Find, Vet and Close the Best Product Managers

Find, Vet and Close the Best Product Managers

Todd Jackson is skilled at identifying excellent product managers. Now Dropbox's VP of Product and Design, he shares his process here.

Todd Jackson has been a part of product organizations across some of the best companies in the Valley, from Google to Facebook to Twitter, after it acquired his own startup, Cover. Now VP of Product and Design at Dropbox, he’s worked with hundreds of product managers — and hired dozens — over the course of his career.

When Jackson was at Twitter, the company surveyed its engineering, product and design teams, asking what they thought and knew about each other’s areas of expertise. While everyone was clear on what engineers did (write code), and the majority could describe the responsibilities of designers, less than half of respondents knew what product managers actually did. This seemed like something the product team, and Jackson in particular as Director of Product Management, should dig into. (Unsurprisingly, it turned out the PMs knew exactly what everyone else did).

As he asked more people what they thought PMs did, he realized that everyone had different answers. “I think that’s because the PM role needs to be purposely flexible, almost by design,” he says. “A PM basically sits at the center of UX, technology and business. You may have heard the quote: ‘The PM is the CEO of their product.’ I think that’s pretty accurate, but it also means they have to do a lot of diverse things well, and good ones are extremely hard to find.”

In this interview, Jackson explains how startups can define the type of PMs they need, source candidates, ask the right interview questions — and, perhaps most importantly, convince them to come work for you.


The best product managers do three things:

  • Articulate what a winning product looks like.
  • Rally the team to build it.
  • Iterate on it until they get it right.

Doing this well—no matter what you’re building or environment you’re working in—requires a specific set of qualities. Jackson breaks them into three categories: Must Haves, Good To Haves and Bonus Qualities:

Outstanding intellectual ability and the ability to synthesize information both help a PM identify what a winning product will look like, and how it will succeed strategically in its market. Excellent communication, leadership and effectiveness within the company culture are required to articulate the vision for that product and get others excited to devote their time and energy. “I’ve never seen a truly great product manager that did not have all four qualities in the Must Have column,” Jackson says.

In the Good To Have column, technical background and entrepreneurial spirit will help a PM gain the loyalty and credibility they need to motivate the best work from engineers and designers. Analytical and strategic thinking are necessary for constant, smart iteration. Most well-known tech companies like Dropbox will only hire PMs who have both columns A and B covered.

The bonus features, like writing code, creating mockups, and running their own analysis is what you might look for in an early hire or on a small team. They’ll maximize your productivity per person. At larger companies, you tend to have more people to specialize in these tasks so PMs don’t usually need to. It’s always nice to have them. They’re just more critical at some times than others in a company’s life. The extra effort should be made for a first product hire, Jackson says.

“This definition of what a PM needs to be and have is probably 70% right for most companies,” he says. “But if you’re a SaaS company with a huge sales team, you might have a different archetype in mind than if you’re a 40-person social app company.” So think about what’s core to the success of a PM at your company and then what the more “elective” attributes might be that are tailored to your industry and product in particular. Actually write the list. It makes a big difference to see it laid out visually when you start talking to candidates.


As you search for a PM, you’ll get a blend of proactive applicants and referrals, but it’s also a good idea to source candidates yourself on LinkedIn. The latter will give you a more refined sense of who's out there with what experience and how that maps to what you need the person in the role to do.

While there is no single successful PM archetype, Jackson likes to think there are a handful of PM personas that can work well. All five of the anonymized profiles below are representative of amazing product managers he knows personally, and show the breadth of diverse backgrounds that can make great PMs. “It’s important to look for diverse experiences and backgrounds,” Jackson says. “Your users and customers are likely a diverse set of people, so your employees should be too. This can actually be a big competitive advantage over other companies that think too rigidly or homogeneously about their hiring.”

The Classic Choice

This is the resume with a more conventional PM background:

  • Computer Science undergraduate degree from a school like Georgia Tech, Brown, Rice or University of Illinois — schools with great CS programs
  • Founded a non-profit community summer program in college
  • Product Manager at a large tech company, worked on advertiser-facing products and then video products

“I like the range of experience here,” says Jackson. “Experience working on advertiser and publisher-facing products, as well as consumer-facing video products around search and discovery. Plus she had the initiative to start a non-profit. This is someone you definitely want to talk to.”

The Rookie Prospect

  • Robotics undergraduate degree from Olin College
  • Course Assistant for a History of Technology Class
  • Product Management Intern at a large tech company

“Whenever you’re talking to someone who has no full-time work experience, it’s a very high-risk, high-reward prospect. So you have to do your best to look for evidence of their capabilities. The number one sign I have here is that they went to Olin College, which some folks might not have heard of, but I know by reputation produces great product managers,” says Jackson. “The PMs I've known who went to Olin were all very technical but also creative. Their course assistant work is a touch of the humanities. It’s a technical background married with creative user-facing experience. Definitely worth a phone call.”

