Your business is growing, your team is expanding, an annual strategy day could help get everyone aligned and excited for the year ahead. But planning it? That’s another task on your already-full plate.
We’ve taken our experience from PPF’s successful ‘Annual Kickoff’ days to create a practical guide that makes planning your annual strategy day feel less overwhelming and more achievable.
Why This Matters
An Annual Strategy Day sets the tone for the entire year ahead.
It’s your opportunity to bring everyone together, celebrate successes, learn from challenges, and create a shared vision for the future. Done well, it energises your team, aligns everyone’s efforts, and builds the momentum needed to achieve your goals.
But it’s more than just a planning session. It’s a chance to strengthen your culture, show your team they are valued, and turn big ideas into actionable plans.
Think of it as an investment in both your business’s future and your team’s development.
Getting the Format Right
Timing Matters
The energy of your strategy day can make or break its success. We’ve found that morning starts work best when everyone is fresh and focused.
Plan for a full day — you need that space to think big and dive into important discussions.
Break up the day with regular 15-minute breathers every few hours and schedule your most challenging sessions for the morning when energy levels are highest.
Choose Your Space Wisely
Environment plays a huge role in creativity and engagement.
Whenever possible, get away from your usual workspace — a change of scene can shift perspectives and spark fresh thinking. Look for a venue with natural light, good ventilation, and enough room for both group activities and breakout sessions.
Oh, and don’t underestimate the power of good coffee and comfortable seating!
What to cover in your Strategy Day
1. Looking Back to Move Forward
Financial Review
Begin with the numbers that tell your story. This isn’t about drowning in spreadsheets — it’s about gaining insight. Look at revenue growth, client retention, and which services had the biggest impact. Understanding these trends helps shape better decisions for the year ahead.
Team Achievements
Celebrate your team’s proudest moments. Allow space for sharing wins, whether it’s completing a major project, resolving a tricky challenge, or improving internal processes. These stories reinforce the value of collaboration and give everyone a sense of collective accomplishment.
Don’t just focus on work achievements, allow time for people to share from their personal lives as well (if they want to), this helps show the team that you are interested in them as a person, and not just for the role they do.
Learning Opportunities
Every challenge presents lessons. Explore what your team learned from client feedback, project hurdles, and internal experiences. This isn’t about focusing on failures — it’s about turning lessons into future strengths.
Pro Tip: Let the team know ahead of the day what input you’d like from them so that they have time to think and reflect and not feel put on the spot.
2. Getting Clear on Where You’re Heading
Mission, Vision & Values Alignment
Spend a bit of time reviewing your company’s Mission, Vision & Values. This helps remind everyone what your ultimate goal is, and when making plans you can continue to ask yourselves the following:
- Does it fit with our purpose?
- Does it take us closer to our goals?
- Is it in line with 1 or more of our values?
Goal Setting
Share the Goals you’d like for the business for the coming year. You could break these down into sections and ask for feedback/ideas from the team on how they could be achieved, or if there any goals they feel would be beneficial to add.
- Client Experience: Discuss service improvements, communication channels, feedback mechanisms, and new service opportunities.
- Team Development: Identify skill gaps, training needs, career progression plans, and knowledge-sharing strategies.
- Operations: Brainstorm process efficiencies, technology requirements, resource allocation, and quality improvements.
- Growth: Explore marketing initiatives, partnership opportunities, new market segments, and innovation ideas.
Priority Setting
Share insights, vote on top priorities, set quarterly milestones, and assign project champions to drive each initiative forward if appropriate.
3. Making It Happen
Resource Planning
Ahead of the day, map current team capacity and identify skill gaps to determine hiring needs and budget allocations. Proper resource planning ensures your team has what it needs to succeed.
Action Planning
For each priority initiative, define clear quarterly goals, key milestones, necessary resources, success metrics, potential roadblocks, and risk mitigation strategies. This step turns strategic ideas into actionable steps.
Communication Framework
Establish a robust framework to maintain momentum:
- Weekly team updates
- Monthly progress reviews
- Quarterly checkpoint meetings
- Annual planning cycles
A consistent communication rhythm helps maintain focus and alignment throughout the year.
4. Building Your Dream Team
Team Structure Planning
Ahead of the day review current roles and responsibilities to identify overlaps and gaps. Map out a future organisational structure and plan for succession paths to ensure sustainable growth. Share with the team any hiring goals for the year, would you like to employ more people, what roles would be key for the goals in that year, when are you likely to start advertising the role.
If you don’t have any hiring plans, share with the team how you will handle increased workloads should that be a factor in your strategy for the year. You don’t want to demotivate the team by making them feel overwhelmed with lots of plans but no extra support.
Growth and Development
Focus on individual development plans, mentoring opportunities, training programmes, and career progression paths. A culture of continuous learning keeps your team motivated and prepared for future challenges.
Making It Stick: The Follow-Through Plan
- Week 1: Share detailed notes and action items within 48 hours. Set up project teams, schedule progress meetings, and distribute individual objectives.
- Month 1: Implement weekly quick-win updates, team leader check-ins, progress tracking, and resource allocation.
- Quarter 1: Conduct monthly progress reviews, resolve obstacles, celebrate successes, and adjust plans as needed.
Practical Tips That Make a Difference
Keeping Energy High
- Start with a meaningful icebreaker, like sharing a client win.
- Mix presentation styles with workshops, discussions, and talks.
- Use visual aids, such as charts, mind maps, and sticky notes.
- Incorporate movement with stand-up discussions and changing seats.
Making It Interactive
- Utilise digital tools for real-time polling.
- Form small discussion groups and rotate leaders.
- Encourage quieter team members to contribute.
Capturing Actions
- Assign a dedicated note-taker.
- Use action templates and take photos of workshop outputs.
- Record key decisions for easy reference.
Common Challenges (And How to Handle Them)
- Challenge: Dominant voices overpowering discussions. Solution: Use structured techniques like round-robin sharing or anonymous input cards.
- Challenge: Energy dips after lunch. Solution: Schedule energiser activities during the mid-afternoon slump.
- Challenge: Conversations drifting off-topic. Solution: Assign a timekeeper and use a parking lot for non-urgent items.
- Challenge: Lack of follow-through. Solution: Build accountability into your regular meeting cycle.
Need a Helping Hand?
Planning an annual strategy day doesn’t have to be overwhelming. If you want a hand with HR compliance or culture then let’s chat!
When your team thrives, your business does too.
