Planning a Leadership Workshop or Away-day?

It is time to bring your leadership team together.  But, how to ensure the effectiveness of the time together?

Every year we facilitate hundreds of impactful leadership workshop and away-days. Here's our perspective on how to ensure the success of your leadership ‘get-together'.

Convening your leadership team is especially crucial during the following events. These ‘special occasions' are becoming more frequent. How many of these apply to your organization?

Let's begin with the end in mind. That is, with your goals for workshop success. To guide you, here is a list of the top 5 goals set for leadership workshops and away days.

In planning for the success of your leadership workshop, it can be helpful to address anxieties, risks and concerns up front. In that way, you can plan to prevent them.

We don’t just turn up and facilitate a workshop or away day.

The process of ensuring success involves some or all of the following components (based on your needs).

Here are some reasons why we believe leadership workshops really matter:

Why use a facilitator for your leadership workshop or away day?

Here are some of the reasons to use a facilitator for your leadership workshop or away day:

1. Engagement and Participation

  • Active Participation of Leaders: Enables leaders to fully engage in discussions without the responsibility of steering the meeting or managing the agenda.
  • Inclusive Dialogue: Ensures that everyone's voice is heard, preventing dominance by a few.
  • Energy and Engagement Management: Maintains energy and engagement levels, especially in longer sessions, and keeps conversations constructive.

2. Effective Communication and Environment

  • Safe and Open Environment: Creates a platform where participants can express their thoughts freely, with a balance of respectful challenge when necessary.
  • Addressing Sensitive Topics: Facilitates discussions on delicate issues that might otherwise be avoided.
  • Conflict Resolution: Assists in identifying and resolving conflicts that may emerge during discussions.

3. Insight and Perspective

  • Awareness of Contradictions and Biases: Highlights contradictions, gaps, and inconsistencies in conversations and prevents groupthink.
  • External Perspective: Provides an outside viewpoint, offering comparisons with challenges faced by other leadership teams.
  • Stimulating Questions and Tools: Uses probing questions and analytical tools to foster thinking, creativity, and innovation.

4. Structure and Focus

  • Meeting Management: Keeps the meeting focused, manages the agenda and time, and allows flexibility for emerging topics.
  • Navigating Personalities and Politics: Manages interpersonal dynamics and political issues.
  • Customization to Group Needs: Tailors the approach to fit the unique dynamics and needs of the team.

5. Outcomes and Follow-Up

  • Clear Next Steps and Commitment: Helps in agreeing on next steps and assessing commitment levels to avoid setting unrealistic goals.
  • Post-Workshop Follow-Up: Ensures that agreed-upon actions are tracked and progress is monitored post-meeting.
  • Feedback and Evaluation: Gathers feedback on the meeting's effectiveness and suggests improvements for future sessions.


What are the principles?

Here are our key principles re leadership workshops facilitation:

Coaching Philosophy and Approach

  • We are coaches, not consultants. Our job is to help your team clarify the problem and find their own solutions, avoiding dependency on external experts or consultants.
  • Every voice must be heard. Those who usually remain quiet often offer divergent perspectives that can lead to breakthroughs.
  • Everyone is different. Some people prefer quick action, while others need to discuss problems or opportunities more. We honor these differences.

Creating a Conducive Environment

  • We create a safe environment by depersonalizing and depoliticizing issues, enabling people to express their thoughts freely.
  • Many leaders have a rosy view of reality because their teams often nod in agreement or remain silent instead of voicing true thoughts. Our role is to facilitate an open and honest assessment of performance and potential.

Belief in Potential and Growth

  • We believe in people's potential. Failing to unlock this potential carries unacceptable organizational, societal, and personal costs. Thriving is difficult when potential is unrealized.
  • The most significant changes are adaptive, not just technical. A change in mindset and behavior is often necessary. Simply acquiring new knowledge, tools, or skills may be insufficient. We operate in the ‘mind gym'.
  • While focusing on improvement, it's important to recognize progress and celebrate achievements. This boosts motivation and builds momentum.

Performance Evaluation and Strategy

  • We evaluate performance through a balanced scorecard, considering variables linked to sustainable performance and organizational health, including potential, pressure, vitality, and collaboration.
  • We believe strategy and execution go hand in hand. Our role is to increase visibility of the strategic project and initiative portfolio, often bridging the gap between strategy and execution.

Identifying and Addressing Challenges

  • Our mission is to ‘slice the watermelon' – identify projects and initiatives that appear positive (green) externally but are complex and challenging (red) internally.
  • Discussing setbacks and obstacles is crucial for effective planning, building commitment, and resilience, contrary to previous beliefs about it being demotivational.
  • We frame opportunities and challenges to illuminate blind spots and enable new solutions discovery. Our goal is to foster thinking and rethinking.

