Interviewing The Company

As you may have heard before, interviewing is like dating and looking for a fit. The company likes you and you like them. It’s a match! But how do you, as a candidate, figure that out? By interviewing the manager and recruiter. Ultimately, your next manager is the gatekeeper to your future success. They are a major part of the decision for promotion and internal transfers. Furthermore, the manager will be most likely on-boarding you on Day 1, if it’s a startup (there may be a dedicated training team!). Some managers are hands off (expect to be very resourceful and manage up), while some may like to stay involved in everything (expect to communicate updates often). I categorized the following questions based on topics: role, manager, company, and flexibility.

NOTE: Please ask these questions in a conversational manner and don’t read them off like a list! In fact, you may want to jump to General Tips on Asking Questions first.


What would a day in a life look like?

What’s the most challenging part of this role?

What does success look like for this role?

What does onboarding and training like?


What’s your communication style?

How would you describe your management style?

Can you share the hardest decision you had to make in the past 6 months?

What’s your experience in managing this role?


I go back and forth with this because if public information exists about company performance or industry, then it’s wasteful for the candidate to ask these questions. Focusing on the role, management and department goals are more appropriate and valuable. With that said, here are some good questions:

What KPIs would I be responsible for that directly impact company goals?

I read recently that XYZ, can you share more behind that decision?

Flexibility / Travel

Important for those who are seeking flexible working schedules (i.e. work from home / working remotely). To me working from home is earned and a privilege. I don’t recommend asking these questions unless you have personal obligations or you are commuting from a very far distance.

What’s the company’s perspective on remote work / flexibility?

Can you tell me about what the typical work schedule looks like?

Does the role require travel?

General Tips on How to Ask Questions:

  • Have 3-5 questions memorized

  • Treat the interview as a conversation. What came up during the interview? “Can we go back to a point we discussed a moment ago, what was your perspective on...” “Earlier you mentioned an important company initiative for Q1, can you expand upon what would be my role in...” “Earlier you mentioned about the productivity improvements, can you give me an example of a project I might be involved in?

  • Ask about your job, your role in that job and your contribution to that job. Avoid questions that are way too big (macro). “What are the core products for my largest customers?” “How will I work with Product Management & engineering”

  • What not to ask: company, industry, pay and benefits

  • Don’t ask short answer questions

  • Ask to expand upon a topic or ask for their ‘point of view’. “Can you give me your perspective on this..” “I would like to know more about XYZ”

  • Give context - “I was reading a great deal about CS outsourcing, what does that mean for my role and budgets? How will that trend affect my role and how I run CS?

  • When you’re done or out of time, be quiet and stop. “That’s all the questions I have right now, I really appreciate the opportunity to interview, before you go I’d like to leave you with one final thought...”

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