The Management Consulting Refugee

  • Psychology degree from Emory
  • Data Analyst at a startup developing search technology, including web crawling and document processing tools.
  • Senior Business Analyst at a well-known consulting firm

“You see this profile pretty often these days — people who want to get into tech from consulting or finance,” says Jackson. “And a lot of them would make great product managers because they have the analytical thinking and strategic mindset. But you have to make sure they have a true passion for technology and solving user needs. Also, are they going to be willing to collaborate effectively with engineers and designers or just provide directives and assume their instructions will be followed? These are the two most common pitfalls I see when hiring people from this background.”

The ideal version of this profile includes what this sample resume has: some experience working in technology. Technical background is a good indicator of problem-solving ability and a desire to build things. But even then, the culture at some consulting shops conditions people to lead through force or command-and-control methods rather than excitement and influence. “When you talk to these candidates, always ask them about how they lead — and you want to hear them to talk about how they lead through example.”

Engineer/Designer Turned PM

  • Senior member of technical staff at successful SAAS company
  • Software engineer at a small startup focused on productivity software
  • States in her LinkedIn summary that she has “a strong interest in usability and likes direct interaction with users.”

“I love this type of profile because you know if this person actually has the product skills you’re looking for, they’re going to be great at working with the engineers or designers on the team,” says Jackson. “If someone’s entire experience is in engineering, you want to look for other signs that she is a product thinker. Here it’s in the person’s summary, but not every engineer will say something like that.”

In the absence of a clearly-stated interest in or experience with product, you want to look for evidence of the person taking on steep learning curves and growing fast. Did she teach herself new programming languages to work on a project? Did he rise swiftly in an organization? Those actions indicate that they’re entrepreneurial enough to flexibly shift into a product role.

Marketer/Biz Dev Turned PM

  • International Business and Marketing degree, Cal State Poly
  • Co-founder, a startup focused on developing social ads and products
  • Business and Corporate Development at a large tech company

“This one can be challenging because many great marketing and biz dev people can dazzle you — they are really good at talking about tech products, but you have to be careful,” Jackson says. “Can they really build stuff? Have they built anything in the past?”

Let’s say that while at their last company they led deals where they had to understand technical and product integrations — that would be a positive indicator. Also, as a co-founder, this person built and launched products from scratch.

“You can see that a CS degree isn’t always required,” he says. “But it does help. If they don’t have a technical background, then they should have impressive entrepreneurial experience mentioned elsewhere in their past roles.”

Todd Jackson, Dropbox's VP of Product and Design


The typical PM interview has three stages: phone screen or coffee, the one-on-one in-person hiring loop, and the panel presentation.

The screening process is mostly about finding mutual fit. If you’re hiring for a startup, roughly half the time should be devoted to convincing the person to come in and talk to the rest of the team. The caliber of the people you go after and the fact that your startup is probably unknown means you’re mostly in sell-mode.

When it comes to the one-on-one hiring loop, who you choose to include from your side depends on the size of your company.

Let’s say you’re at a small startup with less than 100 people. You’ll want the top PM candidates to speak to your founders, the other PMs on the team (if any), your engineering lead, a design lead, and a business lead.

If you’re at a large company with more than 500 people, let’s say, the rules change. You want these candidates to talk to your VP Product, two to three other PMs on the team, the engineering lead, design lead and business lead.

These are the stakeholders that will probably interact with the person on a daily basis, and they’ll illuminate different aspects of their experience and personality. In all of these conversations, the goal should be to see how well the person fits this list of criteria:

  • Intellectual ability
  • Communication
  • Leadership
  • Effectiveness within the company culture
  • Knows what users want
  • Strategic/Analytical Thinking
  • Technical background
  • Entrepreneurial spirit

Below, Jackson lists some of the questions he’s found to be the most valuable when interviewing product management candidates in person, what he believes good answers sound like, and the responses that should give you pause.

QUESTION 1 (Product Sense): Name a product that you think is exceptionally well-designed – ideally a non-electronic product. Tell me what makes it well-designed. (Testing intellectual ability, communication, and whether they know what customers want.)

WEAK ANSWER: Something superficial or cliché. “If they don’t go into a lot of detail and say something fluffy like, ‘My electric toothbrush is so great, it’s won a bunch of design awards,’ that’s a strike against them.”

