6 Expert Tips On Strategic Planning

With something as layered and detailed as strategic planning, it’s always smart to get outside advice. Even the most experienced strategy teams could use fresh ideas from others. So we gathered some of the top tips on strategic planning from business leaders in a variety of industries:

1. Start with a core team.

“Begin by building a team to own the process and ensure there is representation from all key areas of the organization. Incorporating different perspectives makes it easier to implement and disseminate the strategic plan once it is created. The team must be heard, invested in the process, and agree to goals upfront or the plan will not get adopted.”

‍Paige Arnof-Fenn
‍Founder & CEO, Mavens & Moguls

The City of Bartlett, Tennessee, followed this advice when it rebuilt its strategic plan. The mayor, the aldermen (three of whom were newly elected), and department directors all brought fresh voices to speak for the community. University survey results further vetted their claims. The city also held several work sessions with the aldermen, both to share survey results and to get feedback on the direction. Bartlett built the entire plan in only 13 months.

2. Do it faster.

“Too often strategic planning meetings are long and drawn-out, but that doesn't need to be the case. It is possible to speed up strategy sessions. First, look at the process in advance to determine if there are steps and elements you can cut out entirely.

“Next, at the beginning of your planning, lay out the ground rules that include time limits for conversations, exercises, and activities, and then designate a time-keeper whose job is to call time for these tasks.

“Finally, if people get long-winded, go off-topic, or just get bogged down in their conversations during strategic planning, ask the question: ‘What are we trying to achieve?’ to refocus the conversation. When that question has been answered, ask: ‘Is there anything else?’”

‍Mike Brown
‍Founder, The Brainzooming Group

3. Make plans realistic, measurable, and data-based.

“The three key differences between successful and good strategic plans are:

1. Having a realistic connection between the intrinsic motivations of employees, organization’s goals, and client outcomes.
2. Creating accountable, measurable activity at individual, team, division, and group levels.
3. Continually challenging processes. Decisions should be based on robust, unbiased, intelligent information, not emotion.”

Gordon Jenkins
Founder & Managing Director, The Visible Guy

Good data changes the conversation. In the City of Germantown, Tennessee, city leaders shifted from debating data accuracy and formatting to asking meaningful questions: “How much did it cost?”, “How long did it take?”, and “Did it have the impact we wanted?” Every quarter, the City Administrator reviews key metrics with each department director using concise reports with status icons. Germantown went on to win the 2019 Malcolm Baldrige National Quality Award.

4. Use scenario planning.

“Don't strategize with a single possible future in mind. Decision-makers are rewarded for their vision, but they need to consider the myriad forces in play over which they don't have control. Smart strategists develop multiple possible visions of the future based on combinations of uncontrollable forces. Plan for both short- and long-term. Strategic planning should start with the long term (5-10 years), then fit shorter strategies into it.”

‍Dr. Nardia Haigh
‍Professor & Consultant, University of Massachusetts Boston

The short-term layer matters more than it used to. Many organizations now plan on a rolling 12- to 24-month horizon with quarterly or trigger-based reviews, and our own recommendation is an 18-month planning cycle. Our 2026 Strategic Planning Report found that organizations relying on traditional multi-year planning cycles have initiative completion rates of just 12% to 22%. Keep the long-term view, but review it often.

5. Test your assumptions.

“Do small tests to validate your hypotheses. When implementing strategic changes to an organization, it's easy to get tunnel vision and fall in love with your own ideas. This can cost a company a lot of money if your ideas don't turn out to be successful. Instead, it's best to do mini-experiments to test your assumptions. If you achieve the desired results, then you can standardize the process across the company.”

‍Michael Coleman
‍VP of Sales and Marketing, Medical Marijuana, Inc.

Velosio, a value-added reseller of enterprise software, tested its own software choice this way. CEO Jim Bowman and two colleagues ran a trial, migrating their Excel-based scorecards into ClearPoint. Within three days, the scorecards were constructed and populated, and that trial clinched the decision. Bowman describes the company’s approach to any new system: “get it out there, test it, and evolve it in a continuous improvement process. We don't study the options to the ninth degree.”

6. Make it fun.

“If your team groans when they hear it's time to do strategic planning, shift that mindset by making it fun. This means shaping the process so people can actively engage in and succeed at it.

“You can do that by providing structured strategic thinking exercises that take people off the hook for starting the planning from scratch and allow them to engage in productive conversations based on their areas of expertise. One fun exercise we use is called Pin Prick. In this exercise, participants look at a pesky competitor and imagine every way their company could be a complete nuisance to them. Yes, some wild ideas come up, but people start to think in a new and often unconventional way. The result is often bold thinking that becomes executable strategy. It also makes employees feel like they contributed and affects the overall bottom line.”

‍Mike Brown
‍Founder, The Brainzooming Group

Strategic planning is a learned skill.

There’s a lot to learn about strategic planning. Doing it well isn’t easy, but you have help. At ClearPoint, our software supports organizations from the initial planning stages, through implementation and ongoing execution. Whether you’re a strategic planning pro or just getting started, our software is built to make your job a whole lot easier.