Do you feel guilty when you ask someone the hard questions?  When you really put it to them – not in a demeaning or rude way, but in a direct fashion where you need to know the answers in order to proceed?

It’s odd isn’t it, how guilty we start to feel that we had the audacity to ask these questions?

Maybe I was too hard?

Did I come off too strong?

What will they think because I was so direct?

Depending on who you are asking and the context of the discussion at large I would hope those people feel challenged by your line of questions because you are putting their premise to the test and asking them to demonstrate it’s value.

I still get that guilty pang when going through direct questions, but to date, the responses I have received when asking these questions, have been more positive in nature because I asked them, because people knew where I was coming from and because it challenged them to really think of these answers.  There are always those moments of silence, awkward pauses and struggle to answer, but the conversation that comes next is where the discussion really changes.

Not sure if that whole “feeling guilty for asking tough questions” feeling will ever go away but I do know that when you are leading a team, and you are committed to growing that team, the only way to do so is to ask those hard questions that make your team think, no matter the feelings it brings up in you.  If your motivation is to make the team better, that honesty and integrity will shine through in your interaction with your team.

Want more? Check out my book Code Your Way Up – available as an eBook or Paperback on Amazon (CAN and US).  I’m also the co-host of the Remotely Prepared podcast.


1 Comment

  1. Great post Greg and I agree with you wholeheartedly. And I would also add that we must be willing as leaders to also ask ourselves and allow others to ask us the hard questions too.

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