Business Trends

Seven Realizations About Planning

Why Everyone Needs a Plan for Success and Sustainability

Today I was coaching a spry young and driven project manager of a very successful dealer group and long-time coaching client. We discussed three project plans seeking to improve the processes and remove obstacles to success. This great conversation led me to a lot of reflection on the act of planning itself. I always tell people that coaching without a plan is just therapy. When it comes to achieving results and helping others make them, I’m no spring chicken! I truly began planning while working with high ranking military officials in the combat zone mission briefings in the Army. Then I enjoyed planning in a senior-level leadership role in a dealer group. Now, as an executive coach, it’s my job to help sales managers and sales pros clarify what they want to accomplish most, understand why it’s important, help them create an action plan to achieve their objective, then care for the plan long term. 

As such, I follow up and check-in along the way, sometimes things go great; other times nothing happens at all. This is when masterful coaching comes in. I don’t judge or criticize, I ask them if accomplishing that objective is still essential or if they want to let it go. It’s almost always still vital for them! Then I ask questions to find out what got in the way of their action plan fulfillment. We address the challenge, adjust our plan, and move forward. After having thousands of these conversations, I have come to some simple yet powerful realizations about plans. I share them with you in this article hopes that your plans become as airtight as possible. Regardless I want you to be ready for when they fail because they will, and that’s OK because you’ll fix it!

Realization #1

There is no perfect plan because there is no perfect person!

There are diminishing returns in over planning; thus, trying to create the perfect plan is a waste of time. I recommend deciding in advance how much time to allow yourself for planning. That will help you stay focused and give you a deadline for getting started. Also, this will help you present yourself and others a little grace and dignity when the plan doesn’t work out perfectly. Because after all, the last perfect person walked the earth 2000 years ago, and you saw what happened to him.

Realization #2

Any plan becomes 100% more effective when there is a contingency plan.

My special operations team never ran a mission without a primary plan, secondary plan, and tertiary plan. Since failure is always a possibility, you don’t want to be scrambling to create a new plan at the same time. This leads to undue stress, sloppy execution, and poor results when, most of the time, all you needed was a backup plan in the beginning.

Realization #3

No plan gets accomplished with no desire, no discipline, and no dedication. 

Having a plan without someone wanting to achieve the results from the plan will ensure the plan fails. It’s like giving a four-year-old a plate of steamed okra in hopes of having them eat everything on their plate. They’ll sit there and poke at it with a fork, dump it behind the couch (my kid did that), or maybe try to feed it to the dog. You have to sell the okra, in this case, the plan to the parties involved, get the buy-in! Then watch them eat the okra, in this case, check-in on the plan, and continuously remind them of what accomplishing this plan will mean for them. “You’re going to grow tall and strong from eating this delicious slimy green okra!”

Realization #4

A plan can only maximize results if the plan is maximized with continuous improvement.

Once your plan is underway and you are conducting follow up, checking in, and supporting efforts, this is the opportunity to improve. Things to look for improvement: How can we do this better? How can we do the action items more efficiently? Who else could contribute to these efforts? Are too many resources dedicated to this action item? Is there another step in the plan that doing first would make this step easier? To truly maximize the results of your plan, revisit it throughout, ask those questions and make the adjustments necessary.

Realization #5

Increase a plan’s complexity two-fold and decrease its odds of completion tenfold.

Complexity in planning would be the bane of my existence if I weren’t self-aware enough to know it’s my issue. Because I love planning and enjoy coordinating many moving parts, it’s easy for me to create unnecessary complexity. A plan needs to be simple to execute and big for impact. “How can a plan be simple yet big?”, you ask. A lot of people focus on one objective, and each person has one or two simple action items or behaviors they are responsible for executing. It’s significant because there are a lot of people involved and it’s simply because each person knows exactly what one or two things they do. Start giving people three or more things to do in their plan and watch the whole thing fall apart. When planning, it’s always better to K.I.S.S. (keep it stupid simple). Check for understanding by asking those involved to repeat their strategy back to you. If you can’t explain it to a third-grader, it’s probably too complicated.

Realization #6

A plan’s action items are only as good as the person’s understanding of why, what, when and how to do them.

A leader’s biggest frustration is often when their people don’t take action, which leads me to ask some tough coaching questions. I ask things like, “When did you expect them to have that done by?” “Did you give them that expectation?” and “What training and testing did you give them to ensure they could do that?” and “How did you teach them that process?” and “Why is doing it that way so important? Did you explain that to them?” Often the answers to these questions give the leader the clarity that the person they were planning with didn’t have clarity! No plan is complete unless you can answer this question for each part of the project: “Who does what by when and why is it so important?” Another element that makes for a high level of clarity is by writing the plan details down and ensuring everyone involved reads and signs off on their action items.

Realization #7

To avoid an obstacle, you have to know it exists and a silent disagreement is a hidden obstacle.

Honest communication is essential to effective planning. If you can’t have an honest dialogue with someone, why the heck are you planning with them in the first place? If someone is “yessing” you to death but not executing on the plan, or if you are picking up on body language that they disagree with the plan, deal with it right now. It’s best to get the disagreement in the open so you can adjust your plan, or help the disagreer get over it. Otherwise, plan on having the same discussion soon while adding frustration in the mix, and higher stakes leading to potential blow-ups.

I hope this article on planning makes your work life more successful, enjoyable, and productive! It would be my honor to help you plan your next benchmark to success, so feel free to reach out to my receptionist and schedule a strategy with me at 1-888-921-0221 or email


After leaving US Army Special Operations and serving over two years in combat zone deployments, Sean Kelley #TheCarBizCoach applied those leadership principles to automotive management and successfully led multiple dealerships for over a decade. Sean’s passion for people development led him to become Chief Business Development Officer of DriveCentric CRM, a software company, where he helped them double their annual revenue. As CEO of Car Motivators, Sean works with dozens of dealer groups, automotive tech companies and hundreds of coaching clients across the country. As a writer, Sean’s work and success stories working with his clients have been published in multiple automotive publications. Sean was “Consultant of the Year” in 2018 by Dealership News and ranked #10 in’s top 100 sales coaches. Sean’s engaging presentations have been featured at conferences like Digital Dealer, Automotive Game Changers, Rockstar Automotive, Canadian Game Changers, SLADA, TIADA, and Driving Sales. Sean’s vision is to positively impact the leadership landscape and culture of the 

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