Interviewing at a startup? Make sure you know what you're getting yourself into.

Know what to ask.

You don’t really know a company until you’re working in it.

We all take a gamble when starting a new job, so when looking for that job, we prioritize certain criteria to help base our decision to join:

• Compensation (salary, benefits, equity)

• Flexibility (flexible hours, WFH, 4-day work weeks)

• Title and responsibilities

• Culture/coworkers

• Potential for personal or professional growth

• Potential for company growth (is this a rocket ship I want to get on?)

Let me save you some time.

If you’re looking to join a startup (especially pre-Series B), some of the above won’t matter/is already figured out by the time you apply:

• Expect your salary to be 10%-30% lower than at larger, more established companies (this is very role, city and industry dependent, so checkout sites like GlassDoor or PayScale to get an idea of the cut you’d take).

  • You’re also less likely to get benefits like health, dental and insurance

  • To compensate for this hit, you’ll be offered equity

• The vast majority of startups adopt flexible schedules/work policies

  • Most startups I know let employees work from home and take breaks during the day for personal time (gym, appointments, therapy, etc). If flexibility is very important to you, do ask your potential employer about their policies if not clearly stated on the job description.

• Your title is likely to be inflated, meaning that if you were a Manager at a large company, you might be hired as a Director for a startup. Don’t get too caught up on titles because:

• Responsibilities in early-stage startups are broad, numerous, and ever-changing. My first startup job was “Community Manager” — I spent my days oscillating between logistics, project management, HR, and a sprinkle of content writing. Good/smart startups won’t have extremely specific job descriptions because they know they need generalists who will adapt to changes in priorities.

  • This means that you should find a department that you’re interested in (e.g. Operations, Marketing, Finance) but accept that no two days will look the same.

• By joining an early-stage (and likely fast-paced) startup, you’re de facto prioritizing your professional growth. I learned more during my first year working at a startup than the four years I spent earning my Bachelors and Masters degrees.

  • This being said, the growth is usually unstructured — think more “hands on” experience rather than a formal certification your employer pays for. If this is what you want, maybe look elsewhere.

This leaves us with the “wild cards”:

• Culture

• Potential for company growth

Evaluating Critical Differentiators: Culture and Company Potential

Here is a hard truth: you cannot completely gauge a company’s culture or its growth potential until you’ve been hired.

In fact, you probably won’t fully understand the culture until you’ve worked there for at least one month. Some employees will never learn the company’s real potential because certain key facts (like runway) are usually only known by the executive team.

But there are certain questions you can ask during the interviewing process that will help you determine whether or not a) this is a culture that fits with your personal values/preferences and b) whether this startup is likely to succeed (spoiler: 90% of startups do not succeed).

Questions for Culture

Try to ask the following questions:

1. What are the company’s core values?

   1. green flag: they have defined core values, they list them like they’re naming their siblings

   2. yellow flag: not having values isn’t necessarily a red flag; it’s normal that the founders may have prioritized other things (like building product or raising money) over creating values, but you do want to gauge if they care.

2. [If they haven’t yet defined their values] What do the founders value? What is their working style?

   1. red flag: “laid-back” or “relaxed” — building a company is hard work, you want the founders to take it seriously. Personally, I don’t want to think that the person signing my pay check is “loosey-goosey”

3. What are your rituals or habits?

   1. green flag: they have weekly, monthly, quarterly and/or annual rituals (e.g., town hall meetings, OKR planning, company retreats, etc). This shows intentionality, which is usually felt in other areas of the business as well (focused strategy, hiring plans, roadmaps, etc)

4. Would you say you’re more… (choose 3-5 based on your own priorities)

   1. competitive or collaborative?

   2. flat-levelled or hierarchical?

   3. data-first or intuition-first?

   4. organized or creative? (or pro-systems vs systems averse)

   5. into relationship-based trust or task-based trust?

   6. vision driven or values driven?

   7. into prioritizing shareholder value or stakeholder value?

You can also create your own list — but you get the idea.¹

Questions for Company Potential

Here are the questions I wish I had asked in all of my interviews with startups over the years:

1. You might not feel comfortable answering this, but what is your current runway?

   1. green flag: they answer the question and runway is 12+ months. It’s not necessarily a red flag not to share this information — sometimes, your runway gets shorter and you don’t want to communicate it broadly because you don’t want people to worry.

2. How do you manage your burn/cash flow?

   1. red flag: if they don’t answer this question, or answer it vaguely.

   2. green flag: they have a cash flow forecast, they review spend/burn regularly (minimum once a month), they have controls in place (e.g., not everyone has a company credit card, there’s an approvals process for expenditures, etc)

3. [After learning more about their business model] What is your go-to-market strategy? What are the main tactics you’re deploying to gain market share?

   1. Note: a pre-Seed or Seed startup might still be in discovery mode, so the question instead might be: what have you discovered so far about marketing your product? What’s worked and what hasn’t? Have you found product-market fit (PMF)?

   2. If they haven’t found PMF: What is your plan to find your PMF? (red flag: they don’t have one/don’t know how to answer this question — green flag: they talk about surveying users, doing A/B testing, trying different sales or marketing strategies)

4. Do you have a pitch deck? Would you mind pitching the company to me?

   1. Green flag: they pitch to you! This is a great way to understand the company before joining it and, you can think critically about the product, the market opportunity and competitive advantage.

   2. Not necessarily a red flag if they don’t — they might not have a pitch deck ready (or, if they’re not an exec may not have access to it)

5. Do you have current investors and/or shareholders?

   1. Flags are tricky to gauge here. Having investors is usually a good sign (it means someone believed in the company enough to fund it), but a lot of investors for an early startup could mean a crowded cap table, which is a risk. You’ll probably never know the state of the cap table, so focus on gauging whether or not the company is venture backable.

6. Who does what on your executive and/or founding team? If there are gaps in terms of skills and/or experience, what’s your plan to fill them?

   1. Green flag: responsibilities are clearly delineated, ideally someone oversees Finance (one of the most overlooked functions in early-stage startups). If there are gaps, they’re open about them and have a rough timeline of when they’ll hire for what role.

   2. Red flag: there are clear gaps and no plans to solve them (hiring isn’t the only solution, founders can work with external resources like consultants, mentors and coaches)

These are my baseline; you should have other questions that come up organically as you’re learning about the business, like questions about the revenue model, org chart/reporting lines, founder backgrounds, etc.

Ask yourself some questions, too.

There is always a risk in joining a startup. The key is figuring out how to get to a risk-level that you are comfortable with. This is highly subjective, so think hard about your own risk tolerance.

Questions that might help you:

• Am I okay if I lose this job in a year? In 6 months?

• Am I comfortable not knowing what my day-to-day will look like 6 months?

• Can I/Do I want to build systems and processes from scratch?

• Will I be okay financially if I forego a higher salary and potentially benefits for a few years in exchange for equity that only has a <10% chance of going anywhere/being worth anything?

• Am I in a phase of my career where I want to prioritize ‘learning over earning’?

I love startups, and I think more people should join them — but I also respect that it’s not for everybody.

In case it is for you, I hope this article helped.

1. My personal preferences are: collaborative, somewhat hierarchical, data-first, pro systems, into task-based trust, and equal/balanced on vision/values driven and shareholder/stakeholder value. IMHO, startups that aren’t data first or pro systems will struggle to execute on their vision/mission.