by Rich Hein

How to Prepare for Tough Interview Questions

May 08, 201413 mins
CareersIT JobsIT Leadership

We spoke with industry experts to get the advice that will help you craft better answers to what are some of the most common, and difficult, interview questions.

When companies are looking to hire someone, especially in a leadership or CIO position, they are looking for several things. Often times hiring managers have little precious time with actual candidates to decide if they have the technical ability to get things the done, the business acumen and vision to get IT to align the company’s business objectives and it’s technical capabilities, and finally but certainly not the least important, how someone would potentially fit into the company culture and work with upper management.

For most of us getting interviewed is never an easy process. You’ve got to be spot-on perfect for what seems like forever, many times through a multi-step interview process. You’ve got to know your technology, be ready to articulate effective answers and questions, all the while putting on your most pleasant and positive face. There is no shortcut to acing the interview. It takes, time, dedication, research and practice. In spite of all the preparation even the most seasoned interviewee gets thrown a curve ball every once in a while.

The only hard question to answer is the one you didn’t prepare for. So in order to help you get the job of your dreams we spoke with IT recruiters, staffing firms, CIOs and other senior IT personnel to find out what questions are typical stumbling blocks for those being interviewed, and how to best to prepare for and answer these questions in what could be the longest and most important hour of your career.

Question #1 – Why is there gap in your work history?

Lay-offs, workforce reductions and downsizing

In the recent economic downturn many companies experienced lay-offs or simply went out of business. Senior IT people understand this economic reality and normally won’t hold this against you. That said, hiring managers typically prefer hiring someone who is already employed. According to Matthew Ripaldi, Senior Vice President with Modis, you should not try to dance around it but instead be straight-forward and honest about exactly what happened. “Chances are they already know. In addition you want to make sure you make it clear that it was not performance related and be able to talk about specific accomplishments you had while in the role and references of your work that are readily available. Make sure to rehearse how you’re going to answer that question so that it flows smoothly, and finally, never say negative things about your past employer!”

What if I was fired?

If you were a part of a downsizing or workforce reduction then the answer can be simple and self-explanatory. If the reasons are something you’d prefer not to get into then you had better prepare ahead of time. Scott Saccal, Senior Director and IT leader with Johnson & Johnson Diabetes Solutions Companies says it’s best to take the high road. “For this question, it’s probably best to take the position that the position was not the best fit for both you and your previous employer. Should there be additional probing, it’s important that you be honest but brief in your responses as dwelling on the subject prohibits a discussion on your strengths and potential value in the new job,” says Saccal.

Ripaldi offers this advice, “You’ll want to be honest but keep it short and transition the response into a positive and then the next question. For example ‘It was a blessing in disguise, now I have the opportunity to explore a better matching position such as this opportunity with your company, would you like to hear more?’ Many times it was probably the wrong match from the beginning and you can state that. If it was for personal problems then you can reference that you’ve solved them and now you’re ready for the next phase of your career.”

Harvey Batra, Director of Information Technology at The Truland Group, Inc. reminds readers to always demonstrate your ability to stay current. Let the interviewer know what you did to better yourself during your time between jobs. “Out of work does not mean outdated, be ready to explain how you utilized the downtime time to catch up on either a new technology or fine tune an existing one. Think creative, volunteering is often a great way to make use of this downtime,” says Batra. Employers like to see that potential employees have managed, in a difficult time, to keep it together and improve their skills.

Question #2 – What is your biggest strength?

This is a softball question that is typically followed by the next question on our list. That said, it is an opportunity to demonstrate how your abilities align with their goals. Our experts say that preparation is key to framing this correctly. Use what you have learned from the job description and your online search of the company to prepare an answer that highlights your strength in a way that aligns with the positions objectives. “The most important thing is to know your audience–do some research to think about where your skills overlap with their needs and place emphasis on these areas when talking about your strengths, says Mark Stagno, principal consultant and team leader of software technology search with WinterWyman, an IT recruitment firm.

“Answering the ‘what is your biggest strength’ should tie into your 30 second elevator pitch,” advises Ripaldi. An elevator pitch is a brief, well-rehearsed response that clearly states your strengths and how they align to the position.

As we get older and more experienced we evolve and so should your strengths and weaknesses, according to Batra, who says, “Strengths and weaknesses also change as you progress through your career, so if yours have been static all along, then that is a sign that you haven’t taken the initiative to develop or overcome them.” This isn’t necessarily something an interviewer might pick up on but it is a signal that you need to take your work on the particular weakness a little more serious.

Question #3 – What is your biggest weakness?

“No one is perfect, everyone has weaknesses but how those weaknesses are dealt with and improved upon separates candidates during the interview process,” says Matthew Ripaldi. Whether we like to admit it or not we all have areas where we need improvement. The hard part is figuring out which area to discuss and how best to frame it. In the end, the interviewer is trying to get a feel for how well you know yourself and what you are doing to learn and grow.

“On the weakness, be equally frank and offer examples where you recognized the weakness and also how you mitigated it in a particular situation and I would equally want to know how you are working to improve that weakness,” says Houston Ross, Vice President, COO and CIO of ING Life Insurance Company, Ltd. (Japan).

Scott Saccal offers this last piece of sage advice, “&share a story from your past with examples of how you have been able to successfully take a weakness to a strength that was valued by your previous employer.”

Question #4 – What was your biggest career failure?

