Guest Post: 9 Preparation Tips to Enhance Your Strategic Planning for 2021

Editor’s Note: With planning for 2021 right around the corner, we jumped at the chance to publish some inside tips from experienced planning coach Herb Cogliano. Also be sure to check out Herb’s past webinars for Align on Evaluating Strengths, Weaknesses, and Emerging Opportunities and How to Pick a SMART Quarterly Priority.

by Herb Cogliano, Aspire Growth Advisors

If you’re a CEO planning a strategy session or 2021 kick off with your Executive Team, it’s important to be well prepared. This article will discuss the best ways to prepare and lead the strategic planning process, particularly if you’re going it alone. Here are several useful tips gained from my experience facilitating sessions with different clients over the years.

1.   Set Dates

It’s advisable to set the dates for the quarterly and annual planning retreats (some people call them “advances”) well in advance. And it’s best if a specific rhythm is established (i.e., the second Friday and Saturday before the end of the quarter). The annual planning session is normally two to three days and the quarterly sessions one to two days.

2.   Scan Scaling Up

Have the executive team scan the book, Scaling Up (Rockefeller Habits 2.0), especially the three chapters in the Strategy section and The Priority chapter in the Execution section. The book is available on or you can click here to download a free copy of the Barriers to Scaling Up chapter. Have the executive team take 5 to 10 minutes to complete the 4D assessment to see which of the Four Decisions — People, Strategy, Execution, or Cash — needs the most attention in the upcoming planning session. Take the Scaling Up Quick Assessment here!

3.    Read (or Re-read) Jim Collins’ Classic Articles

Read (and re-read) Jim Collins’ Harvard Business Review article titled “Building a Company Vision.” (Download for $6 at Do this in the first few annual planning sessions until you’re comfortable with your Core Values, Purpose, Profit/X, and BHAG — key elements of the first two columns of the One-Page Strategic Plan (OPSP). Also go to where Collins has several free interactive tutorials to help discover Core Values, discern a Purpose, choose a BHAG, etc.

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4.   Strategic Thinking “Council”

Form the council as discussed in Scaling Up and start meeting weekly to get some critical talk time around the strategic decisions driven by the Strengths, Weaknesses, Trends (SWT) and 7 Strata worksheets. Also discuss the 4Ps of marketing: Product, Price, Place, and Promotion. In most firms, marketing strategy = strategy. Search the internet for Ogilvy’s 4Es of marketing and add those to the ongoing discussions/ debates. Even if it’s just for a few weeks prior to the planning session, these weekly discussions will get the strategy juices flowing.

5.    Employee Survey

A few weeks prior to the planning offsite, conduct an employee survey. Employees’ insights are helpful in determining quarterly or annual priorities since they are closer to the customers and are immersed in the daily processes of the business. Many firms use an online survey tool such as SurveyMonkey to make it easier to administer. We suggest three simple questions:

  1.  What should (enter company name) start doing?
  2. What should (enter company name) stop doing?
  3. What should (enter company name) keep doing?

6.   Customer Input

Along with employee feedback, formally gather customer input. At a minimum, ask them the same three “start, stop, and keep” questions. As discussed in The Data chapter in Scaling Up, it’s easier to pick up patterns and trends if there is a weekly rhythm of gathering input from customers and employees, but this simple three-question survey will get you started if you are new to the process.

7.    Top Three Issues

Send out an email to those attending the planning session to ask them to send back the top three issues they feel MUST be addressed/explored/answered at the upcoming planning session for them to feel it was a success.” Compile these for review at the beginning of the planning session or just prior.

8.  Strengths, Weaknesses, Opportunities, and Threats (SWOT):

If you want to dig deeper than what the “top three issues” question uncovers, lead a separate SWOT exercise with the broader management team prior to the planning session. Or simply send out an email to your team seeking their input on the SWOT and compile the results for the planning session. Helpful resources in identifying important trends are Frost & Sullivan’s annual trends report and Peter Diamandis’s Abundance 360 annual event and quarterly updates.

9.   Find a Facilitator

Find someone outside the company to facilitate your planning sessions. Ask a colleague from another firm or bring in a professional facilitator like one of us Certified Scaling Up Coaches. This allows everyone on the team, including the CEO, to actively participate rather than worry about facilitation. And trained facilitators will know how to discern Core Values, define a powerful Purpose, discover a key strategy, and help the team uncover the underlying constraints in establishing priorities and setting key performance indicators (KPIs).

If you are interested in learning more about effective planning for 2021 book a call with Herb! 

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