Work History

The Human Element

The purpose of this conversation is to get to know the candidate better as a person. The questions are open-ended and do not have right or wrong answers.

The Business Obligation

We’re approaching the point in the process where we need to make decisions. In most cases this is the final interview. Our obligation to the company is to make good hiring decisions. I want to leave this interview with the answers to these questions:

  • Will this person enjoy working at our company and on the hiring team?
  • Will I be able to provide them the support they need?
  • Will I be able to provide them the growth opportunities they want?

A Humane Approach


I typically pick their three most recent roles. I then start at the oldest of those and go through the following questions. Then I move forward to the next most recent and finally to their most recent role, repeating the series of questions each time.

This may sound repetitive, but with a little effort it can be made conversational. I find that discussing the roles chronologically helps to craft a story and provides better opportunity for meaningful follow up questions than traveling backwards through time.

I also like to explain the format of the interview to the candidate before starting so they know what to expect.


I find 60 minutes to be a good length. This requires active time management. If I’ve selected three roles to discuss, I know I have to finish each in about 20 minutes. If a candidate has sufficiently answered a question, I let them know that we need to move on.

The questions

  1. How did you hear about this role and what made you decide to take it?
    This can provide insight into what motivates them.

  2. What were the working relationships and environment like on your team?
    For some candidates the word culture will not immediately call to mind company culture, but that’s basically what we’re after. What was it like? What about it did they like or dislike?

  3. What was something positive about your time there?
    This can help us see what interests or excites this person.

  4. Do you feel like you had the support you needed to grow professionally?

  5. Did you face any obstacles that made it difficult to work as well as you would’ve liked?

  6. If you faced similar obstacles now, would you handle them any differently than you did then?

  7. What led to your leaving this company?
    Being reminded of why people leave companies can help us retain our own staff.

If this was the final interview, I’ll thank them for the time they’ve spent going through the interview process. I also like to ask them if they have any suggestions on how we could do better.

Explain next steps

Understandably, the candidate wants to know when they’ll find out if they got the job. Provide as clear and accurate of an answer as you can.