Rhys Metler Toronto Sales Recruiter
By Rhys Metler, Toronto Sales Recruiter

As a headhunter, I screen and interview candidates regularly, so I know first-hand about putting candidates on the spot with difficult questions… and how stressful it can be!  The only way to handle tough questions is to be as prepared as possible.  In this post I’ve outlined the 13 toughest questions interviewers almost always ask, with guidance on how to answer them.

1. How did you like your last employer?

Never criticize a former employer in an interview.  You might express appreciation for what you learned on that job.  If pressed as to why you left, an appropriate answer can refer to your leaving “to pursue a new and challenging opportunity” or “for a situation which offered more opportunities for advancement”.

2. What kinds of people rub you the wrong way?

This is not a time to get into personal likes and dislikes.  The interviewer really wants to see if you get along well with other people.  A good answer may be that you generally like those with whom you have worked.

3. What are your weaknesses?

Once again, this is not a time to let it all hang out.  The best approach is to list a few “weaknesses” which are actually advantages.  Examples include:  being impatient to get things done, needing to produce a quality end product, or having the tendency to take your work too seriously.  Another approach is to talk about a weakness that you have overcome.

tough interview questions

4. What made you apply for this job?

Be ready to cite several reasons why you think your current level of skill and interest help qualify you for the position.  Also, provide several points why you are particularly interested in the employer (which also reflects the research you have done on the organization).

5. Where do you hope to be 10 years from now?

You should have a basic feel for the direction in which you want to take your career.  Your best answer is that you seek the opportunity to show how well you can perform and hope to go as far as dedication to the job and working intelligently will carry you.

6. May I answer any questions about the job?

Be prepared to ask several good questions about the job (with whom will you work, how is work evaluated, etc.), but don’t focus on salary.

Also, before you leave the interview be sure to express interest in the job and ask what the next step in the process is and when it happens.

7. What kinds of work have you done?

Highlight skills you think are important in the new job and cite examples of successes or unique achievements in past situations.

8. What are the most important factors you require in a job?  How should it be structured to provide you with satisfaction?

Obviously, those questions are asked prior to giving the applicant any detailed information about the job in question.  The answer can be one of many, for example:

•             Freedom to work independently or autonomously

•             Security

•             Overall environment

•             Team atmosphere

•             Responsibilities

•             Compensation

9. Describe a time when you felt ineffective, why you felt ineffective, what you did about it, and what the outcome was?

Again the interviewer is attempting to identify the behaviors they are looking for in this job and those they hope to avoid.  If the person forgets to answer phases 2, 3, and 4 of the question it usually indicates a short attention span and poor detail orientation.

10. What are the most satisfying aspects of your present position?  What are the most frustrating aspects of your present position?

The answers should provide insight into “what makes the applicant tick”.  Is this candidate results-oriented and pleased with the attainment of specific goals?  Conversely, has there been difficulty with interpersonal relationships such as personality conflicts, which may have stymied efforts to reach objectives?

11. Has your job performance ever been appraised?  How were you assessed?  Give both the pluses and minuses.

From the candidates’ answers, the interviewers can usually get an idea of their honesty.  While no applicant is expected to reveal major flaws or serious shortcomings, everyone has some weaknesses and failure to admit them imparts a negative impression.

12. Describe a time when you felt particularly effective.

The interviewer is not as much interested in the activity itself as how it described and the behavior evidenced during the explanation.  If the candidate says, “I’m not sure what you want,” this is considered to be a dependent trait.

13. Were your assignments handled individually or were they a team effort?

Here the interviewer tries to determine whether the applicant is exaggerating his own influence in performing tasks and achieving results.  The question seeks a balance.  For example, “I completed the programming for the customer response module independently.  I served as a member of a task force which completed the specifications for that module.”

You can never be certain which questions an interviewer will ask, but coming prepared with answers to some of the toughest interview questions will keep you calm, cool, and collected, and give you a leg up on the competition.


For more interview tips, check out our Tips From a Headhunter For Job Seekers blog category.  Also, learn more about Toronto Sales Recruiter, Rhys Metler, and connect with him on LinkedIn.

IQ PARTNERS is an Executive Search & Recruitment firm with offices in Toronto and Vancouver. We help companies hire better, hire less & retain more. We have teams of specialist recruiters in Financial Services & Insurance, Marketing Communications & Media, Emerging Tech & Telecom, Consumer Goods & Retail, B2B & Industrial, Technology, Accounting & Finance, HR & Operations, Energy, Mining & Engineering, Life Sciences, and Construction, Property & Real Estate. IQ PARTNERS has its head office in Toronto and operates internationally via Aravati Global Search Network. Click here to view current job openings and to register with us.

Rhys Metler Sales Recruiter

Rhys Metler

Rhys is a VP, Client Services of IQ PARTNERS‘ Sales practice and leads the SalesForce Search recruitment team. He specializes in prospecting new business relationships, client retention and renewals, and building top performing Sales teams in even the most challenging environments.

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