Plans are Nothing. Planning, is Everything.

Using Quarterly Planning as a model for creating Clarity and Alignment

Hello again. I coach leaders and teams on how to improve the way they deliver value to their customers in ways that work for their business. My promise has always been to give you real world examples, not textbook advice or platitudes from an armchair quarterback.

Alright, buckle up. I thought I would change things a bit for this Tidbit. First, a fable. Short, punchy, and maybe even wise. Then we’ll get to the real story — the one that just might change how you think about planning. Trust me, it's worth it.

It goes a little something like this.

A man walks past a construction site while on his way to work and sees two gentlemen building a wall. Curious, he approaches the first worker and asks, “What are you up to?” The construction worker replies, “I am laying these bricks to provide money for my family.” Honest work for an honest cause. Then, the curious man walks over to the second construction worker and he asks the same question, “Sir, what are you up to?” The construction worker raises his head almost as if to look off into the future and then, without turning back to the curious man, joyfully responds, “I am building a cathedral.”

Two different men working on the same project. Two different perspectives, goals, and outcomes. Neither perspective is wrong. The first worker understood his first priority was his family and that his actions would help him provide for them. The second man understood the outcome they were ultimately striving towards. The ultimate goal.

And that's how the Cathedral mindset works in theory. Now, let me show you how it played out in practice with a marketing team I helped align on their own “cathedral”...

Some Background

“Planning” has always been a sore subject for me. On the one hand, I loathe waste. This leads directly to my disdain for spending long hours trying to fool myself and others into thinking we can somehow know everything that will happen more than 30 minutes into the future. After that, the Butterfly Effect is in play and time and chance start playing a fateful game of “watch me swoop and poop on your best laid plans.”

On the other hand, walking into the future with absolutely no forethought is a recipe for disaster. I can’t tell you how many times I have rushed head long into something without thinking and it turned out exactly like Leroy Jenkins in a dungeon.

From this twisted tension tumbles what I believe to be the best value from planning: Clarity and Alignment. Not a plan. Get Clear on the desired outcome for the period in question, (day, week, weekend, month, quarter, year, etc) and then Align on valuable items that might help achieve that outcome. Of course you have to be careful to keep the correct level of fidelity. Plan properly for the proper planning window.

In other words, if we are discussing a plan for the day, focus on getting clear and aligning on daily outcomes. If you are instead discussing a plan for the year, focus on getting clear and aligning on valuable items that help you on yearly outcomes. Don’t focus on daily task type things in your yearly plan. That’s too much detail in the wrong conversation. It’s the wrong planning window.

For example. In our Cathedral story, if the conversation is about our yearly plan, we would not be discussing how we would build the walls. That’s a daily conversation. We would instead be getting clear on what our goal for the year was, building the cathedral, and aligning on what high level items needed to be completed to make that happen.

And that is how I helped a marketing group create Clarity and Alignment.

The Story

I was called in to help some development teams improve their quarterly planning. There are schools of thought and frameworks that would have you focus on trying to know everything going into the planning. And for some projects, that may work. For the rest of life, where being nimble and adapting to the market is important, a different approach is needed.

The goal was to have the team come in to the meeting with their top level goals or outcomes. I personally prefer to use OKRs, but feel free to use whatever structure or framework befitting your situation. The terminology is not important. Essentially, just list 4-5 high level things you could potentially accomplish over the next 3 months. That’s what we had the team’s do.

Next, I had them categorize these desired outcomes, along with any goals they were currently working towards, in what I like to call a Now, Next, Later. Here is a quick example.

In the pictured example, similarly to the marketing teams, we can quickly review any completed goals (Done), review items that were in flight (Now), and then set the bulk of our time discussing if our list of “Next” items made sense. Now, the goal of the conversation was not asking for permission or approval on what was Next. The goal was alignment. Did our “math check out.” I was coaching these teams to take ownership of their homework and knowledge, which is something I believe is central to building empowered, self sufficient teams. We don’t go around asking others if we have permission to renovate our house (unless you have an HOA…sigh) or take a trip to Disney. We should have already done our own homework to decide viability of those ideas. Instead, we use this time to mine for any final advice or insights before we go and spend company funds to have this team execute towards the next goals.

We invited stakeholders, leaders, and the rest of the team to this conversation in hopes that any input would help drive some clarity and alignment.

It was chaotic, confusing, and intense. Pure bonkers. (There were conflicting ideas, unexpected hurdles, and a few “who's in charge?” moments.) Exactly what you’d expect for a first attempt at something new.

And it was beautiful.

The group shined. One team in particular had bought in to the idea of setting up their Jira board just like a Now, Next, Later and it was the star of the show. They were able to clearly articulate how they planned to attack the coming months, while explicitly stating they would learn and adapt along the way. They didn’t discuss daily work, keeping the conversation at that higher level of 3-4 outcomes they wanted to achieve during the quarter.

This brings me to the next key to making this a success. While the team did leave the room with alignment, the secret sauce would be in having some type of recurring alignment checkin after that meeting. The teams decided they would meet once every other week, with a few people from the team and a few stakeholders and leaders. The intent was to revisit the Now, Next, Later, double check their math, and even discuss a few things they were able to deliver towards the goals.

Alignment was achievable. What’s more, it helped drive clarity. The people seemed to understand they were “building a cathedral.”

Landing the plane

I recently ran almost this exact process with a set of marketing development teams. Once you’ve done it a few times — especially in your own space — it just clicks.

You don't have to be two different people: rigid Project Manager at work, adaptable leader at home. If we can navigate household chaos, church ministries, or community projects with flexibility, we can do the same at work.

Quarterly planning doesn’t have to be rigid, painful, or soul-sucking. It’s about being clear on the outcome but flexible on the path to get there.

As Jeff Bezos puts it: Be stubborn on vision, but flexible on details.

The team I’m coaching is early in their journey with this approach. Maybe I’ll have another success story soon.

Until then — keep learning, keep growing.