Dreaded Interview Questions

Recently, I posed the following question to anyone connected to me via my Durham College Facebook account “What is the most difficult question you were ever asked for a legal support position?” I was preparing to discuss interview preparation with students getting ready to embark on their first field placement experience, and thought perhaps there might be a few new zingers floating around out there that I had not heard before.

For the most part, I was wrong. It seems that what constitutes a ‘difficult’ interview question hasn’t changed a great deal over the past 21 years that I’ve been teaching or in the 12 years prior to that when I interviewed prospective employees as a manager.

What I learned from informally surveying my network is that most questions that raise situations that have the potential to cast an eager interviewee in a negative light are considered difficult by new and experienced job hunters alike.

For example, one contact wrote, “The worst/most interesting question I was ever asked in an interview was, ‘name the worst person you ever worked for and why’. Beyond awkward!” Another noted, “I was asked to explain if I had ever had a difficult boss/manager and how I handled that situation. It’s always hard to discuss negatives in a positive way!” Others wrote that they had been asked about their failures or the hardest lessons they had ever learned in life.

What lies at the heart of these difficult questions is the ability to come across as tactful and diplomatic while providing the interviewer with clear insights into how you handle challenging situations without throwing yourself or others under the bus. To do this successfully, you have to prepare. ‘Winging it’ when faced with questions like these is not advisable!

At the end of the day, the interviewer is ultimately evaluating one or more of the following things as you answer questions like these:

  • How you approach challenging situations
  • The quality of your interpersonal skills when dealing with potentially awkward situations
  • Your ability to communicate effectively – with others and in the interview!
  • Your self-awareness – being able to recognize when you need to exercise tact
  • How you take difficult situations and learn from them for the future

For example, assume you were asked about the worst person you ever worked for and why. The truth may be that the person was a miserable tyrant who treated people like garbage. With some finesse, you can communicate this without tanking the interview.

“One of my previous managers had a very strong personality. I don’t know whether he was aware of it or not, but often his management style appeared to make people feel embarrassed or hurt, and it was difficult to be motivated and upbeat in that environment. I’m a very positive and easy-going individual who enjoys interacting with my peers in a supportive environment and have found that people are much more motivated and willing to go the extra mile when they are happy.”

Carefully chosen words in an answer like this help you navigate the tricky question. Implying a ‘strong personality’ allows the interviewer to assign their own meaning. Saying ‘I’m not sure if he was aware…’ allows for the possibility that the person may not have known the impact he was having rather than you making a strong statement about him as a person. Suggesting that people ‘appeared’ embarrassed or hurt indicates that you don’t make assumptions or jump to conclusions. Finally, referencing your personal traits ends the answer you’ve given on a positive note.

Don’t cross your fingers and hope you don’t get asked a difficult question. Prepare for these questions by thinking about them well in advance of the interview and crafting thorough answers that you can turn around to demonstrate what you bring to the table.