3 min read

You should run a 2-day strategy session every 8 weeks. Here's how.

You should run a 2-day strategy session every 8 weeks. Here's how.

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.

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 number. 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.


  • 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.


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 we've already travelled stops our 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 got already coming up and workshop how to do it in a way that aligns with your strategic priorities. Most strategic planning days wind up with us committing to new things when our plates are already full rather than changing how we do the stuff that's happening anyway.

If you already have a big piece of strategic work happening - information management, service level reviews, customer strategy, etc - don't try and do new things. Bring the whole leadership team together to work out how you can make that project a lever for strategic progress.

Each business group can feed in, bringing their expertise to the table, rather than leaving it up to the department who own the work to handle by themselves. 

Day 2

The second day of your strategy session has only one job: planning for action. After all the good ideas that came from yesterday's workshopping session, it's time to make good.

1. Tasks, time and money

Set achievable targets and deadlines that lead to tangible steps over 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 de-prioritising as a result.

2. Premortem

Look at what might go wrong, test your thinking for gaps and assumptions and, where possible, shrink the size of your plans. The excitement and inspiration from yesterday will inflate your optimism bias and make it difficult to stick to your intentions when you return to 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 much 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 wiggle out of it.

Here's a sample agenda you can use to plan your next two-day strategy session.

Good luck!

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