15 QUESTIONS YOU SHOULD ASK YOURSELF IN THE FINAL STRETCH OF INTERVIEWING - MAKE THE RIGHT DECISION FOR YOU
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? (Note: Founders typically own the overwhelming majority of the company and have an outsized amount of power in terms of 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 you’re speaking to is three employees… if they don’t have advisors, it is 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 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? Do they have track records? And… how much of their track record is failing upwards vs. truly knowing their shit? It’s pretty easy nowadays to get references from people in a hyperconnected world. Find out who worked with them and ask them about the exec team. Were they A players or B players where they worked in the past? Is this company suited for them? Dig deep. These are the people you’ll be working with day in and day out, most likely.
Questions about GROWTH
Reality vs. perception: How is the business really doing? What are the goals? Is the business hitting those goals? Why or why not? I know a lot of companies today in Boston that everyone thinks are doing really well… that aren’t. And I know some companies that are total sleeper cells that are doing amazing which no one knows about. Don’t buy into perception. Ask the founders and executive team how the business is doing and cross reference what each other says. Some people are direct truth-tellers. Other people like to apply lip gloss.
Aggressiveness: Are the goals aggressive enough? I’m saying you should literally ask the founders/execs this question and see what they say). You’ll learn a lot from the way they answer that question. You could also phrase it another way: How could this company 10x? I know a lot of companies hitting goals that quite frankly 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? How do you figure this out? Simple. Ask existing employees who are not on the executive team.
Flights: Why have people left this company in the past? Are you hearing the same thing over and over again? If so, speak to the team about that before joining. Granted: I know this takes time to actually find people who have left the company and is not always doable.
Lifestyle: Are there any values for you that are deal breakers in terms of how you want to live your life? Really think about that. You’d be surprised how much a well-intentioned value can truly impact your life negatively.
Questions about THE ROLE
Responsibilities in terms of goals and metrics: What am I directly responsible for and indirectly responsible for in terms of goals and metrics? If you ask a Founder what metrics will I own and they can’t tell you… quite frankly, they shouldn’t be hiring for the role yet. Separately, if you are interviewing for a Head of Marketing role, it’s perfectly fair to ask them direct questions like: “What's your CAC today? What’s LTV? What’s your conversion rate? How do you define conversion rate here? How do you define retention rates here? Let’s review them together.”
Responsibilities in terms of skillset ownership: Now that I know the goals and metrics, are the skillsets I’ll be responsible for (Ex: Growth acquisition marketing + email marketing and CRM/lifecycle teams) going to give me the arsenal necessary to accomplish those goals? Said another way… can I take the hill with the ammo I’ll be provided with on day one, and if not is there a path to taking the hill on day two (or a future day).
Value: Do I have the capability of adding both immediate value and long-term value? This is very important and I think drastically underappreciated and underrated. If you can’t add both immediate and long-term value in a given role, it’s not the right time or place for you. I see tons of people hired who would be great for long-term value, but can’t execute at the scale of the company today. The time will come for the majority of people at which your long-term value is no longer enough (typically in years 3 or 4 of the company), and at which point will be the right time for you to go. It will happen and that’s perfectly ok.
Questions about ME
Learning: What am I going to learn in this role that I want to learn and haven’t been able to learn in previous roles or previous companies? Always push to do 1% better than the day before.
Support: Who is going to help me get there? Whether it’s your direct manager, peers, mentors, etc. Have an idea of who can help you learn and improve.
Progression: How will I progress in this org with regards to things I will own? Is there a path towards more ownership personally that you can EARN. Note: I’m a big believer in putting your head down, doing great work, being recognized, and being proactively rewarded. And I’m also a big believer that you should have a vision for your path within the org to protect yourself in case those who recognize don’t proactively reward you. Look out for yourself.
If you ask yourself these 15 questions, you’ll be well on your way to not just evaluating each opportunity correctly, but feeling really strong in your ultimate decision.
One last final point to less experienced, junior tech people: Often times junior people focus on questions about themselves (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. 😉
