Are you asking safe or courageous questions during
the interview to determine the best fit for YOU?
As you look for a new job, will you take any job offer or are you looking for the right one? What
does the right job mean? Too many times job seekers do not take enough time to reflect on
where they have been in their careers before they actively begin their new job search. When they
receive an offer, they do not have acceptance criteria that help them determine the right fit.
To help you identify what the right role would look like; think back in your career when you
were the most satisfied. What role did you love doing, what type of manager were you working
for and what was the culture like during this time? It comes down to 3 main areas that you need
to have answered about the job and company.
1. Does the culture meet your work values that you need fulfilled to succeed?
2. Will you be utilizing your top 3 skills you excel in the most?
3. Are you doing something that interests you?
Now you know your criteria for the right role, you need to ask courageous questions not safe
ones that will impress the interviewer and have you stand out from your competition. Safe
How would you describe your managerial style?
How would you describe your culture?
Does your company take risks?
The responses will give you some answers, but will they answer the 3 questions above?
Here are more courageous questions to ask:
1. How receptive are you to feedback from one of your employees about something they
disagreed with that you did?
One of your values is being able to speak up (diplomatically of course) when you disagree with a
certain decision or behavior of your manager or peers. You want understand how receptive your
manager and others would be to constructive feedback without fear of retribution.
2. As a manager, what frustrates you about people that work for you?
As often as you can during the interview, ask questions where the manager would be able to tell
you about a specific situation. In this case, you want to know what frustrates him/her, so if you
get the job you will know what behaviors to watch out for in yourself.
3. Is there a project your department is working on now and if so, how are you interacting
with your staff on it?
You certainly want direction from your new manager, but not one that micro-manages your
work. If you asked the safe question, do see yourself as a micro-manager, they might answer no I
am not at all. However, when you asked the question above, you hear he is involved in the
project every step of the way. It could be a red flag for you about his style.
4. Can you give me an example of how you work collaboratively with other departments?
Your idea of how people collaborate can be completely different than others, so by asking what
it looks like in their company, you can assess if it is compatible with the way you work the best.
5. Does the company welcome celebrating special occasions in employee’s lives? What was
the last occasion your department celebrated?
You want a culture that is fun and your idea of fun is celebrating special occasions. Now, if the
person mentions “we don’t tend to celebrate”, you could follow up to ask why and then get a
sense if they would be receptive to it the future.
6. What would be the 3 things that your peers would say you do extremely well?
This question is often asked about you as the interviewer is listening to what you will say. In
some cases, they might follow up with people you are referring to in your answer to verify what
you said. You could ask this question to the manager, potential peer or even HR. Since working
in teams is much more prevalent in today’s business, you want to know more about your
7. I understand the company has a formal recognition program; however, what type of
recognition have you recently given to one of your staff?
If recognition is one of your values, this is a good question. It not only tells you about the
company culture, but also if the manager is generous with recognizing the great work of his staff.
Most everyone wants recognition for the work they do, but in very different ways.
8. Has anyone on your staff been promoted over the last couple of years? If so, what was
the reason why this person was promoted?
If you are looking for development opportunities, you want to know what it would look like. You
also want to know if the person was promoted because they pushed it or the manager led it.
9. What type of work do you delegate to your staff?
You want to work for a manager who delegates, so you can develop beyond your role. If a
manager is not a good delegator, then he/she might be insecure about their role and not want you
to know what they are doing. This could potentially hold you back from promotions or
10. What are the 3 main factors you will be using to determine the right person for this
This question is best asked toward the end of the interview, so the interviewer might use some of
what you have to offer as some of the factors. You do want to find out how you fit in with the
manager and job criteria, so if you could address the concerns in the post interview
correspondence and next round of interviews.
11. What have been the main characteristics of your favorite employees?
When someone is talking about a favorite employee, watch for their body language, tone of
voice and listen carefully for what they say. It will help you determine if you have some of their
same qualities and if not, it will give you more to think about after the interview.
12. What was the company’s most strategic decision made in the last year? Could you
describe how they came to this decision?
You want to work for a company that is planning for the future. By asking this question, it will
demonstrate to the interviewer that you are thinking ahead. It will help you understand what you
might need to do to keep yourself current in your field and continue to add value to the company.
13. Can you give me an example of how and why one of your staff made a major mistake
and what was your response to it?
You want to be able to take risks, but you also want to know your manager will support you in
resolving it not reprimanding you. It will give you a sense of the level of risk taking that would
BE COURAGEOUS BY ASKING THE RIGHT QUESTIONS THAT WILL HELP YOU
MAKE THE RIGHT CAREER DECISION FOR SUCCESS!
Jayne Mattson/Senior Vice President Keystone Associates www.keystoneassociates.com