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Strategic Discipline Blog

Annual Planning & Strategy Meeting

Posted by Douglas A Wick on Mon, Jan 7, 2019

Annual Plan - Your Roadmap for a Successful YearIf you’ve already completed your Annual Planning & Strategy Meeting for 2019, congratulations!

In December I spent 6 days with two of my customers facilitating and leading their Annual Planning and Strategy meetings. 

If you’re not taking a minimum of two days with your leadership team offsite, chances are you shortchanging the process.

The planning portion alone requires one day of minimum investment.  You should:

  • Review last year
  • Brag about victories & accomplishments
  • Discover why and where you failed
  • What contributed to success
  • Determine what and how you can do better next year

Strategy & Planning Tools

ScaleUp companies focus on Four Decisions: People, Strategy, Execution, and Cash.

Your business should determine how you are doing in each decision annually (at minimum!). 

Good tools/metrics to discover this are:

People: Performance Matrix*, eNPS*, Gallup’s Q12*

Strategy: Year over year revenue growth, Client Acquisition Costs

Execution: Profit YOY, Rockefeller Habits Checklist*, Labor Efficiency Ratio*

Cash:   Cash Conversion Cycle*, AR days, AP days, Cash on hand YOY, Bottom line pricing grid*

*represents a tool/exercise Positioning Systems uses to help discover this measure and elevate your growth.

The importance and magnitude of these discoveries require 2-3 days for Annual Strategy & Planning.

Customer’s Focus#1

The two customers I worked in mid-December are at different stages of their progression in the ScaleUp process.  One just started in September, the other’s been a customer for 7 years.   Each had different needs and lengths of time set aside.

The new customer focused on strategy.  They’re business has been growing over 30% this year, with high customer acquisition costs eating profit margins.  We worked on identifying their Inside Advantage, specifically their Core Customer to focus intentionally on who their most profitable customer is.  We also worked on defining their Winning Aspiration/Core Purpose.  Playing to Win - What is Winning-1

Both took a considerable amount of time and energy to discover.  We finished up a bit early, due to the team’s exhaustion from the intense work, delaying our first quarter planning.  We completed this in a 4 hour session the last Saturday in December. (In September we’d created 2019 Annual Plan)

Customer Focus#2  

Since two new team members had been added to the team the past year, we conducted a 5 Dysfunctions of a Team Assessment,  determining the team needed to strengthen their accountability.  We invested 2 hours here.  

Avoidance of Accountability -5 Dysfunctions of a TeamEach team member was asked to share a response to the question:  What is each person’s single most important behavioral characteristics or quality that contributes to the strength of our team? (That is, their strength.)   

Starting with the leader, until all five team members heard from the other team members and responded. 

Then each team member was asked to share: What is each person’s single most important behavioral quality that detracts from their strength of a team? (That is, their weakness or problematic behavior.)

Once again starting with the leader, he listened to all members feedback and responded.

This can be a very uncomfortable exercise. The leader sets the tone. Without the Leader/CEO’s willing engagement and vulnerability their can be argument, even emotional outbursts. 

The next step discovers how committed each team member is.  They are asked, What one or two behaviors will you work on after this exercise?

By revealing their intentions each team member makes a commitment to improve, identifying specifically what they will do to limit and improve their behavior quality that detracts from the teams strength.  The full team is encouraged to help remind each other of their commitments as we progress through 2019.

Outthinker logo-1Another intense exercise for this team was the Outthinker Process.  We invested over 12 hours on this alone.

The team generated over 100 ideas to consider as innovative thrusts. 

Outthinker Process 4th Option - Win Move Crazy Idea Waste Chart-1When we narrowed these down by ease and impact, we identify 4-5 Winning Moves, and several “Crazy Ideas” to pursue.  The COO plans to develop a precise set of questions and rules for his company using the “What would have to be true” Outthinker Process Template to help set objectives to achieve these ideas by the end of the first quarter.  


Once a year is not enough time to invest in the Four Decisions to grow your business. Your quarterly and monthly meetings can be a source of learning, planning, solving for higher Strategic Objectives.  My 7 year customer achieved more the my just starting customer.  However not in terms of what is critical for their growth

Strategy Deeper & Deeper layersIf you’ve ever visited a precious metals mining operation, you find time and extensive hard work, through layers and layers of earth, the search for precious metals are excavated to be used in commerce. Often near the end of the effort, many layers deep, the most valuable results are found.  The Strategic Thinking process is like this: With hard work, sequential collaboration, through time, the strategic decisions have synergistic effects. The result is momentum changing and climatic.

In Create Your Strategic Learning Cycle we shared the nature and importance of continuous strategic renewal in today’s dynamic markets.

Is your leadership team equipped to meet these challenges?

Growth demands Strategic Discipline.

Acheive Execution Excellence BP Guarantee posterPositioning Systems is obsessively driven to improve your business and your team’s execution.  3 Strategic DisciplinesPriorityMetrics and Meeting Rhythms help your business dramatically improve your forecasting, individual and team performance to create alignment. Empower your team to achieve accelerated growth.

As an Execution Decision, Strategic Discipline increases your Profitability.

Positioning Systems helps your business achieve these outcomes on the Four most Important Decisions your business faces:












We help your business Achieve Execution Excellence.

Positioning Systems helps mid-sized ($5M - $250M) business Scale-UP. We align your business to focus on Your One Thing!  To achieve growth, you need to evolve in today’s rapidly changing economic environment.  Have you been avoiding a conversation on how you can successfully grow your business? Contact to Scale Up your business! Take our Four Decisions Needs Assessment to discover how your business measures against other Scaled Up companies. We’ll contact you.

FOCUS Measure What MattersNEXT BLOG – Measure What Matters (FOCUS)

“It is our choices . . . that show what we truly are, far more than our abilities.” ~ J. K. Rowling

John Doerr opens Chapter 4 of Measure What Matters with this quote.  Focus is the title of chapter 4.  It’s the first Decision you face when establishing OKR’s.  What to focus on?  It’s also the first decision in Strategic Discipline’s Execution Disciplines. We’ll learn more from Google on why your choices are critical in your business and personal life, next blog.

Topics: Annual Plan, Strategic Learning, Strategic Planning, Strategic Learning Cycle, Strategy vs. Planning

Challenges of Scaling Up a Business 







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1. Priorities: Determine your #1 Priority. Achieve measurable progress in 90 days.

2. Metrics: Develop measurable Key Performance Indicators. 

3. Meetings: Establish effective meeting rhythms. (Cadence of Accountability)  Compounding the value of your priority and metrics. 

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Certified Gazelles Coach

Doug Wick, President

Positioning Systems


The Strategic Discipline Blog focuses on midsize business owners with a ravenous appetite to improve his or her leadership skills and business results.

Our 3 disciplines include:

- Priorities
- Metrics
- Meeting Rhythms

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