TBM 367: The Wicked "Big Picture" Loop

Some recent stuff:

• I’d love to show you my current product. If your company has a mess of disconnected spreadsheets, decks, and docs to describe the stuff above team-level roadmaps (strategy, goals, investments)—and there’s even a chance in hell to spend $ to save or make $ by fixing that—book a demo. Mention TBM/me, and I’ll try to run it myself. We can’t replace committed leaders (see below), but we can help people with good intentions.

• A short video on roadmap views, and another video on extracting structure from narratives

• One for the tree lovers :smile:

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The loop is as follows:

Executives want to get a "big picture" view of what is happening.

Teams provide that view, but then they are told, "This is too complicated," "This is too in the weeds," or "We need the big picture."

Teams often leave out a lot of information, filtering it down, summarizing, and so on.

"Great, we like this view." Executives like this view.

But a nagging doubt builds. The team is moving slowly. The views never change. Doubt grows. Or maybe a new strategy is emerging. Execs stop paying attention to these views. Meetings missed, etc. You learn that there's back-channeling, and other meetings set up to get the "real story." OKR cycles get missed or are rushed. Suddenly, you learn about new views emerging like the "just the tier 1 launches," or "the engineering roadmap," or ___________.

"We JUST need a P0 CEO list! Just the really important things that we're concerned about!"

Concern grows. For a while, the P0 list is working. Everyone is walking on eggshells, don't let the P0 list slip. The CEO is happy because their needs are being met.

But at what cost?

Meanwhile, teams are complaining about being overloaded. Of there being no real strategy. Of all the plans that get interrupted, new requests, etc.

Even the P0 list starts to suffer.

Then you hit this "oh shit" moment, where someone says, "Wait, we need to see everything!" Often, this happens because the team drops a major ball. So managers go for it.

They expose reality: "50% time to customer requests!"

Leaders: "But why didn't you tell us that? No wonder things are going so slow!"

Managers: "We tried, but then you asked us to simplify! You told us not to make excuses!"

Leaders: "It is your job to push back! Why didn't you escalate this?"

Eventually, the dust settles.

Teams scramble to repackage the truth. A new format emerges. A cleaned-up view. Just the essentials built around the "new priorities."

Leadership nods:

"This is great. This is what we needed all along. Just give us the big picture."

And so it starts again. The cycle repeats itself.

As Human As It Gets

The cycle is as human as it gets, even when you only have one human.

It's like when someone finally tries to get organized. They list out everything—every task, every loose end, every unfinished commitment. The raw, unfiltered truth. It's overwhelming. So they clean it up. Group things. Make a top 5 list. Create a dashboard. Something they can look at without spiraling.

For a while, it works. The simplified version feels good. Manageable. But slowly, it drifts from reality. New tasks never make it on. Old ones resurface. Things slip. Soon, the system is abandoned. Sticky notes reappear. Inbox chaos returns. They stop trusting their lists.

Then something breaks. A missed deadline. A forgotten obligation. The "oh shit" moment. So they go back to the beginning. Dump everything out again. "I need to see it all." And the cycle starts over.

The only time I have personally been able to break this kind of loop is when I hired a coach. Every week, he forced me to turn over every rock. I blocked out way more time than we needed. I gave him permission to keep the pressure on, hold me accountable, call me out on hand-waving, and make sure we followed each thread. From "Did this get done?" to "Do these principles still make sense?" We closed loops. Every week. Sometimes it was boring, and it certainly wasn't magic. But it worked.

It boiled down to staring at the whole picture long enough and often enough to stop lying to myself about it.

Three Approaches

When you consider how hard this can be for one human, let alone a thousand humans, it makes you wonder.

Idealized Discipline

An idealized view is that you can build this discipline across an organization, and that it boils down to being willing to have the hard conversation. "If we could just get real and have the hard discussions, we'd be good."

Lightweight (But Effective) Constraints

Another view is that, at best, you introduce just enough enabling constraints and hire qualified enough people to keep the ship generally moving in the right direction, dealing with the icebergs as they arise. This view is usually skeptical that there's some sort of global discipline that can solve the problem, and that you can deal with the pendulum swings when they get out of hand. It also views any potential process to rein things in (the equivalent of my coach example) as ultimately too damaging and expensive, and also a major hit on ambition and autonomy. The personal productivity analogy here might be that you should run your life a bit fast and loose, ditching the coach, and while that may mean the occasional crash and burn, you'll generally end up okay.

Reactive

Another view is the one that leads to the spiral I mentioned above. It isn't an intentional act of designing a "controlled fall with guardrails" per the latter approach above. And it isn't a deliberate effort to get real, as in the first approach (the hyper-disciplined approach). The constraints are poorly designed and fail to surface issues early enough. By the time the leadership team is onto their next kick/phase, the roots and seeds of the next blow-up are firmly implanted. It is reactive and counterproductive.

Why?

I've given a lot of thought to why companies end up in this vicious cycle.

The first thing that comes to mind is this knee-jerk reaction to anything that seems to defy "simplicity." It is an unwillingness to face things as they are, and the ensuing optics game. If a leadership team is unwilling to sit with reality and explore what is happening, or creates an environment that is unfriendly or unsafe to do so, then you will never "get clear." If they insist on seeing things only as they want to see them, rather than from other perspectives, then the self-inflicted delusion will persist.

From my vantage point, I think many leadership teams intend to adopt either the disciplined approach or the lighter-touch guardrails and minimal, yet effective, enabling constraints approach. The first is more similar to the Amazon WBR, while the second is comparable to many rapid scale-ups. So the intent is good.

But reality catches up to them. Most people don't realize how reactive many leadership roles are. You think your solo personal productivity mission is hard. Now, layer in a massive company with fires cropping up daily. The cognitive load is extremely high. Best-laid plans fall apart. The "magic list of 15 priorities" that seemed like the ultimate forcing function from two months ago quickly dissolves as reality shifts around (and inside) the company.

Ultimately, it comes down to intentionality and accountability. Even "high-performing" athletes need a coach to hold them accountable (often for rest, but that is a topic for another post). You need a mechanism to follow the desired path: either a "weekly coach" type model, or holding to your enabling constraints.

My hunch is that for most teams, even a single day of "blocked for ad hoc meetings" would provide enough flexibility to close the loop. Whatever it takes to inject 20% more intentionality into the day.

I also think that the ideal approach is a mix between the high-discipline and well-designed enabling constraints approach, where you have high discipline on certain recurring tasks, and use the enabling constraints to quickly and effectively surface hot spots.

The way this video discusses “continuous planning” might help: