On Wednesday 27th November 2025 I hosted my first in-person event - the 2025 Visionary…
Want to know how to structure your annual CEO day? As a solopreneur or small business owner, it is all too easy to spend all your time working in your business and not spend enough time working on your business. Taking the time to step away from the day-to-day runnings of the business and have the opportunity to be in CEO mode is essential. Ideally, this should happen regularly, but as an absolute minimum, you should ensure that once a year you have a CEO Day where you plan for the year ahead. Keep on reading to find out how to structure your annual CEO Day.
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What is a CEO Day?
In the simplest terms, a CEO Day is a day dedicated to being in CEO mode. This means you review the performance of the business, set goals for the future and create plans that will enable the business to achieve those goals.
Depending on your business you may take a CEO Day on a weekly, monthly, quarterly or annual basis (or even a combination of those frequencies). The distance between the CEO Days will impact what you spend that day doing. What you do on a weekly CEO Day will be very different from what you do on an annual CEO Day. In my business, I have a CEO session on a weekly and monthly basis, have a CEO half-day on a quarterly basis and then have a CEO day on an annual basis.
For the purpose of this blog post, I’m going to be focusing on a CEO Day that is being held on an annual basis. These days can also be called a Strategy Day or a VIP Day. You might have seen other business owners going somewhere gorgeous like a hotel or spa for their CEO Day, but if you can’t escape for an ‘awayday’ somewhere fancy don’t fret. What you do on your CEO Day is much more important than where you have your CEO Day.
Why is it essential to have an annual CEO Day?
As a solopreneur or small business owner, the reality is you are wearing lots of hats in the business and the majority of your time is taken up by keeping the business running. Your days could be filled with working with clients, marketing your business, general admin etc. This may leave you very little time that is dedicated for you to work as a CEO. That’s why CEO days are so important and powerful. A CEO Day is a day where you clear your diary of everything else and the day is dedicated to dealing with CEO activities.
How to make the most of your CEO Day?
To make the most of your CEO Day there are a number of things you need to:
- Completely clear your diary of all other commitments. This should be a day where you have no distractions and nothing that will force you to switch from CEO mode in to another type of mode.
- Create an agenda ahead of time. I know having an agenda might sound boring to make the most of the day you should have a structure to follow with suggested timings. This will ensure you don’t get completely sidetracked or miss something all together.
- Have easy access to your data. Any good CEO day will involve reviewing your current data to help inform decisions about the future. You don’t want to lose lots of time because you can’t log into your accounting software or your Google Analytics account. Ensure you have the logins for anything you’d need to log into and for data that is on spreadsheets etc make sure that is easy to find.
| TAKE YOUR CEO DAY TO THE NEXT LEVEL BY HIRING ME FOR THE DAY.
For years I’ve been running CEO Days with solopreneurs and small business owners. Running your CEO Day with someone external from your business and with tons of business and marketing experience and expertise makes a massive difference. I’ll support you to face the facts about your current position, dream big about the future and get really strategic about what you need to do in order to achieve those big business goals. So if you are planning on having a CEO Day to create your 2025 and you want to make the day even more productive and useful, book a 2025 Strategy Day. For more information and to book a 2024 Strategy Day click here. |
HOW TO STRUCTURE YOUR ANNUAL CEO DAY
1. Review, and reflect on, the past year
The first thing you should do is review your past year. As a business owner, it can be easy to constantly be looking forward, but reviewing your past performance can help you make better decisions about what to do in the future.
If you had set goals for the previous year review those goals and see which goals you did and didn’t achieve, and try to articulate why you did or didn’t achieve the goal or not. It can be easy to gloss over an unachieved goal, but your “failures”, as well as your successes, teach you valuable lessons so if you haven’t already made a note of the lessons write them down.
Very often over the year, things will have happened that you didn’t anticipate or plan for. Use this time to also make a note of the unexpected highs and lows of the year.
When reviewing the past year you should be coming at it from two angles: data-driven and anecdotal. Looking purely at the numbers can be misleading and so can only looking from a personal perspective. It may be that your revenue was the highest in years, but you felt exhausted the whole time. They could be a service that generated significantly less revenue than the other services, but it brings you the most joy. That’s why it is important to look at the data, but then add your personal reflections as well.
2. Think to the future and set goals for the year ahead
Once you’ve properly reviewed the past it is time to look to the future. For an annual CEO day, the focus is on thinking about what you want to happen in the year ahead. In the first instance, you should get all of your ideas onto paper or a computer. As a CEO I’m sure you’ve got tons of ideas bubbling away. Your CEO day is the time to get those ideas out and decide which ones you are going to move forward with.
