It can be hard to carve out the time to take your entire leadership and management team out of rotation for two days, but when it’s done right, the strategic planning process is incredibly productive. This is where hidden issues are brought into the light, consensus is built, priorities are set and the whole team watches the big picture come together before their eyes.

Having run annual sessions for many years and many companies, I’ve come up with a simple strategic planning template that makes the best use of people’s time and input, so that everyone comes away with clear goals and an action plan for reaching them.


The location

It takes extra effort, but an off-site location is essential. It removes day-to-day distractions and gives participants the distance they need to stop seeing the trees and start seeing the forest. The change of venue resets people’s brains so that they can tackle the issues with more focus and new perspectives.

Bringing your strategic and operational teams together for a continuous, focused session can accomplish what dozens of fragmented, on-site meetings can’t.

Taking things off site also establishes neutral territory where people can talk about the problems. People are conditioned to be upbeat and positive in the office, and it can be hard to let go of those expectations when the annual planning exercise takes place on home turf.

If you can spare the time, break up the annual planning session over two days. This allows the group to focus on the problems day one, enjoy some down time together and then come in the next day having slept on the issues and ready for a fresh, focused discussion on solutions.

As a final point, a rural location usually works better than an urban venue. This isn’t just about giving your team the chance to enjoy some outdoor recreation. Studies show that natural environments stimulate a state of deeper focus, increased engagement and less stress, all of which will enhance the planning process.

The attendees

Choosing who should participate is a critical decision point. The c-suite is a given, but you should also invite anyone with operational management responsibility— typically that next level of management. This is especially important for growth companies where this management layer has more operational pull and can often see things that the c-suite doesn’t.

I also like to invite a board member to participate in a limited role. You don’t want them weighing in on the problems—that input should come from within. But a board member can draw on the insights they’ve collected from their interactions with other companies to provide a different and valuable perspective.

The process

I like to keep the planning process straightforward:

1. Use a simple SWOT analysis to identify opportunities and problems
2. Prioritize the top two or three in each category
3. Set SMART goals that support a solution

For each item tackled, be sure to agree as a group what success looks like. This prevents a situation in which there is some ambiguity about the final outcome. For example, is a sales initiative successful if it brings in a thousand leads or if it results in a half-million dollars of new business?

Most people don’t like to talk about the problems, especially in front of the CEO, so the planning process needs to pull that information out of everyone around the table. I’ll ask each member of the team to list the three problems that are at the top of their personal list. The only rule is that the problems need to be within the company’s control—things like a lack of training, high turnover, low morale, missed deadlines.

Write the problems up on the board, and then consolidate and rank them by how many hits they each got. Then start drilling down and discussing the top three. Talk about the implications of the problem: what effect is it likely to have on the company? Then figure out how you’re going to make sure the problem goes away using SMART goals.

It sounds simple, but having operational experts and decision-makers in the same room looking at problems in new ways can generate breakthroughs. Here’s an example:

During a planning session for a SaaS company I ran a few years ago, we discovered that one of our biggest problems was being late on installation schedules, and it was affecting our profitability and reputation.

As CEO, I knew this was an issue, but I had no idea why until I was in the same room with all of my managers. They told me that integrating our software with legacy systems required them to build complex, time-consuming interfaces.

During the session, we agreed to stop building custom interfaces for each new client and focus our efforts on building an interface toolkit that could be reused time and time again.

The result was a middleware product that not only solved the problem, but actually generated a new revenue stream, turning our biggest weakness into a strength.

The rules

1. No judgement. While the planning process needs to be frank and open, it can’t be judgmental. I try to ban the words “you should.” “You should focus on this product,” becomes “Have you considered focusing on this product?” The problems are important: where the blame belongs isn’t.

2. Choose three. You’ll generate many problems and opportunities during the planning process. The key is to keep consolidating and prioritizing them until no more than three come into focus. These are big issues and big initiatives: addressing too many at once will set you up for failure.

3. Define success. For opportunities, it’s essential to drill down. Look beyond the “what” to the “why.” If you want to open an office in Paris, for example, decide what that office needs to do for you to deliver success. How will it grow your business? What are your revenue expectations?

4. Have a plan. Setting the direction gets you halfway there: creating the action plan gets you the rest of the way. You want everyone to leave with step-by-step instructions so they’re clear on the game plan and their accountability.


Here’s the bottom line.

While you can’t control external factors, annual planning helps you address and control the internal ones that are holding you back. Bringing your strategic and operational teams together for a continuous, focused session can accomplish what dozens of fragmented, on-site meetings can’t.

So get out of the office, start with a SWOT analysis to set the strategy and use SMART goals to set execution and accountability. If you’ve done it right, you’ll walk away with a clear sense of what needs to be done, who’s responsible for doing it and maybe even a groundbreaking insight or two.


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