Life Tool: Annual & Quarterly Strategy Retreats

Charles Moore
Jan 6, 2018 · 8 min read

This post is part of a series. You can start at the beginning or see All of the Tools.

Photo by Paul Gilmore on Unsplash

“…in senior leadership positions, one of your jobs is to reflect, and you have to schedule time to do that.”

The quote above is from Clarence Otis, former CEO of Darden Restaurants, in his Corner Office interview. I referred to this when describing the operating system design principle: reflect on what’s important to you on a regular basis.

One way I do this is to hold an annual “strategy retreat.” In fact, my wife and I do it together. The retreat is a day of investment in deep reflection, which enables essential planning for the coming year.

Greg McKeown shared his perspective on essentialism and the usefulness of a regular retreat:

“So this perspective, this helps to reveal for us the difference between good things and essential things. That’s the whole shift. Essentialism is different to every other productivity system that I’m familiar with in this primary way. It’s not about getting more stuff done. It’s about getting more of the right things done. It’s not about efficiently doing what’s on the to-do list. It’s realizing that the most important thing isn’t even on the to-do list. That’s the insight. That’s what the personal quarterly offsite can do.”

The most important line of this for me is: “the most important thing isn’t even on the to-do list.”

That is, an activity that is focused on just creating a plan (an extension of a to-do list) misses the spirit of a “retreat.” One needs to get away — whatever that means for you — to do deep thinking, to connect with what really matters. Only then, can you create a plan that is effective — in that it will help you get to a destination that is valuable.

Annual Retreat


The retreat typically comes during the week between Christmas and New Year’s, since there is little happening at work and it’s a natural time to plan for the coming year. But in principle, you could do it at any time in which you could create enough time and mental space.

The retreat used to be a full day, and I’d recommend that schedule if you can do it. However, now that I have kids, the retreat is more like 2–3 hours of discussion (when our kid is napping!), with my wife and I having done our separate pre-work over the previous week.


In practice, the retreat happens at my office or a coffee shop, but main idea is to find time and space in which I can work without distraction, think deeply, and think creatively. Greg McKeown suggests getting into nature.


The agenda for the retreat typically includes:

To have those conversations successfully, we do pre-work for the retreat that includes:

Keys for Success

Here some drivers of a successful experience:

Making It Actionable

That last step — making the strategy actionable — is really what gets it off to a good start. One tactic that I have found particularly helpful is to make public commitments.

A few years ago, one of my goals was to improve my knowledge of personal finances. To do so, I invited my friends to a series of dinners at my house, with the promise that there would be an insurance agent, financial planner, investment advisor, lawyer, or similar expert to educate us.

I didn’t have everything planned when I sent the invitations, but because the commitment was public, it helpfully forced follow through.

A few years later, I wanted to build some new cooking skills, using Kenji Lopez-Alt’s nerdy cookbook The Food Lab. Instead of keeping it as a vague goal, I put six dinner and brunch dates on calendar, and invited my friends.

This approach has a key benefit: removing willpower as a barrier to success. Once the commitment is out there, the action just kind of happens.

Resolutions Are Crap

Tricks like this — easy solutions to the behavioral impediments to action — were key to another realization: New Year’s resolutions are crap. Instead of creating a list of things you intend to do or want to do, you can create a list of things that you are doing or have already done.

There’s less ambiguity with this approach, and in a way, much less planning involved once you get started.

It’s about going from “I need to go to the doctor” to “I have an appointment already scheduled for March.”

From: “I need to work out more”

To: “I joined a weekly basketball league” or “I am signed up for a 10K run in June.”

From: “I need to take a break more often. I’ve been meaning to travel more.”

To: “I bought plane tickets to the Bahamas for April and to the Grand Canyon for October.”

The solutions you implement might be different, but the focus on taking real action immediately may be the missing piece to achieving these types of goals.

At the very least, you’ll finally get to that annual physical.

Getting Started

Here’s the world’s simplest action plan: just do it. There’s no need to wait for the next holiday season. Scan your calendar for the next that is mostly free, and schedule your retreat.

Quarterly Retreat

I follow a similar process each quarter to reflect on my personal strategy and my team’s strategy at work. At the start of the year, I block off days for the quarterly retreat (about two weeks before the end of each quarter)

Like with the annual retreat, I try to “remove” myself from my normal environment — typically, working from home or retreating to a conference room, so that I can work without distraction. Regardless of whether I’m physically in the office, my calendar is marked “out of the office,” so that it is not interrupted with meetings.

The questions I use to guide the reflection and planning are in italics below. These are also questions I put to each member of my team when we hold a full-team strategy retreat.

What went well in the last quarter? What went poorly or not as planned?

These questions are a straight-forward reflection of the past. The first step of the retreat is to “grade” progress against each objectives and key result from the previous quarter, and these questions are to guide the reflection on that exercise.

What was the #1 thing that I control that held me back from accomplishing more? What was the #1 thing that I don’t control that held me back?

The first question gets to my behaviors that drove success or failure. The answers typically yield changes to my routines and approaches or skill development objectives.

The second question is meant to the raise the systemic factors that impact success. They are usually things I cannot change unilaterally, but can attack with help from others. For example: “I/we need more resources to…”, “I need permission to…”, “I need clarity from leadership about…”, “I need to get relief from the following commitments to free up time…”

How am I doing relative to my annual goals?

This is a check-in on the larger set of priorities. By the third and fourth quarter of the year, these are often quite different from the beginning of the year. But it is great to revisit those annual goals to make sure I am not missing anything important.

(At work, this exercise is often a prompt to revisit annual goals with superiors and other stakeholders — e.g., “We said we would achieve X before, but I now think Y is more important. Do you agree?”

What state of the world in three months, would make me declare that the quarter was successful?

This question is the heart of developing objectives and key results for the quarter.

What’s different now relative to the last time I/we did planning?

This question helps tease out differences in context that merit different approaches and different priorities — e.g., new commitments, different priorities for my boss, new stakeholders due to an organization change, new knowledge, new competitors.

One of the biggest issues my junior colleagues (and those who are more experienced, but aren’t strategic thinkers) have is that they focus on what’s right in front of them rather than on the big picture. Often, their list of key results simply takes their current set of projects and outlines what three more months of the same work would look like.

But the whole point of taking a step back, of having a “retreat” is to provide room for deeper insights like:

Those types of insights are harder to see without focusing on fundamental outcomes and what’s different in the context.

What do I need to get done today/next week to get off to a fast start?

Much like the annual retreat, ending with clear action steps has proven to increase the odds of success. At minimum, the action steps include communicating with “customers” to get their agreement on the plan (i.e., “does this work for you?”) and with those on whom I’m dependent (i.e., “can you get done what I need to accomplish these objectives?”).

I want to hear your thoughts!

This is a “living post,” in that I’d like your help to add to make it more valuable. What have you tried that is similar? Have any stories about the impact of using a tool like this? Please share!

See All of the Tools for other posts like this.

Charles Moore

Written by

Product and analytics guy. Here, sharing a bunch of random insights from a bunch of random experiences.

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