How to raise tricky questions at work

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We’ve all read the statistic that women only apply for jobs if they meet 100% of the criteria, while men apply for jobs if they meet 60%, and this lack of self-belief can trickle into everyday working life, especially when raising tricky subjects at work. As someone who has asked for a pay rise (more than once), requested a change in job title, and even spoken directly to the CEO about a senior member of staff, I thought it may be of use to share my tips for raising these awkward, and potentially anxiety-inducing subjects. 

Adapt to the person you’re meeting

Whether you’re approaching your line manager, someone from HR, or a Director, think about where would be best for them to have this conversation. If they’re very formal, booking a boardroom or designated meeting space may be best. If they’re quite laid back and would respond to you better over a coffee, it can sometimes go in your favour to suggest a trip to a local coffee shop together; I once secured a pay rise in a Starbucks! 

Make sure they know why you’re meeting 

Continuing from the previous point – make sure the person you’re meeting knows why you want to see them. It’s not fair to blindside someone with a complex conversation if they thought they were being invited for a casual coffee. When requesting to meet with them, explain why you want this meeting, and if appropriate, also send a calendar invitation with the reason you’re meeting as the subject. They need to be prepared just as much as you do. 

Know your worth

You’ve managed to secure a meeting with this person, now is not the time to wobble and be vague about why you’re there. If you’re asking for a pay rise, go in there with specific numbers and evidence for why you deserve that. A while back I was taking on a lot of additional design work, so I worked out how much everything would have cost to outsource and took this to my manager. In just one month I had saved them over £1000; the numbers didn’t lie, and because of this I secured a retention allowance to recompense the extra work I was doing. These conversations can be really awkward, particularly when they’re about money, but you need to be bold! 

How does it impact on the organisation? 

Whatever you’re asking, you need to think how it will affect your workplace. If it’s a change of job title, how does it align with the company’s vision or strategy? If you’re asking for a pay rise, what’s in it for them - what extra output will you provide or have you been providing that benefits them, and means you should be paid extra?  If you’re requesting training that will be costly, how will the skills you gain benefit them? Think in terms of your workplace saying, “what’s in this for me?”, and go in prepared with that answer.  

Command the meeting 

It may sound obvious but go in knowing exactly what you want or need to say. I find it helps to take in notes, so I don’t forget any of the points I plan to raise. Write a few bullet points to make sure everything is covered; once you’ve got this person in a room you don’t want to risk missing anything out! Lead the meeting and make it clear why you’re there and what you want to talk to them about. 

Hopefully these tips will have given you some ideas to apply to your working life; if you don’t ask, you definitely will not receive, so go for it!

(Alice Irvine)