Security Engineer Interview: Conducting Empathetic Interviews

Being good at interviewing others is a skill. Let’s read that again, a little bit slowly this time. Being good at interviewing others is a skill. It is not about being able to ask one question after another to judge the candidate in front of you. It is a lot more than that. In this article I would like to talk about a technique I call “Empathetic Interviewing” which I came up with after conducting dozens of interviews. It is centered around the idea that people remember how you made them feel. It can be used in conjunction with the interviewer’s framework I described in my earlier post.

In a nutshell, empathetic interviewing is about the following:

  • Making the candidate comfortable
  • Recognizing the breadth and depth of responses
  • Changing and reframing questions to get the best answers possible from the candidate
  • Promoting a sense of equality by answering questions.

Making the candidate comfortable: This is the most important thing to start with. It helps establish an initial rapport. There are several ways of doing this:

  • Introducing yourself, what you do, how long have you been at the company.
  • Outlining how the interview is going to be structured.
  • Being open to answering questions during and after the interview.

The above are just a few examples but you get the idea.

Recognizing breadth and depth of responses: Once you have made the candidate comfortable and are in the middle of the interview, for each response from the candidate gauge the breadth and depth of the candidate’s answer. You may wonder how this falls under the empathetic interview umbrella. The key is “how” you accomplish this. One of the most effective ways I have found is to go from open ended questions to more specific ones as the candidate gives you more information. The point at which you feel that the detail of the response has significantly decreased, you can steer the candidate in another direction to expand the breadth. Repeating this will lead you to examine both breadth and depth of a response. For example, let’s take the question which I talked about in a previous blog post – “How do you go about ensuring two parties can communicate without the possibility of eavesdropping on the network?”

If the candidate starts describing how TLS works on a high level, you can increase the depth by asking specific questions around how key exchange would work? types of attacks possible? etc. Once you feel the candidate has reached their “knowledge” limit, you can pivot to another question e.g. what other protocols can be used to accomplish the same goal? In response to which the candidate might start describing an application level protocol like SSH. Rinsing and repeating this process would give you as an interviewer a really good idea of the strengths and weaknesses in the response.

Changing and reframing questions to get the best answers from the candidate: This is yet another important skill. Sometimes candidates get stuck or do not know how to answer a question. Recognizing “when” this happens and altering the question is the skill to develop. An effective technique is to reframe the question in a way that can still give you an idea of the candidate’s knowledge. Taking the same example as above about establishing a secure communication, if the candidate gets lost in the beginning, you can hint by being more specific and reframing – “how do you ensure confidentiality of data between a server and a client”. It is a similar question but slightly more specific which some candidates might pick up on. Note that both this and the above steps let you gauge a candidate even when it is challenging to do so.

Promoting a sense of equality by answering questions: At the end of the interview, finding time to answer the candidate’s question reflects well on you as an interviewer. Interviewing is a two way street where you are evaluating the candidate for the role and the candidate is evaluating the company as well. This is as important as any other part of the interview. The questions that a candidate asks also can show you the amount of research and thought they have put in.

In summary, the outcome of empathetic interviewing is a great experience for the candidate which should feel like a discussion with a teammate. At the same time you as an interviewer should be able to provide an accurate assessment of the candidate. If the candidate ends up working with you in the future you already have a good rapport with them. If not, they still carry a good impression of you as an interviewer. Win-win!

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