want to fill. It also highlights their natural level of curiosity.

Interviewing potential peers

When I’m interviewing someone who’ll work closely with me on different team, I focus on the skills needed to be successful in their job and how they like to work with others (what does a PM think the Designer’s role should be? How does an Engineering Director view the working relationship between Development, Product Management and Design etc.). I want to understand:

Do they know the job?

If they’re interviewing for a Product Management role, can they handle it in our environment? Do they understand what they would and wouldn’t be accountable for? Have they worked in similar environments and made a positive impact?

If they’re interviewing for a leadership role, I want to know if they lead in a manner consistent with our culture (leaders serve their team, ensure their people can grow, and hold their team and themselves accountable).

Do they play well with others?

Their ability to collaborate and help their team and the large org is more important than most of the bullets on their resume. Diving into their experience handling challenges and navigating professional relationships sheds light on how they interact. I want to see them credit their team instead of focusing on their own wins.

Would they fill gaps beyond the job description?

A unique combination of skills, experience or perspective can help this person drive the company forward, so if I spot an interesting area beyond the job description I like to dig in. For example, a PM who comes from a different industry and is particularly data-oriented may see something in a wholly different light when reviewing our usage analytics. She may raise and answer questions we hadn’t thought to ask.

Five questions I ask potential peers:

Most of my questions are role-specific but there are some that apply across a wide swath of candidates.

Why are you interested in this role and company?

I want to know if they did their research and which areas from that research and any previous conversations are particularly enticing. Ideally, they demonstrate that they are running toward this opportunity and not away from their current situation.

What’s the biggest frustration you deal with as a [their current role/role interviewing for]?

This helps me understand the level at which they’re currently working and helps to uncover some innate preferences or biases. Answers may range from technical/tactical roadblocks to communication and collaboration issues. How they communicate these frustrations is critical. Do they fall into griping about other people or do they acknowledge that there is a frustrating situation and shift into how they handle the frustration in a smooth manner?

How do you work with [other teams]? Where do you see overlap and where are their clear lines of responsibility? How do you navigate those gray areas?

We all have to work with other teams that may have similar or opposing goals. In many cases, lines that were once well defined have become fuzzy. Designers are far more involved in product strategy than they were five years ago and some Developers have insightful views into usability, so understanding how this candidate navigates those waters and how she collaborates is important. In some cases, people want to hold tight to strict role definitions and responsibilities, which raises a flag for me.

Can you tell me about someone you’ve helped in your career?

There’s no right answer to this question, though there is definitely a wrong one: “nobody”.

What do you want to learn next?

This question is as important for a peer as for anyone who could join my team.

Interviewing my potential boss or someone “up the chain”

I’ve interviewed potential bosses a number of times from both sides of the table. The first few times were…weird, admittedly. The shift in dynamic took me a bit to get used to, but as I gained experienced, I became comfortable asking hard questions and digging in. I now know that I can only be successful working for someone who expects and values being challenged (in the right way at the right time), so I look for that in my potential boss along with several other factors. I want to know:

Our dynamic

  • Do they expect to be challenged on their assumptions and will they provide perspective and justification for their opinions?
  • Do they communicate well?
  • Will they hold their team (and me) accountable?
  • Will they provide me the feedback that I need to hear when I need to hear it?
  • What can I and those on my team learn from them? (This is hugely important)
  • Will they trust me to execute?

Their potential and plan for growth

  • What does their career path look like and how do they aim to achieve their next step?
  • How will their growth likely impact our team and the company?
  • How does that path map with what I think our team and company need?
  • Is there anything that I might be able to teach them?

The impact of hiring them

  • Does it feel like they have a grip on what they’d be walking into, at least in rough terms?
  • Have they faced similar situations in the past and did they manage them well?
  • Will they guide everyone involved appropriately? Do I think they’ll be able to manage up as well as manage down, representing our team well and shielding it where necessary?
  • Where is their ego based? Is it in the success of themselves or the success of their team?

Eight questions I ask potential bosses:

What role do you see [my team] play in [the ___ organization]?

For example, “what is Design’s role within the Product org?” This question gets to the heart of whether we’re going to be aligned in our worldview. If their answer is significantly different than what I think it should be, I’ll dig in to better understand their thoughts and determine if I may be missing something. If they view the landscape in a manner similar to mine, I’ll probe for any differences to see how they may help my team grow.

Have you helped a company shift from [our current size/scale] to [the next significant level up]? What strategy and tactics have worked for you?

When hiring a senior leader into a growing company, there are typically known areas that need improvement, often related to scaling up to the next level (revenue, company size etc.).

Have you helped solve [a specific pressing challenge our team/company is facing]?

Similar to the scaling question, I like to develop an understanding of where their experience can be directly applied to solve some of the big challenges my team is currently facing. I’m also curious if their solution is similar to what I would expect or significantly different than I think we should go.

How do you structure and interact with your direct team?

I want to know if they’re going to be particularly hands-on or hands-off and the rhythms and processes they like to follow. I also want to understand what changes would likely come were they to join the team.

How will you measure my success and that of my team?

Knowing up front how they view my role and that of the team is critical. This question gets to the heart of their understanding. If the types of metrics they apply match mine, we’re in a good spot, but if they’re significantly different, we need to dig in further. For example, as a leader of a Design team, I would not expect to be measured on revenue but would on customer satisfaction or the ability to hire and train effective teams.

From what you’ve heard so far, what sounds like it is working well and where do you think you can help us improve?

This provides a view into what they’ve learned from their research and previous conversations as well as their understanding of the challenges we face. Their response in terms of how they can help us improve helps me to understand the unique skills they can bring to the table and/or correct any misunderstandings.

How would you spend your first 90 days?

I want to know if they have a plan before walking in the door. My hope is that they have a rough outline of the types of things they will do, but that they aim to hold off on major changes until they’ve had the opportunity to observe and learn from their interactions and the day-to-day reality.

What concerns do you have about the company or role?

The answers to this question can be fascinating , revealing a lot about the candidate. It provides an opportunity to provide more detail and reduce, if not eliminate the concern.

On Interviewing

A few general notes on interviewing:

  • I aim to ask the same set of questions to every candidate for a role with a few additional ones added in based on the conversation. This helps provide an even playing field for candidates.
  • There is rarely ever a “right” answer in my questions as so much depends on the specific person, their background and the role we’re trying to fill.
  • As I noted in T-Triple-C, I have some key attributes I look for in every interview, no matter the role and no matter which side of the table I’m on.


I’d like to wrap up by thanking Vitorio for suggesting this topic. He’s been an active member of the Austin design community for a long time and routinely introduces alternate perspectives and thoughtful responses to discussions.

Photo of “The Bobs” from Office Space from 20th Century Fox

If you have thoughts, questions or suggestions, please weigh in. I’d love to hear them!

Originally published on my personal site.


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