Best Practices, Framework, Operations, V9I2

Strategic Planning

(Photo courtesy of Polina Zimmerman by Pexels)

Do you have a vision for your business 10 years from now? A clear picture of what you want it to be three years from now? An actionable plan for this year? 

What are you doing today, this week, and this quarter that will ensure actually achieving those desired outcomes?

Everyone who starts a business dreams about what this business will help them achieve; however, not everyone invests the resources to gain pristine clarity about their objectives. 

Even fewer business owners develop systems and processes to communicate goals consistently throughout the entire company to guarantee that everyone is working in a focused and disciplined way toward those intended outcomes. 

As a result, much time and energy are wasted. 

The practice of annual strategic planning is a critical piece for achieving focus and clarity and results in measurable movement toward your desired outcomes. While this ideally occurs at the highest levels of leadership in a company, it can be done departmentally or even personally if the vision is not in place at the ownership or president level. 

Getting clarity on a few key questions is the starting point. Why do you exist as a business? What does success look like this week, this quarter, this year, or in 10 years? 

What is the purpose of our work—what business are we actually in? For whom do we exist, or who is our ideal client? What are the values that we expect all our people to hold? 

What is most important right now for us to move toward our goals?

There are various ways of labeling each of these categories—and the names do matter!  However, what is most critical is that you, as a leader in the company, have great personal clarity on the answers to these questions and that you lead in a way that builds great clarity throughout your team.

My first attempt at strategic planning took place in the dead of winter, just weeks after I signed the deal and took full ownership of the family business. 

I knew we needed to move the business from being a “job” to being a “company” and only vaguely understood what that meant. What I did know is that I wanted the leadership to be clear and united on what we were trying to accomplish and how we were going to get there. 

My team headed off to Williamsburg, Virginia, and booked a condo for several days. I was fueled with fresh vision from having just read The E-Myth by Michael Gerber and armed with videos from a business master along with my flip chart and markers. 

We spent two and a half days thinking, debating, and dreaming (interspersed with some good food and a round of mini golf) and returned to work with increased clarity about our individual roles and our shared vision. 

What became readily apparent is that dreaming, debating, and creating a plan were merely the first steps toward achieving our goals. 

Finding ways of communicating that throughout the company in such a way that everyone was fully aligned proved a perpetual challenge—and that only became more difficult as the employee count grew from the original 12 to 45! (More on that in a later column.)

Following are three observations that, from my experience, contribute to effective strategic planning meetings: 


Strategic planning engages most people at a level at which they are not normally accustomed to thinking. As such, getting out of the familiar zone, where they are regularly reminded of their daily tasks and subject to distractions, is extremely important. 

New spaces are conducive to innovative thinking, as the stimuli of a new space can trigger insights that may be fresh and original or that may have been lying dormant for a long time. 

When the budget allows (and maybe even if it is a major stretch!) it can be inspiring to select a place where the customer service is par excellence and the scenery or furnishings are beautiful or particularly enjoyable.

It is critical that you have this time together free from interruptions. If you must report back to work, do so only at scheduled times. Make necessary preparations to ensure that this time can be dedicated to “working on the company” so that when you return to your work in the company you will be effective.


Obviously, you scheduled this time away to work. This is not about the routine, daily tasks required to get your job done, but rather about the strategic part of your role. 

In order to be most effective in this strategic planning, deliberate “downtime” is also extremely important. 

First of all, you need the downtime to allow mental rest from what can be intellectually fatiguing work. Secondly, such indirectly purposeful activities as playing together can do wonders for nurturing team connection and health and as a result, grow the effectiveness of the team when they are at work. 

Healthy relational components like communication, trust, and respect are often built as much through the non-work times spent together as they are when you are professionally engaged.

Be sure to intersperse your actual planning work with some activity the team enjoys together or a new activity where the entire team has rookie status. This allows for some truly memorable moments that can slip into the shared history of a leadership team and that will resurface in conversation for years to come. 

And as always, there ought to be some good food … because who doesn’t enjoy a great meal!


For years, I led the strategic planning sessions as the president of the company. It seemed to be an appropriate way to exercise and develop my leadership role. 

What I discovered eventually was that while I was actively engaged the whole time, I was never able to disengage until the entire event was over. Bringing in a coach or facilitator to lead the planning session allowed me to participate fully in the planning process far more as a peer to the other team members. 

This freed me to focus more fully on the actual issues we were discussing, rather than constantly thinking about what the next steps would be. 

A facilitator also brought some much-needed objectivity to the process and was able to expose the “elephant in the room,” whether they were people, processes, or relational challenges that we found difficult to address. 

While the investment was significant, the returns justified the cost.

Earlier I mentioned Richard Gerber’s book The E-Myth as setting the stage for my strategic planning journey. I still recommend that book (or the more recent version, The E-Myth Revisited).  But there is another work that has become an operational guide in more recent years. 

Traction, by Gino Wickman, not only provides a series of questions to guide the strategic planning process but also gathers the work of other outstanding business authors into a holistic business operating system known as EOS or entrepreneurial operating system. 

This system addresses another significant challenge in business: that of integrating all aspects of the business in a way that aligns all people and processes inside the business to achieve greater effectiveness and results—literally, “traction.”

Here’s my offer to you: if you are a business owner or on the leadership team of a business, I’m offering to send you a free copy of Traction—or at least until my stash of books runs out! 

If you’ll simply scan the QR code below and fill out the form with the requisite information, I’ll get a copy mailed out to you to help gain traction in your business. 

Alternatively, drop me an email at Include your name, address, and your business name and role, and I’ll get it to you that way. 

Don’t miss out on the benefits of good strategic planning to help you achieve your business goals!

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