The Self-Facilitated Annual Planning Session: There are lots of great reasons to DIY — make the most of it.

In the world of entrepreneurship and business leadership, annual planning sessions stand as pivotal moments. They’re the compass that guides our organizations through the uncharted waters of the coming year. Traditionally, many have turned to external facilitators to steer these critical gatherings. However, there’s a growing trend of leaders choosing to self-facilitate their annual planning sessions. In this economy, it’s hardly surprising to see.

I’ve been privileged to sit across countless leaders who scribbled their grand visions on simple paper napkins, turning humble sketches into thriving enterprises. The question often arises: Should we self-facilitate our annual planning, or is it wiser to bring in an outsider? 

If the choice is no annual planning session or a self-facilitated one — the choice is clear.

Today, let’s delve into the heart of this matter, exploring the pros and cons of self-facilitating your annual planning sessions.

The Power of Self-Facilitation

There’s something inherently empowering about taking the reins of your organization’s future without external intervention. Self-facilitation can foster a sense of ownership and authenticity that is difficult to replicate. Let’s delve deeper into the compelling advantages, enriched with real-world examples.

1. Deep Intimacy with Your Organization

No one understands your business like you do. You live and breathe its daily rhythms, challenges, and triumphs. This intimate knowledge allows for a planning session that is deeply tailored to your organization’s unique context.

Example: Consider a tech startup developing a niche software solution. The founders, immersed in the intricacies of their product and market, decide to self-facilitate their annual planning. Their deep understanding of the technical challenges and customer feedback enables them to pinpoint specific areas for improvement and innovation that an outsider might overlook. They can delve into technical jargon and nuanced issues without needing to bring someone up to speed, making the session more efficient and focused.

2. Cost Efficiency

Hiring external facilitators can be a significant investment. For startups and small businesses operating on tight budgets, self-facilitation is a cost-effective alternative. The resources saved can be redirected towards implementing the strategies devised during the planning session.

Example: A small family-owned restaurant aims to expand its services but has limited funds. By self-facilitating their annual planning, they save on consultancy fees, which they instead invest in renovating their kitchen and training staff for the new services. This financial prudence allows them to grow without overextending their budget.

3. Enhanced Team Engagement

When the team takes collective responsibility for the planning process, it can boost engagement and morale. Everyone becomes a stakeholder, contributing ideas and taking ownership of the outcomes. This collaborative environment can strengthen team cohesion and commitment to the organization’s goals.

Example: A nonprofit organization brings together its diverse team for a self-facilitated planning session. By encouraging contributions from all levels, from volunteers to senior staff, they foster a sense of unity and shared purpose. A volunteer suggests a community outreach program that becomes a cornerstone of their strategy, highlighting how inclusive participation can lead to impactful initiatives.

4. Flexibility and Adaptability

Self-facilitated sessions allow for greater flexibility. You’re not bound by an external facilitator’s schedule or methodologies. If a particular discussion needs more time, you can adjust accordingly. This adaptability ensures that critical issues receive the attention they deserve.

Example: During a self-facilitated session, a marketing firm realizes that their digital strategy isn’t yielding expected results. They decide to allocate extra time to brainstorm solutions, something that might not have been possible with a rigid external agenda. This flexibility leads them to pivot their strategy effectively, incorporating new social media trends they had initially overlooked.

5. Cultivating Internal Leadership

Facilitating your own planning sessions can be a valuable development opportunity for emerging leaders within your organization. It allows team members to step up, demonstrate their capabilities, and grow their leadership skills.

Example: An employee at a manufacturing company expresses interest in leadership. During the self-facilitated annual planning, they are given the role of session moderator. This responsibility challenges them to manage discussions, keep the team on track, and handle conflicts. Successfully facilitating the session boosts their confidence and positions them for a future managerial role.

The Challenges of Going Solo

While self-facilitation has its merits, it’s essential to be aware of the potential pitfalls. Understanding these challenges can help you mitigate them effectively. Let’s explore these challenges in depth, accompanied by illustrative examples. The point is here is to shine a light on these challenges as issues to be mitigated. I’ve got some options of how to do so in the next section.

1. Risk of Bias and Blind Spots

Our deep involvement in our businesses can sometimes cloud our judgment. We may overlook critical issues or alternative perspectives simply because we’re too close to the situation. This lack of objectivity can hinder effective planning.

Example: A family-run retail business is facing declining sales but attributes it solely to market conditions. In their self-facilitated planning, they fail to acknowledge internal issues like outdated store layouts and poor customer service. An external facilitator might have highlighted these blind spots, but their closeness to the business prevents them from seeing the full picture, leading to strategies that don’t address the root causes of their challenges.

2. Limited Expertise in Facilitation

Facilitation is a skill that requires practice and expertise. Professional facilitators bring methodologies and tools honed over years of experience. Without this expertise, self-facilitated sessions may lack structure and fail to achieve desired outcomes.

Example: An engineering firm attempts to self-facilitate their planning session but struggles to keep discussions on track. Technical debates consume excessive time, and they fail to cover critical agenda items. Without effective facilitation techniques to manage time and guide conversations, the session ends without clear objectives or action plans, resulting in confusion and lack of direction.

3. Time Constraints

Planning and facilitating a comprehensive annual session is time-consuming. Balancing this with the day-to-day demands of running the organization can be challenging. There’s a risk that the preparation or execution of the session may be compromised due to time pressures.

