S2 Ep 6: What Is Your Best Interview Question for Product Leaders?
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Hope Gurion: With more companies understanding the value of good product management and a shortage of deeply experienced candidates, finding a product leader to lead the function can be challenging. In this episode of Fearless Product Leadership, we learn how to assess potential product leaders from seasoned product leaders themselves when they answer the question “What is your best interview question for product leaders?”
Welcome to the Fearless Product Leadership podcast. This is the show for new product leaders seeking to increase their confidence and competence. In every episode I ask experienced and thoughtful product leaders to share their strategies and tactics that have helped them tackle a tough responsibility of the product leader role. I love helping emerging product leaders shorten their learning curves to expedite their professional success with great products, teams and stakeholder relationships. I’m your host and CEO of Fearless Product, Hope Gurion.
Finding a product leader to lead the function can be challenging, especially for executive teams that haven’t had that role or for founders seeking to hire a first-time head of product. Sometimes they rely on executive recruiters who specialize in the product leadership function, but the role often requires different traits and skills depending on the company’s product management maturity, company stage, business objectives, and level and differences of understanding of what “good product” looks like. How do you get to the heart of what is important to learn about a product leader candidate quickly to assess fit for the role in your organization? We’ll learn a variety of interview questions and what makes for a good answer in this episode, and I’ll share the question I didn’t hear but believe to be critical when evaluating product leader candidates at the end of the episode.
Fearlessly tackling the question “What is your best interview question for product leaders?” are:
Sean Murphy, former VP of Product at Target and VP of Product & Engineering at CustomInk
Rachel Obstler, VP of Product at PagerDuty, former VP of Product at Keynote Systems
Hope Gurion: First, Dave Wascha describes the 4 traits he’s seeking in any product person he hires and what questions he uses to uncover the degree to which a candidate possesses his desired qualities.
Dave Wascha: I spent a lot of time interviewing people. I interview hundreds of people a year. I end up taking jobs that require kind of really growing and transforming the capacity of the company. So, I've spent a lot of time doing this; I stopped counting, but I think as of years ago, I've done 5,000 product interviews in the UK over the last decade and that's at every at level. There are a few things that I ask consistently and over whether it's a senior person or not, just to get a read on the person.
By the time, at this point in my career that I'm speaking to someone, we're not assessing them on whether or not they're a competent product person. I'm really having a discussion with them around values and personality traits and their fit within an organization. I found a few questions to be invaluable in trying to uncover some of those things; because what I'm looking for anybody, whether they're a leader or you know an associate product manager. I'm looking for someone with high integrity, I’m looking for someone who is low ego, I’m looking for someone who sees the value in collaborating in a creative endeavor with a group of people. I'm looking for a lifelong learner; somebody who has kind of curiosity inside and outside of work for how things work and they're all constantly wanting to learn new things and picking up new hobbies and they have a diverse set of pursuits outside of work. I found those three or four things to really be the leading indicators of whether or not someone's a successful product person.
So, I try to focus my questions around each of those areas; high integrity, low ego. I’m really trying to assess that I have some situational questions around times when their integrity has been challenged or when they didn't tell the whole truth. Moo one of the companies that worked for when I first moved to the UK, we really valued this and we we picked a question that we wanted to ask everyone; which is, “What's the worst thing you've ever done at work, that you didn't tell anybody about?” and you get some really - on a work level, I suppose, not a personal level - what's the biggest mistake you made at work they didn't tell anybody about? That can give you some interesting answers, but what you're really looking for there is someone who's really self-reflective and low ego and self-critical. What you don't want to get is someone who says, “Well, the biggest mistake I've ever made, was I said I was going to do 10 things and I did 20 and so I was wrong because I was much better than I was planning on being.” So, high integrity, low ego.
