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Interviews: how to approach awkward questions

8th November 2021

Gabby Rosenberg took to LinkedIn live once again last week to give her view on all the awkward questions we don’t want to ask during interviews. Often the pain of suffering some awkwardness is overruled by the importance of learning what we can about an organisation before we agree to working there. If we agree that it is always best to ask, what is the best approach? Here’s a summary of Gabby’s points…


The importance of asking questions

I have a lot of people contacting me for new roles because they are looking for opportunities to progress. In my experience, this one of the main reasons people search for a new job. As it is such a huge factor driving job moves, it is never too early to ask about progression opportunities. You want to know not what just the job is today, but what the future is for you within that organisation. Moving jobs is one of the biggest decisions we make in our lives, and it is easy to develop tunnel vision on the role itself. Candidates should not forget that they will be working in a brand new environment that might feel ‘new’ for a while, so understanding what it is like to work there from a peer perspective is essential. It is completely okay (and recommended) to request to speak to other team members to ask as many questions as possible; anything that can help influence such an important decision for you is worth asking.


You learn something new…

Often, the responses to these ‘awkward’ questions can tell you a lot about the organisation where you are applying. People will find it difficult to work in an environment that does not align with their personal values, no matter the job description. As I said in my last live, candidates are faced with more job offers than ever, so it is helpful to consider the business’ policies to gauge an indication into the working environment. Candidates ask me if they should query the organisation’s approach to D&I and mental health, and I say a good, contemporary business is able to talk about these topics and their policies. Polices can reveal how much an organisation has thought about important matters. A lot of my candidates look for an organisation with the right maternity and paternity policy and it’s fine to ask about these. If some businesses have ‘old-fashioned’ views, then it is not the right business for you.


Balancing act

Sometimes it is in the framing of the question. How do you request time off for emergency childcare? Or bring up a negative Glassdoor review? A considered question, that appeals to both employer and employee, is the best approach. Here’s some examples;

‘I have childcare set up, however if that care fell on me I would like to know there would be flexibility?’

‘As part of my research I have looked on Glassdoor and there have been some not so positive comments, what are your views on these?’

Give the employer the right to reply. As I have said before, if you don’t ask, you don’t get.


A helping hand

Questions that have little deciding factor on whether an organisation is right for you can be difficult to navigate. Learning a business’ dress code and travel expenses policy is helpful but not always crucial to a first stage interview (unless extensive travel is part of the job). One of the benefits of working with a recruitment company is that they can ask all the awkward questions for you. Usually, because it is your choice to attend that interview, travel is at your expense, but recruiters can about a specific dress code and prepare candidates. When it comes to the big, make-or-break questions like salary, I believe in being honest. It is very British to not ask about money but very few candidates are willing to move for less than they currently earn, so you’ve got to ask! Some clients do go outside of the advertised salary banding, so if you’re only a small margin out you should still consider opportunities.


There is a reason these questions are titled as ‘awkward’ and framing them can become a real balancing act. An employer must dedicate time for candidate questions; this is usually the best way to wrap up an interview. A recruiter’s experience can help frame these questions positively, but whether you use one or not, make sure you ask as they tell you what you need to know in terms of the response to the question, but also about the wider business.

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