Skip to main content

“Breaking down silos is essential in modern organizations. The cross-functional nature of these strategy sessions ensures that breakthroughs are not just vertical but horizontal, tapping into diverse perspectives that lead to innovative solutions and increased collaboration.”

Colleen CiakFractional Chief Marketing Officer

As summer is upon us and many of us are heading out on vacation, we will return to a critical time of the year. For those operating on a calendar fiscal year, the questions become pressing: “What are our 2025 goals, and do we have the budget and resources to accomplish them?” This time is vital as companies adopt diverse approaches to navigate this phase. While there is no one-size-fits-all strategy, the effectiveness of in-person strategy meetings, especially those involving a broad cross-section of a company’s team, is unparalleled.

The Value of Inclusive Strategy Sessions

The power of gathering various departmental members—not just department heads—for a comprehensive strategy session cannot be understated. In today’s distracted world, these inclusive meetings foster greater engagement and innovation. A memorable example from my career involved a company that brought in a successful, retired CEO to facilitate our strategy session. This wasn’t just a top-down information session but a dynamic workshop with active contributions from about 25 team members across various levels of the organization.

During the session, we set clear financial targets like revenue goals, profit objectives, and Net Promoter Scores (NPS). More importantly, we focused on strategic initiatives outside of these standard metrics, crucial for growth. We brainstormed and narrowed down a multitude of ideas to four or five special projects that could propel our business forward. This proactive approach ensured everyone had a say, providing leaders with a comprehensive view of what was required and how it could impact other teams.

Communication and Connection

Breaking down silos is essential in modern organizations. The cross-functional nature of these strategy sessions ensures that breakthroughs are not just vertical but horizontal, tapping into diverse perspectives that lead to innovative solutions and increased collaboration. This is especially true when the strategy involves everyone in goal setting and execution plans, making sure the organizational goals are transparent and understood across all levels.

A study by Gallup shows that only about half of employees strongly agree that they know what is expected of them at work, which can lead to disengagement and inefficiency. Transparent communication during these strategy sessions can significantly clarify expectations and enhance engagement.

Monthly Follow-ups and Real-Time Adjustments

After planning, we didn’t let the projects run on autopilot. Instead, there was a structured follow-up process where each team reported back monthly to the executive leadership about their progress. This routine ensured that the projects received the necessary guidance and allowed for the reevaluation of their viability. Projects that were no longer feasible or effective were promptly replaced, maintaining adaptability and momentum without losing an entire year.

Leadership and Organizational Focus 

Effective strategy reviews demand ongoing commitment from the highest levels of leadership, particularly the CEO or President. As Peter Drucker said, “Only three things happen naturally in organizations: friction, confusion, and underperformance. Everything else requires leadership.”

If senior leaders do not actively model the importance of these cross-departmental initiatives, there’s a high risk that these projects will not achieve their potential impact. Leaders must actively participate in these sessions, endorsing and resolving organizational roadblocks, providing critical decisions, and holding teams accountable to ensure these initiatives remain a focal point across the organization.

Encouraging Cultural Change in Leadership

Introducing substantial changes to leadership practices, especially those that involve a shift toward more inclusive and collaborative strategic sessions, can indeed represent a significant cultural transformation within an organization. For leaders accustomed to a more traditional, top-down approach, the idea of involving various organizational layers in strategic planning might seem daunting or unnecessary. However, the benefits of such a change—enhanced creativity, increased buy-in, and improved execution—far outweigh the initial discomforts of altering established habits.

Dos and Don’ts for Strategy Planning

If you aren’t ready to embrace a whole new process for strategic planning, here are my top dos and don’ts:

Dos of Strategic Planning:

  1. Clearly define objectives and goals.
  2. Involve diverse team members from various departments.
  3. Foster an open and collaborative environment.
  4. Use data and analytics to inform decisions.
  5. Set realistic and measurable targets.
  6. Encourage creative and out-of-the-box thinking.
  7. Regularly review and adjust strategies as needed.
  8. Prioritize actions that align with long-term visions.
  9. Communicate clearly and consistently across all levels.
  10. Provide training and resources needed for effective implementation.
  11. Recognize and celebrate milestones and successes.
  12. Address potential risks and devise mitigation strategies.
  13. Ensure alignment with overall organizational mission and values.
  14. Use feedback loops to refine strategies continually.
  15. Maintain flexibility to adapt to unexpected changes or challenges.

Don’ts of Strategic Planning:

  1. Don’t exclude key stakeholders from the planning process.
  2. Avoid setting vague or unachievable goals.
  3. Don’t ignore the input from lower-level team members.
  4. Avoid relying on outdated data or assumptions.
  5. Don’t forget to consider the competitive landscape.
  6. Avoid creating plans that are too rigid or inflexible.
  7. Don’t overlook the need for resource allocation.
  8. Avoid poor communication of strategy and objectives.
  9. Don’t skip the evaluation of past performance.
  10. Avoid a one-size-fits-all approach, tailor strategies to specific needs.
  11. Don’t neglect potential ethical implications.
  12. Avoid underestimating timelines for goal accomplishment.
  13. Don’t ignore industry trends and external factors.
  14. Avoid lack of accountability mechanisms.
  15. Don’t let biases influence strategic decisions.

At Kate Ryan & Company, we specialize in facilitating effective strategy sessions that harness the collective insights and expertise of your entire team. By promoting an inclusive and collaborative environment, we help ensure that every member of your organization understands and is aligned with your strategic goals. This approach not only promotes a more engaged workforce but also drives meaningful, actionable results.

If your organization is looking to enhance its strategic planning sessions or needs support in aligning team efforts towards common goals, contact us today. Let us help you transform your strategic planning meetings into a powerful tool for innovation and sustained growth, ensuring that your team is not only ready to meet the challenges of today but also to capitalize on the opportunities of tomorrow.