Chartered Occupational Psychologist, Consultant, Speaker and Writer

5 questions to ask your boss now


Ever been through a performance review?

That excruciating, annual, one-way affair where the manager ticks boxes and drives the conversation, and the only question you ask is  ‘What’s my pay rise?’

Of course, for some of us, even this question can seem too pushy – we don’t even try that.

I definitely think we need to have more honest, open and proactive conversations around pay and rewards (women especially), but in addition to that, I think we can do a lot more than this to make our performance reviews – or any formal conversation with our boss – more two-way.

When I managed a team of super-bright, career-driven consultants, encouraging them to raise their head above their challenging individual targets to think about business strategy, or seek feedback on their performance wasn’t always easy (especially, ironically, to ask question one). And I agree that some of these questions can feel stretching or scary, or provide you with answers you’re not necessarily ready for.

But as a manager, these are some of the questions that I was happy to be asked – and some of the questions I asked in turn of my manager. I guarantee they’ll change the sort of conversations you have with your manager for the better.

1. What am I doing well?

It’s really important to know what your boss thinks you’re doing well, and where she or he sees your strengths.  A great boss will have already let you know, but even the best managers can get caught up in the day-to-day and forget to mention it.  If you get the answer to this question, you can replicate it, do more of it, or apply the strength in a similar situation.  It’s also a good check to make sure that what you think you’re doing well is what your boss thinks you’re doing well – if you and your boss have different points of view on this you might want to consider a broader review around your impact.

2. What can I do differently?

The flip side to question 1 above is usually ‘what am I doing badly?’.  But this question isn’t that helpful.  A better question is ‘what can I do differently?’.  This leads to a much more productive conversation, and should offer some actionable insights.  You can dig down into the reasons that your boss wants you to do these activities differently by asking for more detail on how you could do things differently, but getting into a long conversation about your weaknesses probably won’t serve either of you.  Focus on the future, and experiment with more than one way of doing the things your boss suggests for the most growth.

3. What’s the 3-year plan?

Again, a great company and a great boss will make sure you’re up to date on where the company’s going.  But in my experience, communication in organisations isn’t perfect, and not all employees are interested in the bigger picture.  If you’re one of the few who are, it can make a big difference to your career.  You can make sure your activities are aligned to the business strategy, and also look for opportunities for new projects or more interesting work.  Being the first to put your hand up is a must if you’re looking for progression, and ensuring that the things you put your hand up for are the things that are business-critical will ensure you keep your profile strong not just with your boss, but with the wider business.

4. What else is happening in the business that I should be aware of?

A great opportunity to find out what’s happening in other departments, and hopefully see opportunities to leverage work that’s been done by them in your own department.  Sometimes we have our nose so firmly in our own business we miss opportunities to be joined up, and end up doing things twice.  Organisations can waste a lot of time like this.  You are closest to the work you do, and therefore more likely than your boss to be able to spot this kind of opportunity.

5.  How can I support you better?

Sometimes we forget that our boss is dealing with their own challenges in their role, and may be protecting us as well as pushing us.  Asking them how you can better support them will not only build a stronger relationship with them (you really don’t have to do this in a creepy way!), but help to provide opportunities for you to demonstrate how you can step up.

What sort of questions do you ask your manager?

What’s the impact?

What questions have had the best/worst response?

Let me know in the comments below!

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