GOOD ANSWER: First, the candidate will get excited to talk about a product they admire, and it will show. “One of the best answers I heard was about the Micro Kickboard scooter for kids – I remember the candidate getting really excited telling me all the details: ‘I recently noticed how thoughtfully designed my niece’s scooter is. It’s the mini scooter that you see a lot of kids riding lately. It’s got two big polyurethane wheels in front and a third small one in the back, so it goes over cracks and bumps smoothly and prevents faceplants. Also, instead of handlebars that turn, it has a ‘lean-to-steer’ design which is really intuitive for kids, teaching them how to steer by shifting their weight. And it’s also just super easy to assemble and disassemble—basically just two parts that click together.’”

Particularly strong candidates will look at the product from the user’s perspective and talk about the problem it solves. In the above example, “the candidate spoke about how the users of the product (kids) are actually different than the customers of the product (parents) and all the product design and marketing ramifications of that, which I though was quite insightful.” The candidate will have a lot to say and will be very enthusiastic as they speak, especially about the very small details that provide a finished and delightful experience. “That’s how you know the difference between a passionate product person and someone who just wants a job.”

To take it up a notch, you can follow up with the question: “What would you improve about it?” or “If you were the CEO of the company that produced this product, and you wanted to sell 10X as many, what would you do?” Look for educated guesses or reasonable assumptions about the market for the product, who the target buyer is, how the market could expand, the constraints of production, etc. Those are the components that should drive the next best step for the product, it shouldn’t just be a random idea.

Note: It can be easy for PM candidates to prepare for this question. You can make sure they’re thinking on their feet by constraining the space they choose from. For instance, the example must be a physical or non-electronic product or one they have at home.

QUESTION 2 (Technical Skill): In as much detail as possible, tell me what happens when I type into my browser and hit enter. (Testing intellectual ability, communication skills and technical background.)

WEAK ANSWER: Their response might be rudimentary or confused. You could get an answer like, “I see the Yahoo homepage, right?”

GOOD ANSWER: Something like, “Your browser generates an HTTP request. A DNS lookup gets the IP address of the host. The server receives the request, checks for cookies to see if you’re logged in, and eventually generates an HTTP response containing the content you should see. Your browser receives the response, parses the DOM and starts to render the page. CSS, images and Javascript are loaded to modify the page.”

The strongest candidates can answer this question in good detail, taking about five minutes to walk you through the process. This is a good level-setting question for product managers so you can see where they stand technically. They don’t have to hit every single action that happens. Watch out especially for candidates who say they’ve programmed in the last few years but are clueless about this question. That’s definitely a red flag.

If you think that candidates may have prepared for this type of question, you can mix it up by drilling them on specifics at various junctures of their response. Or you can ask them similar questions about the fundamentals of iOS or Android programming if they have a lot of mobile experience.

QUESTION 3 (Leadership): Tell me about a time when you disagreed with engineers and designers on your team. What did you do? (Tests communication, leadership and effectiveness within the company culture)

WEAK ANSWER: There will be allusion to finger-pointing, or mention of blame. The tone of their response will be generally negative, and you might see a dip in self awareness, complemented by a spike in defensiveness. They’ll be more concerned with smoothing over their role in the confrontation than sticking to the facts.

GOOD ANSWER: They’ll demonstrate leadership by diagnosing root causes of the conflict. They’ll show humility. “One candidate told me she couldn’t agree with her engineering and design team on one feature — they all wanted to build it and she didn’t. She said, ‘Okay let’s time-bound it. We’ll do the idea, but if it doesn’t pay off in four weeks, we’re going to change it to this other idea.’ I thought that was a great solution to avoid gridlock.” The candidate knew when to push back and when to disagree and commit.

A candidate who ends their response by saying what they learned from the situation and how they applied these lessons going forward should get serious bonus points.

QUESTION 4: What are all the implications of self-driving cars? (Tests strategic and analytical thinking and entrepreneurial spirit.)

WEAK ANSWER: A response that is boring, cursory, or disorganized. They might throw out some obvious answers, like unemployment for taxi drivers, or self-driving big rigs. But they won’t go deeper into the ripple effects in other industries that will create a whole new wave of businesses. They’ll stay in the inner ring of cause and effect.

GOOD ANSWER: Showing vision and imagination, they’ll paint you a picture of what could happen. Maybe car seats will be arranged in a circle around a coffee table! No one will own cars anymore, which means no one will have garages anymore. “I got an amazing answer to this one the other day: ‘Google will open-source the software for self-driving cars so that any manufacturer can build them, the way they offer Android,’” says Jackson. “I have no idea if that will be true or not, but I thought it was pretty creative.”

Most importantly, the answer should come packaged in some sort of organizational framework. Maybe they’ll say how life will change for drivers, and then the auto industry, and then urban planning. Ideas should be presented within themes, not as a free-association jumble.

