Hiring For Startup Fit - Bradfordcross.com

I’ve hired three CEOs, dozens of executives and managers, and hundreds of employees into early stage Seed and Series A stage startups. I’ve been exposed to hundreds of early stage teams through my network and the startups I’ve built in Consumer, SaaS, Enterprise, Deep Tech, Biotech, Fintech, Agtech, and other markets. So I’ve seen a lot of data on which backgrounds and traits work in startups versus which don’t.

The easiest way to find folks that are most likely to be a fit for startups is to find people that have already been working in early stage startups. That said, you often find great people that haven’t worked at startups before. They may come from bigger companies, later stage startups, academia, or fresh out of school. Regardless of the source, the question is always the same:

Who is going to be successful in an early stage startup environment?

Startups have unique characteristics which require people to have unique traits. The earlier the stage of the startup, the more pronounced those unique characteristics are, and the more important it is to hire for startup traits. Let’s dig into the most important traits and how to interview for each.

The 7 Most Important Startup Culture Traits

Growth Mindset — the most distinguishing startup trait is the maniacal focus on customer growth and personal growth.

Ownership Mentality — proactively seeks highest value responsibility and takes accountability for it.

Resolves Uncertainty — leans into the unknown with an active curiosity to clarify, create, and experiment their way to novel solutions.

Humility and Empathy — self-reflects, sees the bigger picture, understands and cares about the needs of others.

Grit and Intensity — bias for action with the determination and persistence to achieve a goal.

Velocity and Productivity — shocks others with speed, quality and volume of their work.

Clear and Precise — can articulate a clear direction that is magically both detailed and simple.

Now that we’ve outlined the traits, next we’ll just describe each trait in a bit more detail and provide interview questions for each.

Growth mindset — the most distinguishing startup trait is the maniacal focus on customer growth and personal growth.

Either your startup grows fast, it’s failing, or it’s not a startup. The defining characteristic of a ‘startup’ versus any other business is that startups are meant to have scalable fast growth. They can take in venture capital and use it to grow faster. Since startups are focused on growing so fast, there’s a lot of pressure. It’s hard to grow fast enough, and it’s quite stressful when you aren’t. It’s also stressful when you are growing fast, because it’s difficult to keep pace with all the change and things breaking from the scale. If the startup grows so fast and you don’t grow as fast as an individual, then you wont keep up. The startup will ‘run out ahead’ of you, and keep hiring you new bosses. Some people talk about great startup CEOs and team members as learning machines — they just keep surprising you by getting better so quickly in so many different ways.

There’s another side to all this growth. First, it is very stressful and it burns people out a lot. Of course everyone would say they want personal growth, but it’s tiring to have a constant pressure to grow important metrics and for you to grow to keep up with the growing scope of work. It can also feel very unsatisfying to constantly get something to be good enough to work, and then move on to the next thing. If you want to go very deep and master something — for example I worked with a guy at Google who was absolutely amazing and he chose to go very deep into compilers. He could have grown into a critical technical leader at startups too, but he chose to grow in a different way with a deep specialization. He can roughly understand that by making C++ code run faster, he’s making everything at Google faster, and therefore impacting the user experience. He doesn’t need to obsess about products, markets, or rapidly learn new skills in areas like sales or marketing. Si you might think of him as growing vertically deeper in a specialized skill, rather than growing horizontally broader across skills, as is often required in startups.

Interview questions

What’s the fastest you ever grew something?
What’s the most aggressive goal you’ve ever set? Did you hit it?
Describe your process for learning something new?
Name an experience where you were dealing with something that grew so quickly that it spiralled out of control and how did you deal with things breaking?
What’s the most pressure you’ve ever been under and how did you deal with the stress?
When have you been under pressure to grow, but haven’t been able to? How did you deal with it, what did you try?
Where have you worked hardest on to grow in the past few years, and what’s your #1 goal for the next few years?
How would joining our team get you closer to becoming the person you want to be?

Ownership mentality — proactively seeks highest value responsibility and takes accountability for it.

Startups have very little resources and management. You have to be self-directing with a high level of autonomy. You have to create the output yourself, not just look around for other things in place already or places to delegate the work. All the work is mostly ‘core work’ that is on the main production line and critical to company results. There aren’t any places to hide and work on secondary less important projects with less pressure and visibility. You must be able to manage the stress of owning high pressure core results. Everyone is expected to see what’s most valuable, and to use their nose for value to seek out and find ways to have higher impact. There’s always more work to own than people to own it, so we’re looking for those who will grab open work and take accountability for it, not people that will avoid important work that they see and could take on, but instead avoid and claim that it wasn’t their job.

Interview questions

When’s the last time you proactively just took ownership of something because nobody owned it?
If the team is dropping a few responsibilities, how do you decide which to pick up?
How do you decide what has the highest impact on any given day?
What’s the biggest thing you’ve ever owned?
What’s the longest you’ve ever owned something?
How do you decide what you should own?
How do you identify things you should drop?
What if you own something and you don’t think its as important as something else that you think you should be doing?
What do you do if someone else owns something, they are doing a poor job, and you think you can do it better and should own it?
What are your favorite mechanisms for holding yourself accountable?
When was the last time that you could see you weren’t hitting your goals, and you pivoted to do something differently and then started hitting your goals? How did you know you weren’t hitting your goals? What did you do to pivot?

Resolves Uncertainty — leans into the unknown with an active curiosity to clarify, create, and experiment their way to novel solutions.

Enjoys resolving the unknown and is comfortable with ambiguity. OK with 90% of their work being thrown away as part of the navigation process. Most people aren’t accustomed to throwing away a lot of work because they are used to doing incremental work on top of established work, so it’s not so often that you expect to work super hard for a few months, figure out that the thing you’ve been working on is a dead end, then throw the work away. Must like to experiment. Is excellent at taking various bits of information and synthesizing them into a coherent direction. Goes into seek-and-destroy mode; finds areas of uncertainty that can yield biggest wins, and takes initiative to find solutions.

Interview questions

What’s the most stressed out you’ve ever been over something uncertain at work?
What’s the most ambiguous instruction you’ve ever gotten and what did you do about it?
Give a recent example when the team was stuck on an unknown and you resolved it.
What is the hardest problem you ever solved?
What problems have you paused or given up on?
Tell me about a side project you’ve worked on?
What project was most heartbreaking to abandon because it solved a problem perfectly but it was the wrong problem?
Did you ever try to start a business or help someone else starting one?
When’s the last time you came up with a novel solution to a problem?
What’s the coolest experiment you’ve run in the past few years?
What’s the gnarliest bunch of information you’ve had to aggregate and synthesize in the past few years? What was your final output?

Humility and empathy — self-reflects, sees the bigger picture, understands and cares about the needs of others.

Doesn’t take themselves and their opinions so seriously that it impedes their ability to learn and work with others. Looks first at what they can be doing differently before looking at what others can do differently. Doesn’t participate in a culture of blame. Keeps a service mindset — focusing on how they can make life better for customers, teammates and others around the business. Is deeply connected with the customer needs.

Interview questions

When was the last time you felt strongly about the value you were providing to the customers of your company and why?
Where can you most improve in the next few years of your life?
What do you most wish you could go back in time and change about the past few years of your life?
When is the last time you’ve messed something up really badly at work and what did you do about it?
When did you last help a teammate with something?
What’s the worst conflict you’ve had personally or professionally in the past few years? What do you think was the cause? Could you have done differently to help?
Give a couple of specific examples of how you work with your current team
When do you prefer to work together vs work independently?
What are you most proud of in the past few years at work? What could be better about it and what would they do differently now?

Grit and Intensity — bias for action with the determination and persistence to achieve a goal.

