Five Ways to Tank Your Strategic Planning Retreat

Fourth quarter rituals for many organizations include holding a strategic planning retreat. For some it’s a holiday treat, for others it’s as welcomed as a hard block of fruitcake. Retreats have a bad reputation because it’s so easy to stumble over the details. Anyone who knows what good meetings look like, also knows that they don’t happen by circumstance. Avoiding the following five pitfalls might keep you in the clear when planning your next retreat.

1. Ignoring the Elephant in the Room

Strategy is worthless if your house isn’t in order. The best-prepped strategic retreats will not go anywhere without people. And if any key staff member is upset or has an outstanding problem, your strategic planning meeting will likely be disrupted. Give your employee the opportunity to voice issues or concerns privately. Make sure you clarify your intent is to clear up any problems that may inhibit his or her full participation during strategy session.

2. Refusing to Use a Facilitator

If you were having a party for 100 of your closest friends, would you improve your efficiency by hiring a caterer, or would you cook for all of them? Why take on the extra stress? A strategic planning meeting is no different. Hire a facilitator and you can be fully engaged in the strategy and planning, and leave meeting process and structure to someone else. The return on your investment will be worth the time and money.

3. Inviting Everyone

The old cliché of “too many cooks spoil the broth” couldn’t be closer to the truth. While it is imperative that key employees have a voice in planning, not everyone has to literally be at the table. Groups between 10 to 15 people are the ideal size for strategic planning meetings. The key thing to remember is be inclusive, but don’t invite everyone to everything.

4. Forgetting to Explain the Process

A good facilitator will make sure to explain the strategic planning process and outcome of the meeting from the get-go. Use shared strategic planning language, understand the elements of a strategic plan, and be clear on the desired outcome for the meeting. By making sure that everyone starts on the same page, you eliminate any confusion that might derail your meeting.

5. Ending on a Low Note

The best way to get people jazzed about the plan is to have them visualize success. Do that by asking your team to draw a picture of what the company will look like if you achieve your strategic plan. Have them really explain it. How many employees? What is the office like? Who are your customers? What is the media saying? Etc. That way everyone leaves the planning session seeing a connection between the work of the day to a future state of success.


How will you make your next strategic retreat a success?


One Comment

  1. JOHN KAGUMU says:

    Found the article, informative and educative but too brief.



What is 13 + 12 ?
Please leave these two fields as-is:
All fields are required.

Free Guides & Resources

Setting OKRs that Work

A FREE downloadable guide and canvas to build Objectives and Key Results.

SWOT Assessment Guide

A FREE downloadable guide and canvas to complete a SWOT analysis, synthesize it into Competitive Advantages, and then use your SWOT to create SMART goals.

Guide to Create KPIs with 100 Example Metrics

A FREE downloadable guide to learn the basics of Key Performance Indicators with 100 example metric sources for ever department of your organization.

Free Guide for Writing Better SMART Goals

Download the FREE guide to learn how to create goals that have impact in your organization.

Free Guide to Build a Growth Strategy

A FREE downloadable guide and canvas to create a growth strategy that clearly defines where you play and how you’ll win.

Goals/OKR Cycle Guide

A FREE downloadable guide and canvas to establish a quarterly rhythm for OKRs and Goals.

OKR Essentials Cheat Sheet

Download the free cheat sheet to guide you through building and refreshing OKRs.

Join 50,000 Other Leaders Engaged in Transforming Their Organizations

Subscrbe to get the latest agile strategy best practices, free guides, case studies, and videos in your inbox every other week.

We Believe in Empowering Teams to do Amazing
Work, Consistently and Passionately

Success isn’t a list of flashy logos. It’s about helping anyone who wants to lead a great organization.
If that’s you, join our list of clients – you’re in good company:

Armen EZR Multnomah RHA SEO Monitor
Chobani Cisco Armen KIA Patagonia
Concordia College Davenport Fairbanks St. John's Washoe County School District
Boys and Girls Club BSA Cancer Society Maryland Food Bank Make A Wish
CMPD Long Beach San Francisco City of Sparks Washoe County