QUESTION 5: What aspect of product management do you find the least interesting?

WEAK ANSWER: A PM who complains about doing nitty gritty work (e.g. taking notes, scheduling meetings) and implies that these things are beneath them.

GOOD ANSWER: A great PM understands that they need to lead from the back, and they relish their role as an unsung hero. The candidate doesn’t have to say they love the tough nitty-gritty stuff, but they should get points for acknowledging the grungy parts of PM work and why it’s important to be in service to the team and mission their supporting.

QUESTION 6: Why do you want to work at this company or on this product?

WEAK ANSWER: “X industry/company is getting a lot of buzz. Everyone is talking about it. It’s really hot right now.”

GOOD ANSWER: Clearly passionate about the industry, company or project. Look for specific ideas and plans for what they’d want to do and how they want to make things better. This indicates that they really did their homework and have thought deeply about the company. In particular, keep your eyes peeled for long-term thinking, which indicates commitment to the industry or type of product. For example, is the person talking about what robots or drones will look like in 5 or 10 years? Or do they just talk about how robots and drones are exciting now? Here are some examples:

  • I’ve always wanted to work in X industry, I’ve done Y and Z in the last couple years to really prepare for this career move.
  • Company X has a huge competitive advantage because of Y.
  • I have been using product X for a while, and I really like feature Y. I think feature Z could really improve growth/engagement/monetization and here’s why...

You want people who are excited about the space, not just this one opportunity.

Panel Presentation

After a candidate has made it through all the one-on-one interviews, you should stop and evaluate. You have the chance to save everyone a ton of time if they’re not a good match. So make sure that it’s a good fit on both sides (and that everyone’s equally excited) before proceeding to the next phase of the process: The panel presentation.

“I like to ask candidates to come and give a presentation in the office around a conference table for 8 to 10 people,” says Jackson. “This is a good way to see how they do in a group dynamic, how they present their ideas, and how clearly they express themselves.”

The prompt he gives them is pretty complex:

PART 1: What product or service has launched in the past two years that you believe is particularly revolutionary? What does this product improve for its customers? What about it is well-designed? How will the product impact market conditions and the competitive climate in its industry?

PART 2: Identify three areas of the product that could be improved. Explain how you would change the product to address these issues and how you’d test whether these changes had a positive impact.

Candidates are asked to present for an hour with 15-20 slides.

“I’ve seen some really great presentations,” says Jackson. “A really memorable one was about Class Dojo, which is educational software. The candidate actually set up the environment like a Class Dojo classroom so all the people on the panel got gold stars when we asked good questions. It was really entertaining and interactive. But really you’re looking to see how deep the person goes in their thinking. How fluidly do they communicate? Presentation matters. Most importantly, how do they deal with Q&A on the spot, because PMs have to be able to handle a constant flow of hard questions.”

Bottom line: You want PMs who are spokespeople. They have to be able to represent themselves, their work and the work of their teams every day. Their job will be good communication. They have to be clear, organized in their thinking, and quick on their feet.


Once you have a candidate you love, it can be tragic to lose them. The close is like a gymnast sticking their landing. It’s really what matters in the end. Ironically, the close process starts at the very beginning of your interaction with a person.

First and foremost: You need to over communicate and remain in frequent contact with all candidates. They should never feel confused or unsure of where they stand. Be hands-on. Don’t delegate this to recruiters. Stay involved and available. There’s nothing more damaging to candidate experience than someone feeling like your company doesn’t care about them.

This seems obvious, but there are a few closing tricks that are specific to PMs.

“I like to think about the reward centers in the PM brain,” says Jackson. “There’s several big ones I can think of: having impact, delighting users, sense of purpose/mission, having autonomy, getting recognition, financial outcomes, learning/growth, etc. In my experience, more than other disciplines, PMs tend to care most about impact and autonomy.”

This is unique. Engineers are often motivated by really interesting technical challenges. Designers can be motivated by craftsmanship and feeling of community. Of the reward centers that are important to PMs, one will stand out more for a candidate. It’s different for everyone, but you want to figure out what that one, most influential factor is. You can even ask a candidate to stack rank them in order of importance.

Once you know what drives them, describe in detail how that will manifest in their role at your company. For example, if autonomy is most important, talk about the opportunities they will have to lead projects on their own. If user delight is most important, talk about past releases that have gotten enthusiastic reception. If impact is most important, talk about how what they’ll be doing rolls up to move the needle on a company-wide objective.

“If you can honestly describe to them how they’ll get the reward they want most, you’ll close some great candidates,” says Jackson. “Just make sure you deliver on whatever you promised. The only thing more important than hiring the best PMs is keeping them.”