It is the strategic planning time of the year again and wow, it sure did come around quickly—and not soon enough. This year, as we all know, is one to put in the history books.

As we plan 2021, here is a quick process I have followed each year that really works to drive alignment in teams and individual ownership of the plan.

Catipult.AI can walk you through this process.


Strategic planning is art and science. The art comes from the discipline to keep discussions strategic, rather than tactical and the science in mapping a plan that is data-driven rather than opinion-laden.

To generate the best outcome of your strategic planning time and make sure that the participants walk away as owners in a plan upon which everyone is aligned, I like to segment sessions in terms two levels:

  • Level One: In this level resides the overall vision of the organization and the macro-level KPIs the organization needs to achieve. In this bucket are assignments and milestones that the management team (if applicable) assigns to its individual members to execute.
  • Level Two: The management team / individual departments. In this space, the management team takes Level One objectives they helped create and cascades them down into their own plans for their departments.

Here is how to execute Level One and Level Two planning sessions.

Part One / Level One: You and Your Strategic Team

Step 1: Re-assess Your Outcome.
Re-evaluate your three-year vision. Where is it you and your company want to be in three years given what it experienced in 2020? Even if you are in the middle of an existing plan, I recommend a re-evaluation of that strategy considering what was experienced in 2020.

Step 2: Determine what needs to happen to get there.
There are seven business drivers to your company, each driver participates in delivering the outcome you want to achieve. This next step takes the outcome you created in Step 1 and breaks it into key performance indicators that answer the question “what” needs to be achieved in each driver to create the defined outcome.

Step 3: Build a plan to accomplish the “what.”
The plan you build is answering the question: “How will we achieve what it is we need to accomplish in order to make our three-year vision a reality?” Individual answers to the question will be contained in what we call milestones or rocks. Milestones and rocks are not to be confused with tasks. Tasks are the small things necessary to accomplish the milestone.




Part Two/ Level Two: Your Strategic Team and Their Teams

When Level One is complete, it is time for your strategic team to work on their own departments. With the context created above, the strategic team will now determine what it is they need to accomplish to drive the corporate vision and the milestones that they have been assigned to own in Level One.

Each strategic team member should evaluate their departments using two variables:

  • The plan created above and
  • A common set of strategic questions. Using the same context and question set creates a common language and framework for the ultimate strategic planning meeting.

Members of the strategic team should repeat the exact same three steps they completed in Level 1, but on their own departments and through the lens of the company’s objectives.

By having team members create their own plans, a culture of accountability and ownership is strengthened, if not created.

Part Three: Putting it All Together

Parts one and two can happen at the same strategic planning offsite. Typically, when I lead them, the offsite is two days with the first day dedicated to part one, the second to part two, and the half-day is dedicated to the presentation of the individual plans.

I use Catipult.AI to walk teams through building their plans quickly, efficiently and in alignment with each other. Catipult.AI contains an advanced, fast-paced strategic planning module with more than 100 strategic planning questions that help establish visions, KPIs and outcomes for all levels of the organization.

Once the plan is completed with the milestones and rocks necessary to drive its success, management teams then use it as their weekly stand-up meeting agenda. Catipult, in other words, is the fastest strategic planning and alignment framework on the market. The software also nudges people to complete their milestones and acts as a virtual accountability coach for executing your strategic plan.

A Twist:  Your Health is Driver: One

The first business driver in Catiupult is “you.” If individuals are not meeting their personal, professional and health goals, the company will suffer. There is no way around this scientific fact. In Catipult, every member of the company using it will be asked to establish their goals in line with the business objectives. This is a powerful reframing of business that drives results by directly tying job performance with desired personal outcomes. By having health and wellness data in one system, it further streamlines operations by giving people a single portal, rather than dozens, to access.

Our partnership with LifeOmic’s Corporate Wellness Program integrates health data and individual goals directly into your strategic plan. Those goals are kept private to the individual, but the experience of seeing their health objectives being projected as just as important as business objectives is powerful. Individual health should increase and company performance and execution on the strategic plan should follow.


Here are some additional resources to help your process:

Catipult Software:

Catipult JumpStart Strategic Planning Workshop:

Get Catipult free for one month: