“He who has learned to disagree without being disagreeable has discovered the most valuable secret of diplomacy.”  – Robert Estabrook

The skill of challenging effectively is a constant area of focus – not only in working with my clients, but personally as well.

There’s no doubt about it, challenging is challenging. It’s a tricky skill to master and is often found in the too-hard, too-awkward, too-uncomfortable basket. The same basket you’ll find giving feedback and mastering difficult conversations, BTW.

However, being able to effectively challenge ideas, people, strategies and our own assumptions, is crucial in the workplace. Without enough challenging, poor-quality decisions proliferate and innovation dies. With unskilled challenging, aggressive cultures develop, fear abounds or soft-soaping is the name of the day.

The trick is knowing how. 

So, I’ve put together a few openers which can help to get you started.

Here are 20 ways to challenge effectively:

  1. I have a different perspective…
  2. Can we play Devil’s Advocate here for a minute?
  3. What other alternatives have you considered?
  4. Looking at this scenario, what have we not taken into account?
  5. Are there some assumptions we are making here that could be challenged?
  6. What are our current paradigms we need to be aware of when looking at this?
  7. What are the potential risks?
  8. Do you mind if I challenge that idea?
  9. Can I bring another idea into the mix?
  10. Here’s another angle to consider…
  11. Let’s put ourselves in their shoes…
  12. What’s missing?
  13. Are you aware that…
  14. Let’s look at the worst/best case scenario.
  15. This is going to be a tough conversation… (sometimes framing a conversation that is about to focus on challenging can help prepare everyone)
  16. What are the obstacles and challenges in us/you achieving this?
  17. What would X say if he/she was here (referring to someone you all know helps to form a different perspective)
  18. We’ve listed why this is a good idea. Let’s consider why this is not a good idea for a moment…
  19. Why do you say that….tell me more (getting others to explain what’s behind their thinking can sometimes be enough…)
  20. In telling the story, what are you noticing?
  21. That’s a bloody stupid idea. (Just joking. Don’t say number 21 unless you wanna be THAT guy)

End note: remember, so much of our communication is non-verbal, so be aware of what you are saying with your facial expressions and body language – finger pointing and table thumping  are ones to ditch for starters.

Thanks to Allan and Travis for your ideas 🙂

What tips for challenging can you add to the list above?