business planning day

The Power of a Planning Day for Your Business + FREE Worksheets

by Derkia Thomas

  |  03.27.23  |  

Reviewed By: Stephanie Love

One thing we often hear from small business owners is that they’re too busy to dream about the future. Sound familiar? That’s why blocking off time for a “planning day” is essential.

This dedicated day provides an opportunity for business owners and their teams to focus on long-term planning and strategy, without the distractions of day-to-day tasks.

Of course, when you’re busy, it can seem impossible to find time for planning. However, that’s exactly why it’s so important to make the time to do it. How else will you put all your innovative ideas into action?

Here’s how your business can benefit from a planning day, whether you want to focus on marketing, long-term growth, brainstorming or adding new services.

Modern Small Business Playbook

Marketing-focused Planning

When was the last time you reviewed your marketing strategy? Don’t worry — we won’t judge. It’s difficult to find time when you’re focusing on running your business, but revisiting your strategy might lead to smoother processes.

A good rule of thumb is to review your marketing plan quarterly, if not monthly. Do you need to make drastic changes this often? No, but it would benefit you to examine what is and isn’t working for your business.

On your dedicated planning day, you’re able to:

• Prioritize marketing tasks
• Re-allocate resources effectively
• Analyze goals and timelines
• Ensure that your marketing efforts are aligned with your business strategy

This will also help you avoid marketing emergencies and making last-minute decisions, which can be costly and stressful.

Additionally, if you’re looking to keep your staff motivated, a marketing planning day could do the trick. By reflecting on your business and marketing goals, you’ll reignite your team’s passion and commitment to achieving your objectives.

Want to come up with social media content, for instance? Let their creativity flow with TikTok trends or how-to videos.

This will also enable you to communicate your vision and values more effectively to your team, customers and stakeholders.

During your planning day:

• Analyze your current marketing strategies
• Identify areas for improvement
• Research new trends, tools and techniques

Long-term Growth Strategizing

How amazing would it be if your business could run itself a few years from now? When you’re working on a day-to-day basis, it’s hard to visualize that future.

Short-term gains provide immediate benefits, but they may not be sustainable in the long run. By prioritizing long-term growth , your business can develop the solid foundation needed to withstand challenges and thrive in the future.

One key benefit of focusing on long-term growth is that it encourages your company to invest in itself. This can mean investing in new products or services, upgrading technology and equipment or hiring additional employees. 

Long-term growth also allows a small business to build a loyal customer base. By providing high-quality services and cultivating strong relationships with customers, your business can establish a positive reputation and attract repeat business. 

Over time, this can lead to increased revenue and profitability.

Increasing customer retention by just 5% boosts profits by 25% to 95%. — Small Biz Genius

When you focus on long-term growth, you’re able to build a strong sense of purpose and direction for the company, inspire employees and attract customers who share your business’s values and vision.

Brainstorming to Become Better

Brainstorming days can be incredibly beneficial because they allow employees to come together and share their ideas. 

By pooling their collective insights and experiences, teams can find unique and innovative solutions to problems that seemed impossible.

You’ll also help foster a sense of connection and teamwork among your employees. When individuals feel that they are working towards a common goal, they are more likely to be invested in the success of the business. 

We’re talking about a boost in motivation and productivity, as well as improved communication and collaboration.

In addition to improving team dynamics, brainstorming days help break down barriers between departments. Bringing together individuals from different backgrounds and skillsets, help teams approach problems from multiple angles and find more effective solutions. 

This cross-functional collaboration is invaluable when working to stay ahead of the competition. 

Expand Your Offerings to Stand Out

Let’s talk about your service offerings. Can you quickly identify which service is your money maker and which may be underperforming?

When you set aside a planning day to look at the services you’re offering, you can evaluate the services you’re offering and determine if there are any gaps.

This is also a great time to consider the needs and wants of your target audience. What potential new services could meet those needs? 

This process is what helps you identify your business’s competitive advantage , attract new customers and retain existing ones. This can lead to increased sales and revenue for your business.

Service development also improves your business’s reputation and brand image. By demonstrating your commitment to providing high-quality services, you establish yourself as reputable and trustworthy.

This leads to positive word-of-mouth referrals and increased brand awareness, which, as you may have guessed, further drives business growth.

Having planning days is crucial to the success of any business. By dedicating a day or two each month to planning, your business can ensure that it’s on the right track and constantly evolving to meet the changing needs of your customers.

Ultimately, a planning day is an investment in the future of your business and drives long-term success, but sometimes you need help beyond planning. When you’re ready to run your business more smoothly, check out The Modern Small Business Playbook .

