Encourage Challenges - March 2024

Encourage Challenges - March 2024

What do these disasters have in common?

  • The 1986 space shuttle Challenger explosion
  • The 2008 financial crisis
  • The 2024 Boeing airplane malfunctions
  • The patient (one of far too many) who woke up from anesthesia to see that the wrong leg had been operated on

They were all preventable because each one of them was primarily caused by poor communication. Specifically, there was clear evidence in each of these catastrophes that people tried to speak up and met:

  • An unwillingness to hear anything contrary to those in leadership roles' preconceived opinions
  • Poor listening, exhibited by a repeated dismissal of concerns
  • A “kill the messenger” culture where it felt unsafe to speak up for fear of retaliation – another expression for this is, “speaking up against management here is a career-limiting move”

Want to prevent even small-scale disasters, as well as achieve greater team results? Make it safe for people to challenge you. Here are a few ways to expand that safety zone:

  1. Invite the Debby Downer types to your meetings. Too often, we steer clear of them when they say, “That will never work,” dismissing them as negative. You’re better informed and prepared though if you ask them to tell you more about what is wrong. Keep them closer. Ask for their help to prevent the problems they have identified along the way.
  2. Make a specific ask for feedback. For any new idea you bring forth, insist that your team give you feedback on one thing that is good about it and one thing that is not so good. This is much better than the blanket, “What do you think?” That’s too open-ended when you are trying to build up challenger safety.
  3. Host failure storytelling parties. Every one of us has a success story that has a lot of failure chapters in it. We wouldn’t be where we are without those key learning opportunities. Reinforce the framework of learning through challenges vs beating yourself up with guilt.
  4. Regularly use “pilot projects” as a way of hardwiring innovation. Pilots are all about learning before jumping in with both feet. Trials and PDCA (Plan-Do-Check-Act) cycles are ways to be sure data is guiding decisions, not just feelings. Feelings are valid sources of information, but safer to live by the “trust but verify” motto to prevent groupthink or blind loyalty to a fundamentally faulty idea. A great go-to question to show it’s ok to challenge during a pilot (or anytime) is, “What are we learning from things not going as we planned?”
  5. Manage your ego. This might be the hardest thing to see in the mirror, leaders. Note when you find yourself defending, wanting to say “but…,” interrupting, feeling attached or convinced of rightness. It’s not that you are necessarily wrong. But these signals can serve as a reminder that it’s time to pause and listen. Self-confidence borne from being right is fragile. Develop lasting self-confidence by creating a safe, trusting place for your team to land and by trusting yourself enough to not feel threatened by questions.
  6. Become aware of your signature non-verbal signals and learn to manage them. Be careful about that sigh, frown, pursed lips – ask a good friend to tell you what yours is because you may not even realize it. You might even say to your team, “I am beginning to realize that when my defenses go up, so do my eyebrows. I don’t want this to get in the way of you sharing different points of view or asking me questions about decisions I’ve made. I’ll work on my eyebrows and my defensiveness, and I want you to work on being brave enough to disagree with me. We’ll all be better for it.”
  7. Become at ease with ambiguity, messiness, unfinished business. Going ahead with something because you have so much time and energy invested already, or because the deadline has arrived and you said you would is a little like marrying the wrong person. It gets the deed done that you agreed to, but (speaking from experience) even more messiness is ahead. Make it a group norm to question everything, e.g., “Is now the right time, is there anything we’re missing, would it be more prudent or risky to wait,” etc.


A leader with a team who will be courageous because they know they’ll be heard is going to achieve great things. Get to building or expanding your safety zone.


Jo Anne Preston In Jo Anne's current role as Organizational and Workforce Development Senior Manager at the Rural Wisconsin Health Cooperative (RWHC) her aim is to offer to leaders straightforward tools and inspire the courage to use them.
Leading The Way In Five Mintues A Day

Lead the Way in Five Minutes A Day: Sparking High Performance in Yourself and Your Team, by Jo Anne Preston is currently available for purchase.

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