How to Get Your Quarterly Planning Done in Two Days

Why top-down and bottom-up both fail in practice, and the middle path that gets a company aligned on quarterly goals without burning a month of executive time.

Most companies run their quarterly planning one of two ways, and both of them usually fail.

The top-down approach is what most people learned in enterprise. The executive team disappears for a week, comes back with five to seven company goals, and cascades them down. Each layer sets goals that supposedly ladder up to the layer above. It’s clean on paper. In practice, the people closest to the work weren’t consulted. The goals feel handed down. Nobody owns them; they just try to comply with them. And by the time everything cascades through all the layers, the quarter is a third over.

The bottom-up approach sounds like the fix. Ask each team what they think their goals should be. Roll them up. The executive team synthesizes and refines. This is the ideal model in a world with infinite time. In practice, it burns an entire quarter on planning itself. Almost nobody actually does it, and the ones who try usually give up halfway through.

The middle path isn’t a compromise between these two. It’s a different sequence.

The core principle is the one we’ve written about before. [@Luis Pieruzzini - include title and link to this article here.] It’s much easier for you to course-correct the team’s thinking than for the team to reverse-engineer yours. Planning should be designed around that reality.

The full sequence

Here’s what a well-run quarterly planning process actually looks like when you compress it. In practice, this is roughly two working days of actual meeting time, spread across a week to allow drafting in between.

Step 1: The framing group drafts directional guidelines. (Half a day)

Get two or three people in a room who have their pulse on where the business needs to go. This is not necessarily the CEO plus the org chart. It’s the people with actual context, wherever they sit. Sometimes it’s the CEO, a founder, and a senior operator. Sometimes it’s a CEO and a couple of function leads. The composition matters less than the caliber of thinking.

The job of this group is to draft directional guidelines. Not full OKRs. Not target numbers. Just the qualitative priorities for the quarter.

Something like: “Our biggest issues this quarter are increasing retention, growing sales in the enterprise segment, and reducing interest payments on our debt facility.”

That’s it. No percentages. No specific KRs. If you have strong feelings about a specific number, don’t hide the ball, name it. But mostly, this stage is about scoping, not committing. The goal is to give the rest of the organization enough guidance to think clearly, not to hand them a finished plan.

This is the phase where focusing on inputs matters more than outputs. What you produce here is a set of inputs to the team’s thinking. You’ll get outputs back from them in the next steps.

Step 2: Executive alignment on scope and ownership. (Half a day)

Bring in the executive team, or the layer of leaders who own each functional area. Walk them through the directional guidelines. Get their feedback. Refine as needed.

The critical part of this meeting is claiming ownership. By the time everyone leaves the room, each priority has a leader whose name is on it. Not shared ownership. Not “the marketing team.” A specific human who will come back with the OKRs for their area and be accountable for delivering them.

You also want to leave with rough agreement on the guidelines themselves. Not perfect. Rough. The point of this meeting is to give people enough scope to think inside the broad shape of the plan, not to lock the details of the plan.

Step 3: Owners draft OKRs with their teams. (One week, mostly async)

Each executive takes their area of responsibility and drafts real OKRs. Targets, guards, and diagnostics for each priority. (If those terms are new, we wrote about them in “Measuring What Actually Matters.”) [@Luis Pieruzzini include link here.]

For smaller teams, the executive can often just pull three or four people into a room and draft it collaboratively. For larger teams, most managers do this through one-on-ones. They draft, share, iterate. A lot of team members won’t have the context to make good top-down contributions, but they’ll have sharp opinions on the pieces that touch their work.

This step takes about a week. It’s mostly async. The leader is doing the driving.

Step 4: Executive review and dependency mapping. (Half a day)

The executive team reconvenes. Each owner presents their OKRs, what they’re going to achieve, how they’ll measure it, and, critically, what they need from the rest of the company to succeed.

This last piece is the one most companies leave implicit and then regret. If the sales lead’s plan assumes engineering will ship a specific feature by mid-quarter, that dependency has to be surfaced now, in the room, with the engineering lead present to confirm or push back. Otherwise, you’ll discover the misalignment in week eight, and it’ll be too late.

Expect a few iteration loops. The CEO gives feedback. Owners refine. Sometimes, it takes two or three passes across different meetings. That’s fine. What matters is that everyone leaves this stage with OKRs that are actually owned, with dependencies mapped and agreed upon.

Step 5: Publish via all-hands. (One meeting)

Roll out the quarterly plan in an all-hands meeting. The CEO frames the quarter at the beginning and closes at the end. Everything in between is the executives presenting their own OKRs. Not the CEO reading them out. Not the deck someone else built. Each owner gets up and says, “Here’s what I’m committing to, and here’s what I need to make it happen.”

That’s the sequence. Two working days of actual meeting time, spread across roughly ten calendar days. Some drafting and thinking in between. A published plan at the end.

Why the sequence works

The design of this process is doing two jobs at once.

Job 1 is producing a coherent set of quarterly goals. That’s the obvious thing.

Job 2 (less obvious but more important) is producing goals that are actually owned by the people who have to deliver on them. The reason the sequence starts with directional guidelines instead of specific OKRs is that specific OKRs handed down feel like assignments. Directional guidelines that owners then translate into OKRs feel like commitments. Potentially the same content on paper, but a wildly different psychological experience.

The core principle that runs through the whole sequence: you never set the goals in the final form yourself. The goals are always the summarization of what the people who own them decided. Your job is to shape the direction upstream and course-correct downstream. The middle part belongs to them.

How the cadence adapts down the org

The sequence above describes what happens at the top of the company. There are similar mechanics apply as you push it down through the layers, with one important adjustment.

The more junior the employee, the more directive their manager needs to be. A senior VP will draft their own quarterly goals and defend them. A mid-career manager usually needs some framing from their leader before they can draft. A junior individual contributor often needs to be told what the priorities are, not asked what they think they should be.

That’s not a violation of the principle. It’s the principle applied to reality. Ownership requires the context to make good decisions. When someone doesn’t have that context yet, forcing them to invent goals is not empowerment, it’s abdication and lack of support.

The middle manager’s job near the bottom of the cascade isn’t primarily to set goals. It’s to make sure their team has internalized ownership of the goals that got set. That happens in the invitation-to-challenge conversation. “Here’s where we’re going this quarter. You said you want to own X. Here’s what I think success looks like. What do you think? What am I missing?” The lower you go, the more developed of a plan you’re bringing to the person. But you still bring it as an invitation, not a decree.

One more thing to include: The executive hiring test

A useful tell for whether a senior hire is going to work out. When you’re at the final stage of hiring an executive, have them do exactly this planning process for themselves, for their first six months.

Draft directional guidelines. Propose OKRs. Identify dependencies. Present it back to you.

You get three things out of that exercise. (1) You see their analytical thinking. (2) You see whether they actually understand the mission and can translate it into priorities. And (3) when they start on day one, they know exactly what their job is (after you’ve helped them refine their perspective).

That’s more useful than any interview loop.

The bigger point

Most planning processes fail not because the goals are wrong, but because the process didn’t produce ownership.

You can write beautiful OKRs and cascade them cleanly and still end the quarter with a team that never really committed to them. Or you can produce slightly rougher OKRs through a process that made people co-authors of what they’re committing to, and watch the same team overdeliver.

The plan matters, but the way you produce it matters more.

Two days of well-designed meetings, spread across a week, will get you further than a month of the wrong ones. The trick is knowing which meetings actually count and running those well.