Low ego is crucial, I think, for a product person because they need to be able to work with, collaborate, problem-solve as a group, without egos getting in the way of those kinds of things. With leaders, one of the questions I really like to ask is, “What's been your best day at work?” and that usually catches people off guard, although now that I'm giving you the list of questions, I'm sure people will be prepared for them; but what I'm really looking for there is how do they define the things that motivate them and success and what is good at work. Inevitably, really successful leaders, their answers will really be in the context of they helped the team do something or they helped somebody get promoted and it's really about the team and others. Whereas, someone who's earlier in their career or more of an IC [individual contributor] or perhaps less suited to being a leader, would really talk about an individual accomplishment, “When I shipped this thing or I got this decision made” or something like that. There's nothing wrong with those, it's just helps you suss out what they find important, what they're naturally going to find motivating, what their default mode is going to be, certainly under times of stress etc. and so, that's a really interesting way of starting a conversation, “What's been your best day at work?” and people will often try to describe a generic best day. Then I’ll say, “No, actually, what's the specific best day? Tell me about the day” and then I will follow up with, “….and what's been your worst day at work” and that's really helpful because it speaks to what do people find de motivating. What do people - if they found themselves in the position where situation conflicted with their values or their integrity how do they deal with it? Again, leaders are just human beings like everyone else and you really want to them to help you understand how they might fit in the organization and what do they find motivating what don't they motivating?
So, I found those to be really helpful questions when I'm interviewing each level. I love asking the question, “What do you do for fun?” because again, that helps you know you understand a couple of things about a person that you're talking to. One is they have a diverse set of interests, are they lifelong learners. I think it's fairly well worth considering at this point, that certainly with engineers, there's a correlation between being a musician and being a really good engineer and I've found a similar correlation in my personal experience with being a pro and having kind of nerdy diverse, maybe the eclectic interests outside of work. I've hired people that were stand-up comedians, I’ve have hired people that designed role playing board games, I've had hired people who you know ran kind of boutique clothing kind of e-commerce sites in their spare time; inevitably or someone who sold kit to make concrete lights at farmers markets and those are some of the best product managers that I've worked with because they've had a really diverse set of interests outside of work. It also under really helps to understand again, what motivates them, what kind of environments do they enjoy, what are they when they have discretionary time, how are they spending it and are they going to be successful and motivated in the environment and what you're hiring them or not? I think that certainly, with somebody in my role that's half the job in interviewing is.
My role I'm not really assessing whether or not they're going to be a good product manager, its assessing whether or not they're going to be a successful product manager in the environment in which were operating. Then again, this goes for leaders like everybody else. So, yeah, best day at work, worst day at work, what do you do for fun? I used to have a favorite product, all of it is now when everyone's prepared for that question and so you get a kind of pat written kind of rote answer and that' not interesting or particularly helpful in in assessing people.
So, those are my typical go-to and that again, is for someone who's just out of college and someone all the way up to someone who's on hiring to be a chief product officer.
Hope Gurion: Next, Zabrina Hossain shares the two questions she uses to assess competency and technique for a prospective product leader and whether they possess a mindset for continuous improvement.
Zabrina Hossain: My go-to interview question that helps me to assess potential product is actually pretty loaded, because I can learn a lot from this question. My favorite question is, “Take me through a product that you led from strategy inception, through to launch.” This question helps me to understand a lot of things based on the person’s answer. Taking a product from the ideation phase, all the way through to launch requires product craft knowledge, a mix of hard and soft skills. It also helps me to understand how they create a product vision and then subsequently, get a team to rally around that vision. Do they deeply understand their user and the problem they're trying to solve and it also helps me to see how they supported their team during the development of that product, and then, support the go-to-market launch plans. Then, my favorite follow-up question to that is, “Based on what you learned from that product, what would you do differently?” This helps me to understand if the PM is continually learning and iterating on their own methodologies, based on their experiences, which is incredibly important.
Hope Gurion: Next, Anthony Marter describes how he turns the table on his product leader candidates, to see exactly how curious they are to truly understand the company, the role, the customers, the markets to be successful in being a product leader at his organization.
Anthony Marter: So, assessing product and assessing fit for a product manager and a product leadership kind of role using one single question. To me, this is not one single question, it's a series of sort of ways that I approach my interviews. So, whenever I'm interviewing, I usually do it in two stages. The first stage is where I bring the candidate in and I tell them I'm looking for you to ask me questions and so by doing that, I'm assisting a number of things. I'm just going to find out whether this is the right organization for them. Is it the right fit, just kind of like basic kind of stuff; but my sort of undercurrent here - I wonder if anybody will actually end up watching this podcast, that will be funny - is that I'm looking for them to show curiosity and business acumen. Are they asking any really probing questions about how this organization works? Are they asking me questions about how this organization makes money? Have they got a concept of actually, it's about the revenue, it's about the fact that we need to connect what we're doing to outcomes? Are they asking any questions about our markets: where are our markets, who are at markets doing, do we know, do we have a route to market? Also, things like what is our organization's financial structure? That's telling me all they actually thought through how their product is going to get funded. So, that's kind of my go-to, is actually saying, “Hey, interview me, interview my organization” and then what I'm looking for is that that that is hopefully emblematic of their approach to the role.
