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5 Mistakes CEOs Make with Annual Strategic Planning
September 27, 2023

Every year, executive teams at leading companies around the world gather for their annual strategic planning offsite. These meetings are key for setting the course for the upcoming year and ensuring alignment among key stakeholders. However, all too often, these offsites end up being a costly and unproductive use of time. In this article, we'll explore the top five mistakes that contribute to the inefficiency of these crucial gatherings.

1. CEO as Facilitator, Not Team Member

One common mistake is having the CEO take on the role of the facilitator during the offsite. It's essential for the CEO to be actively engaged in the strategic planning process, however acting as the facilitator creates a couple of issues. On one hand it can create a divide between them and the rest of the team. The CEO should be a part of the discussion, contributing their insights and ideas, rather than solely managing the conversation. When the CEO assumes a facilitator role, it can stifle open dialogue and hinder the free flow of ideas, leading to missed opportunities for innovation and alignment.  Additionally, managing a productive session takes focus, the CEO should put their attention on the strategy, not managing the clock.

2. Lack of Preparation

Another significant issue that plagues annual strategic planning offsites is a lack of preparation. Without adequate preparation, team members often enter the offsite without a clear understanding of the current state of the company or the goals for the future. This lack of alignment can result in a disjointed and unproductive meeting, where important issues are left unaddressed or team members are blindsided by unexpected issues. To maximize the effectiveness of offsite meetings, it's crucial to ensure all participants have a chance to provide their input, are well-prepared, and informed.

3. Unrealistic Goals

Setting unrealistic goals for the year ahead is a surefire way to frustrate and demotivate your team. While it's essential to aim high and challenge your organization, setting unattainable objectives can lead to disappointment and burnout. It's crucial to strike a balance between ambition and achievability when setting annual goals. Engage in realistic discussions about risks and resource requirements during the offsite to ensure that your team leaves with confidence in their ability to execute the plan.

4. Lack of Alignment 

An offsite meeting should serve as a platform for achieving alignment among team members. Unfortunately, many organizations leave these gatherings without reaching a consensus on their strategic direction. This means that participants may leave the offsite with differing interpretations of the strategy or lacking a shared vision for the future. To prevent this mistake, Katahdin Group facilitated sessions close with what we call a “blood signing” where everyone agrees to the goals and metrics before leaving the session. 

5. Absence of Clear Governance Plan and Ongoing Strategy Meetings

Once the strategic plan is established during the offsite, it's vital to have a clear governance plan and ongoing strategy meetings in place to stay on target and execute the plan effectively. Without this framework, the strategic plan frequently becomes an artifact that collects dust on a shelf, rather than a dynamic roadmap guiding the organization's actions. Regular strategy meetings and a clear governance structure ensure that the plan remains a living document, subject to adjustments as needed to respond to changing circumstances.

Especially in today’s distributed world, the annual strategic planning offsite is a valuable opportunity for executive teams to align their vision and set the course for the year ahead. These common mistakes can undermine the effectiveness of these gatherings. By addressing these issues, your organization can transform what might have been a waste of time and money into a productive and strategically advantageous event.


Learn more about Katahdin Group’s strategic planning offering that has helped CEOs and their teams find clarity and drive growth for more than 20 years.

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