Managing Challenge

Do you want to be an effective leader? You may be an MD, or a self-employed. It doesn’t matter, you will still need to challenge others skilfully and effectively and be able to deal with people who challenge you.  How can you do that?


Do you feel you have the ability to have robust conversations with others where mutual challenge is present? What is the value of this kind of conversations? Allowing challenge in discussion means that all parties are able to reach greater breadth and depth in debate, and consequently better outcomes may emerge.


Thinking about yourself as a challenger

When was the last time you had to challenge others? Would you like to share the type of situation you were in? We are going to share just a few areas most managers find tricky.

  • When you have to challenge poor performance
  • When you just disagree with someone
  • When you want to test out what your team is capable of


A member of your team does something you disagree with. What will happen if you:

  1. Do nothing about it
  2. You go grumbling behind people’s backs
  3. You bottle it all up 
  4. You challenge him/her back in a very blunt and robust way


The cost of getting it wrong may be one you are not prepared to pay. You are entitled to disagree, of course. But you need to speak up to create a great outcome. You need to practice the art of voicing your concern and put it in a challenging, yet positive way. How can you do do that? Have you heard about the Poop Sandwich technique…? It’s a technique for giving feedback that involves sandwiching critical, truthful feedback (the poop) in between two slices of praise. How would you say it works?

The Poop Sandwich technique…


In a study at the University of Chicago, behavioral science professor Ayelet Fishbach conducted a simulation in which she divided a class in half and instructed one half to give negative feedback to the other. Amazingly enough, the half receiving feedback thought “they [were] doing great.”

Remember you challenging someone is not about your emotional need to express yourself, it’s about the usefulness of feedback to the recipient in helping him/her adjust and improve. In Horowitz’s words, “[s]tylistically, your tone should match the employee’s personality not your mood.” Research has found that the type of feedback that people prefer to receive is dependent on whether they’re an expert or novice.  How does that work? Beginners need positive feedback and encouragement to gain confidence in their new endeavor, while experts are more likely to seek out negative feedback.

As with any other aspect of your professional life, tackle challenge with these three goals in mind:

  • empathy
  • purpose
  • directness



Becoming a good challenger is an art, a skill that gets better with practice. If you wait to challenge until a difficult situation presents itself, you will feel anxious and probably will not have a great outcome. Use challenge as a valuable resource, a sharp precision tool. Approach challenge as a frequent, real type of conversation.

In a future post we will discuss how we can challenge poor performance… Don’t forget leaving your comment and sharing!


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