Example: The CEO of a mid-sized company takes on the role of facilitator but is constantly interrupted by urgent operational issues. Their divided attention leads to a poorly organized session with insufficient materials and an unclear agenda. As a result, the team feels frustrated, and the planning outcomes are subpar, affecting the company’s performance in the following year.

4. Difficulty in Managing Group Dynamics

Facilitating discussions, especially on critical and sometimes contentious issues, requires skill in managing group dynamics. Ensuring that all voices are heard, navigating conflicts, and keeping the team focused are tasks that can be challenging without facilitation experience.

Example: In a self-facilitated session at a healthcare organization, dominant personalities monopolize the conversation, while quieter team members hesitate to share their insights. Important perspectives are lost, and underlying tensions remain unresolved. Without the skills to manage these dynamics, the session fails to unify the team or harness its collective intelligence.

5. Potential for Groupthink

Without an external perspective, teams may fall into groupthink, where dissenting opinions are suppressed, and critical analysis is lacking. This can lead to strategies that are not robust or innovative.

Example: A software company’s leadership team, all with similar backgrounds and experiences, self-facilitates their planning. They quickly agree on a strategy without challenging assumptions or exploring alternatives. Later, they discover that competitors are adopting innovative technologies they hadn’t considered. Their lack of critical debate and diverse perspectives during planning leaves them behind in the market.

Striking the Right Balance

Understanding the pros and cons equips you to make an informed decision. If you choose to self-facilitate, there are strategies you can employ to address the challenges.

1. Leverage Internal Expertise

Identify team members who have facilitation experience or natural aptitude. Provide them with the support and resources they need to lead the session effectively.

2. Adopt Structured Methodologies

Utilize established planning frameworks to guide your session. This can provide the structure that an external facilitator might offer, ensuring that discussions are productive and comprehensive.

3. Encourage Open Dialogue

Create a safe environment where all team members feel comfortable sharing their thoughts. Establish ground rules that promote respect, active listening, and constructive feedback.

4. Allocate Sufficient Time for Preparation

Recognize that facilitation requires preparation. Allocate time to plan the agenda, materials, and activities that will make your session successful.

5. Seek External Input Where Necessary

Consider bringing in external perspectives in specific areas. This could be through guest speakers, industry reports, or consulting with mentors. This can help mitigate blind spots and introduce fresh ideas.

Enhancing Your Self-Facilitated Sessions with Complimentary Resources

While self-facilitating, you don’t have to navigate the process entirely alone. There are resources designed to support leaders in crafting effective strategies and facilitating meaningful planning sessions.

Here are some examples of toolkits that can be helpful.

Firstly, the Strategy 360 Overview provided by coach.win. This tool offers a comprehensive framework to assess your organization’s current position, identify opportunities, and develop robust strategies. It guides you through a 360-degree analysis, ensuring that you consider all critical aspects of your business environment.

Additionally, the Annual Reset program available at coach.win can be instrumental. It provides a structured approach to reflect on the past year, learn from experiences, and reset your vision and goals for the future. These resources can complement your self-facilitated sessions by providing the structure and external insights that might otherwise be lacking.

Finally, the Paper Napkin Wisdom toolkits available via papernapkinwisdom.com. You’ve got access to 1000s of lessons learned from hundreds of top entrepreneurs. In the podcast you will find solutions to every imaginable business problem. In the Paper Napkin Wisdom book you have Key Questions to navigate creating action items to move past them. 

Conclusion

Self-facilitating your annual planning sessions is a viable option that offers several benefits, including deeper team engagement and cost savings. However, it’s crucial to be mindful of the potential challenges, such as bias and lack of facilitation expertise.

By proactively addressing these issues and leveraging available resources, you can enhance the effectiveness of your planning sessions. Remember, the goal is to create a strategic plan that propels your organization forward, and whether you choose to self-facilitate or bring in external support, the focus should always remain on achieving that objective.

5 Key Takeaways

1. Deep Organizational Understanding: Self-facilitated sessions benefit from your intimate knowledge of the business, leading to tailored and immediately actionable strategies.
2. Cost and Engagement Advantages: Saving on external facilitator fees and boosting team ownership are significant pros of self-facilitation.
3. Awareness of Challenges: Recognizing potential biases, time constraints, and facilitation skill gaps is essential to mitigate the cons effectively.
4. Utilizing Structured Frameworks: Adopting established methodologies and encouraging open dialogue can enhance the success of self-facilitated sessions.
5. Leveraging External Resources: Complimentary tools like the Strategy 360 Overview and Annual Reset can provide structure and external perspectives to your planning process.

Take Action

Ready to elevate your self-facilitated annual planning sessions? Here are some steps to get started:

• Explore the Strategy 360 Overview: Visit coach.win/strategy-360-overview to access a comprehensive framework that will guide your strategic analysis and planning.
• Implement the Annual Reset Program: Check out coach.win/annual-reset to systematically reflect on your past year and set impactful goals for the future.
• Prepare Thoroughly: Allocate time to plan your session agenda, materials, and desired outcomes using the insights from these resources.
• Foster an Inclusive Environment: Establish ground rules that promote open communication and ensure all team members are heard.
• Seek Support When Needed: Don’t hesitate to reach out for guidance or clarification on utilizing these tools effectively. Subscribe to the podcast of Paper Napkin Wisdom — there’s gold in those small ideas, they have the power to change your world.

By taking these steps, you’ll be well on your way to conducting a successful self-facilitated annual planning session that positions your organization for growth and success in the coming year.