Align your goals with the opportunity

The right way to interview for early-stage startups

You are someone who has 2+ years of experience and has worked with at least one startup already. You have tasted the energy of being on a scaling startup and this time when you’re jumping boats, you want to go to an early-stage startup - increasing your skin in the game.

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How do you evaluate if an early-stage startup fits you?

By early stage, I am referring to companies where they are “pre-PMF” (still figuring out what the customers want) and the sustainability of the startup is, at best, questionable.

Before the first interview:

Don’t interview an early-stage company just because you want to get in the “interview mode”. If you want to get into interview mode, practice at a bigger company. It hurts them lesser if you drop off after taking 4-5 hours of their time. Here are the things that you evaluate while you’re still to get to interviews:

1. Think through what you want from this job.

It could be as simple as “Just want any job” to “Want to work in a consumer FinTech company in the growth team so that I can start up later in the same space”.

Just get your objective out. Even if it’s vague, it will help you think clearly.

Read this - you’ll learn about what each type of startup has to offer & you’ll quickly get a sense of what fits you best.

2. Evaluate the role.

Visualise this: A friend’s goal is to have a career in Product Management but the recruiting startup is only offering a marketing role. Should he explore this opportunity?

Sometimes as optimists, people end up internalising “anything is possible”. Is this career switch practically possible - yes probably, but might be very few such examples. Before deciding to take a leap of faith, look around in your professional or friends’ network for examples of successful/failed switches. Talk to them openly. Don’t assume.

3. Evaluate the industry.

Visualise this: A friend is passionate and wants to work at an EV/climate tech company but is now interviewing at a startup that’s building B2B software for Real Estate companies. Should she explore this opportunity?

Sometimes you know deep inside that even if you get the offer letter at favourable terms, you won’t take it up. If it’s a “hell no”, move on. Stay in your current place until you figure out a place that would keep you more satisfied than your current workplace.

If you’re still at this stage, pause reading here. Bookmark this newsletter link and come back to it when you are interviewing.
Use this list of startups to identify the startups and reach out to them. 

After 1 or 2 good interviews, but before receiving an offer:

1. Compare the compensation range with your long term goal.

Ask the founder/recruiter for the compensation range explicitly if not discussed yet. If they say “depends...” or something like that, tell them your expectation up front - or at least whatever you feel is non-negotiable - like it could be cash component or ESOP expectation or something else.

If it’s going to be completely out of range for them, better to let them know beforehand.

What some people might tell you. 😂

2. Will you learn from this team? Will you enjoy the working style?

You tend to move towards the average of the 5 people you spend the most time with. In an early-stage startup, if you don’t feel excited about the people who have already interviewed you and the others who are going to interview you, it’s a dead end. Success in early-stage startups is all about people.

Real-life story: A friend was interviewing for a Director level Tech role in a Series A startup. After 2 rounds of interviews, it was clear to him that there’ll be less flexibility / independent thinking in his work because the objectives of the company are very clearly stated for the next 12 months already. He politely denied it and moved on - it saved 10s of hours for both of them.

Apart from these interviews, going through all existing employees on their Linkedin will give you a vibe if you’re excited about working with them.

3. What are the company's growth prospectives? And does it match your expectations?

Technically, startups are supposed to grow fast. But every founder thinks differently. Some build slower than others, optimising for different variables/reasons. Sometimes a startup that grows 5x in 3 years could be a better choice for you than a startup that grows 5x in 2 years if other parameters fit better.

Evaluating a company's growth prospects is subjective, but trying to get inputs from employees/founders about how are they seeing things evolve and what their targets are, would give you visibility. Also, check out point 3 in the next section.

After the offer:

1. Do a ref. check on the team:

Collect feedback about the co-founders as well as your next manager. Try to look for informal connections (cold or warm) instead of asking them for referrals.

💡 Some questions you can ask people who’ve worked with the founders/manager:

1. The best thing about working with them?

2. The worst thing about working with them?

3. Any anecdotes of their experience with them.

If you liked the manager but are not sure about the overall culture - REQUEST to chat with more people in the team. Say that “you enjoyed existing conversations but are still not clear; and want to understand the working principles and culture better.” Don’t hesitate.

2. Can you have a tough conversation with the founder?

The first step in testing trust & communication transparency is having honest conversations as early as possible.

💡 Sample questions to ask founders:

1. What do you like about me? What do you think will be my shortcomings?

2. How do you see my career trajectory here?

3. Why are you building this company? 🙂

Try to see what happens in scenarios when you have a contradicting opinion of the founder? Does the founder evaluate it rationally? Or did it make the conversation tense?

You’re getting the hint of what is happening now and what would happen in future.

3. Talk to investors:

Not just their current investors, but generic investors in the market.

Ok. Most investors might not want to talk to someone just because they’re having a job offer at a startup BUT if you’re joining in a high risk-reward state (senior position in a small founding team), cold contact existing/potential investors.

💡 Sample questions to ask investors:

1. What are they bullish/not bullish about in the market/approach?

2. How would they stack the startup against other early-stage startups in their portfolio?

3. Risks in the startup? (If they say “none”, there’s a high chance that you should ignore their previous answers)

If you enjoyed this article, do share it with other folks in your network and let me know what more you’d like to read about! ❤️❤️❤️