Company growth gets harder over time, not easier. And a big reason for this is that most companies get quarterly planning wrong — especially bootstrapped and “lifestyle” businesses.

First things first, your job as founder and/or leader is to ensure that the company is on the right trajectory at all times.

“But Paul,” you might say, “what about day to day execution?!”

Execution is table stakes. If you and your team can’t execute, stop reading this now and get that under control.

If you’re still with me, think of it this way:

Going from $0 to $1M in annual revenue is an act of brute force. If you’re at that stage of your company, you’re better off skipping this post and getting back to work.
Going from $1M to $10M in annual revenue is about doubling down on what’s working (eg, processes, people, customers, etc).
Going from $10M to $100M+ is generally about saying “no” to more opportunities and taking bigger swings with your initiatives.

The purpose of quarterly planning meetings is to verify your overall strategy and ensure that your plans align accordingly.

Here at Strata, for example, I want our company’s strategy to be aligned with 2X revenue growth each year. This is our intended trajectory and, each quarter, I pull my leadership team together to keep everyone’s efforts aligned.

Quarterly Planning Framework

There are two non-negotiables for me:

The Quarterly Planning Meeting needs to be offsite. If your team works from an office, the meeting needs to be at least 10 miles away. If your team is fully remote, the meeting needs to be face-to-face somewhere else.
You — the founder and/or leader — need to set the narrative and have a goal in mind. For me, a successful Quarterly Planning Meeting is one that allows everyone to walk away with a single document that outlines the 3-5 goals (or Rocks) for each team by the end of the meeting.

As you’ll see shortly, the meeting itself is relatively intense — despite being spread out over ~2 full days. By having the meeting at some off-site location, you’re minimizing distractions for your team. And, candidly, new workspaces tend to make people just a bit more creative.

So here’s the playbook once you’ve set a date and location for your own Quarterly Planning Meeting:

60 days out: block the calendar off — two days for the meeting, add an additional day before and after the meeting for travel.
30 days out: if you haven’t already, book travel and hotel. Bonus points if you pre-select lunch and dinner plans for the team.
14 days out: send out an agenda to the team. This should include your narrative (more on that in a moment) and the hour-by-hour agenda for the meeting itself.
7 days out: check-in with each attendee one final time. Make sure they have what they need, they understand the narrative you’ve sent and that they understand what you expect them to bring to the meeting.
0 days out: it’s meeting time!
7 days after: each attendee’s direct reports should understand the goals that have been set for the team and the overarching company strategy that led to those goals.
30 days after: by now, you’ve shared the company’s quarterly goals with the entire team — you’re doing monthly All Hands meetings, right? 😅

The Narrative

If you don’t set the narrative, one will be made up for you — and I guarantee you’ll hate it.

To put this another way, you can’t properly plan for the future without a hard look at the present. If you’re reading this post, you’re responsible for writing the narrative. Here’s a look at how mine looked a couple weeks ago:

TLDR

We need to [Objective #1] and ensure [Objective 2].

Purpose

As we near the end of Q2, we’ve learned a couple things…

From a marketing & sales perspective:

[Learning #1]
[Learning #2]

From an internal perspective:

Learning #1]
[Learning #2]

As we head into Q3, we need to [Objective #1] and [Objective #2].

On the first point (re: [Objective #1]), we have [REDACTED]. We should address the variables we can control (eg, [Example #1], [Exampled #2], etc) and keep an eye on the variables we cannot control (eg, [Example #3], etc).

On the second point (re: [Objective #2]), we have already seen the benefits of [REDACTED]. We should [REDACTED].

None of this should come as a surprise, of course. We need to [REDACTED].

So, please rest up as we head into this next meeting. Please set aside an hour or two to think about the things below. And please come to Osprey ready to share your thoughts, ideas and concerns. 🙏

With this narrative, I’ve clearly outlined my view of the current/past quarter and presented company objectives that I believe are important.

At this point, the rest of my leadership team needs to either refute my thoughts and present their own. Or they need to draft their plans accordingly.

Which reminds me…

Planning vs Strategy

Most companies spend too much time on planning and not nearly enough on strategy.

These also tend to be the companies that look up one day and ask themselves, “how in the world did we end up here?”

Nine times out of ten, it’s because “the strategy” is usually some vague financial target. And then “the plan” becomes a list of things that are defined by nothing more than affordability.

That’s playing to lose.

Strategy is about choosing what the company will do, what it will not do, and why.

You know you’re truly talking strategy when it feels like a bet. And once you’ve aligned your team on the strategy, the planning efforts exist to serve that strategy entirely.

The Meeting

You’ve put in all the prep work, here’s how the two days roughly break down:’

Day 1 (8:00pm-12:00pm)
- What went well last quarter? What didn’t go well last quarter? Everyone comes prepared with the good, bad and ugly. This isn’t about pinning the blame or taking the credit, it’s about “breaking the ice” and getting into the flow together. I like to coax everyone into throwing at least five bullet points on each list.
- 1-3 higher level discussion topics (aka strategies) about certain ideas that I may have presented in the narrative that was sent out prior. The team is welcome to bring their own topics for this part too. The key here is to ensure that any topics discussed here are “big enough” to matter — if you’re at $1M or less in revenue, these topics should be worth at least $100K in revenue or cost-savings. You can multiply the numbers upwards as you grow.
Lunch. Go get something to eat. Walk as a team, if you can.
Day 1 (1p-5p)
- Confirm the existing Mission, Vision and Core Values. Re-write them, if necessary. Take as long as you need. This is important.
- Confirm your 3 year goals. Then confirm the 1 year goal. These can be however you define success (eg, “we will do XXX” or “we will have YYYY”) — it doesn’t matter if you’re right, it’s about getting alignment on the definition of success so that whatever trajectory you set over the next few hours aligns.
Dinner. Go have some fun together, you’ll talk about work… but try not to, if you can.
Day 2 (8a-12noon)
- Every attendee presents the top 3-5 goals (ie, Rocks) their team should deliver to align with the previous day’s discussion. Don’t debate things yet, just get everyone to disclose their thoughts on their own team / efforts — you’re writing this down into a central document somewhere.
- Once everyone’s outlined their goals, it’s time to discuss. I like to let the team pick where we should start. By this time, anyway, there’s usually a clear idea of where the discussion will start — more often than not, it’s probably your product.
Lunch. Go get something to eat. Walk as a team, if you can.
Day 2 (1p-5p)
- You’ve probably been debating things for hours. I wouldn’t be surprised if tempers flare at some point too. That’s a good thing. But it’s your job to keep the discussion moving towards a resolution.
- By end of day, you should have a single document — we use Google Docs — with 3-5 goals for each team. It’s important that the owner of each team fully agrees with their goals and that the rest of the team is aligned with those goals. It’s that simple. And that hard.
Dinner. You and the team are probably drained by this point, don’t skip this chance to bond.

The Aftermath

I prefer to share the goals and strategy widely across the company – not just my direct reports. This is the best way to ensure that everyone understands why we’re doing the things we do.

Beyond that, we check-in weekly on the goals/rocks to get a sense of whether we’re “on track” or “off track.”

Test this format at your company and let us know how it goes! Send us an email with any questions or results! (hello@stratapt.com)

How to Execute Quarterly Planning for your Clinic