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Key elements of a 'strategy planning day' for your business.

Is the thought of the strategic planning process too daunting for you to consider? Many small business owners and CEOs are inclined to put this off, thinking that such planning requires extended time away from the workplace, a commitment of additional resources and the risk of falling behind with critical deadlines.

But while it’s true an in-depth strategy planning session may take several days, there are alternatives that make the planning process more feasible for busy executives and their teams.

One such option is what’s called a “strategy planning day”—a single, focused day (at a venue generally offsite) with a schedule of intensive activities that are designed to “generate ideas [and] be done in an environment that stimulates freedom of thought and involve the right people.”

The structure of a strategy planning day may vary, depending on your business needs and other circumstances. But certain elements should be included in order to get the most bang for your buck. These include:

A skilled facilitator. It’s tempting for the CEO or owner to lead a strategy discussion, but that’s not necessarily in the company’s best interests. An objective third-party, skilled in encouraging a free-ranging discussion (but not letting the discussion get out of hand), is generally more effective in getting people involved than a business leader with “skin in the game.”

A clear view of key objectives. A vague goal of “strategy” is unlikely to move the needle in terms of efficient business planning. As part of the preparation phase, it’s vital to outline specifically what goals you intend to achieve by the day’s end—be they new product ideas, ways to enhance customer service, a revamped approach to vendor relations, etc. Knowing the “why” behind the planning session helps everyone involved stay focused on the task at hand.

Want additional insight? Read 4 Step Guide to Strategic Planning now to learn more

A request for outside-the-box ideas. At least a brief portion of the strategy planning day should be set aside for brainstorming that adheres to no prescribed limits. Encourage team members to toss out the “craziest” solutions they have for ongoing business problems. The goal is to uncover some kernel of an idea that might lead the way to a genuinely practical solution that’s so far eluded the best minds in your business.

A few constraints. At the same time, introducing some constraints into the strategy discussion may serve to overcome commonly held misperceptions. John Jantsch of Duct Tape Marketing notes that business leaders “sometimes can’t get past why something won’t work thoroughly enough to get behind any sort of unified plan.” Addressing these constraints, he says, “give everyone a common point to attack when trying to determine strategies that will help eliminate or overcome the hurdles.”

A SWOT analysis. Analyzing your company’s strengths, weaknesses, opportunities and threats is always a good idea. When you allocate a set period of time for SWOT analysis, it helps to frame a broader discussion of your company’s place in the marketplace, its standing with respect to competitors, current (and future) forces driving sales, and so on. A strong SWOT analysis also helps to set the baseline for future strategy day sessions.

A list of planned action steps. The end result of a strategy planning day is having concrete action steps to implement upon a return to “business as usual.” Each objective should come with its own list of proposed actions, including specific steps to overcome existing roadblocks to success. Assign action steps to a team or to individual team members, along with a schedule for getting things done. Keep interest alive by promoting the work of these teams and individuals with everyone in the organization.

Following your strategy planning day, it may be time to embark on a broader approach to strategic planning. TAB’s “Strategic Business Leadership” process is designed with small and mid-sized businesses in mind. We invite you to download our free white paper today and learn more about how strategic planning can help guide your business toward greater success.

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How to run a successful strategy day

Business planning in an agile age

How often have you heard that you need to spend more time ‘on the business’ rather than ‘in the business’? Your team strategic planning offsites are one of the most valuable ways to spend that time – if they’re done well. If you think of every business decision as a series of conversations, this is where the most important conversations for your business’s future will take place.

However, if you’ve ever experienced a strategy day that was quickly (or best) forgotten, you’ll know turning those conversations into a realistic, meaningful strategy isn’t easy.

So if you’re planning to run a strategic planning session to get the next financial year off to a good start, this guide may help you align your team, and strengthen your business’s performance in the year ahead.

“ If every business decision is a series of conversations, your strategy day is where the most important conversations for your business’s future will take place.

Success starts with a plan

Before you work out who to invite and set the agenda, think about where you are right now in the strategy process – and what you need this meeting to achieve. What time frame do you want to discuss? Are there any limitations you need to put on the scope of discussion?

Once you know the objectives, you can work out who needs to be involved to help shape and take ownership of the outcome. Ask them to share any ideas or issues they’ve been considering, and give them some guidelines on how to prepare before the meeting.

