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My Interviewing Strategy

I’ve found that interviewing for a new job can be super stressful and it reminds me of speed dating, “Let’s get to know each other over the next few hours to see if this relationship can work”. With such a short time window, there’s not much time to ask “fluff” questions like “if you were a tree, what kind of tree would you be”. Instead, I’m more likely to ask some of the following questions to get a better understanding of what I’m about to step into. If the company can’t answer some of these questions, it’s not a deal breaker, but can be a red flag about this place.

With that being said, I hope these questions help you during your interviewing process!

Business Strategy

  • What is your biggest concern for ?
  • What was a major success for over the past year?
  • What was a stumbling block for over the past year?
  • What does your ideal customer look like?
  • What is your business model (i.e. how does make its money)?
  • Any thoughts of expanding to other markets (such as, if the company sells a particular type of medical device, are there any thoughts of making other devices or add-ons for the main device)? If not, why?
  • Who would you say are your biggest competitors? What differentiates you from them?

Software Development

  • What is the current architecture of the software?
  • What is the direction that is moving to?
  • What is your current tech stack?
  • What development methodologies (TDD, Pairing, Mobbing, XP, etc…) are you using?
  • How do you maintain quality?
  • What is one quality you appreciate it a teammate?
  • What is one quality that gets on your nerves? How much work is new (greenfield) vs maintenance (brownfield)?


  • What would you consider to be a big success over the past year?
  • What would you consider a failure or stumbling block over the past year?
  • What is the best thing about working at ?
  • What is one thing that be improved about working at ?
  • What determines “success” for this role? How would you measure / know it?
  • What does a typical day look like for this role?


  • How many vacation days? How many sick days? Are they from the same bucket (i.e PTO) or different buckets?
  • Is there a 401(K)? If so, what’s the vesting period (i.e. how long until the employer contributions become yours)? What’s the employer contribution?
  • Is there a training budget? If so, is it per person, per team, per department? What do you typical training expenses look like (books, videos, conferences, or in person training)?
  • When does open enrollment begin for insurance? Am I covered on day one or is there a waiting period?