It's December (yup how did that happen?), which means planning season is in full swing. Conference rooms are booked solid. Memos are being written. Spreadsheets are multiplying. And somewhere, a poor operations person is trying to reconcile why three different departments all claim they need the same headcount to solve what appears to be the same problem.

Sound familiar?

Here's the uncomfortable truth: most organizational planning is broken. Not because teams don't care, or because leaders aren't smart, but because we're planning around org charts instead of customers.

I might be one of the only people who truly loves planning. Why? Because it’s the opportunity for the organization to come together and do the thing they said they do all year long: collaborate.

Every organization does planning. Even the most agile, "we don't believe in long-term plans" startup eventually needs to talk about budgets, headcount, and what the next quarter or year looks like. You should plan. It's essential for alignment, resource allocation, and making sure everyone's rowing in the same direction.

But here's where it breaks down: most companies don't have a clear philosophy on how they plan.

The result? You end up in one of two dysfunctional camps:

Leadership gathers in a room and writes "big bet" memos. They're strategic, well-reasoned, and ambitious. Then they cascade down through the organization.

The problem: The people who will actually execute the work weren't in the room when the plan was created. Product didn't talk to Customer Success. Marketing didn't talk to Sales. Engineering found out about the new initiative when it hit their inbox.

By the time you start Q1, you're not executing—you're negotiating. Every team is scrambling to figure out how this top-down plan affects them, what they need from other teams, and whether the dependencies even make sense.

To avoid being top-down, you tell everyone they can participate in planning. Democracy! Inclusion! Every team gets to write their memo!

The problem: You get 47 different planning documents. Marketing has their template. Customer Success has theirs. Sales has a completely different format. Each team is optimizing for their own success metrics, their own initiatives, their own world.

Then some unfortunate soul—usually in Operations or Strategy—has to reconcile all of this. They're hunting for duplications (why are three teams all building onboarding experiences?), trying to identify dependencies (did CS know that Marketing's timeline depends on them?), and basically playing organizational Tetris.

Everyone just spent 6 weeks planning, and somehow nobody actually planned together.

Here's what both approaches miss: the customer doesn't care about your org chart.

When a new customer signs up, they don't experience your "Marketing Quarter 1 Strategy" or your "CS Onboarding Pillar." They experience a journey:

That journey cuts across every department in your company. It requires Marketing, Sales, Product, Customer Success, Support, and probably others to work together seamlessly.

But your planning process treats those teams as if they're solving separate problems.

The result? You get:

There's another issue that comes up during planning season, and it's the one that makes leaders squirm: ownership.

Who owns onboarding? Who owns retention? Who owns expansion?

In theory, everyone knows the answer. In practice, nobody wants to say it out loud.

Why? Because naming an owner feels political. It feels like you're saying one team matters more than another. It creates tension. So instead, we dance around it:

All of which is true! But also meaningless when it comes to planning.

Here's what happens when you avoid naming an owner:

The irony is that avoiding the ownership conversation doesn't make it less political—it makes everything MORE political.

What if, instead of planning by department, you planned by customer experience?

Here's how it works:

Before anyone writes a memo or requests headcount, answer these questions as a leadership team:

This gives you a shared view of reality. You're not talking about "Marketing's goals" or "CS's goals"—you're talking about the customer's experience and what needs to improve.

Once you know which experiences need to improve, form squads around those outcomes—not departments.

Example: Instead of this...

...Do this: Form a "First 90 Days Experience Squad" that includes:

This squad owns ONE shared OKR: Improve the customer experience in the first 90 days, measured by activation rate and time-to-value.

Here's where you solve the uncomfortable ownership problem.

Yes, the squad owns the outcome together. But one person is the DRI (Directly Responsible Individual)—they're the primary owner who:

This isn't political—it's practical. Someone needs to be in charge. But framing it as "we all own the customer experience, AND this person is the DRI for this specific part of the journey" makes it feel collaborative rather than territorial.

Now here's the magic: instead of each team writing separate memos that get reconciled later, the squad plans together from day one.

They use a shared template (like the one you can download here) that forces them to:

The result: You start Q1 ready to execute, not negotiate. Everyone already knows what they're building, who they need it from, and why it matters.

Let's make this concrete with an example.

Traditional Planning (Broken):

Q1 Reality: Three teams discover in January that they're all trying to solve the same problem three different ways. They spend weeks negotiating who owns what, debating metrics, and arguing about dependencies. By February, they're behind schedule.

Customer-Centric Planning (Fixed):

"First 90 Days Experience Squad"

Current Customer Experience: New customers are overwhelmed. They don't know where to start, can't find relevant education, and 30% churn before achieving value.

Desired Customer Experience:

What We're Building Together:

Dependencies Made Explicit:

Q1 Reality: The squad starts executing on day one. They meet weekly to unblock dependencies, adjust based on customer feedback, and track progress against their shared OKR. When challenges arise, the DRI makes calls quickly because everyone already agreed on the customer outcome.

Customer-centric planning requires a fundamental mindset shift:

Old mindset: "What is my team going to do this year?" —> New mindset: "What customer experience are we improving together?"

Old mindset: "How do I get resources for my initiatives?" —> New mindset: "What do we need to deliver this customer outcome?"

Old mindset: "Who owns this? (and I hope it's me)" —> New mindset: "We all own this, AND this person is accountable for driving it"

This is uncomfortable at first. It requires leaders to:

But the alternative—continuing to plan in silos while pretending you're customer-centric—is worse.

If you're in the thick of 2026 planning right now, here's how to course-correct:

Before anyone writes another planning document, gather your leadership team and map your customer journey. Identify the 3-5 experiences that matter most to your business next year.

For each critical experience, identify who needs to be in the room. Not who wants to be in the room—who actually needs to do the work.

Give every squad the same template (download mine here) so they're all speaking the same language. This makes it dramatically easier to identify overlaps, dependencies, and resource conflicts.

Have the hard conversation. For each squad, who is ultimately accountable? Make it explicit, make it clear, and move on.

Block time for squads to plan together—not just share their plans, but actually write them collaboratively. This is where the magic happens.

Create a shared view (spreadsheet, Airtable, whatever) where every squad's dependencies are visible. This is how you catch conflicts before they become Q1 surprises.

Your customers don't experience your organizational structure. They experience a journey that cuts across every team in your company.

If you keep planning by department, you'll keep getting:

Customer-centric planning isn't just a nicer way to plan. It's the only way to plan if you actually want to execute.

The question isn't whether you should plan. It's whether you're going to plan around your org chart or around your customers.

2026 is coming. Which one will you choose?

[Download the Customer-Centric Planning Template]

Ready to transform how your organization plans? Get the full template and start planning around customer experiences, not org charts.

I can hear some of you saying: "We're agile! We don't do big annual planning!"

Great. Two things:

The philosophy applies whether you're planning for a year, a quarter, or a sprint.