Systems Thinking and Tools

  • We employ systems thinking to help executives embrace the full complexity of their organizations, strategies, and teams, looking beyond just people and events.
  • In all interactions, we bring non-judgmental awareness, empathy, and understanding.
  • We provide cutting-edge tools and analytics to accelerate the transition from insight to action.
What might the flow of the workshop look like?

The workshop will be tailored to your specific needs, reflecting the opportunities and challenges facing your organization, team or strategy.

However, most leadership teams begin by engaging with your team and its members at their current stage. Typically, this involves two key elements:

  1. Where is the team now? Each team member shares their perspective on performance, potential, pressure, vitality, and collaboration as they currently exist. This discussion often yields surprising insights into the team's actual state.
  2. Where is the strategy now? The team collectively reflects on its strategy or strategic priorities, evaluating their level of confidence and ambition at this time. This provides revealing insights into the current state of the strategy.

These factors then shape the conversation and set the agenda. For instance, is the team satisfied with its current state and strategy? Where does the team aspire to be in 3, 6, or 12 months (depending on the chosen timeframe)?

Based on the current state of your team and strategy, the focus will shift to specific opportunities or challenges, such as:

  • Shared Vision of Success: Do team members have a shared and compelling vision of success? This involves individuals sharing their visions of success in their own words, rather than simply reciting the mission statement.
  • Clarity and Alignment: What is the level of clarity and alignment regarding key priorities, desired results, and purpose?
  • Effectiveness of Team Dynamics: How effective are the ways of working and interacting within the team? This encompasses both the effectiveness in completing tasks, while also bringing out the best in each other.
  • Key Success Factors (KSFs) and Risks: What are the KSFs and risks (including those normally hidden) associated with executing key strategic priorities and initiatives?


What does the facilitation involve?

Facilitating a leadership workshop, includes some or all of the following (based on your needs):

What do others say?

Here are some quotes from our clients about our approach to facilitation:

1. “We've been operating under a lot of pressure, but by the time the workshop was over, I could already feel that the level of pressure had reduced.”

2. “We had been putting off certain conversations for a long time, but I feel we started them today.”

3. “I didn't think we were aligned, but now I'm feeling a lot more confident that we are all pulling in the same direction and focused on the key business priorities.”

4. “Today, we worked really well as a team. We looked beyond our own functional areas of responsibility to the key priorities for the leadership team as a whole.”

5. “I am feeling re-energized – this comes from getting clear on our priorities and our purpose.”

6. “I no longer feel that I am going it alone; instead, I feel that I have the backing of the team when it comes to my key strategic initiative.”

7. “We are not meeting together often enough as a leadership team.  But, today shows what we can achieve in just a few hours when we do.”

What are Strategic Conversations and why do they matter?

Strategic Conversations are those critical discussions that often don't occur amidst the busyness of day-to-day activities. The capacity to engage in such conversations is vital for strategy development, as well as for managing performance and risk.

Additionally, the ability to have these conversations is a key indicator of the health of an organization or team. It requires balancing tension and cohesion within the team, enabling individuals to express their true thoughts, and challenging groupthink.

The Pitstop approach is steeped in the principles of Strategic Conversations, Appreciative Inquiry, and large format conversations for change (e.g. World Cafe, Future Search and Open Space).

What is the role of data / analytics?

Do you want to get to the heart of the issue quickly? This can be achieved using our analytics. It captures essential information for your leadership team, highlighting areas of agreement and disagreement.

The analysis takes just 15 minutes online and gathers perspectives from leaders, stakeholders, and teams ahead of the workshop. This information will then inform the workshop's objectives and ensure that the conversations are grounded in reality.

The data is used to guide (or more precisely, expand) the conversation during your leadership workshop. This is especially crucial for preventing groupthink and highlighting potential blind spots or biases, particularly in regards to complex issues and sensitive topics.

Why the idea of a pitstop?

The ‘pitstop' is a technique tailored for sustained performance in dynamic, high-pressure environments. Its appeal to leaders lies in the need to deliver ambitious strategies with increased speed, agility, collaboration, and innovation.

However, an interest in racing or pitstops is not a prerequisite to benefit from this approach. The associated tools and frameworks are crafted to reframe business opportunities and challenges, depersonalizing and depoliticizing them. This helps in addressing blind spots and fostering more creative solutions.

What about an annual conference and large numbers of attendees?

The annual conference can help to accelerate and sustain both organizational performance and health, especially given the newer approaches like pitstop.  Find out more here.

Pitstop-inspired Conferences & Events are based on a lot of published research.  You can explore this through our books.

“…an actionable agenda that managers can use for accelerating growth. “

Prof. Frank Cespedes,


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