How to ask the tough questions at work

Sometimes getting what you want in life can be simple as just asking. But when it comes to your career, it isn't always that easy.

A raise, a promotion, extended leave, flexible working hours - these are all things we may want from our job, but are reluctant to ask for.

At some point in your career you’ll likely find yourself asking the tough questions of your boss. So, how do you do it in a way that will hopefully lead to an answer you want?

Come prepared

It’s important you prepare how you’ll present the question and also think of how you’ll respond to the questions you’ll receive in return.

  • If you have more than one question, or important points to back up your question, write them down. This will be a valuable reference if you get flustered.

  • Make sure you’re completely open and honest about what you want and why. Present facts, not more questions.

  • If you’re asking for a raise or a promotion, have a list of compelling and valid reasons why. “I want more money” is not a good reason, but “I have taken on a huge amount of responsibility and leadership, and I’m worth a great deal more to you than last year” is.

  • Don’t forget, you and your boss are both human, and both are bound by standard employment laws. If you have a pressing personal matter that requires you to take extended leave, such as a close relative who is ill, then lay those facts out there.

  • Remember that the aim is to find a mutually agreeable solution, not for either party to be forced into a corner.

It’s all about the timing

Bursting into your boss’s office at 9.01am before they’ve had a coffee, or during your lunch break when they’re guiltily scoffing a pie will not grant you a great reception.

Strike when your boss is at their best and not under pressure. It might be best to make an appointment and find somewhere private to talk so you get their undivided attention.

Be direct and be patient

Don’t preface your question with a lengthy background story about what’s to come - nobody has time, or patience, for that. Instead:

  • State your question first and then provide background explanatory information if it is asked of you.

  • Silence can be golden. Once you’ve asked your question, be patient and allow space in the conversation for the other person to think and respond in their own time.

  • Try not to be emotional. Even if you are addressing a personal life matter, such as flexible work hours to care for a family, it is a business conversation, so adopting a professional demeanour will go a long way.

Don’t get defensive

If your question is met with a resounding no, a maybe or no answer at all, then the natural response is to ask why.

There’s nothing wrong with that, but try to shape your “why” in a more productive way. For instance:

  • How can we work together to solve this problem?

  • Is there a halfway point or similar solution to what you’re asking for?

  • Suggest a follow up meeting to give your manager time to come up with a solution.