Summary

The article outlines five key questions a candidate should ask during an initial interview to assess the company's fit for their career goals and personal values.

Abstract

The author emphasizes the importance of a candidate being proactive in evaluating a potential employer by asking targeted questions during the interview process. These questions are designed to uncover the structure and challenges of the engineering team, the company's financial health and growth prospects, the specifics of the role being offered, and the company culture. The article suggests that by asking these questions, a candidate can discern whether the company aligns with their professional aspirations and personal work-life preferences. The author also notes that posing insightful questions can elevate a candidate's standing in the eyes of the interviewer, demonstrating competence and selectivity.

Opinions

The interview process is a two-way street, serving to establish mutual fit between the candidate and the company.
Understanding the size and structure of the engineering team is crucial for determining if the work environment suits the candidate's preferences.
Acknowledging and addressing the company's current challenges is important for aligning the candidate's skills and interests with the company's needs.
The company's stage in the funding cycle and its product-market fit are key indicators of stability and future prospects, especially in a startup context.
Inquiring about the reasons for hiring and the expected contributions of the ideal candidate helps clarify the role's importance and potential for growth within the organization.
Asking about the interviewer's personal motivations for joining the company and their retrospective insights can provide candid insights into the company culture and quality of life.
Good questions from a candidate are seen as a sign of strength, reflecting the candidate's self-worth and discernment in choosing their next career move.

5 screener questions I ask interviewers

As a candidate, make your own list of questions.

After all, you’re a talented professional in a growing field. You have other options. The interview is about establishing good fit. For you and the company.

Having sat on both sides of the table, I’ve seen some things.

I’ve developed a short list of questions that I like to ask when sussing out a company.

The questions

These questions are my screener questions. I use them in the initial conversation with a new opportunity.

For most of these, even a technical recruiter should be able to answer them.

If there’s interest, I’ll write another post about deeper process, management, and quality of life questions that you can ask in a later-round interview.

1. How big is the engineering team & how is it structured?

Working on a small team is very different from working in a large engineering organization.

There’s no wrong answer. It’s just a matter of what you are looking for.

Red flags:

The engineering team isn’t structured at all
You’d be unsupported in the role
There’s no room for growth

2. What are the biggest challenges you’re facing at the moment?

This question aims to understand what kinds of problems the engineering team is working on.

Also, what problems is the company as a whole addressing?

You’ll want to pay attention to the words they use when answering. This question generates a lot of good material for you to re-use in your later interview rounds.

Red flags:

They pretend like there aren’t any challenges
The challenge is company threatening, like “we don’t have customers”
Technical challenges that don’t overlap with your skills/interests — it’s okay to want to learn from a new job, but if you’re not interested then you should pass

3. Where is the company in the funding cycle & how is product-market fit?

I ask this question because I’m interviewing at mid-stage startups. I want to get an idea for runway, sales, and business trajectory.

If you’re not interviewing at startups, this one will be less important. But you do still want to know where you fit into the company’s revenue model.

Some alternatives/corollaries to this question:

Are you profitable? What’s your planned timeline for becoming profitable?
How do you make money? What’s the business model?
How much are you planning to hire in the next year?
Are company sales/financials transparent throughout the company?

These all assess the company’s growth and business model. It’s important for startups.

But it’s also important for established companies. Maybe you want to work for a big name but the answer to, “How do you make money?” is, “We take military contracts” or, “We sell users’ data to advertisers.”

Red flags:

The company isn’t profitable and doesn’t have a clear plan to get there
You can’t explain the business model to your dad/grandma/uncle/sister
Lack of transparency or defensiveness about company financials

4. Why are you hiring for this role now? What would it look like 6 months from now to hire the perfect candidate?

Asking about the “perfect candidate, 6 months from now” is a great strategy to uncover what the hiring manager is really looking for in the role.

It shows how the job aligns with the organization.

When a company allocates new headcount, it’s because there’s a problem. Developers are incredibly expensive to employ. There must be a big problem worth solving.

In the description of the ideal candidate, you’ll get to decide if you want the job that’s being described. Are those challenges exciting?

Red flags:

The role is nebulous, undefined, or there’s no good answer
You get conflicting answers to this question from different people
You don’t want the role as they’ve described it

5. Why did you choose to join this company? What do you wish you had known when you joined this company?

Now, I’m mostly interested in mission and culture.

I want to know if it’s a good place to work. Do people actually enjoy working there? How is the quality of life?

I find that these questions are a good entry point to talking about culture. Specifically, the “what do you wish you had known” opens the door to talk about the darker side of the company — if there is one.

Red flags:

Grind culture with long hours, catered dinners, etc
No clear mission or vision for the company
Anything that doesn’t match with what you’re looking for in a company culture — everyone is different

Asking hard questions = strength

An interesting thing happens when you ask hard questions of your interviewer.

Good questions indicate competence.

They show you value yourself.

You’ll find that the interviewer’s opinion of you as a candidate goes up when you ask difficult questions. It shows you’re selective about where you’ll work and what problems you want to work on.

It’s almost as if you become exclusive. It gives the impression that you’re oversubscribed.

And, of course, you are! You can only take one job. So, any other interviews will be a “no” eventually. Start thinking from that position of strength.

More resources

I’ve written previously about saying no to bad opportunities, how to land interviews, and knowing your worth.

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