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When (and how) should you ask recruiters highly sensitive questions?

The job hunt can be a nerve-racking time. So what if you have a tricky question that absolutely needs to be asked – and you don’t know how and when to ask it?

The majority of candidates go to interviews armed with astute and pertinent role- or company-related questions. Their queries will help the candidate determine if the job is right for them – whilst also (hopefully) impressing the interviewer.

But some questions are much, much harder to pitch correctly.

Your questions might be entirely practical: maybe the salary has not yet been disclosed or there are not details about the benefits package. You might not want to make this one of your feature questions as you don’t want to risk creating the impression that all you are interested in is the money and perks.

Alternatively, your questions might be highly delicate. Happily, you might have just discovered that you or your partner is pregnant. At some point you are going to have to broach maternity or shared paternity leave. At the sadder end of the spectrum, you may have just received a potentially devastating medical diagnosis and – whilst this will not immediately affect your ability to perform the role – it might have future implications.

You may have deeply personal questions regarding your target company’s support for, or policies preventing discrimination against, ethnic minorities, employees who are LGBQT or physically challenged.

On a less sensitive level, you might have booked a once-in-a-lifetime dream holiday, which means you will be jetting off to a different continent during the very period in which your new boss would be expecting their perfect new hires to be settling in.

Whichever scenario relates to you, you will naturally need to time your query very carefully. You don’t want to risk dissuading the recruiter with a red flag at the very outset of the process. But if you leave it to the very last stages, then you might be concerned that this will appear dishonest and untrustworthy…

So, how do you ask these difficult questions?

Easy: you don’t!


At Insure Recruitment, we ask those questions for you. We believe in supporting all our candidates throughout the entire recruitment process. Mostly this will be helping you to identify the best opportunities for you or ensuring you are properly prepared for interviews. But occasionally, you will also need us to ask the difficult questions for you.

Our intimate relationships with our clients and our extensive sector and professional expertise means we know exactly how and when to ask.

More importantly, we know precisely how to get the answers you need.

Don’t let difficult questions prevent you from boosting your career. Call our team on 01483 668700 or email us today at for more information.

Discover the many unmissable opportunities our clients have on offer: register with our Candidate dashboard today.

We will help you find your dream insurance or financial services job.

No question.



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