Then, the second stage is the more formal typical kind of skills interview. There's one question and this one I won't claim credit for, it actually came from one of my team; it is, “If you had a magic wand, what would you change in your current organization to make product management better?” and that's been really enlightening because you separate out the people who only have a surface understanding of what it is that they're doing, from the people who really understand the pressure side of it. How can I be more effective through the way that I work, not just by working harder? That magic wand kind of question really challenges people to go, “Well if I dropped all my assumptions, what could I do?” Sometimes, it's also insightful to then say, “Okay, well please help me understand why those things are not happening in your organization as well” because it then gives me insight into how are they as a leader, can they manage and can they manage stakeholders who they’re obviously bashing their head against to try and get these things changed or are they even pushing that change at all? They're just going to be throwing out their hands and going, “I've had enough of them. I'm out of here.” So, that that is true to be a really insightful question as well.
Hope Gurion: Next, Swapna Malekar shares why she seeks to understand how potential product leaders think about decision-making, with her go-to-interview question.
Swapna Malekar: So, in terms of the go-to interview question or a set of questions that I ask, when I want to assess potential product leaders. One of the things that jumps out to me is about a person's decision-making style, whether they are more of a consensus driven individual or more of a collaborative individual. So, one of the questions I always ask would be, “Is consensus always a good thing?” So, that is a questions I ask in a different format, depending on the conversation that I'm having with the potential hire; because again, as Canadians, we are so predisposed to being nice to each other, to be respectful, which is great, but at the same time you want to be agreeable, even in difficult situations. We don't take a decision unless everybody on the table has agreed on the solution. However, the responsibilities of a product lead is to push boundaries, make those tough hard decisions that are best for the team, for the organization, but they might not be agreeable with all the decision makers or all the stakeholders on the table. So, you need to disagree and commit at some point. This question allows me to evaluate how does a candidate think about consensus and collaboration and do they even know the difference between the two and when would they use consensus as a decision-making tool versus collaboration as a decision-making tool and how do they form that judgment during their decision-making process, I would say. So, that among a set of other questions, helps me understand the potential of a product lead when I'm hiring somebody for my team.
Hope Gurion: Sean Murphy shares the two questions that help him determine whether the product leader candidate has both relevant experience and a working style that will match the needs of his product team.
Sean Murphy: Here's my go-to question and really most of my interviews center around two questions: my first question that I ask people is, “Hey, what is your greatest professional accomplishment?” and then I spend 15 minutes talking about it. I go deep into the timeframe, the challenge, the roles what the person did versus what other people did, what the metrics were what were the pivots along the way, and I'll spend 15 minutes going deep on that.
Then, my second question is pretty similar, I tee it up. I then say, “Hey here's what the role is that you're interviewing for today, here are some of the problems that we have. Now, I want to hear about what is the closest thing that you've worked on related to this problem, whether it was a success or a failure either way let's talk about that and I'll spend another 15 minutes going deep just into that particular scenario.
Those are my two questions. Otherwise, I do things around people's cultural fit or working styles, those types of things, but really number one, what is your greatest professional accomplishment and two, what is your greatest accomplishment or failure that's most related to the problem we're facing today?
Hope Gurion: Finally, Rachel shares the three questions she relies to understand how prospective leaders think about the people and business responsibilities of the product leader role and what evidence signals for her that the interview went well.
Rachel Obstler: I would say I don't have a single go to question. The reason for that is that that sometimes you ask a question and you get exactly what you want and some really good stuff out of it and sometimes you don't. Everyone is different, and so I think you need a good set of questions to give people an opportunity to really shine. I've had times and I've asked people a question I thought I got pretty crappy answer and later I asked them another question and they answered the first question with this great answer. Sometimes it takes people to warm up a bit. So, I think it's hard to have one, but I will share a couple that I use, that have a good percentage result.
