A Startup Hiring Framework

11 min readOct 22, 2020

If there was one thing that I prided myself as one of the first executives at Coursera, it was being able to hire people who were far smarter, more talented, or more experienced than I was. At a start-up where there are so many major decisions that have yet to be made, so many critical insights yet to be observed, so many twists and turns yet to be navigated, talent (at every level) becomes the difference between success and failure. But hiring well is actually really hard to do. And in the crazy, intense pressure cooker that is an early-stage start-up, it can be easy to let your hiring process or your bar slide.

As I’ve moved to the investor side of the table, I’ve been surprised that sometimes it’s even the VC pressuring the CEO to “just get someone in there.” But while “just getting someone in there” might solve a short term challenge or plug a leaky hole, startups are all about the upside. And you need to hire for that upside, even if it means enduring the short term pain of not having someone in the role. There are also real costs to bad hires, particularly at the executive level. I recently met with a company who had made the wrong VP of Sales hire (something that is unfortunately quite common). They waited about a year to act on it and are now effectively a year behind in their sales build and, correspondingly, their revenue.

This post is a response to questions that I’ve gotten from founders on how to hire. In it, I’ll share the hiring framework that I used, some sample interview questions, and the thinking behind the framework. My framework is a mash-up of the hiring process that I used at Teach For America, Google, and then adapted for the early days of Coursera. The framework can be applied to any role and different levels — though how you weight the different elements to the framework will vary. I hope you find it useful!

Start-up Hiring Framework:

Leadership and achievement

Record of past achievement (in any capacity)
Ability to influence and motivate people
Grit. Attitude toward challenges.

Comment:

Leadership is important at every level, not just for those who manage. For most roles, it was the single most important attribute that I would look for. While there are many aspects of leadership, the three areas that I would focus on were achievement, ability to motivate and influence others, and grit.
Achievement was one of the trademark things we would look for at Teach For America (TFA) — -the idea is that if someone shows achievement elsewhere (regardless of what type of achievement it is) they are likely to achieve again. I found this to be true not just with TFA teachers but in startup land as well.
In the early stages of a startup persistence and ability to maintain a good attitude in the face of challenges is paramount, and a real defining characteristic of those who succeed. As the company scales, this trait still matters, but to a much lesser degree.

2. Ability and desire to learn

Ability to learn from experiences
Introspection

Comment: This is the newest addition to my framework. I added it after a few years at Coursera after observing that the common trait among those that thrived was their ability and desire to learn. Startups change rapidly and so do the roles within them. The people who thrive were those with a learning mindset — -they loved reflecting on what we had done, what worked, what didn’t work, and how we could do it better next time. They also relished the opportunity to develop themselves as an operator and leader — -what were they doing that was facilitating their success and what were they doing that was holding them back? This trait was something I began to look for in the interview process. This trait also happens to be a key trait that I look for in entrepreneurs that I work with.

3. Strategic and creative thinking

Problem-solving ability
Ability to be generative with ideas

Comment: Google called this section general cognitive ability. I never felt comfortable with that. Am I really able to determine their general cognitive ability through this type of interview? But what I can assess is their strategic thinking skills, their ability to break down programs, know what questions to ask, as well as their ability to be generative. I’ll get more into the questions I used to assess these things, but it’s worth mentioning that sometimes to get an accurate read on some of these dimensions you need to go beyond the interview. Having them produce work products aligned to the actual type of work that they would be doing is a great way to see some of these skills in action.

4. Role related knowledge and experience

The exact things I was looking for would vary by the role and function I was hiring for

Comment: Role related knowledge and experience matters, particularly if there is no one else in the company that has those skills and experience. As I built out the enterprise team at Coursera, I used to joke with my leadership team that “at least one of us needed to know what we were doing.” But functional expertise is not the only thing that matters. When hiring for functions outside of your own functional background, I have found that people (including myself) overweight functional expertise. Functional expertise may make someone competent in a job — but it’s these other attributes (leadership, strategic thinking…) that makes someone exceptional. Shoot for exceptional.

5. Cultural fit

Mission alignment
Values alignment
Ability to deal with ambiguity

Comment: There is debate on whether and how to hire for fit. I firmly believe that hiring for fit, especially in the early stages is critical. But I also believe that you need to define what hiring for fit means. It can’t be about finding people you’d like to “have a beer with” or you risk building a homogeneous workforce. We all know that diverse teams are smarter, more innovative, and ultimately more successful. As a startup founder, you need to bake that diversity into your DNA from the beginning, and that includes building a hiring framework and process less prone to bias.

For me (and for most of the companies that I work with) the most important aspect of fit is that deep alignment and passion towards the company’s mission. It also means making sure your values are aligned, and that they are comfortable working in a startup environment.

Framework Aligned Question Bank:

This is a list of sample questions aligned to the above attributes. Instead of asking a large number of questions, I would focus on a few and really dig in to understand what the individual was thinking and feeling.

1. Leadership and achievement

Achievement: What is the professional achievement that you are most proud of?
Influence and motivate: Tell me about a time when you had to motivate a group of people towards a goal.
Influence and motivate: Tell me about a time when you had a conflict with a colleague.
Influence and motivate: Describe a time when you struggled to build a relationship with someone important. How did you eventually overcome that?

Comment: The main thing that I am looking for in the “influence/motivate” section is their ability to understand the feelings/motivations/desires of someone else and use that understanding to accomplish something. I don’t believe you can make someone do something that they don’t want to do (or if you do it probably won’t work out well in the end). You can, however, understand someone else’s motivations/interests and use that to find common ground. That’s what I am looking for.

