In my last article, I made the case that proper annual planning needs two days.
One day is rarely enough to review the year properly, strengthen the leadership team, reconnect with the long-term vision, decide what matters most for the next 12 months & turn it all into a focused 90-day plan.
But then I speak to businesses that spend three days on annual planning.
Three full days.
At that point, I have to ask: what are you actually doing?
Because unless your business is dealing with something genuinely exceptional, three days of annual planning sounds less like disciplined business planning & more like a junket.
There are usually long presentations. Large amounts of data. Endless discussion. Plenty of good food. Possibly a nice location.
Then everyone leaves with a very large strategic document that nobody ever looks at again.
That is not effective annual planning.
That is corporate theatre.
More Time Does Not Automatically Create Better Thinking
There is a belief that spending more time on planning means the business is being more strategic.
It does not.
More time can simply create more space for people to overthink, repeat themselves, disappear down rabbit holes & discuss things that have very little impact on the future of the business.
Good annual planning should create clarity.
It should help the leadership team answer some very straightforward but important questions:
By the end of the planning process, everyone should understand the direction of the business, the priorities for the year ahead & what they personally need to deliver.
You do not need a 70-page strategy document to achieve that.
You need honest conversations, strong decisions & a plan people can actually use.
The Real Problem May Be What Happens During the Rest of the Year
When a leadership team needs three days to work out what is happening in the business, the annual planning meeting may not be the real issue.
The issue may be that the important conversations have not been happening throughout the year.
Problems have been left unresolved.
Strategic issues have been pushed aside by operational noise.
Performance has not been reviewed regularly.
The leadership team has not made time to step back, think properly & address the bigger issues affecting the business.
Annual planning then becomes the place where the team attempts to deal with everything it has avoided for the previous 12 months.
No wonder it takes three days.
A strong leadership team should be reviewing its numbers, solving important issues, checking progress against its priorities & keeping the long-term vision alive throughout the year.
Annual planning should bring that thinking together.
It should not be the only time the leadership team thinks strategically.
Are You Planning, Or Are You Producing a Document?
Another reason annual planning expands to three days is that the team becomes focused on producing a comprehensive strategic plan.
Every possibility is examined.
Every department contributes pages of information.
Every initiative is documented.
Every risk is listed.
Every idea is captured.
It feels thorough.
It may even look impressive.
But the more complicated the plan becomes, the less likely anybody is to use it.
A plan is only valuable if it helps people make better decisions after the planning meeting is over.
If the plan is too large to remember, too complicated to explain or too detailed to use in weekly decision-making, it is not a useful plan.
It is a report.
Three Days May Mean You Are Avoiding the Hard Choices
Effective planning is not about capturing every good idea.
It is about deciding which ideas matter most.
That requires discipline.
It also requires saying no.
No, we cannot pursue all 15 opportunities.
No, everything cannot be a priority.
No, every department cannot have six major initiatives.
No, we cannot keep adding work without removing something else.
A two-day planning process creates useful pressure.
It forces the team to get to the crux of the issues.
It forces people to make decisions.
It forces the leadership team to turn a large number of possibilities into a small number of meaningful priorities.
A third day can sometimes remove that pressure.
Instead of making the hard call, the team keeps discussing.
Instead of choosing, it keeps adding.
Instead of simplifying, it creates more complexity.
Clarity creates confidence.
But clarity only comes when leaders are willing to make choices.
There Are Times When Three Days Together Makes Sense
There will be exceptions.
A family business may need additional time to work through ownership matters, succession, family relationships or the role of the next generation.
A company going through a merger, major restructure or significant change in ownership may need deeper discussion.
A leadership team that has recently changed may need time to build trust & establish how it will work together.
But that does not necessarily mean the annual planning process itself requires three days.
It may mean the business needs a separate ownership meeting, family council, leadership development day or strategic retreat.
This distinction matters.
In a family business, the needs of the family, the owners & the business frequently overlap, but they are not the same.
Trying to solve all three areas in one annual planning meeting can create confusion, frustration & an agenda that stretches forever.
Give each conversation the time & structure it deserves.
Do not throw everything into annual planning & then congratulate yourselves for being thorough.
Annual Planning Should Produce Action, Not Exhaustion
The measure of a successful annual planning process is not how many hours you spent in the room.
It is what happens when you leave it.
If not, another day probably will not fix it.
Annual planning should create alignment, clarity & action.
Two well-structured, well-prepared & properly facilitated days should be enough to review the past, strengthen the team, reconnect with the long-term vision, agree on the annual priorities & build a focused 90-day plan.
If you regularly need a third day, take a hard look at what is filling the agenda.
You may not have a planning problem.
You may have a preparation problem, a leadership discipline problem or an inability to make the hard choices.
And no luxury retreat venue is going to solve that.
Is Your Annual Planning Actually Producing a Useful Plan?
Before you book three days, ask yourself what you are really trying to achieve.
Are you creating clarity, making decisions & agreeing on the most important priorities for the year ahead?
Or are you filling the agenda because nobody has been dealing with the big issues during the rest of the year?
A strong annual planning process should leave your leadership team aligned, confident & ready to act. It should not leave you exhausted, overloaded & carrying a strategic document nobody will ever open again.
If your annual planning has become too long, too complicated or too operational, let’s have a conversation.
I help leadership teams cut through the noise, get to the crux of the real issues & create a practical plan they can actually use in the business.
This section gives you quick access to 3 links - to articles, blogs, podcasts & stuff that will help you to create a better business & lead a better life.
Have productive meetings through better structure.
Reflect on progress and celebrate successful milestones.
Shift from constant activity to purposeful productivity.
We are here to help you live a better life by creating a better business. We are real-life business owners with years of experience & a strong desire to make a huge difference to the lives of entrepreneurs.
If anything here resonates with you or you would like our help, then please get in contact. Just reply to this newsletter & let us know who you would like to speak to…. Or visit our webpage & contact any of our team from their own pages.
If you know someone who would benefit from reading this, then please forward it onto them. 💖
If you’d like to learn more about any of these tools or would like to find out how I can help you achieve a better life through creating a better business, then book a free Discovery Call with me.
We’ll talk about what you want to get from your business & your life & come up with a plan to do that!
Debra Chantry-Taylor
Certified EOS Implementer | Accredited Family Business Advisor | Entrepreneurial Leadership & Business Coach | Speaker & Workshop Facilitator
