15 Questions You Should Ask Yourself in the Final Stretch of Interviewing

So, you've been interviewing with a company you're really excited about. You like them. They like you. Great. Hooray.

You're in the final stretch. You've interviewed with everyone. You've met the CEO. The exec team. Your peers. The People Ops team. You're in alignment on compensation and what a package may look like. And you're now really trying to challenge yourself to assess the opportunity.

So, what questions should you be asking YOURSELF before you decide to make the leap?

Experienced executives ask questions about the following in this order: Leadership → Growth → Culture → Role → Me.

Questions about LEADERSHIP

• About the founders: How confident am I in the Founder? How confident am I that this founding team is THE team to see this vision through? (Founders typically own the overwhelming majority of the company and have an outsized amount of power over where the company goes.)
• About the Board: Do the Founders have great people around them both at the Board of Directors level and Board of Advisors level? I don't care if the company is three employees, if they don't have advisors, it's a massive red flag. It's also a massive red flag if a mature company's Board of Directors sucks. If they lack industry experts. If they lack Operators. If they lack people who are incredibly smart, strategic, and have a vision for where the world is going… run.
• About the executive team: How strong is the executive team? Have they demonstrated the ability to win and scale companies in the past? Track records? How much of their track record is failing upwards vs. truly knowing their shit? Easy nowadays to get references from people in a hyperconnected world. Find out who worked with them and ask. A players or B players? Is this company suited for them? Dig deep. These are the people you'll work with day in and day out.

Questions about GROWTH

• Reality vs. perception: How is the business really doing? What are the goals? Is the business hitting them? Why or why not? I know a lot of companies in Boston everyone thinks are doing really well that aren't. And some total sleeper cells doing amazing that no one knows about. Don't buy into perception. Ask the founders and execs how the business is doing and cross-reference. Some people are direct truth-tellers. Others apply lip gloss.
• Aggressiveness: Are the goals aggressive enough? Ask the question directly. You'll learn a lot from the way they answer. You could also phrase it: how could this company 10x? I know a lot of companies hitting goals that aren't that impressive and/or are 1/10th that of their competitors moving 10x faster with better teams and better products.
• Destruction: And vice versa, what would totally destroy growth? What if XYZ happened? Play out scenarios.

Questions about CULTURE

• Reality vs. perception: Are the values on the website actually practiced day to day? Do they practice what they preach? Simple: ask existing employees who aren't on the executive team.
• Flights: Why have people left this company in the past? Are you hearing the same thing over and over again? Speak to the team about that before joining. I know this takes time and isn't always doable.
• Lifestyle: Are there any values that are deal-breakers for how you want to live your life? Really think about that. You'd be surprised how much a well-intentioned value can impact your life negatively.

Questions about THE ROLE

• Responsibilities in terms of goals and metrics: What am I directly and indirectly responsible for? If you ask a Founder what metrics you'll own and they can't tell you, they shouldn't be hiring for the role yet. If you're interviewing for Head of Marketing, ask directly: "What's your CAC? LTV? Conversion rate? How do you define conversion rate here? Retention rates? Let's review them together."
• Responsibilities in terms of skillset ownership: Are the skillsets I'll own (e.g., growth acquisition + email CRM/lifecycle teams) going to give me the arsenal necessary to accomplish those goals? Can I take the hill with the ammo I'll have on day one, and if not, is there a path to taking the hill on day two?
• Value: Do I have the capability of adding both immediate and long-term value? Drastically underappreciated and underrated. If you can't add both, it's not the right time or place. I see tons of people hired who'd be great for long-term value but can't execute at the scale of the company today. For most people, the time will come in years 3 or 4 when your long-term value is no longer enough and the right time to go arrives. It will happen and that's perfectly ok.

Questions about ME

• Learning: What am I going to learn that I haven't been able to learn in previous roles? Always push to do 1% better than the day before.
• Support: Who is going to help me get there? Direct manager, peers, mentors. Have an idea of who can help you learn and improve.
• Progression: How will I progress in this org with regards to things I'll own? Is there a path to more ownership you can EARN? I'm a big believer in putting your head down, doing great work, being recognized, and being proactively rewarded. I'm also a big believer that you should have a vision for your own path to protect yourself in case those who recognize don't proactively reward. Look out for yourself.

If you ask yourself these 15 questions, you'll be well on your way to evaluating each opportunity correctly and feeling strong in your ultimate decision.

One last point for less experienced, junior tech people: you often focus on questions about yourselves (Me) and the role. Level up your thinking and push yourself to ask the real questions that matter about leadership, growth, and culture. It's not just what a company can do for you. It's what you can also do for your company (customers + fellow operators + execs + founders + board). Good luck out there. 😉