Planning Is a Practice, Not a Product

#29 || The messy middle of strategic planning, and how to get it right.

Street art in the Bowery, NYC (2017), Melissa Daimler

“Who does this really well?”

That was the question a client asked me recently during one of our preparation sessions for their executive team’s strategic planning offsite. The two co-founders I was working with had been running their business successfully and profitably for 16 years. Yet this year, they wanted more structure. Their executive team was asking for more clarity and cross-functional alignment.

They were using the OKR (Objectives and Key Results) framework, introduced by Andy Grove at Intel in the 1970s and outlined in his book High Output Management. The model gained momentum after investor John Doerr introduced it to Google in 1999, where it became central to the company’s approach to focus and alignment. Since then, OKRs have gained widespread adoption because they’re a simple and powerful way to translate strategy into action.

So when my client asked me who does strategic planning really well, I paused. Longer than I expected, or cared to admit.

Because the truth is, it’s hard to name a company that consistently gets this right.

It’s not that the people aren’t smart. Most teams can pull together a plan. I’ve been on plenty that were great at setting goals, writing OKRs, building out timelines in a spreadsheet, and turning it all into a beautiful slide, ideally with those three core pillars.

The more challenging part is what happens after the planning session, especially if those follow-up conversations aren’t seen as part of the plan itself.

Once the plan is set, most teams don’t revisit or reference it until the end of a quarter. Priorities change. New leaders join. And the plan quietly becomes irrelevant. The spreadsheets and slide decks are buried deeper in Google Drive, hidden beneath the “real work” and the day-to-day documents that everyone is focused on.

The Hard Part Happens in the Middle

Here’s the part most teams don’t realize. To create a strong strategic plan, you must be skilled at planning.

The real work isn’t just filling in OKRs or stacking everything into a spreadsheet or slide. It’s the middle part, where teams are working out how actually to make it all happen. The daily conversations, tradeoffs, and decisions that need to happen week after week if we’re ever going to reach those significant annual outcomes. These are the moments when we figure out who’s actually making the call, what needs to happen first to launch the product, and what kind of headcount it will take to get it all done.

These are the real planning moments, if we use them well, because they’re the exact challenges teams will face during execution. Planning the plan is really an opportunity to practice those conversations.

Getting opportunities to work through these problems builds the team’s trust and strengthens its ability to bring potentially divergent perspectives back to clarity. A solid plan isn’t just a product of smart people with good ideas. It’s the result of working through tension together. Tensions arise from striking a balance between keeping the plan simple enough to be realistic and specific enough to be meaningful. Grounded in current reality, but still aspirational enough to stretch people and teams.

I’ve been both the leader driving this process and the facilitator helping teams work through it. In both roles, I’ve found that the best teams don’t just build a strong plan.

They build the muscle of planning.

They build practices that help them clarify, prioritize, and work through challenges together.

Here are three questions that not only lead to a stronger, more aligned plan but also help you achieve it. They also help establish the foundation for how the team will continue to plan over time.

1. Who Is Accountable, Really?

It sounds basic, but a surprising number of plans fall apart because no one’s sure who’s actually on the hook. Every objective needs a clear owner, someone who’s accountable for forward motion, even if others are involved.

There are great frameworks that can help, such as DACI or RACI, which enable teams to establish a structure for how they contribute and make decisions.

So often, we try to be the “nice” leader and accommodate multiple people being accountable. In DACI terms, that might mean two people marked as the Driver, or even two Approvers.

I’ve done this. I’ve been that “nice” leader. I thought I was being inclusive and flexible, trying not to step on toes or create conflict. But what I’ve learned, usually the hard way, is that’s not actually nice. It’s just unclear. And when decisions need to be made quickly, and no one’s sure who to turn to, that lack of clarity turns into friction quickly.

What would’ve been helpful to the team was choosing one accountable person up front. One clear owner who knows they’re on point.

That’s what these frameworks are for. Not because acronyms fix everything, but because they give the team a shared language for how decisions get made and who’s responsible for what.

Clarity doesn’t create conflict. It prevents it.

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2. What Are Our Priorities, Really?

Most teams try to do too much. The plan starts out focused, but by the end, it turns into a wishlist.

I know this one firsthand because I’ve been that leader who tried to sneak in just one more priority. I’ve buried sub-priorities inside bigger ones. There was one year when I had just come in as a new leader and enthusiastically told the team, “We have 10 priorities this year. Get excited!”

We didn’t get to all 10. Or even 8. The ones we did complete were often surrounded by competing demands. The team was stretched too thin. The work moved the company forward, but if we had fewer priorities, we would have been able to make a more significant, sustainable change that year.

What we missed was the feeling of momentum. That clear sense that we are making progress on what matters most.

That’s what happens when everything’s important. Nothing is.

The real work of prioritization is about saying no to good ideas so you can execute on the right ones. That’s not easy. But it’s the difference between a team that’s busy and a team that’s effective.

And when new priorities arise, the team needs to be able to have the hard conversation about what gets pushed or taken off. In every company I’ve worked in, this has been the number one issue we grappled with.

It’s incredibly challenging to take something off the list. It’s much easier to keep everything on the priority list and tell ourselves we’ll just work harder. But it never worked out that way. We accomplished more, but by the end of the year, we were so exhausted that there was no real energy to create a new annual plan the following year.

Why bother? We know how this really works. It doesn’t.

3. When Are We Checking In, Really?

The plan doesn’t live in the annual planning meetings. It lives in the check-ins, the discussions, the honest conversations along the way.

That’s why having a clear cadence for reviewing and adjusting the plan is critical. Without that rhythm, even the best plans fade into the background.

A planning cadence becomes energizing, not exhausting, when it’s part of the work.

I’ve found that the best rhythms to practice are weekly, monthly, and quarterly.

Weekly: Make It Part of the Work

This is where most plans fall apart. The weekly team meeting gets filled up with “all the other work” beyond the plan that was just built.

A 30-minute check-in on part of the plan helps keep it visible. What moved forward? What are the blockers? What are we focusing on next week?

Pro tip: Try holding team meetings later in the week. I used to have Monday morning meetings, and it created anxiety at the start of the week. Thursday or Friday meetings give people time to reflect on what happened, and to get aligned on what they’re focusing on next.

Monthly: Back on Track

A monthly check-in with key drivers on initiatives is a great way to assess what’s off track and identify the support needed to course-correct. Ideally, it’s just another hour tacked onto your weekly team meeting. Over time, it doesn’t require much preparation, as those updates have already been happening on a weekly cadence.

Quarterly: Look Back and Look Forward

Too often, quarterly planning becomes a readout instead of a discussion.

The best quarterly reviews I’ve been part of include a dashboard or summary sent out ahead of time. That frees up the meeting itself for what really matters: the learning.

What worked? What didn’t? What do we need to change going into the next quarter? Who deserves acknowledgment for doing work aligned with our values and behaviors? What surprised us?

This is where planning becomes part of the work itself. And when you acknowledge what actually moved forward, it creates momentum to keep working the plan.

The Plan Is Just the Start

The best teams treat planning like a practice. They revisit it. Adjust it. Stay in a relationship with it.

The plan becomes planning, and the priorities become the work.

You don’t need a perfect process. You just need a repeatable one that builds honesty and trust into how you set direction, and flexibility into how you stay on course.

And that team I was working with on their 2026 strategic plan?

We had a great start, not just in building the plan, but in the conversations themselves. They got clearer on ownership, asked better questions, and practiced converging when it was time to make a decision.

And the best part? They’re still having those conversations. Because they didn’t just walk away with a plan. They walked away with practices for having the hard conversations and building the clarity they and their teams are craving.