The Clever Way To Question Your Boss

by Glenn Fisher

Is there a wrong time to ask questions?

Before we answer that, let me ask you some questions...

Have you ever closed the fridge door really slowly whilst peeking inside to check that the light does definitely go off?

There’s no shame in it.

And I bet good money that at some point in your life you’ve put a vacuum cleaner nozzle to your hand or face to find out how strong the suction is.

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Or when they put those ‘widgets’ in beer cans... you must have tried to rip open the can (or at least peak down the spout) to see what the ‘widget’ looked like?

You’re inquisitive.

And believe me, that’s a good thing.

Questioning the norm, challenging assumptions, asking why this does this or that does that... it’s so important to furthering your knowledge and in turn advancing at work and in life.

But consider that first question again: is there a wrong time to ask questions?

Einstein said "The important thing is not to stop questioning." Yes, yes, yes... BUT!

As Michael Masterson recently suggested, when it comes to business, "asking the wrong person the wrong question can be damaging to your long-term success."

The dumbest way to question your boss

Michael says you shouldn’t "ask questions of someone more powerful than you if you have reason to believe they don’t like you..."

It’s a very good point.

The question might be valid but asking it outright of a boss who you think might be out for your head is plain dumb.

For example, let’s say you’ve noticed a particular administrative procedure is unnecessary. Somewhere along the line work is being duplicated and it’s wasting time, money and effort.

You waltz up to your boss (who’s already thinking, what does this jerk want now?!) and pointing out their error you say:

"Louise (that’s your boss), why do we do X, Y and Z, when we could just do A and save time, effort and money?"

Through gritted teeth Louise smiles and says "good point, well spotted... let’s change it."

You proudly (and a little bit smugly) stride away pleased with your good work.

Behind you though, Louise is rubbing two fingers on her cheek like Peter Kay, planning all the crappy jobs she’s going to give you and already plotting your inevitable downfall.

This, my good friend, was the wrong way to go about things!

Hey look, your heart was in the right place. I’m a firm believer in the philosopher Bertrand Russell’s opinion that, "in all affairs it’s a healthy thing now and then to hang a question mark on the things you have long taken for granted."

I hate it when you notice something that’s not working as well as it could and first answer you get is "Well, uh, that’s how we’ve always done it?"

As I say, question the norm, challenge assumptions... but be clever about how you do so!

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You might be lucky and have a boss (or be a boss) who welcomes questions and challenges from their staff, but it’s the way of the world that you will at some point run into an authority figure who isn’t so clued-in and resents your new thinking.

So how’d you get round it, get your point across and perhaps start to soften that prickly relationship?

The clever way to question your boss

The first thing you need to do is give up ownership of your idea. You’re actually going to give the credit away.

But don’t worry; it’s a good thing in the bigger picture.

You see what you need to do is wait for an opportunity where you can float the idea in such a way that your boss or the authority figure picks up on it themselves.

Instead of asking ‘why do we do this...’ suggest ‘we could do this...’

By taking the question out of the equation, you take away the threat.

Don’t say the whole idea... just the gist. Feed the seeds and then let them grow.

Yeah you might not get complete credit for the idea, but you have got your point across and you’ve done so without causing offence to your boss.

And one better, your boss will know it was your idea and will know that you let them take the credit for it. For them it’s a signal that you’re willing to play ball and work together - and that will help things enormously going forward.

So don’t ever be ashamed of seeing if the fridge light goes off, vacuuming your hand or trying to spot an elusive ‘widget’, being inquisitive is an excellent quality to have...

And questioning the norm and challenging assumptions is essential to your success.

But know when to hold back!

We all inevitably meet with some authority figure that we don’t see eye to eye with in our careers... so to make sure you advance in yours be humble, willing to compromise and think of the bigger picture.

Do so and you’ll avoid making enemies, build stronger business relationships and the doors to success will be swung wide open for you.