When preparing for a job interview, most people will anticipate the questions that may be asked of them. Questions about experience working with volunteers, assigning and monitoring work delegated to employees, and familiarity with office software applications are fairly typical.

But beware those questions that may not be expected and potentially could trip you up as a job candidate. These are not questions the employer asks intending to harm your chances. They are motivated by a keen interest in how you deal with the unexpected and to learn what makes you tick. They absolutely should relate to the performance the job requires of the successful candidate and whether you have demonstrated these competencies in your career to date.

A classic example is a question asked by the CEO of one of the client organizations I frequently work with. He likes to start interviews (after the usual introductions and pleasantries) with this question: “So, Tim’s or Starbucks?” Let’s reflect for a moment on what is likely going through the manager being asked this question:

• If I answer “Starbucks” will they think I spend lavishly? Will they think I need a harder jolt of caffeine in the morning because I’m slow to get started? Or, will they think I just prefer Starbucks?
• If I answer “Tim’s” will they think I am a loyal Canadian? Will they think I relate to people of all economic strata? Or, will they think I just prefer a double-double with a cruller in the morning?

The fact is the CEO doesn’t care where you get coffee or which brand you prefer. His reason for asking the question is to see how you respond to the unexpected. And, “sorry, I only drink tea” is not a good answer.

Are you ready for these questions?

I’ve collected tough interview questions that business and not-for-profit leaders ask of candidates seeking employment in their organizations. Here are twelve challenging ones. Practice your answers and create a file of your own interesting interview questions so you can be a masterful candidate at future job interviews.

• Why do you do this work (or why do you work in this sector)?
• Personal self-awareness is the key to hiring the right team and deploying a team effectively. Tell me exactly what you do well and what you don’t do well.
• What is your legacy with previous employers – when we contact them what will be the one thing they will say about your time there? Remember, think about what past employers will actually say.
• Share an example of where you picked or hired great people, mentored them and inspired them. What great accomplishment(s) resulted from your decision to select and prepare the individual(s)?
• Tell me about a work experience where you had to deal with something that seriously tested you, professionally and personally, and how you managed the situation (e.g., the outcome).
• Where have you failed and what did you learn from it?
• Describe a situation that reflects your tolerance for risk.
• Give me your objective assessment of our organization based on what you’ve learned – good and bad. How would you make us better?
• When have you had to confront something that was very difficult?
• Which aspects of your interpersonal skills would you most like to improve, and why?
• How have you made your current or previous organization an exciting place to work for others (staff and volunteers)?
• Based on your most recent performance review or feedback from your supervisor, what areas would he or she cite where you exceeded expectations, and why; met expectations, and why; needed improvement, and why?

Related interview preparation skills and techniques to hone

Be concise. Donald Trump offers this advice: “Business is no place for stream of consciousness babbling, no matter how colourful you think you’re being. Whatever you’re doing keep it short, fast, and direct. It’s also more polite.” This is especially apt for a job interview. You and the interviewer likely will have one hour to determine whether you and the job requirements are an excellent match, so don’t squander your chances by being unnecessarily chatty.

Use humour (although appropriately). Employers want to see you as a a person who is friendly and whom existing staff will enjoy working with, not just a skilled taskmaster who achieves goals.

Prepare. Research the employer and what they’re expecting from you. Take time to link your best accomplishments in previous roles to the needs of the prospective employer. Think “P-A-R” or Problem, Action, Result. Whether it was a human resources issue, an advocacy challenge, an event deliverable, or some other major outcome, structure answers to define the problem you faced, the action you took, and the result you realized. The PAR approach also will help you to be concise in communicating your experience.

Be proud. There’s nothing wrong with trumpeting your achievements so long as you are measured and honest. You need to be a champion if you’re going to be the number one pick for the job.

Understand the interviewer’s task. I subscribe to Lou Adler‘s advice that interviews should be about fact-finding. I know some candidates I meet find this approach to an interview off-putting because I need specifics about their ability to do what the employer requires, not generalities. When you tell me you did (or can do) something, I am going to probe for more detail. As Adler recommends, the interviewer should get examples and quantify everything. “Ask for facts, figures, dates, names, and measurements. Be skeptical. Interviewing is a fact-finding mission, not a popularity contest.”

Content is © Jack Shand and is reprinted with permission.

Jack Shand, CMC, CAE, is president of Leader Quest, a management consulting firm providing expert advice to not-for-profit organizations since 1997. Leader Quest specializes in executive search/staff recruitment, strategic planning, governance, and organizational reviews. Jack can be reached at 905-842-3845 and 1-877-929-4473, or jack-at-leaderquest-dot-com.