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Top 7 Tips for Conducting a Successful Strategic Planning Session


Team at Planning Session

ari Strategic planning sessions seem to evoke emotions of excitement and dread about equally. The energy around making big plans and thinking about a prosperous future goes hand in hand with worries about agreeing on how to accomplish goals and the process to get to that agreement. 

Given most companies have planning sessions coming up with the year’s end in sight, we chose successful strategic planning as the topic for our November coach webinar and brought in a prolific strategic planner, Executive coach Jennifer Faught, to help us out. 

From her scores of strategic planning sessions as an entrepreneur and as a coach with Petra Coach, Jennifer has seen common practices of companies whose strategic planning is focused and effective as well as practices of companies who fail to run efficient strategic planning. 

For Jennifer, the process boils down to four key steps:

  • Reflect on current performance and positioning
  • Understand targets and priorities the company could pursue
  • Choose targets and priorities the organization will pursue
  • And Mange the plan to maintain focus and allow for flexibility

Yet many of these steps and the transition between them requires overcoming the real challenge of strategic planning: building alignment amongst executives and the whole organization. 

To help simplify this challenging and critical endeavor, Jennifer presented 7 tips for effectively identifying the things your team will do in the planning period and aligning the team around accomplishing them. 

1. Choose an Off-Site Location

Jennifer recommends getting out of the regular office and into an energizing space for planning sessions. This can increase creative thinking and reduces distractions. “When you’re away from the office, you aren’t going back to your desk and getting pulled into something,” Jennifer says. 

2. Set Ground Rules and Hold Everyone Accountable

Keeping your whole team focused during planning requires establishing and enforcing some ground rules around communication and process. Jennifer recommends phones and computers not be allowed in the planning room, save for one to take notes or enter information into Align. Additionally, “The conversations had in the room must be confidential,” says Jenifer. “You can broadcast the plan and the outcomes, but don’t disclose the discussion that got you there.” 

3. Keep The Energy Up

Jennifer recommends taking care to maintain energy and focus in the room during potentially long days of planning. Taking regular breaks for a stretch or breath of fresh air can keep people alert along with avoiding sugary snacks and drinking water. Keeping energy up also means making sure the right people are in the room. “It should be a privilege to be in the team that is working on the business to make it better,” says Jennifer. “Any negativity or including people who don’t want to be there, will drag down the energy of everyone else and impact the output.” 

4. Build Trust in the Room

Jennifer recommends starting off sessions with ice breaker exercises to get people emotionally engaged in the day and to create an environment of trust. Vulnerability creates trust, and high trust teams perform better. “Establishing this trust will ensure your conversations and strategic planning discussions go better,” says Jennifer. For more information about building trust and creating a safe environment for honesty and vulnerability, Jennifer recommends checking out David Horsager’s The Trust Edge or Dr. Brene Brown’s Netflix Special

5. Use an Agenda Focused on Outcomes

Jennifer suggests companies set goals around the things they want to achieve during the session. For instance, this typically is to determine priorities and enter them into a tracking software. “When you move into each section of the day, remind the team what the outcome is for that section,” says Jennifer. “For instance, for moving into the SWOT (strengths, weaknesses, opportunities, threats) analysis,  is to identify the one thing we could do in the next 90 days to move the business. It means focusing on planning not solving.” Not getting into the weeds and staying focused on outcomes is key to keeping planning on focus and moving forward. 

6. Make Sure Leadership is Aligned

The most common downfall of strategic planning sessions, according to Jennifer, is when the executive team comes into the session without a unified vision for how to move the business forward. Aligning the company team becomes impossible when the executive team is splintered. Hosting a pre-planning session with a draft of company priorities creates a united executive team even before planning. While the output of preplanning can still be a draft, it serves to focus the executive team around what needs to be planned during the larger group session. Jennifer recommends Partick Lencioni’s The Five Dysfunctions of a Team for tips on how to build alignment in the executive team.  

7. Push for Outcomes

Jennifer’s final tip for leaders is to push for specific outcomes during planning sessions. Avoiding weakly worded strategic priorities lacking alignment and ownership helps ensure the team owns execution. Jennifer recommends consistently tracking, and assigning ownership of tracking, using a software tool like Align. “If more than one person owns a priority, then nobody owns it,” says Jennifer. 

For the rest of Jennifer’s webinar and plenty more insights into running an impactful strategic planning session, watch the entirety of the webinar below. 


If you would like to learn more about how technology can improve your strategic planning and execution, join an Align Advisor for a demo of Align today!

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