TBM 401: Solving Problems the Hard Way

A Career Altering Experience

One of the most formative experiences in my career was working for a leader who did the hard work to shape a couple of workstreams, assign owners, and, most importantly, push us hard to build good habits and tempo. It wasn’t easy, by any means. We operated this way for a full year, and the results were incredible (and personally very rewarding).

And I’m not the only person who feels that way. Whenever I chat and catch up with my old team members, inevitably someone will say something like, “Hey, is it just me, or was working with [leader] one of the best experiences of your career?” and someone will chime in, “Yes!”

(Note: Thanks from all of us.)

That year still shapes how I try to approach things today.

I Didn’t Fully Appreciate…

I say try, because it is hard. I never fully appreciated at the time how hard it was, especially when it comes to:

• The advocacy they must have been doing behind the scenes to defend how we were working, and to advocate for our work when it didn’t produce immediate results

• The patience to keep modeling good habits and to coach us back into a zone when things diverged.

• At the time, I did not realize how much of that shaping was discovery work. The lanes were not obvious upfront. They were co-designed with the team, argued over, tested, and revised. It was messier than it looked from the outside.

So importantly, they let us be the heroes in our own stories, instead of pulling all the air out of the room and making it more about them (they certainly could have, and a lot of the credit would have been warranted).

It Is Hard

A lot of leaders start the quarter or year strong, like New Year’s resolutions. It lasts a couple of weeks, and then things drift. Mental models diverge. People avoid the hard conversations and elephants in the room that have gradually bubbled up and accumulated. Or they freak out and make an ad hoc stab at reining things in (”Oh no, it is mid-quarter, we need a plan!”).

I’ve certainly let this happen at times. I’m not immune. Keeping a team “working small and thinking big,” moving that rolling cone of uncertainty down the tracks, is hard. You are constantly needing to course correct (without over-correcting and trying to steer against the drift). You need to sense and respond to the current terrain, while keeping future paths in soft focus.

More Details

I remember asking them at a time, filled with early-career naiveté, something like, “Is this a framework, or something?” Paraphrasing from what I remember:

No, just stuff I picked up along the way. It really is about the lanes, though. You have to break down the right lanes.

They can’t be too vague, but they can’t be too specific. Ideally, they are relatively independent. They should last a while, but you need to be willing to reshape the lanes or make the hard decision to retire one or pause it. They need owners as well—one or just a couple. Once you’ve got the lanes sorted out, it is really about the right habits. What are you going to do this week to move things forward? What happened last week? What are your near-term goals? Longer-term goals? What are your KPIs, and what can you realistically move? What’s getting in the way? It is pretty simple, actually. Most important: talking about it as a team or team of teams. Making decisions together.

We ran the whole thing out of a single doc. Every week, the team would copy forward last week’s lanes and a couple of the columns, then add some stuff. It was terribly manual, but I think that was the point. Manually pulling it together forced you to think about it, and then talking about it together helped you calibrate, decide, and leverage the hive mind.

What I also did not appreciate then was that arriving at the lanes was itself part of the practice. It was collaborative, iterative, and sometimes frustrating. The first version was never the right version. The learning happened in the arguing, the reframing, and the small adjustments over time.

Wait, Everyone Does That!

In my current role, I meet with hundreds of teams and companies to explore exactly how they work, and have collected hundreds of versions and variations of this type of doc. I see how common it is. Back when I first experienced this, I was too green to know how relatively “standard” the idea was, but also how hard in practice it can be to mobilize humans to “stick with” the program and not break the chain, and let the whole thing slip into a performative (or zombie) process. It is like we invent all sorts of reasonable excuses for why it doesn’t make sense, or why it’s OK to try it and stop.

I let this leader and some of the teammates read this post, and pass along any comments, and the leader in question added a comment here:

Tell people that even we slipped into that, when I lost influence with X, and I kind of gave up on my own promotion. I also knew things were winding down, and I was psyched that we’d all find new and exciting things to do. While I would say I’m pretty good at getting this going, I’ve also failed to get it going.

Another ex-team member who has gone on to awesome things added a reminder that:

As you get more senior, the lanes get broader, and your distance from the lanes where things are actually happening gets further. The skills partially translate, but it becomes more about leading people who lead people who lead lanes. But you can’t lose your ability to relate to the people in the thick of it, and operate and understand at that level. Plus, you realize that not all lanes are created equal. You’d never approach a 0/1 effort with 0/1-like lanes the same way as you run something later on.

There are so many ways to pretend you’re doing this, pretend you’re making progress, pretend you’re “aligned,” and pretend your lanes are coherent. It is also so easy to prematurely converge and put some things out there because you just want planning to go away so that you can go back to the real work. Operating under the radar can sometimes feel safer and more productive.