Action oriented and actively resolves blockers. Bravely makes a first try right away, doesn’t get caught up in analysis paralysis. Executes quickly, proactively, intelligently, and systematically. Maintains balance so they don’t burn out, and has the endurance to keep pushing hard until they achieve a challenging goal. Being persistent enough to make it in a startup environment requires both a ton of energy and a way to replenish your energy. Most startups fail, and even the ones that succeed fail a ton along the way. That’s why the startup community has special jargon for failure like ‘fail fast’ and ‘pivot.’ So we need people who aren’t surprised to fail, who get up quickly, and who try again and again until they get it right. Resiliency is a critical capability, because otherwise we simply aren’t going to make it through all the failure.

Interview questions

Walk me through the worst blockers you pushed through at your last company?
Give an example of a case where you hit a roadblock and failed. What did you learn from it?
How do you recharge your batteries after a tough grind?
What kind of systems or tools do you use to strike a balance and make sure you don’t burn out?
How do you manage stress?
Give an example of a case where you pushed through a roadblock to success?
What was the most difficult problem you had to solve in the past couple years? How did you go about it?
How would you motivate somebody in your team to overcome a problem? What would you do?
What do you do when you’re stuck? Give examples from the past.
What do you do if you have an interpersonal issue with your colleague?
What do you do if others are stuck?
Can you think of something you worked on that you had to give up?
When was the last time you were surprised how quickly you got a big project done?
Tell me about your track record of projects over the past few years — which ones did you think you executed on best and why?

Velocity and Productivity — shocks others with speed, quality and volume of their work.

In startups, growth is our #1 goal, and as long as you’re headed in a reasonably correct direction, then speed wins. The work has to be both fast and good, and we’re looking for what are sometimes called things like ‘10xers’ or ‘rock stars’ — which are just monikers for being the most productive people in the world in their roles. There’s really no way around it — startups are under high pressure to grow fast, but don’t have enough time, money, and people. Startups pull off miracles only because they manage to hire extraordinary people that really can do many times the work of their peers and solve problems others can’t solve.

Interview questions

What’s your “mutant superpower” — what are you remarkably good at that serves as your greatest strength? Why do you have this power — did you start early, train hard, have a natural gift? What do you think can be done to increase your mutant power?
If there were any reasons why you got higher quality work done faster than other people, what would those be?
What would you say our output is like relative to peers? If it’s significantly different in some ways, what are those ways and why?
Can you think of any examples where you’ve gotten a lot done and the team wouldn’t have been able to deliver without your contribution?
Geek out for a minute — what’s the neatest thing you’ve been studying lately?

Clear and precise — can articulate a clear direction that is magically both detailed and simple.

Explains things in clear and simple terms. Understands the vision for what they’re working on and can get anyone to understand it regardless of their role. Is analytical, systematic, articulate, and broadly aware of social and business context, so that they always distill information and and explain things in a context-aware manner. Is a great synthesizer — can take in complex information and explain things in simple terms with sufficient detail to get everyone to understand what’s important relative to their role. Drills down into precise details — doesn’t wander and remain at a high level.

Interview questions

What does the project do that you work on right now? What are the customers and what are the goals?
How would you describe your company’s vision?
What’s the most complex thing you’ve worked on in the past couple years? What is the simplest description you can give of your hardest problem that has enough detail for me to really understand what you’re talking about?
Tell me about the last time you laid out a highly detailed plan and what it was for?
Tell me about the most complicated coordination situation at work in the past few years and how you pulled it off?
What’s something you’ve done recently at work that the largest number of people had to interact with?
What’s something you’ve done recently at work that made sense in context but would seem totally crazy from the outside?
Explain the most important decision you’ve had to make in recent years and how you went about it analytically?
If I asked you to come up with your own onboarding plan for the first three months after joining us, what’s the simplest description you can give right now that contains adequate detail?

How to run the process

There are three key aspects to running the startup traits screening process; booking a dedicated time slot, training interviewers, and backchannel references.

