This past weekend my husband woke up with a start. Sliding his eye mask off his face and blinking at the morning light he immediately noticed that I was about 4 inches from his face and staring at him intently.

“Good morning,” he said sleepily, “Can I help you?”

“I found tickets to Paris in the mid-600’s,” I said, “I think we should go.”

For a year, we’ve been talking about taking our girls on their first international trip. But the timing has always been funky. School activities, sports, camps, visitors, other pre-planned trips. But this weekend I just got the bug to start looking with different criteria.

Forget going when it’s convenient, I thought, let’s just go when it’s cheapest and we’ll figure out the rest.

After some enthusiastic pitching, my husband relented. By breakfast we had booked our flights, our Air Bn’B and excitedly sharing our news with the kids.

Our kids’ reactions were been mostly what I wanted. Excitement, questions, ideas. But as we started to discuss the trip more, some tension arose. 

“Why did you choose France over Italy?” our older daughter asked, “You know I’ve been studying Italian since last May.”

“How long is the flight, again?” our younger daughter wanted to know, “You know I’m anxious about flying over a big ocean.”

As the girls shared more questions and concerns, I noticed my own reactions carefully. When they showed excitement, enthusiasm and appreciation – I felt buoyed and excited for the trip ahead. I loved them. I have perfectly wonderful children.

When they shared concerns, fears and questions – I immediately felt defensive. Am I detecting selfishness and ingratitude? Do you not understand this Paris we are talking about here?!

After a few moments of internal combustion, I felt a familiar sensation: 

This Paris thing may have benefitted from a bit more thought.

A joke in our marriage is that I am “the engine” and my husband is the “brakes.” I provide forward momentum for our family’s projects and plans; he brings thoughtfulness and practicality. I love improvisation and have tried (and discarded) dozens of hobbies. He’s played violin since he was 3 and still only considers himself “decent.”

 I’m an optimist. He’s a pessimist.

(In my head, I can hear him correcting me, “I’m not a pessimist – I’m a realist.” Which may be true…but doesn’t fit as tidily into the narrative I’m currently weaving. So let’s treat them as synonyms for now.)

Fueled by said realism, my husband tends to plan ahead, be careful in his commitments and explore the downsides of things. Over time, I’ve found this to be an invaluable complement to my own nature. 

It turns out, “Have you thought this through?” is not the sound of a door slamming on my dreams. It’s an invitation to prevent something that optimists and spontaneity lovers often experience: Preventable Disappointment.

According to decision researcher and author of “Thinking Fast and Slow,” Daniel Kahneman, pessimists consistently get a “bad rap” – especially when it comes to group decision making. At best, groups perceive pessimists as a drag – slowing down progress. At worst, they are seen as negative nellies and nay-sayers that seed doubt and fear and dim group morale. Seeing the group’s reaction – a person with pessimistic qualities may feel silenced, singled out and blamed – and choose to withdraw rather than engage in a head-on conflict with group think. 

The problem with this scenario is that the pessimist’s (ahem…realists!) skill at forecasting difficulty can be a major asset even if the group moves forward without changing course. They aren’t “raining on your parade.” They want a contingency plan for rain on parade day. 

On the other hand – optimists are often overvalued on teams for their skill at rallying others to reach for the improbable but ever-enticing future. And this is too bad, because while optimists can be great cheer-leaders and storytellers, they also be astonishingly overconfident and inflexible.

Luckily, the trampling of the pessimists and the loss of their important insights – is actually a preventable tragedy. 

Kahneman suggests a process called a Pre-Mortem. Sounds like a downer…but it’s actually pretty fun.

The goal is to combine the optimist’s capacity for “dreaming the dream” (we are going to PARISSSSS!!!) with the pessimists ability to predict misfortune. It’s a format that can be easily facilitated in families, work teams and on boards. 

If you want to try it, it goes something like this:

  1. Gather all stakeholders together and let them know there is a decision to be made and their input is requested. Ideally, be clear about the decision-making process (eg. consensus-based, majority rule or  leader(s) decides with input). “Hey kids, we’d like to explore the idea of going to Paris for a week in late April. We know this will affect you – so we want to get your input before we make the final call.”

  2. Invite people to imagine the decision has been carried out and write about two different possibilities:

    • Have them write down their optimistic ideas for how this trip could be amazing:Imagine we took a time machine to the future – and we’ve already been to Paris. It turns out, this whole trip is an incredible success. What happened?”
    • Have them write down their pessimistic ideas for how this trip could be an epic fail:  “Imagine we travel to the future – and we’ve already been to Paris. It turns out, this whole trip was an epic fail. What happened?”
  3. Invite everyone to share what’s on the two lists.

    • Spend extra time exploring the epic fail and considering how/whether issues could have been prevented, mitigated or reduced. “You make a good point about not being able to communicate. What could you do to prevent that from ruining your trip? 
  4. Recalibrate. Does the visioning exercise bring up new ideas that should be considered instead? Explore those too! If not, move forward with the decision – applying the lessons learned from the exercise.

  5. Appreciate the Group: Once the group decision is made, make sure to thank the pessimists and optimists alike for sharing their gifts in the process.

If you try it with your family, board or team, I’d love to hear it goes! Maybe like the famed queen of Parisian music herself, we will all find ourselves saying: “Non, je ne regrette rien.”

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About the Author: Kate Cockrill

A little about me... I am a social scientist, facilitator, and professional coach. Through my business: Kate Cockrill Coaching, I support mission driven managers and directors with 1:1 career coaching, leadership coaching, team workshops, and retreat design. My clients include leaders in healthcare, education, research and social innovation.

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