TLDR: Don’t suffer in silence.

You know how we feel pain? Evolution selects for pain because it steers organisms away from certain kinds of harmful situations. When you try to lift something, and pain starts up in your back, it’s your body (and eons of evolution) telling you “maybe find a different way to do this before you hurt yourself.” Pain is the catalyst for change. Pain is useful!

Organizations don’t technically feel pain, but people in them certainly do. Whether it be endless overtime, dysfunctional meetings, ugly exchanges, missed deadlines or what-have-you, team members bears these pains. Prolonged exposure burn people out.

Unlike, say a finger that reflexively informs the nervous system of pain, people in an organization can choose to absorb the pain, or to let it propagate/fester. I want to convince you to not absorb the pain, at least not as a matter of course.

Why? Because if the organization doesn’t feel pain, it will not learn, and it will not protect itself. When you simply absorb the pain, you get in the way of potential change. To put it differently, you are blocking the flow of information necessary to make proper organizational decisions. Don’t be a painkiller, be a catalyst for change instead.

So should we just be squeaky wheels all the time? Isn’t there a time for fighting through the pain? Here’s my framework for evaluating when is the pain worth it.

• Is it passing pain, or chronic pain?
• Is it a calculated pain, or a random and/or unpredictable pain?

Time for a 2x2:

1. A passing, calculated pain is like the floor burn you get when you’re diving for a ball. E.g. a well planned spurt of overtime. It hurts, but its a short duration, and hopefully there’s clear pay off. This kind of pain is probably fine to absorb.
2. A passing but “random” pain is like a sort of flare-up in your back. An example here might be an unexpected bout of fire fighting. You might consider absorbing this kind of pain and “be a team player about it.” More often than not though, it points to overlooked problems in the organization. (E.g. why don’t we have better QA? Or preventive measures?)
3. The line between passing and chronic random pain is pretty blurry. As these kinds of flare-ups become more regular, it is more and more likely that a real problem needs to be diagnosed and addressed. Absorbing this kind of pain is like gorging painkillers to deal with regular flare-ups in your back. The pain points to some chronic misbehavior (e.g. you’re sitting too much, and your posture is terrible.) One day it will fuck you up. Don’t absorb/tolerate this kind of pain.
4. Chronic, calculated pain? Well, that’s just an abusive organization. Get out of there.

In an organization with people of mostly good intent, if you truly experience a chronic pain, it is usually because it cannot be properly fixed at your level. (Otherwise, as the recipient of the pain empowered to fix it, you would have fixed it already.) Passing the pain up the organizational hierarchy gives the org a chance to address it at the right level. It may not fix things, but hopefully focuses attention.

So. Don’t suffer in silence. Share the pain, it’s the adaptive thing to do for both you and the organization.

Corollary – Organizational Pain and the King Lear Problem

…or why you should celebrate the people bringing bad news.

This idea has a frustrating twist when looked at from the managerial point of view. I think of this as the King Lear problem, i.e. do you have a cultural habits/mechanisms setup to get reports of pain/dysfunction from your org quickly and accurately? The more powerful you are (i.e. the more you can shape the fate/reward of those who report to you) the more your reports are incentivized to “shape” the information they share with you.

• In benign cases, they are doing the right thing to conserve your bandwidth, filtering for you only what you need to know.
• In pathological cases (as alluded to in part one) they are hurting themselves and the org by absorbing brokenness in the org without telling you.
• In malicious cases, they are actively misleading you for their own gain.

Without some mechanism of keeping your ears close to the ground and/or cultivating alternative information channels, a senior leader can lose touch with reality on the ground without realizing it. Note that the King Lear effect is the default case! It will happen to you if you do not actively work to break out of the bubble. 

I have no good comprehensive answer for this. However, at the very least it calls for not shooting the messenger, and for institutionalizing blameless post-mortem processes. If as a senior leader you get mad at and/or begrudge the bearers of bad news, soon you lose access these flows of information. If you punish cries for help and displays of pain, the org will learn to suffer in silence until it collapses.

And then it is too late.