Trust Opens Windows

Betsy Block
5 min readOct 10, 2023

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A photo of my waste basket with crumpled up papers
Childs drafts, making way for creativity!

Even when we are with the people we trust the most, we instinctively hold on to our “shitty” ideas. We know they are unformed, and incomplete.

What would it be like if we had the trust in our teams to freely throw into the mix EVERY idea, to truly be generative, and to access the best of our collaborative creativity?

Matt Damon reflected on the creative process when he and partner Ben Affleck were working on Good Will Hunting, which went on to win Best Original Screenplay at the 1998 Academy Awards:

“[Ben Affleck] said ‘Judge me for how good my good ideas are, not how bad my bad ideas are.’ That, to me, is the most important thing when you embark on a collaborative process with somebody. You gotta get the window open to throw every idea in there. And not be afraid to have shitty ideas. Because we all have shitty ideas, and sometimes you need the shitty idea, and then you iterate on that, and they iterate on that, and then it builds into a good idea. But you have to feel free to express it. … [Trust is] what’s really at the root of [collaboration]…”

If you only hear good ideas in your meetings, you are stifling creativity

We all have an easy time holding on to our bad ideas. But we can celebrate the bad ones as a means to unlocking creativity. One colleague of mine does some of her training sessions with “What’s the worst _____ ever?” She gets folks to intentionally design the worst thing ever. This unlocks not just laughter, but also rampant creativity. The team starts to have fun building on each others’ bad ideas, but out of those bad ideas comes the freedom to share all the other ideas without worrying about what is good and what is bad.

In fact, “Worlds Worst” is a well-known improv format. The format, adapted for meetings, is quickly generative and oddly inspiring because our brains often access what we don’t want faster than what we do want. The key here is to pay attention to the “bad” or “worst” and be able to reconstruct that information into the “good” and “best” and “possible”!

I suspect there is some useful psychology happening here. The old “what do you want for dinner?” conversation is helpful: given the full breadth, we all tend to get stuck. Psychologists call it choice overload. We put ourselves under a lot of pressure to come up with that one choice… or that one good idea… but what we don’t want? Wayyyy easier, right?

Creating the space for bad ideas

Your team isn’t made up of improv actors so that first moment where you say, “let’s come up with ideas so we definitely don’t reach the goal” might just feel awkward. A few ideas to get the team into the zone with you:

  • Model it. If you are the leader, be the first to throw in the worst ideas you can think of. And come up with really, really bad ones.
  • Scaffold it. Give the team advance notice and encourage them to come with ideas written down. You can even have folks turn in the information on paper and draw them blindly to start.
  • Game it. Make a prize or incentive for getting voted the worst idea.
  • Make it consistent. Doing this only once will reinforce mistrust. Set the expectation and commit to doing “bad idea generating” regularly.
  • Notice power. How power dynamics shows up in every team is different. Ensure you think about who is exercising power over others and design to allow everyone to show up on equal footing. If you have loud talkers who take up too much air time, then favor writing down ideas.

No judgment

The challenge of this process is the risk of compromising inclusivity: any game that gets loud can shut out the introverts or those with more to risk in a conversation. Moreover, allowing people to edit each others’ ideas at the outset will shut many out.

The key, then, is to ensure that ideas can be put in judgment-free and unedited. Bring the team into agreement about how & when ideas get edited. This doesn’t have to be complex, but it does have to be clear. Consider using a poster or dry erase board notation to indicate when you are in the no-judgment zone, and define clear norms about how team members support and reinforce this.

Watch communication improve

For one of my clients, we are leveraging team coaching to establish new collaborative partnerships (silo busting!). The sponsor asked for metrics, and I dug back into my evaluation days to look at a validated survey instrument for measuring collaboration. In the items that measured communication, some of the keys were around ability to discuss things openly and feeling “safe” to surface conflict. Giving levity and space to be generative is a clear path to open communication when done with intention — frequently, consistently, and systematically.

Get to Shitty First Drafts

Back when I taught in grad school, I inherited a syllabus from another professor that included the “Shitty First Drafts” chapter from Anne Lamott’s Bird by Bird. [In fact, if you haven’t read it, please stop now and read it.] I wish it was a required primer for all of us about not just writing, but problem solving in general: both to get ideas out in the open, but to remember to chunk them and get to the second draft. You start with the child’s draft, where every idea is thrown onto paper without regard, without caution. Much like Ben Affleck counseled Matt Damon for Good Will Hunting.

Lamott reminds us that starting with good ideas is a “fantasy of the uninitiated” and most of us don’t have a deity speaking into our ear with the ideal words or ideas at the outset of a project. This is equally true for teams as well as individuals, but teams need a slightly different path to begin the practice.

The challenge I offer you is to establish the trust to then cultivate the practice of creating and valuing the child’s draft — then you can see the creativity and ingenuity flourish.

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Betsy Block
Betsy Block

Written by Betsy Block

We help small to mid-size nonprofit leadership teams navigate strategic changes intentionally, effectively, and confidently through coaching engagements.

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