The Fine (and Necessary) Art of Challenging Others

We avoid difficult and challenging conversations because we’re afraid of the negative consequences these conversations might create.  The problem with this avoidance is that the negative consequences of NOT having these conversations are probably greater than any consequences of actually having them.

Because of our avoidance we: 

• Accept unacceptable situations and circumstances 
• Fail to grow into deeper and more consequential relationships 

• Spend time being angry- often unnecessarily 
• Don’t get the full picture and proceed with our judgments based on limited information 

Let me say this very clearly – when you don’t challenge others, either on their behavior, their words, or their points of view, you dishonor them. I say this because when you withhold a challenge you are assuming the other person won’t be able to deal with your challenge, or that they are too far in the wrong to ever come to your – obviously correct – point of view.  

There’s nothing easy about having a challenging conversation, even, or perhaps especially, with someone to whom we are close. Here are a couple of ideas about how to think about and act on these interpersonal and professional challenges: 

• Have an honest conversation yourself about your intentions. If you aren’t trying to create a positive outcome for both parties, in the long run, think again about whether you are properly prepared.
• Consider the potential of the other person, and consider how your challenge might simply be calling them to that potential. If you believe they’re better than what they’ve shown, let them know you want to see more of the good stuff.  
• Don’t let people get complacent. It’s easy for any of us to lost vision and drive from time to time. A challenge from you might be what the other person needs to re-energize and focus their efforts.  
• Don’t use challenging language routinely – don’t beat the drum of trying harder, sucking it up, raising your game, or whatever other tired language you can find. Challenging conversations need to be substantive, curious, and focused on where the person is in their life and career, and not just a crack of the whip on their flanks. 
• Be open to the revelation of your own contribution to the problem you’ve identified for them. As you challenge another person, and if you’re truly open and courageous in that conversation, you may learn a great deal about yourself and the impact of your behavior. 

I’ve been on both sides of deeply challenging conversations. I’ve been the challenger and the challenged. In both roles, I have become a better person.  

Are there risks to challenging others? Of course, especially if you’re challenging someone powerful or autocratic. But think about your legacy – will you look back at your career and lament the conversations you had, or will you lament the ones you didn’t have?

Challenging another human being can be a profound service, in some cases changing the trajectory of their lives – and likely yours as well.