I spend a great majority of my work life sourcing and interviewing software engineers, product managers, and other technical professionals. After years of doing so, I have found some questions to be exceptionally useful at identifying if a candidate aligns with the culture and “why” of the teams I build.

What do you want to be when you grow up?

Very few candidates are not shaken when I ask them this question. Your instincts probably tell you that you should repeat the job description for the position you’re interviewing for as what you would love to do for the rest of your life. What you don’t realize is that the ideal of this question is to dive deeper into what motivates you as a person.

Particularly in software, the “lifespan” of someone beyond two years is virtually unheard of at a single position, let alone organization, so I try to be realistic and work within the constructs of reality.

One candidate (whom we eventually hired) I’ll never forget because it was the fastest response I’ve ever received to this question: “I want to be an author, but generally just love making things people use.

That told me several things:

  1. This candidate knew exactly what they wanted in the future, which leads to deeper questions about setting long term goals and achieving them, and overall work ethic.
  2. This candidate had a passion for reading and learning; few things are as important in software as a deep interest in constantly learning.
  3. There are a lot of ways I can align these passions for writing and making things people use to helping the rest of our team which will give deep purpose, and hopefully play, to the day-to-day for this individual.

What accomplishment are you most proud of in your life?

From this, I hope to gain an understanding of the level of effort a candidate puts into things. For example, a clear picture can be drawn when someone responds with “I saved for 7 years to buy a boat my son and I can fish the pugent sound” versus “I filed the most bugs of any engineer on our team last year.”

Both are great accomplishments, and nothing to scoff at, but the individual who saved for 7 years showed a great deal of commitment and grit and stuck with a goal that was truly meaningful to him and his son; and while it had nothing to do with software, you can safely bet that person applies the same effort to their work. To be clear, testing and finding bugs is an exceptionally important value in the software industry, but that is more of a task based mindset that is hard to identify the actual work that went into the task. Were they all unique bugs? Were they all part of the same project? Were they known but not yet filed? It is much harder to get a clear picture of that persons grit from that answer.

What things do you dislike most in the software industry?

Here we try to identify triggers and cultural elements that may or may not align with the team. For example if a candidate responds that they really want to be left alone to do their work because that’s how their most efficient, I certainly sympathize, but our scrum teams meet at least once per day and are in constant collaboration, so that would be alarming.

Similarly, if a candidate outwardly labels a specific technology I guarantee I will prod deeper into that, because that generally indicates a lack of willingness to leave their comfort zone. A C# developer will likely prefer C# to node.js, but to outwardly disparage node.js would be an indicator that they simply are not interested in learning the advantages/disadvantages between the two.

It’s all magic

In the end, it’s all instinct and intuition, but these are some of the key questions I ask every single candidate because I have had great success with these questions leading into others that create great conversations with candidates.

What really matters most is that you stop the whiteboard interviewsas I’ve shared about in the past.


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