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How to Hire a Brilliant Product Manager

Updated: April 1, 2022

At the First Round Capital talk, Todd Jackson, the VP Product of Dropbox, discussed how you can find, evaluate and close top Project Managers for your company.

We loved the concepts at his talk and made a summary for your ease!

The Project Manager’s role is commonly vague.

From an internal survey on Twitter for engineers, products, and design. They’ve found out that most of the answers show that the PM roles and responsibilities are not clear to them.


So what does a Project Manager do?

Project Managers have the responsibility for the success of a project. From initiation, planning, and design. To execute, monitor, control, and closure of a project.

The PM is the CEO of their product.”

Todd Jackson, VP Product of Dropbox


As Todd’s definition, a Project Manager needs to articulate what a winning product looks like. Rallying the team to build it and iterating until they get it right.


What kind of qualities of people who can do this job?

Qualities to look for your future Project Managers can be divided into three categories.

The must-have should have, and bonus qualities.



1. Outstanding intellectual ability to process and synthesize info
2. Excellent Communication
3. Demonstrated leadership
4. Strong culture fit



1. A knack for knowing what users/customers want
2. Strategic / Analytical thinking

3. Technical background

4. Entrepreneurial Spirit



1. Writes code
2. Creates designs
3. Runs quantitative analysis


After having these qualities considered, a question to ask for yourself is this –

What responsibilities do my Project Manager will perform in my company. And what are the qualities I am looking for?


Here are the 3 steps to hiring your next Project Manager:


1. Searching for the right candidate

When finding your Project Manager, remember that there will be no single PM archetypes but there are a handful of personas you can choose from:

a. The Slam Dunk the resume that shows classic product manager pedigree

This candidate is a graduate with a Computer Science degree from Brown University. Became a Software Engineer for a summer program in college. Associate Product Manager for video and advertising products and then a Product Manager for a large tech company.


b. The Rookie Prospect very high risk = very high reward

This one doesn’t have full-time experience because you’re hiring them straight out of college that’s why it’s a high-risk and high-reward candidate.

But what make this person interesting and the factors that you might want to take a shot on this person are these:

1. They went to Olin College, which is a great school for Project Managers. They are technical but in touch with creativity.

2. The diversity of experiences that are shown on the resume. This person is on the technical and creative user-facing aspects.


c. The McKinsey Refugee these are people from consulting/ finance to tech


People from McKinsey makes a great PM. Their analytical thinking and strategic mindset make them stand out as a candidate.

But before considering them as a potential candidate, you have to check and have these questions answered:

Do they have a passion for users and technology?” “Are they going to be willing to collaborate effectively with engineers and designers?”

You would like to know if they are really in for the right reasons.


d. The Engineer/ Designer turned PM engineer or designer that has product skills

Signs of a Product Manager (that can be found on this resume):

  • Focus on usability
  • Direct Interaction with users
  • Familiar with different programming languages. And the willingness to learn whatever is needed for the task at hand (which shows entrepreneurial spirit).


e. The Marketer or BizDev’er turned PM

Marketing/ BizDev’er people often dazzle you talking about products. But measure if they can really build a product.


A good point to talk about this one,

Is the CS degree or technical background required to be a Project Manager?

“It is not strictly required but it helps. And if you don’t have one, you better spike on the other attributes,” says Todd Jackson.

Images Source: Find, Vet and Close the Best Product Managers, Todd Jackson VP Product of Dropbox


2. Interviewing and Evaluating

There are 3 phases to assess your potential candidate:


1. Phone Screen (or coffee)

This is more finding a mutual fit and if you’re a start-up, half the time you’re convincing them and you’re on sell mode.


2. 1:1 Loop – Who should Interview?

You need at least 5 to 7 people and here is a great panel to interview the candidate:


For a small startup (<100 people)

(2) Founder(s)

(2) Other PM(s)

(1) Eng Lead / VP
(1) Design Lead
(1) Biz Lead


While for a larger company (>500 people)

(1) VP Product

(2-3) Other PMs

(1) Eng Lead

(1) Design Lead

(1) Biz Lead


In our fast-paced world, where change is constant and technology evolves. You’ve got to know and ask the right questions to see if this candidate has the qualities you’re looking for. And see if this person has the potential to grow and thrive in your company.

These are some good questions to ask in the interview that will hit the qualities we’re looking for in your future PM:



“Name an app you really like and tell me all the features that the team had to build to create this app. Tell me how you’d improve it.”


Qualities to look for: intellectual ability, excellent communication, and technical background

Bad answer: “I like Instagram it’s simple and fun to use”

This shows a superficial thinker who also doesn’t get into product details

Good answer: “Instagram is fun and simple because of many details done right. Editing is powerful but easy to use, etc.”

The candidate has a detailed answer and is excited to talk about the product details.



“In as much detail as possible tell me what happens when I type “yahoo.com” into my browser and hit enter.”


Qualities to look for: intellectual ability, excellent communication, and knowing what users want

Bad answer: “Mmm. I see the Yahoo homepage?”

The candidate is a little clueless

Good answer: “Generate HTTP Request, DNS lookup to get Host IP…”

The better answer is that the candidate knows the basics of HTTP request and response loop and he/she will walk you through it. It is a 5-minute worth of technical details.



“Tell me a concrete example where you disagreed with the engineers and designers on your team. What did you do?


Qualities to look for: excellent communication, leadership, and strong culture fit

Bad answer: “Contains yellow flags”

The candidate answers with finger-pointing or assigning the blame for something to someone else. There will be a lack of self-awareness and has an overall negative tone while answering.

Good answer: “Shows Leadership”

A good answer would be that they diagnose the root causes of a problem, communicates openly with respect, and demonstrated humility among the team. Has concrete ideas for avoiding gridlock, knows when to push back vs. disagree-and-commit, and has an overall positive tone.



“What are all the implications of self-driving cars?”


Qualities to look for: strategic /analytical thinking and entrepreneurial spirit

Bad answer: “Boring, superficial, and disorganized”

A bad answer would be, is that the candidate doesn’t frame their answer. Only talks about the consumer experience

Good answer: “Shows vision and imagination”

A better answer is that the candidate shows vision and imagination. He/she organizes and frames his answer very well. Example: “Ride-sharing will be more efficient, Google will open-source all its software, Uber will be worth zero, there will be a competition between Google, Uber, Tesla, Apple. “


3. Panel Presentation

After going through the interview, if you see that it’s a good fit on both sides, ask the candidate to present a presentation.


Here’s the prompt Todd gave that contains intricate topics to the candidates:

A. What product or service has launched in the past two years that you believe is particularly revolutionary?

  • What, specifically, does this product or service improve for its customers?
  • Which aspects of the product or service are especially well designed?
  • How will this product impact market conditions and the competitive climate in its space?

B. Identify three areas of the product that could be improved.

  • Explain how will you change the product to address these issues, and how would you test whether these changes had a positive impact.

In this way, you’ll be able to see how this deep this person goes, how he communicates, see them in a group dynamic, and most importantly how he handles tough Q&A on the spot.

You want a Project Manager who is spokespeople.


4. Closing your next Project Manager

After searching and evaluating, we know now that we want the PM for our company. Here’s how you close them:


a. All the usual stuff

  • Maintain free contact
  • Be hands-on (don’t delegate to recruiters)
  • Talk to your investors


b. Things that are unique to Project Managers (Rewards Centers in the PM brain)

  • Having Big Impact
  • Delighting Users
  • Autonomy
  • Recognition
  • Financial Outcome
  • Learning/Growth


Out of these reward centres, impact, delighting users, and autonomy are the factors that motivate the PM.

So the framework is this, find out which reward centre they respond to and

prove to them they’ll have [the reward center they like] at your company.

But also ask yourself the same thing, “am I willing to give this person autonomy, impact, growth… at the company?” If you are, prove to them otherwise and you’ll close some great Project Managers.

Finding the right person to join your team is not an easy task. It will need a lot of work. But we hope this summary will help ease it out and serve as your guide to build a strategy for finding your next Project Manager.