That Burning Feeling When You’re Right

Roy Rapoport
4 min readOct 3, 2021

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But on the plus side, he was right

“The reasonable person adapts themselves to the world: the unreasonable one persists in trying to adapt the world to themselves. Therefore all progress depends on the unreasonable person.” (George Bernard Shaw, slightly modernized and de-gendered)

I talked a little bit about what happens when a person is not exactly aligned with the organization within which they try to operate in Candor, Bluntness, Impedance Matching; one of the fundamental benefits of not being entirely aligned with your organization is the potential for good that can come from that lack of alignment, as you help your organization move in a certain direction. The challenge with not being entirely aligned with your organization is that the further away from popular and policy-based stances[0] you are, the more thoughtful you need to be, because the harder it will be for people to listen to you. Which seems like as good a time as any to tell you about John (not his real name).

A long, long time ago, I worked at a company that was trying to change the fundamental way in which it did deployments and engineering and ran its servers. They had a bunch of smart people, who had already made some decisions on this front (“We’ll move from MySQL to SimpleDB, it’ll be great!” for example). They also hired John, who became my peer and coworker.

And here’s the thing you need to know about John: He was incredibly experienced, and profoundly smart, and deeply opinionated. He had some brilliant ideas about how to manage infrastructure in the cloud, that were years ahead of where we were. He was transformational.

Well … In theory.

He was … deeply opinionated

So John went into meetings with all these other smart people who had made some decisions, some of which were unwise, and told them these decisions were unwise. I recall a meeting where he literally asked “who’s the idiot who made the decision to do X?” and someone else in the meeting said “yeah, so that was me… “

Five months after he started at our company, he left our company, having been fired. Literally none of his ideas were adopted by the company until many years later, after some painful lessons and some people who were more effective in talking about this had come to work at the organization.

Because John was right. And he was a heretic. And he was ineffective. And while effective heretics change the world, ineffective ones … well, ineffective heretics get to feel warm for the rest of their “lives” in the organization in which they operate [1].

Being right is deeply emotionally satisfying for many people. I’m one of them. But also? It doesn’t really matter. Being right, and having people not listen to you because you’re ineffective at persuading people that you’re right (and obviously continuing to keep the lookout for the possibility you’re wrong) doesn’t mean you work with dumb people — it means that you don’t know how to be persuasive. It means that you don’t know how to lead.

Which gets us to this 2x2 matrix of the possible outcomes from heresy, depending on whether the heretic in question is right or wrong and separately from that effective or ineffective.

I’ve been an ineffective heretic (I still, sometimes, am). I’ve talked about this before.

Real Talk

What’s the point here? Well, at least partially it’s “look, Aaron! I finally wrote that blog post that you asked me to write some time ago!” But less trivially, the point is simple:

It’s seductive to be right. It’s emotionally satisfying. It’s particularly satisfying when you’re right about something big, and about something your org is very wrong about. But being right is nothing. It’s not a prize. It’s an obligation. It’s an obligation to be effective, or try as hard as you can to be effective, in persuading others, because otherwise you have squandered an opportunity — an obligation, I might say — to be an effective heretic. Because leadership is setting a north star and getting people to adjust course to move closer to it.

Being right is useless without being effective.

[0] See The Overton Window
[1] With thanks to Terry Pratchett

Postscript
In a moment of absentmindedness, I published this post so I could get some other people’s opinion about it, and had neglected to mark it ‘unlisted’. The end result was obvious in hindsight, with this blog post being shared by a bunch of people who find it useful (which is incredibly flattering), but it means that there were further edits to the post that I never got around to making before it went public. Oh well — at this point, I’d hate to add useful information in case people who already read it don’t want to come back.
So that means that the next blog post will likely be a sequel to this post, talking a little about some related topics, including
• How do I know if I’m an ineffective heretic?
• What can I do to be a more effective heretic?
• How can I notice this in others and help them be more effective?

Stay tuned.

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Roy Rapoport

I have goats. I work in technology. You know most of the rest.