Committed to a Planning System, but Feeling Boxed In?

August 22, 2024

I know that, like most entrepreneurs, I have a tendency to change things on a dime. I have no fear of change, and quite honestly feel that sometimes blowing things up creates the best outcome. I have used several business planning systems to manage company planning and goals, and we are currently using EOS (Entrepreneurs Operating System). I appreciate the value that the system provides to my team, but sometimes the rigidity of it makes me crazy.

And so, sometimes I break with the system. I recently cancelled a quarterly planning session and completely rewrote the following quarterly agenda. I wondered, had I gone too far?

I asked several planning experts what they think about how much flexibility was necessary or too much, without giving them the specifics of what I had done. Here is what they had to say.

“Do you have any thoughts or stories about business planning systems being too rigid, and when leaders need to go off script? And is there a limit to how far off they should go?”

Entrepreneur’s – the Original Crazy-Makers
I love the descriptions I got back of entrepreneurs and their behaviors. Some of my favorite phrases included “wandering minds,” “shiny objects” and “raging visionary.” If you are an entrepreneur, you know exactly what they are describing. (These experts are also visionaries, so these comments come from a place of pure love.)

The overarching theme of the responses was that entrepreneurs are ALWAYS off script.

Your Company and Team Need Reliable Structure
So, here's the deal - a planning system exists to help harness that crazy entrepreneurial vision and provide framework for the team.

“EOS is meant to compartmentalize these (entrepreneurial) thoughts into appropriate times and meetings for discussions,” says Don Maranca of JDSM Enterprises. “Visionaries love and hate EOS at times. They may feel it’s too rigid and it doesn’t allow them to express their creativity. They also feel that it’s the best thing they’ve done because it allows them to express their creativity at appropriate times, creating discipline with their team to execute on what matters most at the right time.”

I knew the book “Traction” by Gino Wickman was going to be a game changer as soon as I started reading. It walks entrepreneurs through the process of developing a one-page vision and strategic plan that is similar to many other systems I have used, but then it takes it further. It operationalizes everything - down to scorecards, management and running effective weekly meetings. It prescribes the exact agendas for the weekly leadership meetings.

I acknowledged my visionary tendencies and implemented the system, but sometimes it does still feel restrictive. When is it okay to deviate from those standard agendas and tools?

Structure Isn’t Always What’s Needed
There are times when you may be forced to adjust. If you have been in business long enough, you have certainly had your plans derailed by forces outside your control – key employees’ turnover, economic collapse, pandemics. During those times, you can’t just run the normal meeting agenda.

George Black, author of “The Next Level Entrepreneur” and founder of LiveTrulyFree.com, cautions against too rigid a system. “A big mistake that companies can make, whether they are starting out or they are an ongoing company, is to think that they have to follow their rigid plan, budget, or system,” says Black. “When these companies are hit with challenges in the marketplace, economic headwinds, business opportunities, etc.; they have little ability to react well and quickly.”

If you haven’t hit a pothole yet, it’s just a matter of time, and as Black points out, it’s not just tragedy that could send a company off of the original plan. There are also positive changes that can happen in the marketplace and opportunities a company might need to be receptive to.

“I have never seen a truly unique and great company that sticks to the script! I have seen many mediocre companies follow the structure to the T,”  says Max Kozlovsky, owner of Quest Advising and host of the Practical Leadership Podcast.

I didn’t tell the experts what my special circumstances were when I asked them these questions, but it was due to a business acquisition opportunity. After reading their responses, I definitely felt better about my temporary process deviations. We had a unique opportunity in front of us that fit our vision, and we needed to take it.

Know the Rules Before You Break Them
Maybe the goal isn’t to shackle the entrepreneurs to a rigid set of rules, but to provide a framework and to adjust as needed when special circumstances arise.

“I think you have to know the rules of a system in order to know what you’re breaking and why. I think that the script is for the team, and the team needs the script,” says Mary Reilly-Magee, an Implementor with EOS WorldWide. “There’s actually a lot of freedom within the (EOS) tools once you know what they are and how to use them. Then it’s creative city after that.”

Reilly-Magee was our original EOS Implementor, and she trained us on the proper use of the tools and systems. After our recent business acquisition, we added a weekly meeting using those same tools to manage the goals and issues specific to the merger of the two businesses. Acquiring another company was a huge and completely new focus for our leadership team, but the structure was effortless to spin up because the team already knew how to use the systems. We were able to focus all our energy on the actual tasks at hand.

Kozlovsky shared a great comparison between business leadership and comedy styles as they relate to structure and experience: “Most top improv comedians started their careers doing stand-up with very well thought out and structured routines that had little wiggle room to adapt to the audience and the conditions. As they developed their skills, they were able to use a general set of improv rules to build flexibility and adaptability to their routines.”

“Same is true for management teams. The newer they are to planning and structured sessions, the more closely they need to stick to the script.  But as they develop skills and are guided by skilled coaches and facilitators, the more room there is to invest time in areas that will ultimately prove to be more valuable to them, the team and their business.”

I think that moving forward, I will change my verbiage from “breaking script” to “improvising.” It just feels like a more informed, intentional move within a framework than a reckless and haphazard jump off a building without a parachute.

Let Your Vision Be Your Guiding Force
For some entrepreneurial situations, it may be less about jumping off a building without a parachute, and more about allowing yourself to be blown off course. Most planning systems start with a clear vision and core values for a reason. Those foundational activities should provide purpose and direction to all of your decision-making as a company.

Black puts even more emphasis on knowing your true north than he does on the system, “If you begin with direction and develop strategies to get there, pivots are easy and tactics like budgets, business plans, goals, and systems all make sense. There is no going “off script.” You can change strategies in a moment while staying on track, because you know your direction. Plus, you’ll never chase “shiny objects” that could kill your business.”

I found Black’s book to be incredibly beneficial in terms of understand how to fully define a vision and to understand what a “next level” goal looks like. We regularly pull his Next Level-thinking into our EOS agenda as a sanity check for the goals we are setting.

The verdict – Some flexibility is necessary 
Clearly entrepreneurs have a natural tendency to explore and change things up. While a well-defined vision and a reliable system can provide guidance, it’s obvious that flexibility is still key. But how can we monitor ourselves as entrepreneurs and provide our companies with the correct amount of structure?

“If changing the agenda becomes the norm, then there’s something else going on that’s keeping the team from accomplishing what’s on the agenda that has been proven to work...”, explains Maranca. “It (your system) shouldn’t be so rigid that it puts the fire out from passionate leaders. Nor should it be so undisciplined that results are never achieved.”

Please share your journey in the comments.
Do you struggle with a planning system? Embrace it wholeheartedly? Somewhere in between?

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Thank You, My Fellow Crazy-Makers

A heartfelt thank you to all of these amazing experts, not just on their contributions for this blog, but also for the inspiration and guidance they have provided me throughout my entrepreneurial journey.

Mary Reilly-Magee, EOS Implementor

George Black, Podcaster: Get Business Savvy YouTube channel, Author of the Next Level Entrepreneur, Founder of LiveTrulyFree

Max Kozlovsky, Owner of Quest Advising and Host of the Practical Leadership Podcast

Don Maranca, JDSM Enterprises, TAB Facilitator / EOS Implementor