How to Run a Successful Strategy Day for Your Leadership Team

Are your strategy and business plan still relevant and fit for the future?

When was the last time you stepped back to look at it with a fresh perspective and reflect on your current reality or changing external environment?

Is your leadership team bogged down in the day-to-day pressures of running a business?

In today’s volatile, uncertain, complex and ambiguous (VUCA) world, strategy can’t be static. It must evolve, flex, and respond to change. And unless you press pause, you risk:

• Losing sight of your purpose and goals

• Losing sight of your customers or clients

• Making decisions based on habit

• Missing new opportunities or threats

• Staying stuck in outdated ways of thinking

A strategy workshop (or leadership away day) is a dedicated time and space for leadership teams to focus on long-term planning and strategic direction, free from daily operational pressures. It's a chance to step back from the day-to-day and consider the big picture, ensuring alignment and a shared vision for the future.

Tips, questions and facilitation ideas to design and run a successful Strategy Day

Why You Need to Make Space for a Strategy Workshop

• Strategic Alignment - Ensure everyone agrees on the organisation's goals, priorities, and how to achieve them.

• Improved Communication - Create a safe environment for open dialogue and healthy debate about the future and challenge the status quo.

• Enhanced Creativity - Step outside daily operations to generate fresh ideas, identify new opportunities, and innovative solutions.

• Reduced Risk - Spot obstacles, blind spots and external changes (economic, social, technological) and develop plans to respond.

• Increased Efficiency - When everyone understands the strategic direction, decisions are quicker and more aligned, saving time, effort and resources.

• Better Decision-Making - Clarify what matters most and make decisions that drive the business forward.

• Motivation and Engagement - Re-energise your leadership team around shared direction, purpose and priorities.

Tips for Facilitating a Productive Strategy Day

• Be clear on outcomes - What do you want to get out of the workshop? Be specific: Do we want decisions? Prioritisation? Alignment? A plan? Clarity on ownership?

• Keep it focused - Don’t be tempted to cram too much in with a long agenda. Choose three or four themes or strategic questions and leave time for in-depth conversations and creative thinking.

• Change the space - A strategy day should feel different from a regular meeting, so moving away from the office helps to remove distractions and creates a fresh perspective. Look for a venue that feels fresh, creative and different (not just another boardroom) to inspire fresh, innovative thinking.

• Ditch the table - Boardroom tables can reinforce traditional hierarchy and power structures. To create more openness, equality and more dynamic conversation, sit in a circle or a horseshoe.

• Warm up - Begin with something reflective or fun. Ask people to share what they’d like to get out of the day, what they’re proud of, or what they’re finding challenging. If you want something different, there are dozens of resources online on ice-breakers, but choose something that feels right for your people and your culture.

• Create space for private thinking, as well as group discussion - Use the 1–2–3 model: Start with solo reflection, move into pairs or trios, then share insights and discuss with the full group. This ensures deeper thinking and broader participation. This supports introverted people who like to think before speaking and may get dominated by the extroverts.

• Keep the energy up - Vary activities and use movement, change locations, or shift between sitting and standing.

• End with action: Conclude with specific next steps, ownership, and a timeline. Don’t leave without decisions.

• Facilitating it yourself? Stay neutral where possible, ask more than you tell, and be clear about roles: who’s leading the discussion, capturing notes, and managing time.

• Bring in an external Facilitator - they bring clarity, neutrality, fresh challenge and the skill to manage energy, group dynamics and tough conversations.

How do you structure the day?

The structure of the day should be based around your goals, culture and priorities. Here are some tools you can use:

• Strategic frameworks (SWOT, PESTLE, Ansoff Matrix)

• Business Model Canvas and capability mapping

• Decision-making tools (prioritisation grids like the Eisenhower Matrix, stakeholder maps)

• Creative exercises to unlock fresh thinking

• Time for individual reflection and thinking as well as group work.

Key themes to include:

• Where are we now, what’s working and what’s not?

• Where do we want to go from here and why?

• What’s changing in the wider world?

• What behaviours or structures are holding us back?

• How do we stay aligned through growth, change, or challenge?

• What capabilities will we need for the future?

• SMART goals, KPIs or OKRs - What action will we take, when and who owns what?

10 Questions to Ask Before Planning a Strategy Day

Here are 10 quick questions to ask before planning a Strategy Workshop:

1. Do we need to step away from the day-to-day and look at the big picture?

2. Has our strategy, purpose or vision drifted or lost clarity?

3. Do we need to review our priorities or build shared accountability around them?

4. Are we aligned as a leadership team on where we're going and how to get there?

5. Are we facing a period of change, growth, or external uncertainty?

6. Are we stuck in old ways of thinking or doing things simply because 'that’s how we’ve always done it'?

7. Have we welcomed new leaders, directors or team members who need to get on the same page?

8. Are there behaviours, habits or silos that are getting in the way of collaboration or performance?

9. Do we have key decisions or trade-offs to make that require input and commitment from everyone?

10. Would an external Facilitator help to create an open forum for us to think differently and move forward faster?

If you're answering yes to several of these, it may be time to make time to focus on your strategy.

Would you like help to plan and facilitate your next Strategy Workshop or Leadership Away Day?

Polly Robinson, Growth Space

At Growth Space, our approach is to create engaging, energising and purposeful Offsites and Away Days. We bring

• Strategic tools, frameworks, structures and practical tools.

• Challenge and fresh perspective to encourage new ways of thinking

• The right balance of purpose and results with energy and fun

• Warmth and the ability to build rapport and create psychological safety, so everyone has a voice.

If you want help with your next strategy session, let’s talk.

• Call: 07966 475195

• Email: polly@pollyrobinson.co.uk

• Book at time to meet via Zoom or Teams via Calendly >

• Explore Strategy Facilitation at Growth Space >