Frameworks…

Another observation is that many frameworks and practices flirt with the core principles here—work small and think big, ownership, shaping the lanes, balancing stability and meaningful levels of detail, etc.—but they pretend things are a lot more stable and repeatable than they really are in practice.

You can’t break everything into clean tickets. Goals don’t always neatly align with quarters. There are tons of work, goal, milestone, problem, solution, opportunity, blah blah blah shapes to deal with, and like the quote above, no way you’d treat them all the same way. It saddens me that so much of the spirit of Agile, which I find very consistent with these ideas, became “training-wheel-ified.” All the important and hard stuff got replaced by quirky little frameworks, named practices, named roles, etc., under the banner of teaching and somehow solving the “predictability” challenge with “the business” vs. doing the really important (and hard) things.

You can put whatever label on what you’re doing, but at the end of the day (as dumb and cliche as it sounds), it is about what you do, what you change, what happens, and what you learn.

Lanes Of Lanes

I spent the last couple of days working with an inspiring team at a big enterprise. Thanks if you’re reading! It was an incredible experience.

One thing that struck me was this fascinating mix of various cascades and mental models for “laddering,” and then the fractal concept of lanes repeating over and over. Some lanes were more project-like, program-like, or product-like. Some were wider and narrower, risk profiles all over the place, but that was where the real work was happening. What’s the context, what is the intent, what are we doing now and next, a softer focus on later, and what routines do we have in place to calibrate what everyone is sensing?

That continuous activity at multiple levels of the org is what gives you that ability to sense what is “actually happening.”

We see this in how customers use Dotwork as well. There are standard, as a leader proudly explained, “boring” OSes, and really cool, quirky OSes, but the magic is in the routines and sensemaking. The goal isn’t the perfect rollup. It is the right resolution for the right discussion, and it allows jumping up and down in elevations when needed to find the lanes in question. “Layers” of a value pyramid are less objects that “roll up” than they are frames, lanes, and perspectives.

The Here And Now

I wanted to end on a more philosophical note.

Looking back on this experience was a good reminder that this is tough stuff. It is human stuff. We can hold ourselves accountable for shaping the “right” lanes that are somewhat durable yet spiky and strategic, but then also surrender ourselves to the idea that, especially if things are working, all lanes change and eventually go away. We have the agency to spend our time doing things with intention and a nice balance of urgency and thoughtfulness. Still, we can surrender to the rolling cone of uncertainty and the beauty of the different futures that might emerge.

Finally, the opportunity to be with a group of people and get into the zone like this is not a given. Sometimes it can feel fleeting and out of reach during our careers. But when you have the opportunity, and you can help foster that opportunity, then seize it!

Basics

So how do you “do” this lanes thing? I’m sure you’ve already been doing something like this, but at the risk of not explaining it:

1. Define a small set of lanes (3-5)

Not too many. Just the main drivers and levers that seem capable of moving things forward. Spend time agreeing on the shape of each lane, including risk profile, complexity, experimentation friendliness, and the kinds of practices it likely needs. Look for lanes that are stable enough to get into a groove, but not so rigid that they cannot evolve when reality shifts. Depending on your role you might be defining these at different “levels”.

2. Write a short intent for each lane.

One or two lines. Direction, not work. Something that conveys strategy and purpose without turning the lane into a task list. The detailed work lives elsewhere inside the lane, where actions and changes get tracked week to week. This separation helps avoid confusing motion with direction. Remember, you’ll be returning to this every week for a while (hopefully), so make it good.

3. Put real ownership on the lanes.

Usually one to three people. If there are multiple owners, they need to commit to genuine co-ownership, not ceremonial representation.

4. Bling out the lanes with just enough information to reason well.

Clear near-term work. Metrics that can be influenced in the near term. More directional, lagging signals, such as goals, risks, and current value. Always include what is being done this period, along with what was carried over. Over time, this becomes less about documentation and more about learning to see drift early.

5. Keep the lanes in one shared place and copy them forward each cycle.

No clean slate (unless you are a completely new team). The migration itself becomes part of calibration. Carrying things forward forces attention on what changed, what stalled, and what disappeared—keeping history available matters more than most expect.

6. Review frequently and plan deeper resets less often.

Weekly or biweekly touchpoints keep things honest. Occasional deeper reviews create space to see lanes in the context of bigger lanes, re-check assumptions, and reset if needed. Periods of divergence and convergence are normal. The shape of lanes and ways of working should not be expected to remain constant. When drift appears, do not wait for the big reset. Adjust in the moment.

7. Work with a depth of field mindset.

Hard focus on what must move now. Soft focus on what lies ahead. Awareness of the rolling cone of uncertainty helps guide tradeoffs. Some lanes are project-shaped. Others are more open-ended. Both are valid as long as each lane continues to earn its place.

8. Refactor, pivot, or retire lanes as part of ongoing practice.

Some lanes stay stable for a long time. Others change shape as understanding deepens. The point is to keep adjusting so the lanes remain useful.