Attitude toward challenges/persistence: Tell me about a time when you experienced a significant challenge.
Attitude toward challenges/persistence: Tell me about a time when you had to work very hard to reach your goals and be specific about what you achieved.
Attitude toward challenges/persistence: Tell me about a time you failed?

Comment: In the “grit” section, I am looking for how someone responds to a challenge. At one extreme, do they blame someone else? Or do they take a certain joy in the challenge? Do they view it as a learning opportunity? Do they stay positive or spiral into negativity?

General leadership: What is your superpower?
General leadership: What is a misconception that others have about you?
General leadership: If I were to call your manager/colleague/direct report, what would they say about you?

Comment: Invoking their manager/colleague/direct report tends to lead to more authentic and true answers than the typical what are your strengths/weaknesses questions.

2. Ability and desire to learn

Ability to learn from experiences: What is something that you had to learn to be successful in your last role? How did you learn it?
Ability to learn from experiences: What new things have you tried recently?
Ability/desire to learn: What are some areas that you are currently working on as a leader?
Ability/desire to learn: Tell me about a time that you received difficult feedback. What did you do with the feedback?
Introspection: After several of my other questions (i.e. greatest achievement, challenges ect), I ask if you had to do it again, knowing what you know now, what would you do differently? What did you learn from the experience?
Introspection: After a role play or work based assignment, I ask them to reflect on the assignment? How did they feel like it went? What would they do better next time?

3. Strategic and creative thinking

Problem-solving ability: I generally used real life case studies that my team was dealing with to get at this attribute. I wasn’t looking for a right answer and understood that the candidate would not have complete context, but I wanted to see how a candidate thought. What types of questions did they ask? How did they reason through the problem? These exercises can also be take-home problems.
Problem-solving ability: Tell me about a time when you had to solve a very difficult strategic or analytical problem. What was it?
Problem-solving ability: Tell me about a time when you used data to make a decision?
Problem-solving ability: What are some of the questions that you would want to find answers to over your first few months on the job?
Ability to be generative with ideas: What are some things that you would change about our product? What are some product ideas that you think could be interesting?
Ability to be generative with ideas: Give the candidate a case study of a challenge that you are currently facing. What are several different ways that they could solve it?

4. Role related knowledge and experience

As I mentioned, the exact things I was looking for would vary by the role and function I was hiring for. If possible, it’s great to have them produce some type of work product here or engage in some type of simulation. For customer facing roles, we always had final round candidates do a role play. For strategy roles, we asked them to put together a strategy deck on some challenge we were working on.

Describe your process for (XXX).
How would you think about hiring/building out your team? What would you look for?
What is the difference between good and great in your role/function?

5. Cultural fit

Mission alignment: Why do you want to work at XX company?
Ability to deal with ambiguity: Tell me about the most unstructured environment you’ve ever worked in?
Ability to deal with ambiguity: Tell me about a work environment in which you were able to do your best work?
Ability to deal with ambiguity: Tell me about a time you were frustrated at work?
Values: Who is a leader that you’ve worked with that you admire? Why?
General fit: Why are you leaving your current company? What are you hoping for in your next role?
General fit: When are specific examples of times that your work has felt most meaningful to you? What have you learned about what drives the most meaning for you in your work?

Background and Why Structured Interviews Matter

As I mentioned, my hiring framework is a mash-up of the hiring rubrics/process used at Teach For America (my first employer), Google (my second employer), and then modified to fit my needs as a start-up executive at Coursera.

Of all of my hiring experiences, Teach For America (TFA) was the most formative. At TFA every member of the staff (regardless of your role) would spend several weeks a year conducting structured interviews with literally hundreds of college seniors. A structured interview most simply means using the same interview process for every candidate applying for the same job. We would ask candidates behavioral and hypothetical interview questions, and then rate candidates using a rubric across a set of attributes that were shown to make effective TFA teachers. One’s rating would be calibrated against the rating of one’s colleagues and discrepancies would be debated. The rubrics and scoring would be adjusted every year based on the actual efficacy of the teachers. It was incredible to have this type of interview process and rigor hammered into me so early in my career.

The problem with not having a structured interview process is that we are human and we make snap judgements fully rooted in whatever biases we have. The snap judgment can happen in as little as ten seconds (more on that here), and then we spend the rest of the interview confirming that judgement. A structured interview forces you to tie your questions back to the attributes and values that are important to a job and then evaluate them based on their answers. It makes sure we are consistent across candidates and allows us to bypass our biases and focus on the skills/competencies/experiences that matter. It also creates a common language among an interview panel to debate and discuss the merits and drawbacks of different candidates.

While I mostly have been diligent in following my own framework, there were a few times that I let my organization deviate and paid for it dearly. The most notable time was in the early days of building the enterprise business at Coursera. We had exceptionally aggressive goals and virtually no one in the company had enterprise experience. We knew we needed to hire to hit our goals, so we let the framework slide and hired a few people in sales and account management based purely on their most recent experience. The lack of fit was evident right away. While we were eventually corrected for those hires, my organization took a major morale hit. I also want to acknowledge that it was probably a terrible experience for those individuals who we had hired. We could have prevented this with a better hiring process, something I own as the leader of the organization.

And perhaps that’s the biggest thing that I hope you take from the post. Have a framework and a process — it doesn’t have to be this one. Use it and evolve it. I hope this guide has been useful to you! If you have any q’s, feel free to include them in the comments.

Thank you to Connor Diemand-Yauman, Rebecca Taber Staehelin, Viggy Rajendran, and Thea Knobel for your feedback on this post!