As a candidate before any interview call, whether an introductory call or a technical screen, I always prepare with a listen of questions I should ask. Most times I am allowed to ask the other person some questions and I never want to be empty-handed.

The types of questions I ask generally fall into two buckets:

1. Specific questions related to the company, team, industry, or specialty that usually have distinct answers.
2. Open-ended questions anyone can answer to help me learn more about them, the team, or the company.

For the first bucket, specific questions with distinct answers are good to ask to get introductory ideas of how the company and team operates. The questions I usually ask here are: what is your tech-stack, how large is the team, what your cash flow numbers look like, etc. I ask these purely to gauge the health, growth trajectory, and/or start conversations that may lead to more interesting topics or problems.

My favorite types of questions to ask fall into the second bucket. These usually catch people off-guard because they require a bit more thought. Are you ready for them?

What type of people are successful here?

Some teams are built to be completely autonomous and shut off from others. Some teams are extremely open. Some are so small that everyone works with everyone, and some are so large that they see new faces every day. All teams work differently, so this question helps me determine what type of people thrive with the culture at the company.

Follow-up questions:

• What type of people are not successful?
• Who are the “heroes” at your company?
• What characteristics do the most celebrated people have in common with each other?

What made you choose to join this company?

Besides money to pay the bills, it’s interesting to learn why people choose to work for an employer. They don’t need to have moving stories, but hopefully, they can mention something more substantial than a paycheck. This can help guide your next questions and gauge enthusiasm from candidates.

For me, happy and thoughtful employees are better than resentful, passive employees that only to come in for a 9-5pm routine. I don’t think there’s an exact science behind it, but I think if people care about their job, they work harder and smarter to meet the team’s needs and strive to build a great team and product. This is my experience.

Example answers I received:

• Value alignment with the company
• Meaningful, purposeful, impactful work
• Talented, intelligent, diverse, engaging, and/or passionate team
• Excellent work/life balance
• Opportunity for career growth and/or mentorship
• Awesome product or service
• Respectful/non-competitive atmosphere

It’s a great sign if someone can list multiple pros. This question usually provides insight into the company culture.

What is something currently challenging the team?

My purpose with this question is to see if the person cares enough about the team and company to see outside their day to day tasks. I think it’s important to work with people who not only care about themselves but the health of their team. If they see weak spots, they should point it out and if at all possible, work to improve it.

Example answers I received:

• Poor cross-team communication (technical, non-technical, company details, etc)
• Inefficient engineering processes (ex: non-standard deployment pipelines across projects)
• Not able to grow fast enough to meet demands (This one always irked me. If it’s a chronic problem, that is a problem. But this is also a good problem to have.)
• Products with no customers

Follow-up questions:

• How might you address those challenges?
• How might you close those gaps?
• Do you have the support necessary to drive change? If not, why?

What is your dream for this company?

This question sprouted off the previous “challenge” question during an actual in-person interview I had earlier this month. The person answering it altered my question a bit and I thought it was beautiful.

He said the there are many challenges the team is facing, but he was also looking even further into the future of the platform and said what he wanted. He’s aware of the road blocks but wanted to tell me about his end goal.

I think this is a great question because it means the employee has aspirations for the company and dreams of improving something, whether it be a product, service, process, or something else.

Follow-up questions:

• What steps are necessary to reach those dreams?
• How reasonable is it to meet some of these goals within the next 5 years?
• Are there smaller goals you can think of that can build up to reach this larger dream?

Never go to an interview empty-handed

These questions can be asked to anyone to talk to, technical or non-technical. These aren’t trick questions but do require the interviewer to do some introspection or provide thought. If they fail to do that or cannot come up with some answers, take that as an opportunity to raise red flags.