A lot of the work can be done in advance by pulling together the data everyone needs to know (such as current financials, what strategies have worked and haven’t worked in the past, competitor and customer analysis, current roadblocks) and making sure they read it before the day itself. A team offsite is not an excuse for a 100 slide PowerPoint presentation – you need to maximise the time for problem solving and idea generation.

And all this all needs to happen at least four weeks before your strategy session –  Harvard Business Review’s roadmap  suggests 60 days to develop a successful offsite.

Know your role as leader

As a  recent US survey of top CEOs  revealed, the role of a business leader is now more like ‘Designer-in-Chief’ – rather than having all the answers, you need to ask the right questions to inspire a creative response from the team.

Nowhere is this more evident than during your strategy session. If you plan to facilitate the meeting, it will be hard to also play an active part in the discussions. You may also want to downplay your own opinions upfront, to encourage a more open conversation.

Consider getting others in your team to run specific parts of the agenda so you can sit back and contribute. Those who suggested a specific topic might want to steer that discussion. Or you could bring in an external facilitator for the day.

As the business leader, the strategy offsite is your meeting and you will have the ultimate say on the agenda. But be prepared to be flexible – for example, post it notes on the wall can note session timeslots so you can move them around in case a new opportunity (or issue) arises.

“ The role of a business leader is now more like ‘Designer-in-Chief’ – rather than having all the answers, you need to ask the right questions to inspire a creative response from the team.

Not all frameworks involve a SWOT

A strategy framework is a great way to quickly visualise and share where you are and where you want to go – but planning tools don’t begin and end with a SWOT analysis.

One of the limitations of a SWOT is not understanding the context for each strength, weakness, opportunity and threat. Your weaknesses may not be as important as your strengths or opportunities – and you also need to know how those strengths compare with the market or where you want to take the business. It can end up being a brain-dump with no clear sense of direction.

If you want to organise big issues into manageable categories to focus discussion, other framework options include Kaplan and Norton’s  balanced scorecard , or a self-rating across  specific capabilities  that matter most to your business, customers and industry. Macquarie’s benchmarking results, such as the recent strata management and legal reports, can give you some ideas on how you measure up.

New ways to get ideas flowing

You’ve got all the right people in the room, so set aside time in the agenda for problem solving and idea building. To generate really creative responses, these three techniques can help.

1. Steal ideas from another industry

If you have a specific challenge, look outside your industry for examples of where that has been solved before. For example, if you’re worried about customer loyalty, ask everyone for examples of other sectors that manage this really well. The idea for  packaging roll on deodorant came from a ballpoint pen   – so challenge your team to think outside the square.

2. Set up some constraints

Blue sky thinking can be fun, but it doesn’t always lead to practical results. So put some roadblocks on a brainstorm – this could be as simple as saying ‘you can suggest anything except X, Y and Z’ – and insert the ideas that come up every single year.

3. Ask for truly deviant ideas

Often people will sit on an idea because they think it's not good enough – but with a bit of team effort that idea may spark the best solution. So challenge the team for a high quantity of ideas, as crazy and ridiculous as they like. You never know where they may lead.

Narrow in on the right direction

Two things need to emerge during your strategy planning session. One is an agreed over-arching direction for the year – ideally something you can summarise in one or a few words. Options might involve people, efficiency, productivity, security, market change or scalable growth.

Once you have this, your priorities will become clear. If, for example, you’ve come up with 40 different initiatives during the day (or are still carrying those tactical ideas from the last strategy day),  HBR  suggests using a simple ‘archery’ exercise to make sure you hit your target.

Hang your direction (or a few top line strategic directions) on the wall as a target with two circles: the bullseye and the outer ring. Now write every initiative on a post it and place it where it should go – will it achieve the goal? Bullseye. Is it slightly relevant? Outer ring. Completely off-topic? Outside the target.

This should lead to a manageable list of high-impact initiatives – the second thing you need to agree at the session. Then, if you have time, work out who is responsible, how the outcomes will be measured, and the timeframe for execution.

Close with clarity and a sense of purpose

By the end of your strategy day, everyone should be inspired to achieve the direction you’ve set as a team. Ask one question to check everyone is on the same page: ‘What has become clearer after today?’

Then document your strategy in a single page, and set a time for a review on progress – ideally each quarter.

Given the pace of change in today’s markets, there’s no time to write and review a 40 page strategy document or wait a year for the next collaboration. Like every other aspect of running your business, it might be time to give your strategy sessions an agile shake-up.

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How to use ‘planning days’ to improve your workplace

As a business owner or team leader, there are many ways you can make a great workplace for your employees.

