There are two internal adversaries in every organization that if not managed will grind progress to a halt. These are

• time
• other people’s assumptions

Mismanaging time is first an operational problem that gives rise to cultural problems in organizations. Other people’s assumptions, managed or not, is first a cultural problem that gives rise to operational problems.

Or put another way: culture creates habit and habit creates culture.

Time as an adversary isn’t just about the urgent-important tradeoff matrix, it’s also about the risk tradeoff in “pay with certainty now” vs “pay a lot more later, but maybe”. Most organizations will opt for the “maybe pay later” gamble. After all, deferred expenses are better than current expenses.

The dark side of this gamble, unlike real financial instruments, is that the interest rate is not known. Engineering teams complain about the accumulating tech debt. Product teams worry about losing their competitive advantage or falling behind well-heeled competitors. Marketing teams push to catch the latest trend. Sales teams notoriously sell on product features that aren’t fully released. Analytics teams yell at the clouds about their forecasts of the upcoming train wreck that no one has time to hear about. Compliance / SecOps warn constantly about vulnerabilities. Legal needs to update language. And it’s all very exhausting.

Something will go kablooie, somewhere.

At some point the tech debt will be too much and the Engineering teams will put their foot down, push for centralization, and insist that everything needs to be rewritten from the ground up. The right way this time.

A competitor will jump ahead and Product will go into “Release! Release! Release!” mode.

That marketing trend that everyone rushed to catch without having proper time for diligence will have extraordinarily negative ROI.

Logo retention will fall because of overpromising and underdelivering.

Analytics’ forecasts will have come true, but since no one was listening, did they really forecast anything? And they’ll hear “deep dive!” from ten executives faster than any one of the million dashboards they’ve already set up so that people can self serve their own damn deep dives can load.

There will be a material non-compliance or a security breach. Somebody is losing a job.

The lawsuits will have arrived and the settlements won’t be too far behind followed by layoffs to pay for the settlements.

The problem isn’t so much in adopting a “maybe pay later” mindset. The problem is that we kicked the can one too many times. The problem is that orgs don’t actively set aside budget to fix stuff. The problem is a failure to realize that we are not ever actually building things, we are maintaining and upgrading. The problem is an inability to measure the value of maintenance and upgrades. These are not just costs.

This mismanagement of time (and hence effort) is an operational problem. More process. More tickets. More RACI. More weeklys. What it leads to is a cultural problem. Frustrated staff. Blaming and finger pointing.

In the inevitable post mortem, someone, somewhere sitting in an armchar will say “But why does it take them so long? Can’t they just …”.

Enter our second adversary: other people’s assumptions.

For whatever reason, everyone else’s job is simple. It’s like reading a click bait headline: “You could get your job done quickly if you did this one thing” except people act this out.

This mentality kickstarts the operations-culture death spiral. Eventually, someone senior enough believes the narrative of “that job over there shouldn’t be this hard”. And now, re-orgs! Consultants! Another senior management layer!

It’s a maddening pattern that is everywhere.

A lack of empathy for the needs of each team to solve their here-and-now operational pains is at the heart of all of this. It’s not to say that every team should feel entitled to operate in their perfect environment, overstaffed with every initiative getting 100% attention. [sorry, for practically every business this is unsustainable]. It’s also not to say that borrowing is bad — quite the opposite! borrowing is good — but we must actively pay off that debt. Empathy is to say that there is some debt that is growing and becoming expensive. We don’t have to wait until it is noticeably expensive to start addressing it. It’s The Little Prince and the baobabs.

As for managing other people’s assumptions: again empathy. If you find yourself saying, “Can’t they just …”, shift that to a mindset of compassionate learning. Learning what your colleagues do with excellence. Learning what constraints they have to work with. Learning what tools they have to work with. Often, the other side is operating extremely efficiently with the tools they have. Maybe they don’t have updated tools or know of other tools. And instead of engaging in “can’t they just …”, we can engage in, “do you need help? / how can I help?”. Other times we may find that “holy crap, what they are doing is hard and they’re not wrong in clamoring for more resources / smarter execution / etc”.

Now, if you know me, you know I don’t like to fill up on whine. The reality is tackling these two adversaries is hard. It’s why most orgs eventually devolve into a toxic culture — it’s easier to not have empathy. It’s easier to trivialize other people’s work and it’s easier to say “this is what’s best for the org”. As a consequence, orgs eventually are left with two sets of people: those who lack empathy and those who are suckers for punishment. Everyone else is transient.

The “solve”, if you will, is to recognize what I said earlier: culture creates habit and habit creates culture. Do we want a good culture? Develop habits that lend to this.

If decision making, especially, around how departments, teams, individuals spend their time comes from at least one layer higher in the hierarchy, then the burden of empathy begins there. As leaders are we listening, acknowledging, and compromising to the needs and pains of those who have to execute on our asks? As those who have to execute, do we understand the constraints around which orgs have to optimize around? Are we adequately expressing the problems through the metric lenses that leadership has to operate under? Every one of us leads decision-making and executes on decision-making. And empathy has to exist at all layers.