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Building the Relationship: Questions to Ask in Interviews

Victor Wieczorek and Edward Dunnahoe are involved in the hiring process for the Threat & Attack Simulation Team at GuidePoint Security. With abundant experience as both interviewers and interviewees, they offer advice on the kinds of questions you should be asking in your interviews.

Edward Dunnahoe: There’s often an emphasis on being prepared for the interview and the questions that the interviewer is going to ask. In our experience, not a lot of people ask us questions though. So we’re going to walk through some categories to give you ideas of things that you can be asking, to make sure that the job is the right fit.

Victor Wieczorek: A lot of people fall into the trap of the interviewer talking 90% and the interviewee only talking 10%. The cadence is rapid-fire questions throughout the initial screening, finally leaving the last 5-10 minutes to, “Do you have any questions for us?”

You’re put on the spot after being berated with tons of questions about yourself, but in essence you are interviewing the company just as much as they’re interviewing you. You have responsibility for at least 50% of the relationship and it’s on your shoulders to sustain. Just like any relationship, it’s two-sided and in this case it starts with the interview.

Get A Grasp of the Culture

Edward Dunnahoe: One of the things you should be asking about in your interviews is culture. You don’t want to be looking for another job in six months because you find the culture isn’t a good fit. Malcolm Gladwell makes a point about big fish in a small pond. Some people prefer that, while others desire to be a small fish in a big pond.

It’s important to know what kind of vibe you’re going to get from the company that you’re considering. For instance, at startups there’s not necessarily a lot of documented procedures. People make things up as they go in some cases and that might stress some people out. You may like a military structure where there’s a procedure for everything, just follow the checklist, do your job, and then you’re done.

Also, understanding how teams communicate really comes into play, especially with remote positions. We have people all up and down the East Coast, so we use Slack as a method of communication. It’s very important to us that people remain engaged and come to events, as we only see each other face-to-face about three times a year. You want people to be familiar with other team members’ skillsets, that way if you need help doing something you’re not familiar with, you know who to go to and you have a relationship with them. So it’s good to ask about interaction dynamics between the people on the team as well.

Victor Wieczorek: The key is to find out how each role contributes and communicates in a team. This isn’t going to unlock all your answers, but it starts a dialogue. You have to be very active in this—you can’t just throw that question out there and hope the interviewer gives you all the information you need. So be present in the dialogue and try to pull out all the different pieces that could be critical to your career in the future.

Understand the Leadership Background

Victor Wieczorek: A key area to ask about is leadership—understanding what their background is and where they come from. Do they know the challenges that you’ll face in that role? I’ve worked at companies where the leaders are so far detached from the technical delivery of what we do, that they have a hard time understanding. It’s a little easier when you have some common ground, so understanding the leadership background is essential. Best-case scenario, they can talk about walking the walk that you’re about to undertake, or at least understand where you’re coming from so you’re not fighting tooth and nail for every little thing.

Edward Dunnahoe: At my first security job, I reported to a project manager with no technical background and it was probably the worst job I’ve ever had. I got a lot of good experience there, but reporting to them was incredibly frustrating because they didn’t know what the job required. At GuidePoint Security, we have partners that have been doing this for several years. They can still hop on a call and explain technical vulnerabilities to our clients if we get tied up with a conflict. If we need more licenses for a tool, we don’t have to go to war for it. It allows us to focus on getting work done and writing new automation tools, instead of having to build a formal business case to get somebody to loosen the purse strings a little bit. It makes it a lot easier to get things done in my opinion.

How leadership engages with the team is especially big for us. We’ve built relationships with our management and we feel comfortable going to them with problems and criticisms. It’s important to know what that receptiveness is going to be like. In a lot of companies, people feel that if they bring negative things to their supervisor it will be turned around on them. That makes you feel insecure when providing meaningful feedback that might actually make the organization better, so you just quit doing it. Having that openness and accessibility is very important.

Find Out Your Potential to Contribute

Victor Wieczorek: I like to ask about how I would contribute to the team. This question gets you and the interviewer talking about what the possibility and potential is in the role, so you can come in and tangibly see that needle move. At GuidePoint Security, we’re obviously working to increase the security of our clients, so I want to see change in an environment after we do a red team or any kind of assessment. I derive personal reward when we come back the next quarter and see things improve. That’s what you’re trying to get—a sense of what makes you feel like showing up every day or how you can make a difference.

Uncover the Major Stresses

Victor Wieczorek: What are the teams’ most hectic times? With this question, you’re trying to uncover what the stresses are in the job. Maybe your current life objective is starting a family or a side business, and you want a job that has relatively low stress and responsibility. Or maybe you’re looking for that next challenge or level up. That’s certainly an individual decision that the interviewer can’t make for you, and it’s probably not likely to come up in a normal interview. November and December tend to be really hectic times for us, where a lot of people on the team are challenged to do things at a tempo that’s atypical for the rest of the year. Understanding what those potentials are and what those stressors might be helps you gain understanding of how you would fit in that particular job.

Recognize the Workload

Edward Dunnahoe: Understanding the workload is obviously important too. This strikes that work life balance chord—making sure that you’re making time for your personal life and hobbies. Getting into this industry is obviously a very steep learning curve. You have to marry the job if you want to advance quickly. If you’re willing to put in the time and effort that it takes to go get certifications and study, that’s great. Everybody needs to go through that phase in their life, but once you get further in your career that may not be the case anymore.

Recently I’ve tried to start unplugging and getting away from my computer in the afternoons to do some woodworking. It’s good to have that kind of breakaway and to shut off your brain every once in a while. But on the other end of the spectrum, if you’re invested in getting certifications, you need an understanding of what kind of time commitment outside of your normal business hours that will require. Make sure you ask appropriate questions to set a baseline and make sure your expectations align with your potential employer, whatever they might be.

Realize Growth Opportunities

Edward Dunnahoe: Career trajectories may differ depending on what your aspirations are. Like I said, if you’re just starting out you might want to hurry up and climb the ladder, while others may want to learn at a gradual pace. It’s a good idea to ask about what the expectations are for whatever role you’re coming into—and also, where do you go from there? What are the opportunities for growth? Is it a place where you can build your career?

Some places have specific certification requirements for particular roles. If your expectation is to get into a higher position at some point, then it’s good to know what those opportunities and requirements are. Do they offer technical training? Having the ability to take certification training and not have to pay for it is a pretty big deal for me. But you may find that a company has no training budget whatsoever and any training that you want to take is all your responsibility.

Victor Wieczorek: Additionally, work-life balance and anti-burnout are huge in our industry. What does the team do to combat that when they see it? What’s the PTO or Time-off policy? What are some other things the team does to take a break or help you avoid getting lost inside the business and getting burnt out? These are all valid things to understand and consider.

Overall, I hope we left you with some questions to ask in your interviews, to start that dialogue and to build the relationship from day one. As an interviewer, I want to understand that you’re engaged and that you’re going to take control of your career. What are you passionate about, what can you contribute, what is your self-worth, and who are you? Be engaged in the process, build on the relationship, and find the right fit for you.

Edward Dunnahoe: Whenever we interview people and they don’t ask questions, it makes me wonder if they’re really interested in the job. Are they going to stay here for six months or six years? So demonstrate that you’re interested in the position if you truly are and make sure you walk in knowing what your expectations are. As long as your expectations match the reality, you’ll be in a good place.