In this post:
- Why you need regular strategy sessions
- Why eight weeks is the magic number.
- How to run a great strategy session.
- Free template for a 2-day session.
Strategy is the most important job of any leader. It's why we have leaders. You're the ones who can see the big picture and connect to the work people do everyday.
But while strategies are great, and 3-5 year plans are important, they can be too abstract to take priority over the urgent and unexpected things that pop up on the daily.
Keeping those big dreams alive and making them real doesn't come easy, but it is the most important function of your job and the time you spend together as a leadership group.
Why you need regular strategy sessions
Strategies are great, and 3-5 year plans are important, but they can be too abstract to take priority over the urgent and unexpected things that pop up daily.
Strategic progress is the most important job of any leader. It's why we have leaders. You see the big picture and connect outcomes you want to the work people do every day. But most of your leadership team meetings probably get hijacked by operational rats and mice. You quickly mention an email before you get stuck into the real stuff, and half an hour is lost. Your phone rings, so you step out.
It's a wasted opportunity, so you need dedicated time for strategy. Keeping those big dreams alive and making them real will never come easy, but you have to try. Strategic progress is the most important function of your job and the time you spend together as a leadership group.
Why eight-week planning works
Unless you carve out a regular cadence of dedicated strategy-only time, it will not happen by accident. I've found eight weeks to be the magic numbers. It's why Not An MBA was eight weeks long - students stay motivated and invested, without getting bored or skipping sessions.
8 week planning works because:
- It's long enough to do something important, but short enough to stay motivated about
- Change that isn't implemented within 8 weeks is exponentially more likely to fail
- It's outside of regular planning cycles (quarterly, annually) and thus picks up more initiatives that are in-train or mid-implementation.
How to run good strategy sessions
But how do you use that time well?
Here are some ideas for exciting and engaging strategy days that will keep your big-picture moving forward.
Logistics
- Spend your time out of the office so that people bring fresh perspective to the conversation.
- Put it in people's calendars with enough time to plan for it. Let them know this is a critical part of their job as leaders - not an "extra" to add to their existing workload.
- Order good catering. It's easier to think well when we're fed and nourished. Food brings people together.
- Spend two days. It alleviates some of the pressure on Day 1 to get into "decision-making" mode and disrupts the time-boxing of a regular workday.
Agenda
Here's a sample agenda for your strategy away time.
Day 1
1. Remind people of your goals and big-picture plans.
Distribute hard copies of your most recent strategic document and keep them handy throughout the day. Make strategy the focus and the lens through which all conversations take place.
2. Celebrate success
Talk about what's gone well over the last eight weeks, sharing how you've made progress. You've achieved more than you realise, and you've forgotten half of it. Measuring the distance already travelled stops goals from feeling like hypothetical future states and repositions them as work-in-progress.
3. Scrutinise failure
Use problems and disruptions as valuable learning experiences. Debug something that went badly and take immediate action by changing a process, policy, or rule that will make it harder for the same failure to happen next time. The people who made the mistakes don't have the mandate you do to fix it, so don’t just theorise—make the decision while you’re there.
4. Rally around a shared project
Look at the work you’ve already got coming up and workshop how to do it in a way that aligns with your strategic priorities. Most strategy days end with committing to new things when plates are already full, rather than changing how to do the existing work.
If you already have a big strategic project happening—information management, service reviews, customer strategy, etc.—don’t try to add more. Bring the leadership team together to work out how that project can become a lever for strategic progress. Each business group can contribute their expertise, instead of leaving it all to the department that “owns” the work.
Day 2
The second day of your strategy session has only one job: planning for action. After all the good ideas from yesterday, it’s time to make good.
1. Tasks, time and money
Set achievable targets and deadlines for the next eight weeks, with clearly defined roles and responsibilities. Agree how you’ll communicate these intentions to your teams, and make trade-offs in the room about other projects or funding that may need to be de-prioritised.
2. Premortem
Look at what might go wrong, test your thinking for gaps and assumptions, and shrink the size of your plans where possible. The excitement from yesterday will inflate your optimism bias and make it difficult to stick to your intentions back at your desk.
3. Implementation
Spend your final session of the day doing. Put things in your calendar, draft memos to staff, reallocate budget, and make initial phone calls to get the ball rolling. Committing in the room gives you a head start and makes it harder to back out later.
4. Book in the next one
Use the momentum and excitement to get the next session in the calendar before everyone leaves. That way, you’ll be fired up to come together again—and you can’t wriggle out of it.
Here’s a sample agenda you can use to plan your next two-day strategy session.
Good luck!