Just like any of the other questions here, how you frame your answer is what’s important. You always want to try to highlight the positive. “I would first share that I’ve never had a career failure, but that, I’ve had career learning opportunities that have resulted from adverse situations,” says Saccal.

Houston Ross offers this as a possible template for your answer, “In a rush to deliver on a major initiative I failed in leading my team. There was a major system rollout that had been underway for over two years. Toward the end when success was in our sights I stretched the team too much and we skipped what seemed to be unimportant steps and those very things came back to haunt us as we went live.”

One great tip is to have a story that demonstrates to the interviewer that learning from that particular failure helped save the bacon at a future date. “Most of us have heard this question before; it is not that we should be afraid of sharing this, but the key is in sharing how we learned from this failure and applied this learning in the future. IT professional’s need to focus on the learning rather than the failure itself,” says Batra.

Question #5 – Why are you leaving/left your last position?

This question, according to experts, presents the interviewee an opportunity to tell their story. “It’s crucial to articulate your career mission and to highlight in a positive way your accomplishments in the previous position and how these contributed to your development as a professional. This allows you to then transition into speaking about the new role, and how it not only capitalizes on your pre-existing capabilities, but permits your continued growth and development,” says Saccal.

The all too common answers like “I want to grow,” “I am looking for new challenges,” and “I am seeking new opportunities in this industry” are all well and good but what’s more important than that according to Harvey Batra is the follow-up question. Here is some food for thought:

Example – I want to grow.

“Can you explain why you couldn’t find these growth opportunities in your existing/previous role?” asks Batra.

Example – I am looking for new challenges.

“Does your current or previous environment lack challenges?” asks Batra.

Example – I am seeking new opportunities in this industry.

“Why this industry, why not another one? Can you explain?” asks Batra.

One possible answer might go something like, “I was with Planet Express for ten years and I worked my way up to IT director. My goal has always been to be a CIO in the shipping industry and there is no other more senior role for me to advance to in my current organization. So in order to continue to move my career forward I have been looking for external opportunities.”

Question # 6 – If you were leading a development project and the project was tanking what would you do?”

The interviewer is attempting to gain insight into your problem solving abilities, strategic-thinking and how you handle adversity. “The key management principles that you want to convey is that you remain calm under pressure, that you are able to triage the issues that pose the highest risk to the project, and that there are periods of adversity in all projects,” says Saccal.

Harvey Batra offers this as one possible answer, “Leading a project is very similar to leading an army to war; if you know you are going to lose then why would you do it. Pause, Regroup and Reassess the situation. Finding the root cause is always key, but accepting and correcting the cause is even more important.”

Question #7 – Are you a job hopper?

With the tech jobs and business markets being what they are, it’s not uncommon to be in the workforce for a number of years with one or two short stretches at a company. However you need to have solid and sound reasons for leaving each job and be able to effectively communicate them to potential employers. Most people in technology understand that if you’re not staying current with technologies you’re going to get passed, so there’s a certain amount of appreciation for leaving a job when things get stale and problems are no longer interesting. That said, if you veer too far in that direction, companies will view you as lacking loyalty. “Once you fall into a category of being perceived as a job hopper, it’s hard to overcome that. The line of what constitutes a job hopper is subjective; therefore you want to make sure you’re thoughtful about any job changes you make,” says Stagno.

Question #8 – Are you a leader?

When you get to the upper echelons of IT, it becomes less about the technological capabilities and more about how you motivate, lead your people, and collaborate with those around you. Think about your career and résumé and try to find a few anecdotes that demonstrate your leadership skills. You need to make sure the interviewer understands that you have what it takes to get all your subordinates and coworkers moving in the same direction and the wherewithal to get your projects across the finish line.

Question #9 – Can you effectively communicate highly technical information to someone who doesn’t understand programming?

When you get to the senior level of technology management, the game changes. You’ll speak with people from all aspects of the company and you’ll need to be able to speak a different language with many of them. You could, for example, be explaining the intricacies of the development project at hand to the CIO, in this case you’d want to cover only the high level tech information and focus more on how it helps the business. In the same day you may need to meet with the developers to figure out why the developers are telling marketing that they can’t have a feature built into the project. This may be a high-level, in-depth, tech-heavy conversation. With the in-depth knowledge of why, you now need to explain this to the people in marketing in a way and language that they understand. Then there is explaining things to the end customer who will have a completely different perspective, and different set of communication skills and needs.

The best way to answer this question is with preparation and knowledge of your industry and job. Choose something you are well-versed in like cloud technology or virtualization and explain it as you would to a non-tech person. It should be, short, succinct and understandable. Practice, practice, and more practice is key to getting this right.

Question #10 – I see you were with your last company for 5 years and you weren’t promoted. Any idea why?

For this question our experts advise that interviewees should speak about what they have control over. Stick to things like competencies, and capabilities and the accomplishments that have been achieved. “You should acknowledge that while you consider yourself to be ambitious, that you are also aware that companies promote people at different rates and for different reasons. Finally, you should mention that you are pleased with your position as long as you are experiencing growth and delivering value for an organization and being appropriately recognized as such,” says Saccal.

Final thoughts

Conveying the value that you will potentially bring to a company is a difficult task. The best plan is to prepare and practice. Having a friend act as the interviewer, or answering your questions while looking into the mirror are viable options. Whatever you do remain calm and remember that the bottom-line for all parties involved is to find out if this is relationship is worth investing in.