So, one of them is, I ask people an example of a really good relationship that they had with engineering and what characterized it. Then, I asked them “and then what's an example of a poor relationship and what characterized it?” and a good answer for me as someone who can answer both of those with some sort of specifics about what went wrong, especially with the second one; but then if they talked about what went wrong, what they learned from it. When I have people who said I've always had good relationships with engineering, there's a little bit of a warning sign, because I've had challenging relationships with engineering, then work at them really hard to get them to work. It may not be a signal that there's anything wrong with that person, I think it's a signal that they never had a challenging one, but they don't recognize when they do. So, that one I think is a good one, it also tells me a lot about how they think about engineering how they think about that partnership.
The second one I like, is asking people about a business case that they built, because that helps me understand how they think, how they reasoned through logic, how they figure out if something's a good investment or a bad investment and how good they are at numbers. I feel and believe very strongly in looking at metrics; I think your gut and listening to customers is very important too, but I think metrics are important and the ability to understand that a business case is not actually a number, but it's a mechanism to understand how when assumptions change, your results are going to change. The people who can answer it in that way, I know, can do business cases.
The last one I like to ask, is about a team that someone has built or managed and it's a good starting point to have a really good discussion about their management philosophy, how they've hired people in the past, how they've developed people and beyond that, what it really tells me is are they oriented around management or not. I've had a lot of interviews where I'll ask someone about building and managing a team and I actually always start my interviews here; I always start my interviews with the people side of things. Sometimes, the answers we'll get from people are all around product strategy. I just asked you about a team and you're talking to me about product strategy and I think said that a lot of people are in a lot of companies don't orient around building a team. It's either a sign of a company that focuses on product strategy but not your people, or it's a sign that it's a manager it's not very mature and hasn't had a lot of management experience or hasn't gotten to the point where they can think about people in this way or think about how do I construct the team , how do I fit together the pieces, how do I get the right skills that I need, how do I develop people.
So, anyway those are those are some of the go-tos and then the last thing I will say about this, is that a good interview for me, is one where I learn something and doesn't matter what it is, but if you say something or thought something that I’ve never thought before, I never thought about before, I love that because that also means that it wasn't time that I wasted.
Hope Gurion: Clearly, from the answers our product leaders gave in this episode, there isn’t 1 magical go-to-question that reveals everything they need to know about how well a prospective product leader will perform in a role with such a diverse set of responsibilities. I’ve included in the show notes a recap of the 14 enlightening questions our experienced product leaders shared and what they’re seeking to learn. I was surprised that no one asked the question that I think is one of the most enlightening when interviewing product leaders, which is What have you found to be the most effective ways to measure success of a product team and why? I like this question because this is not straightforward for many product leaders nor for most companies so it reveals how deeply the candidate has experienced this, how they’ve experimented with different approaches, how they think about the intersection and measurement of customer and business value, about transparency, metrics, accountability models and coaching and development of their team and whether that approach is likely to work within your organization.
If you’re a CEO in need of help assessing a prospective product leader for your organization, I’d love to be of help. Contact me on Linkedin or Twitter or schedule an initial consultation with me using the Contact Me page at fearless-product.com.
14 Best Product Leader Interview Questions
To reveal character and motivation:
What’s the worst thing you’ve ever done at work that you didn’t tell anyone about?
What’s been your best day at work? Specifically, what’s was your worst day at work?
To understand depth and relevance of product competence:
Take me through a product that you led from strategy inception through to launch
What is your greatest professional accomplishment?
What is the closest thing you’ve worked on related to our role and was it a success or failure?
What have you found to be the most effective ways to measure success of a product team?
To understand depth of business competence:
Tell me about a business case you’ve built for an investment
To understand learning and curiosity mindset:
Based on what you learned from the product you launched, what would you differently?
If you had a magic wand, what you would change about product management at your organization?
You interview me—what questions can I answer for you?
What do you do for fun?
To understand how the leader thinks about team and relationships:
Tell me about a team you’ve built or managed
Tell me about what characterizes a good/poor relationship with engineering
When do you want a consensus for a decision?