How to Evaluate Startup Culture: 6 Key Question Topics to Ask During the Interview Process

Whether you’re early in your career or as a career transitioner - if you’re new in the tech space - or even seasoned - it can feel daunting to get traction towards that first/next role. And make asking tough questions in your evaluation of the company feel risky.

Not all startups are created equal, and we each need different things from our employment in different stages of life. There are plenty of stories out there about startups, and while some are myths, I’m sure many are true. For context, I run Hustle Hunters and through our early stage startup recruiting and broader talent consulting, have had the opportunity to partner with many incredible early stage companies over the past 3 years that are building for the marathon and not just the sprint, where their employees are treated like the number one asset they are. They are still doing big, audacious things - but set up to maintain balance and health of their employees while doing so.

Figuring out which type of company you’ll be joining is part of your job when entering a hiring process.

Interviewing should be a two-way street, and here are some angles to help discern what life will be like “beyond the interview” at the startups you’re interviewing with.

1: What happens when things go wrong

Interviewing teams want to see how you think, and how you’ll approach problems. The most annoying interview experiences are often when hiring teams challenge candidates beyond their comfort zones to see how they’ll react to the pressure and discomfort - knowing that much of being part of a startup includes exploring and beginning to codify the unknown. Similarly, you should be intent on learning what happens internally when things go wrong. This is an easy topic to dodge with general statements, so be sure to ask around specific examples like “what happened the last time you made a mistake?”, “Does the data analytics team feel pressure to always be right? Or are they encouraged to make calculated guesses and learn from misses?” or “what is the last team that didn’t meet their quarterly KPI’s. What impact did that have on the organization?”

2: Speak with others of similar identity in the process

It’s totally fine during the interviewing process for you to ask to speak with someone that identifies similar to you. That could be with respect to many categories, including race, gender identity, caregiving status, education level, professional background, etc. This’ll give you a chance to meet a potential colleague, build your network in the industry (regardless of outcome here), as well as identify potential hurdles you’ll face in your new environment.

3: Understand the support you’ll have

Even the “best” employees often have a slight learning curve as they learn their new organizations, due to the nature of the startup space where each company runs in it’s own unique way as it builds innovative solutions. Imagine yourself 4 days into this new role as you come across an acronym that must be internal jargon as Google didn’t return any answers. Who will you be able to reach out to without feeling like you’re being a burden? Is there anyone else in this function to lean on? Will there be an onboarding buddy to help you integrate and understand cultural norms within the organization (especially if onboarding and working remotely)? Will you be expected to be the internal expert on a function you’re just learning, or will you have internal mentorship available?

4: Is there life outside of work?

Asking the team about hobbies and other non-work interests can be a fun way to learn about the balance employees are afforded, as well as learning the flexibility teammates experience. Startups often have a reputation of being rife with burnout. Evaluating the tenure of employees, the hours folks are regularly working, and the focus on time or output/impact can help see what aligns with your target lifestyle. It was such a gift in my startup career to learn that doing big, hard work didn’t mean you couldn’t ever close your laptop.

5: It’s ok to be blunt

Early in my career, I was on a sales team that rarely hit it’s quota, and interviewing a slate of new candidates and being worried about addressing the lack of success we’d faced as folks were evaluating the potential financial impact that their commissions could have in this new role. But only one candidate asked the question, so I just stayed silent. Questions like “Which teams have hit their KPI’s in the past 2 quarters?”, “how long did each of the past SDR’s do that role for? Where are they now?”, “especially in light of the recent layoffs, how much runway does the company have?” that dig into both company and role upside can be important parts of this process.

Especially if you’re in a position where you’re being courted by a company, giving them the opportunity to show you how they’ll support you (with whatever you need) can show you a lot about the type of organization you’ll be joining. And if there just isn’t enough flexibility so you’d be home by 6pm most day to let your dog out - maybe this really isn’t the organization for you. We want to join workplaces where we can be ourselves at work - We’re not trying to sneak in the back door.

6: Leadership

Having an amazing idea and being able to translate that into a fully functioning team that grows and scales smoothly are never a given. Evaluating the executive team directly in conversation, and/or by asking other employees about their trust in the leadership is important. Try asking “what is something that the leadership team could do better?” or “can you give me an example of why you have put your trust in the CEO?” to uncover more about this important facet of the business.

Who should we be asking these questions to?

Tact and strategy play a big role here, as often the questions you ask an interviewer are more telling with respect to the signaling they are looking for than the answers you might have given throughout the rest of the conversation. Especially in a setup where space for candidate questions are reserved until the end, how you spend those scarce ~5 minutes are very telling of where your priorities are. If not given much space to ask your questions, I recommend leveraging your recruiter’s insight as to who you should tap for these answers. Often times, the recruiter will take it upon themselves to ask these questions discretely and get you answers without having to risk your time or social capital to learn critical details (this is my favorite part of our work). Your recruiter is your champion, although this resource is often underused and forgotten about once the hiring manager is part of the process. With respect to questions in general- it’s best to tailor your questions to the scope of each interviewers role in the organization. For instance - if you get the chance to interview with a CEO, ask the deeper questions that only the CEO might be able to answer.

Time is our most valuable resource and the decision of which company we plan to spend our next career chapter with is important. You’re about to be part of a startup whose innovation might very well change the world - make sure it’s the change, team and environment you’re wanting to be part of - and you’ll thrive.

Nikki Adamson, Founder + CEO @ Hustle Hunters, Mama to Izzy