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Uncomfortable questions

How comfortable are you in asking uncomfortable questions?

That sounds like an oxymoron, but it isn't. I have a spectrum when it comes to how comfortable I am asking uncomfortable questions ranging from 'not comfortable at all' to 'it comes naturally to me'.

When I look more deeply at that spectrum, I notice that I'm closer to 'not comfortable at all' when I'm either not very knowledgeable about the topic or when I don't particularly care about the outcome. And I'm closer to 'it comes naturally to me' when I'm very passionate about the outcome, or when I'm comfortably knowledgeable about the topic.

It is as though my brain is making an evaluation each time to ask, is it worth asking the uncomfortable question based on what I know and how important the outcome is to me.

As Product Managers, one of the key skills we bring to the table is our ability to ask uncomfortable questions. And this is a trait that is becoming increasingly necessary in every role. After all, if someone had to simply follow orders and execute, their role is likely to soon be automated away.

If you're struggling to ask uncomfortable questions, then spend time acquiring more knowledge about the topic and cultivate an interest in the outcome. The importance of the caring-about-the-outcome factor is so vital that the concept of skin-in-the-game is widely touted.

Not doing so is detrimental in the long run.

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