The Red Flagger

A caution-ary tale

Painting by Andrea Eisenberger

**The Hannalyst will be off through Labor Day – enjoy the rest of summer!**

Some years ago, I worked with a person I’ll call Sam. Sam was smart, proactive and genuinely wanted to serve our mission and improve our work. One day, we were in a meeting where someone suggested a moonshot idea – something that would push us way outside our comfort zone, but also have an outsized impact if we actually pulled it off. Sam raised his hand with gusto, and then listed all of the reasons that it would never work. I remember having weekly check-ins with him and he always came prepared with bullet point after thoughtful bullet point of hedges. Here’s how we could avoid this. Here’s why we should be careful of that. After each session, I felt as deflated as he felt triumphant. Because he felt like he was making a real contribution, while I thought he was constantly making us smaller. Crucially, he never, ever offered solutions. He was what I like to call a red flagger.

Everyone has worked with a red flagger. Some of us have been the red flaggers. Maybe you’re reading this piece and realizing that…[gulp]...you are the red flagger. And it’s a relatable disposition, right? Red flagging looks like agency and it looks like rigor. That person is usually viewed as responsible, sometimes even moral in what they’re doing, regardless of whether or not what they’re saying is useful or correct.

It’s easy for this to become a pattern because there is no accountability for what didn’t happen. There is no scoreboard for the essays that didn’t get written, products that didn’t get built, treatments that were never developed. Which is why being a red flagger is so appealing. Individually, you’re rewarded by that feeling in the moment that you’re making a contribution. Institutionally, you’re rewarded by absolving yourself of any responsibility should something go wrong.

Still, you might think that the person who raises all the flags but never figures out the solutions would always be viewed poorly, but in fact that’s not the case. In reality, we judge action more harshly than inaction. And to be clear, in many cases that makes sense. If you push someone into a lake and they drown, you’re definitely at fault. But if you just happen to walk by the drowning person and opt not to jump in and save them, that’s not great but you’re not going to be prosecuted.

But the weird thing is that even when intentions, motivations and consequences are all exactly the same, we still tend to view harmful inactions as less immoral, and as better decisions, than equally harmful actions. It’s called omission bias and it explains why the person who does something that blows up is always pegged as guilty. While the person who fails to prevent the blow up, even if they definitely could have, is usually just pegged as unlucky.

There’s a better way to dissent

That asymmetry is why red flaggers think they’re contributing something real and confuse their habit for productive dissent. We all know that real, authentic and thoughtful dissent is crucial to progress – great organizations (not to mention societies) can’t function without it. But productive dissent requires engaging with an idea in earnest and then ultimately proposing a way through it, two characteristics not usually found in red flagging.

There is some interesting research testing the difference between red flaggers and productive dissenters and it found that only productive dissenters actually help create new lines of thought within the group. Red flaggers may provoke a discussion, but only one that serves to reinforce the original position. In other words, rather than triggering new and original thinking, red flaggers cause others to double down on what they already thought. On the other hand, productive dissenters force a true kicking of the tires, and in doing so open up the conversation to new ways of thinking about the problem.

The authors’ theory about this is that red flaggers carry no real risk, so they don’t inspire anyone else to carry risk either. They aren’t putting any real stakes in the ground (i.e. new ideas), so no one else feels pushed to do that either. Instead, the conversation devolves into circles of performance between the people pointing out problems without solutions or substance, and the ones defending what they already believe to be true.

The problem is that red flagging has become culturally dominant.

This is most obvious at work – everyone knows a Sam. He’s not hindering progress intentionally, he’s playing to a system that rewards his style. Most organizations have too many nervous stakeholders looking over their shoulders to act with anything other than caution. Whether you’re looking at an earnings call that is max only a few months away or staring down a grant agreement that’s up for renewal in a year, it’s hard to justify taking even a medium swing, much less a big one. Even if you know that’s the only way to make a meaningful impact. The risk feels like it’s right in front of you, while the benefit feels distant at best because that’s how the system is structured.

But it’s become prevalent in society too. Take AI – flagging the danger is seen as the responsible act, no matter how true it is. So both the narrative and the focus has turned towards containment instead of towards productivity, as if this is a choice we have to make. And to be clear, I’m not saying that we shouldn’t be cautious, but I wonder what would happen if we approached building (and policymaking) for extreme benefits with the same zeal that we have for containing the worst.

I recently had a conversation with someone at a very well-funded philanthropy about an idea some colleagues and I have to build a process to help young people figure out how to design their own futures through the AI transition. She said she loved the concept but that they had made the decision to focus all of their efforts and money on preventing the most catastrophic AI scenarios they could think of. And while that’s a worthy cause, it struck me that a lot of possibility is getting left on the table with an approach like that. They were mistaking vigilance for vision, forgetting that it’s possible – and necessary – to have both. Basically, the whole organization had become a Sam.

Which brings me to the biggest problem that I think a red flagging culture creates: we forget what we’re for because we only focus on what we’re against.

My problem with Sam wasn’t that he didn’t work hard, or that he wasn’t professional, or that I didn’t see him genuinely trying to achieve the mission. It’s that by becoming the person who only saw the problems, he’d lost the ability to develop convictions, analysis and ideas of his own.

And I worry that this is happening to us collectively. I feel clear on what we don’t want as a society because I read about it every day. AI that takes every job. A planet so hot it’s uninhabitable. Politics so broken that we hate each other. Disease so rampant that we can’t contain it. These are as easy to articulate as they are to understand and fear.

What is so much harder to grab onto these days is what we do want. It has to be more than the opposite of those catastrophic hypotheticals. It requires vision and thoughtfulness, imagination and – especially right now – productive dissent.

I saw a great quote the other day:

“It’s amazing how many people choose the certainty of a miserable situation over the uncertainty that might get them out of it”

Sam would never say that he’s in a miserable situation but the trade is similar. He’s choosing the certainty of being seen as responsible over the risk of being wrong on something that matters. But in doing that, he makes himself a benign player – never breaking anything. But never building anything either.