Book a dedicated 30 – 60 minute screening session just for startup traits

I recommend a 30 – 60 mins ‘culture fit’ screening. Build your own set of interview questions for each trait by cherry picking those from above and adding your own — try to give each section a mostly equal amount of time, but it’s ok to spend more time in areas of biggest concern based on the candidate’s background.

Many times ‘culture fit’ is treated as secondary and bolted on to the end of another screening step, so there’s less time for it. The questions and responses are normally fuzzier, less strictly interpreted, and ultimately just based on likeability. It’s critical not to let cognitive biases rooted in likability blur the vision of the interviewer to the extent that they prefer candidates that are more like them in superficial ways rather than candidates who demonstrate stronger startup traits. This risks building monocultures of the same profiles who are all very similar and like each other, but who lack the diverse skills required to make magic at startups. The degree of importance and uniqueness of startup traits means that they should really be treated more as must-have skills that you screen for explicitly.

Train interviewers to conduct longitudinal interviews

Longitudinal Assessment > Self-Assessment.

Interviewers should be trained specifically how to assess candidates based on what they did, not what they report about themselves. A lot of the ability to assess these traits comes from the interviewer’s active interpretation of how the candidate describes things they did in the past, rather than to simply administer a skills exam. Internal calibration is also very important here – the team should be aligned on what each trait means and how it translates into behavior. It’s not uncommon to have very different notions of a trait like persistence, only to later realize that you have someone in the company who isn’t really persistent at all and they’ve already hired a bunch of other people who aren’t very persistent either.

Asking candidates to self-assess is foolish in many cases, as they’ll just report things they think you want to hear. The key is to get into the details of their real experiences over time, and calibrate against your needs and expectations. They’ll report they knock down walls, but when you ask what the biggest wall was, it barely registers as a day to day blip on the radar at your startup. They recall a ‘dealth march’ where they had to deliver a new feature for a customer in 6 months, but it’s totally normal for your team to have to react to a customer request like this every two weeks. They say they are easy to work with, but in all the stories of their conflicts, they never seem to see their role in anything. A great example of this is the scales sometimes used in hiring for grit. Many people have realized that a self-assessment scale will have limited utility, and what really matters are examples of actions from the past.

Conduct backchannel reference checks

Backchannel references > candidate references.

Do backchannel references, don’t just take the word of the candidate. The more senior the hire, the more important it is to find your own references and find references from people you trust. People are really biased, so it’s not unusual to see a big delta between what a candidate says and what their peers say, even if they aren’t being intentionally misleading. Use the interviews to suss out areas of potential strength and concern, and then reach out to backchannel references to test your hypotheses and make a final decision.

When hiring is competitive, I sometimes see people fail to follow through with the reference checks, and it often comes back around to bite them. I’ve also done checks, received critical feedback that told me I should not have proceeded, but then brought people in anyway, or started with a ‘trial phase.’ People sometimes say things like ‘well he wasn’t super sharp and didn’t bring in the numbers back when we were on the same team, but it has been like five years now so maybe they are better and you could give them a try at your company?’ Just to be clear, this reference check maps to ‘no.’ If you really need help right now and you’re desperate to hire, it can be tempting to map this check to a ‘maybe,’ or try things like a ‘trial phase.’ Conduct your backchannel checks, and hold the bar to people who have a record of strong recommendations. Don’t give people a try that have spotty records — if people say they didn’t do great when they worked together, then it’s a no.

In Summary

Startups are uniquely focused on fast growth, and require people with specific traits that are well suited to the environment of constant uncertainty, change, failure, challenge, and relentless pursuit of serving customers and winning. These startup traits are so important and unique that they should really be treated as must-have skills and interviewed for explicitly.

I’m planning specific follow ups on topics like ‘who can make the transition from a big company to early stage startup,’ so if you have any specific questions about your startup or specific candidate scenarios, hit me up on twitter, linkedin, or email.