What makes successful startup employees
I was writing this article already when Spencer Allen actually tweeted asking people what indicates startup aptitude? I got busy with Quin and put this in drafts but over this holiday break I decided to finish it. Here was the original tweet:
I wanted to explain what I think makes someone successful in startups because I don’t think it’s “hustle”. In fact, the longer I’ve been doing startups the less I think “hustle” is as important as the rest of the traits I’ll go over. Hustle isn’t unique to startups and I’ve seen some of the most intense workaholics get fired or just generally be unsuccessful in startups because they lack the following more important traits. Since someone asked about interview questions on these too, i’ll include that as well.
Resilience
“Do not judge me by my success, judge me by how many times I fell down and got back up again.”
― Nelson Mandela
I’ve worked in small startups with 3 people burning money and up to large enterprises like Microsoft which had ~100K employees and one of the major differences is the need to be resilient.
Resilience is “the capacity to recover quickly from difficulties”. When I worked at Microsoft I remember knowing that even if I make an absolutely massive mistake, the worst mistake of my career, Microsoft won’t even notice it. I could mope around, give up, and not contribute a thing and Microsoft, was an organization, wouldn’t even feel it.
In a startup you really have to pull your own weight at all times. If you make a massive mistake in a startup (which you will, we all do) you need to go from “oh shit” to “fixed it” to “ok, I learned my mistake, here’s how I can prevent myself or anyone else from making this mistake again” quickly without skipping a beat.
In a startup there’s a good chance you are the expert in your subject area since the team is small. You may be the only one in that subject area at all! The team needs you to get back on your feet quickly or else the entire team and company will be impacted. This doesn’t mean the mistake shouldn’t make you feel sick to your stomach (the worst feeling), give you anxiety, or feelings of hopelessness, but it means you are able to manage those feelings at least until you can solve whatever the problem is. Then go order some donuts, take a bath, and cry later for self care.
Interview question:
“Whats a time something went completely wrong or some big mistake and how did you recover from it? What measures did you put in place to prevent it from happening to others?”
Adaptability
“The most successful people are those who accept and adapt to constant change. This adaptability requires a degree of flexibility and humility most people can’t manage.”
― Paul Lutus
One of the most obvious differences when you work at a small startup vs a large company is the breadth of tasks you have to do and how fast you need to pick new skills up and execute on them to stay ahead or catch up. When I’ve worked in companies even at the size of 300+ you start to become specialists in one part of the overall business. For example, as you get larger, you might have a team setup with a scrum master, project manager, analytics, data science, operations, sales, QA, engineers, product, copywriter, support agents, managers for those people, etc etc etc list goes on. In addition, projects are more planned out and long running generally because you have everyone focused on their little piece of the pie and can afford that up front time.
On the other hand, in a startup of ~10–15 people you’ve got the CTO doing HR, engineers doing customer interviews, the designer trying to wrangle some CSS, VP of product writing code, and founders replying to helpdesk tickets. Why? Well, because someone has to and you are trying to adapt to new information and don’t have time for people to pick it up.
A real example from my time at Vault was we learned that the product we were building as B2B wasn’t working out (the why is for another time). We were trying to sell to business owners with employees but found out, actually, self-employed people wanted this more and the sales cycle was so much faster. While the backend system generally was left the same the frontend needed a total overhaul along with the branding and marketing. Our backend engineers had to jump in and do frontend along with our VP of Product. We rewrote the web based app in a native app with React Native. Our frontend engineer was going out and doing customer interviews during this time too.
It paid off! TechCrunch even picked it up. This lead to more press, customers, and eventually, being acquired by Acorns. That whole pivot I believe took <60 days. By comparison, I remember a project I helped manage and it took dozens and dozens of senior engineers who were experts in front-end months to implement a redesign which the redesign itself took months as well.
This is one of the most fun parts of startups though for me. When I talk to companies about joining them it’s one of the questions I always ask: “Will I be able to work on more than just engineering?” It’s a big reason why I joined Quin. Will and Bryan (the founders) not only said yes but encouraged it.
Interview question :
“Tell me a time you had to volunteer for a job outside of your job description to help out your team or a project? How’d you feel about that experience?”