At first, don’t filter yourself. If it is something you think you’d like to do in your business write it down. Then afterwards you can relook over all of your ideas and start to think about what is feasibly over the year ahead. What is feasible will depend on a number of things such as team size, money available for investing, your available time, the knowledge/skills required etc.
Once you’ve worked out what is feasible it is time to turn those ideas into specific goals. There are numerous ways you can set goals. Some common goal-setting techniques used in business are SMART goals, SMARTER goals and Good, Better, Best goals. The technique you use doesn’t matter, but they should be written in a way that you, and ideally someone external, will easily be able to tell when you have achieved the goal. As a bare minimum, you should have financial and impact goals. Check out the 3 essential financial goals for solopreneurs and small business owners.
3. Services, Pricing and Financial Forecasting
Now that you have clear goals for the year ahead it is time to review what you sell (your services and / or products) and how much you are charging.
Go through your current services and products and decide if you are going to continue in the same fashion, continue but adust or stop selling altogether. For the services or products, you decide to adjust or stop selling think about when in the year you’d ideally make those changes. Then if your annual goals included the addition of new products or services then you’ll need to decide when those additions will be available in your business.
Once you’ve got a clear list of what you’ll be selling across the year the focus moves to the pricing. If you are selling more than one thing then it is important to think about how the pricing across your whole service or product suite looks. There are general rules such as people expect to pay more for a one-to-one service than a group service for example. People expect that if they work with you over a longer period of time it will be cheaper than for a one-off.
Once you’ll want to start your revenue forecasting. Plot out sales for each product and/or service for the whole year and see if your financial and impact goals are physically possible.
4. Marketing and Sales
You know what you are selling and for how much, but how are you going to create the demand in the first place? Having a comprehensive marketing and sales strategy is key for your business.
In your annual CEO Day, you don’t want to go into specific detail such as what you’ll be posting on Instagram on the 24th of May. You want to be concentrating on the overarching strategy of your marketing.
- Will you be selling via launches or on evergreen?
- What marketing channels will you be using?
- Will you be using organic marketing, paid marketing or a mixture?
- What are the possible buyer journeys a client could experience?
- What are your key messages?
You’ll also want to think about the resources required to deliver the marketing and sales strategy. You’ll want to think about whether you can deliver the strategy with your current resources (software, personnel and money) or whether you’ll need to make new investments.
5. The Plan
Now it is time to bring everything together so you can see everything in one go. Depending on your personal preferences at this stage you might decide to have a topline plan that outlines what is happening on a quarterly or monthly basis, or you might want to go even more specific than that and plan on a weekly basis.
You’ll want to start off by marking major activities such as your holiday, launch dates etc. For big goals such a self-publish a book you’ll want to reverse engineer the process leaving time for writing the book, editing, getting a cover designed, pre-order campaign etc.
Your plan should be created for the different responsibilities that exist within the business. Even if you are the only person in your business at this point I want you to treat every different responsibility as if it was done by someone else. Not only does this mindset when planning make it easier if you decide to grow a team for your business. But it also ensures that when you are planning you can properly assess whether your plans are too ambitious. For example, if you decide that you are going to run a massive launch at the start of January, but December is a very busy time for client delivery and then you want to take a week off over Christmas then you’d realise for your launch to be successful you’d need to either do the launch prep extra early (in November), get external marketing support in December or the date of your launch would need to be moved. If you were only creating a plan for marketing this could be easily missed as “marketing” isn’t busy in December, but client delivery is and since you are marketing and client delivery a change needs to be made.
This is why having a topline monthly plan so you can see the main priorities of each strand of your business is so important. It allows you to properly see the full picture and identify issues before they arise.
That’s it. You now know how to structure your annual CEO Day.
Committing to taking one day away from your business and having an annual CEO Day is so important. I’m sure if you use this structure you’ll be able to come away for your own CEO DAY ready and raring for the year ahead.
The structure I’ve shared is the exact structure I’ve used for years when working on my own business and with clients who have a Strategy Day (Annual Planning version).
Running a CEO Day by yourself can be tricky. You might not have the analytical mind to properly review your finances and marketing data. You might have a money mindset that impacts your approach to pricing. You might not have the knowledge for creating an effective marketing and sales strategy. And you struggle to take your big goals and create a plan to achieve them.
If you think any of those things might hold you back then I can help you. You can book a Strategy Day (Annual Planning) with me and I’ll guide you through the process, ensure that you don’t skim over the bits that aren’t your strengths and be the external support to ensure you have strategically thought through everything and have the best plan possible for the year ahead.
To find out more, and to book, click here.
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