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• Staying stuck in outdated ways of thinking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 >

Planning an Offsite or Away Day? Start With These 10 Questions

If you’re planning a leadership off-site, strategy workshop or team away day, pause before you start booking venues or building slides.

Off-sites, Workshops, and Team Away Days can build trust, clarity, and momentum, or leave your team asking, “What was the point of that?”

Before sending the calendar invitation, ask these ten questions to help you design an off-site that delivers meaningful results and avoid the “nice lunch, no outcomes” trap.

10 Questions to Answer before holding an Off-site, Workshop or Away Day

1. What are we trying to achieve?

Every offsite should have a clear why. Without it, the day risks feeling vague or performative. Being clear on the purpose shapes everything: format, facilitation, outcomes, and energy. Without this clarity, the day risks feeling vague or performative. Ask:

• What’s the problem or challenge we’re trying to solve?

• Is it to solve a problem (misalignment, disconnection, lack of clarity) Is it to respond to a shift (new CEO, strategy change, growth) or is it to unlock new ideas and momentum?

• Why now?

Try this: Write your purpose in a single sentence — and use it to brief your team, venue or facilitator.

2. What outcomes do we want?

Get specific. Whether your off-site, away day or workshop is about setting strategic priorities, exploring culture and values, building trust, communication or collaboration. Outcomes don’t need to be rigid but they should be meaningful, specific, and linked to business needs. Ask:

• What decisions do we want made?

• What conversations need to happen?

• How will we know if the day has been successful?

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3. Who should be in the room and why?

The impact of your session depends on who’s involved. Off-sites are more impactful when the right people are present and when you’re clear on what each person brings. Consider:

• Are we including decision-makers and people with insight and lived experience?

• Are we bringing the right mix of perspectives, roles and personalities?

• Do we need external stakeholders, new hires or future leaders in the room?

• Is there anyone whose absence will limit our ability to move forward?

4. What do we want people to think, feel and do afterwards?

A successful offsite should shift something mindset, motivation, behaviour, or direction. Avoid vague goals like “alignment” or “team bonding.” Ask:

• What impact do we want this to have?

• What new behaviours do we want to see?

• What conversations are overdue?

• What actions should people commit to?

5. What’s likely to get in the way and how will we handle it?

Tension, cynicism, unspoken issues, unresolved conflict, cynicism or fatigue. Every offsite has potential blockers. Ignoring them doesn’t make them disappear, but designing with them in mind makes the day more honest, useful and inclusive. This is where a skilled external facilitator can help to surface the tough stuff and move forward constructively.

Ask:

• What’s not being said?

• What might stop people being honest?

• How can we create a safe, inclusive space?

6. Is everyone clear on why they’re invited and what’s expected?

Offsites work when people show up ready to participate, not just spectate. When people feel prepared, they engage more fully and bring better energy to the room. So, make sure people know:

• Why have they been invited

  What the day is (and isn’t) about

  What are they expected to prepare or bring to it?

  What kind of mindset is expected

7. How will we balance, structure and flexibility?

Too much structure can kill creativity at an off-site or away day, while too little can lead to chaos. A well-designed day includes:

• Time to reflect on the big picture

• Space to connect as people

• Opportunities to make real decisions

• Flexibility to adapt in the moment

A structure around presentations and breakout can feel stale and rigid, so build in movement, variety, and breathing space, so include plenty of opportunity for individual reflection, small-group work, open conversations, and collaborative planning.

8. What will make this feel different to a regular meeting?

Your offsite should feel like a different kind of conversation, not just another agenda-heavy session. The best workshops spark insight because they feel different. Ask:

• How can we use a different space or setting? That’s the value in getting away from the office, to somewhere new, away from distractions.

• Can we include storytelling, vulnerability or creativity?

  How will we make it human, not corporate?

9. How will we make sure this leads to action, not just good intentions?

Too many offsites end with a flurry of ideas and no real follow-through. Creating accountability makes sure you see real shifts. Before the day ends, build in:

• Time for decisions, priorities and next steps

• Clear next steps and timeframes

• Clear ownership (who will do what by when)

• A plan to revisit and track progress in a month, a quarter and a year.

10. Should we bring in an external Facilitator?

If you want honesty, momentum, and real progress, consider working with a facilitator. A good facilitator holds the space, creates safety, encourages participation, and ensures real outcomes, not just good vibes. Especially if:

• There’s low trust

• You need to shift dynamics or challenge the status quo

• You want leaders to participate fully, not run the room

• You want actionable outcomes

A brilliant offsite doesn’t just happen. It’s designed with intention, curiosity, and care. Start with these questions, and you’ll already be ahead of most teams that simply hope for the best.

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Are you planning an Away Day, Off-site or Workshop and looking for support?

Whether you’re planning a leadership strategy day, team away-day, or culture workshop, I’ll help you design and facilitate a session that delivers real outcomes,

We’ll bring people together with purpose, create space for the right conversations, and leave with clarity, connection and action.

If you’ve got ideas, plans or challenges that would benefit from getting people in a room together, I’d love to hear about them.

• Give me a call on 07966 475195

• Book a time straight into my diary: Calendly >

• Email me: polly@pollyrobinson.co.uk

• Learn more about Growth Space Workshops & Facilitation >

Not sure if you need a facilitator?
Read my blog: Do I Need a Facilitator for My Away Day?