Positivity
“I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”
― Maya Angelou
When I was at Simple I remember we had a phrase we used ironically: “Hail Simple”. As an inside joke we even made a Twitter account. It was a gag to poke fun at Silicon Valley companies who have the team “Drinking the Kool-Aid” so hard it was like a cult. One place I worked at I remember them telling employees all the time it was a “war”. GitHub around that time was especially concerning from the outside looking in as they would tout that nobody had quit even at 150 employees. People in tech especially switch jobs often and the fact you are a business for 5 years and nobody had ever quit seems like it could be problematic (and as someone who interviewed more than a couple GitHub employees I first-hand know there were some serious culture issues). I’m hyper aware of not trying to create a team or culture that is so positive it’s actually detrimental but a strong positive culture is crucial to success of a startup.
In practice being positive at a startup means not shooting down people’s ideas on the spot. It means not thinking about only the negatives. I remember at one place I worked a designer and a software engineer reimagined how a product of ours could work. They spent a lot of time and research on it including a prototype that could be installed in you browser. They presented it to one person on the sales team who’s first reaction was “This wont ever work. Nobody would buy this.” I’m sure you can imagine how that felt. A more positive way of responding could have been “I love this concept because it really integrates seamlessly into the experience. One issue I see with this however is that it conflicts with how our partners do…” (eventually they presented it to the CEO and he absolutely loved it).
In the end this leads to a team that’s apathetic. They come in, do exactly what they’re asked and only what is asked, and check out. “Ticket pushers” as I would describe them. Why would you work hard if all you’re ever given back is issues, concerns, and negativity. You don’t know what you’re doing right ever. All you ever know is what’s wrong with what you did.
A successful startup employee, and team, knows how to respond to people in a way that positive like this and they know how to take feedback on what isn’t the best idea. They provide positive and negative feedback and can process positive and negative feedback without getting down on themselves. They can separate the good from the bad in an idea. This will lead to a more collaborative, happy, and innovative team. If you’re someone who’s an Eeyore you’re probably not going to be successful in a startup.
Interview question :
“What was the biggest failure in your career?”
Note on this one: you’re looking for why it was a failure and what they learned. You might follow up with a “why was it a failure” if they don’t offer that up. You want to see if they are blaming others, if they’re just overly negative, etc. You want to see that they learned from the experience (positivity) and explain what worked well (the positives outcomes) and what didn’t work well.
Creativity
“Creativity is inventing, experimenting, growing, taking risks, breaking rules, making mistakes and having fun.”
― Mary Lou Cook
Often people tie creativity to the arts. Creativity is really the skill of using imagination in practice. You can be a creative accountant, lawyer, or even factory line worker. A great example of a factory line worker is the toothpaste factory story which is fairly well known in the software industry. The gist is a toothpaste factory randomly produced packages once in awhile with empty boxes with no toothpaste costing the company money. Lots of time and energy went into solving this issue with complex solutions with the machine until one day someone had the idea to just buy a fan to blow the empty boxes off the conveyor belt. They fixed an $8 million dollar problem with a $20 fan. The important part here for startups is the solution didn’t require an engineer even. Just a dash of creative problem solving.
When you’re at large companies you can get away being less creative. You aren’t lacking any resources. You can force that square peg through the round hole with enough force and money. Solving that empty box problem at a place like Amazon they probably would have hired a team of researchers and experts and setup a whole scrum team. I’m sure the solution would have ended up more elegant than a fan but why work harder for the same outcome when you can just be smart about it?
In a startup you don’t have the time or money to burn. You have big ambitions, small team, and incumbents have a lot more money and people than you. Creativity is the only way you can get ahead. Creative solutions from startups are like Dropbox referral campaign to earn free storage to get users which had them grow 3900% in 15 months or Acorns rounding up loose change to get millions of investors the big investment firms couldn’t acquire. Neither are hard technically compared to the systems the incumbents had. The creativity to come up with those solutions was key.
So, when backed into a corner of no money, time running out, and only a handful of people, you need to find a way and this is why creativity is so important to everyone on the team. How can, for example, your product team or marketing team release a “feature” with no dev resources? How can the dev team build something that would normally take a year in 3 months? Both of these I’ve been in orgs that have solved them. One of those companies was acquired and the other has grown to be a unicorn.
Interview question :
“What’s a task or goal you’ve been given that was seemingly impossible but you found a way to make it happen.”
Conclusion
This is how we’ve hired at Quin and we haven’t had to work long weekends and late nights to build and complete an entirely new product that doesn’t exist in the United States from scratch in less than a year. The engineering team merged 750 PRs (1 PR per person every 2 days!), 140,000 lines of code (400+ lines of code written per person per day!). But, the most important stat: we ended the year with a functional product with real customers non-friends and family customers. I truly believe it’s because everyone on the team has a strong skillset in the traits above: Resilience, Adaptability, Positivity, and Creativity.