You don’t need me to convince you that it’s important to be happy at work, because we all spend a lot of time there. Being happy at work is good for everyone’s general health and wellbeing. Plus, it helps you and your staff to achieve more if you are happy and reaching your goals.

What is vital is to communicate with your staff about the future. You might have a great vision, but does everyone else know about it?

Workplace planning days are a way to make to open such communication channels and make the workplace great.

So how do you run one?

Depending on the size of your team, aim to schedule annual strategy meetings as a group, whether it is a department, or the whole company. Make regular workplace planning days a genuine place to exchange and transmit information.

Start with an empty agenda and open it up for everyone’s input.

On the day, ask everyone to come up with ideas about, “How we could do better as a business”. Don’t flag this ahead of time. What you want to do is open this up. You want free thinking, so people feel free to say everything on their minds.

Give participants sticky notes to put down their ideas and make it fast and exciting: “Fix the lights!” “Business development” “Get me suchandsuch software program”. Nothing is too big, nothing too small.

As a group, gather together these sticky notes and group them into three areas: operational; technical; and aspirational

These thoughts will allow you as the boss or decision-maker to see what needs fixing. Often bosses don’t know what the problems in the workplace are, communication will help you find out.

“More face to face time with clients” “Schedule WIPs for 9.15am not 9am”

Head into the day with a few ideas of your own. Find out the vibe in the office about what I like to call “the birthday issue”. Is everyone expected to chip in? That sucks. What’s the rule and does everyone like it? How would you like it to work? It’s not a company responsibility. A good way to deal with it can be that the person whose birthday it is brings the cake. Get the team’s buy-in on what they want and institute that.

During the gathering of suggestions, someone needs to collect the data and ensure that these great ideas are captured on sheets of butchers’ paper and put up in the workplace.

Then each person can take responsibility for crossing off their own suggestions as these things start to be done in the office.

As a business owner or team leader, you need to prioritise what you can and can’t achieve in the business. During the planning day, make a list of action items and issues from the ideas raised which you can immediately address and get as many of them working as possible.

People may love their workplace, but hate that their computer doesn’t function properly. They may not like the person sitting next to them. They may resent always being the one who cleans the office fridge or tidies up after meetings.

Find out what people like and what they don’t. Even the simplest thing can be a fly in the ointment of a potentially great workplace.

This article first appeared on Women’s Agenda .

About the author

Women’s Agenda

Women’s Agenda is a publication for career-minded women who want to stay ahead of the conversation.

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Why you need a Business Strategy – and how a Planning Day can help

Having a strategic plan for your business is great – it’s essential. It helps business owners to see what’s working, and what isn’t. From there, a plan can be developed to resolve and improve – so that the business runs better and goals can be achieved.

There are so many different things a business owner can try to do to improve their business.  However, without a clear business strategy , owners often get distracted. They sometimes waste time, money and resources (Shiny Object Syndrome!) doing things that don’t actually help them make progress.

This is why it is important to develop clear goals and the specific strategies to achieve them. Then there’s the implementation plan – to actually make it happen.

Your business goals should be based on comprehensive research. They should be focused on attracting customers, strengthening performance and resolving challenges.

Your business strategy enables you to 

• make good, future-focussed decisions
• avoid guessing and reactive decision making
• control your business 
• minimise risks 

It also ensures that the implications of any particular strategy on other parts of the business are clearly understood and taken into account. For example, to increase sales you may need time and money to develop and implement a marketing plan, more team members or more equipment.

At DFK Everalls, we can facilitate a strategic planning day with you and your senior team. We can help you identify the opportunities in your business, evaluate them and decide on the strategy going forward. 

We ensure you continue to move in the right direction – towards success!

How to establish a direction for your business strategy

Where is your business now, and where do you want to be? 

We start the business strategy process with your values and business purpose . We will help you identify your business’ 

• opportunities and 

Then we evaluate and prioritise these issues to develop specific goals for your business. 

These could come in the form of fixed targets – or they could be more general, like improving the quality of the product / service or the efficiency of your team. They may also be based around overcoming roadblocks that have been impeding growth in the past.

Our key role here is to make sure these goals are measurable and attainable – and consistent with your business values and purpose. 

Build a roadmap to success

Time to get out the whiteboard and markers!

We love a good brainstorm.  It’s a great way to map out everything we need to do to utilise your strengths , optimise performance, take advantage of opportunities, mitigate weaknesses and overcome challenges. 

We guide the development of your overarching strategy that will help you achieve a competitive advantage through an efficient and effective business.

The strategy develops objectives for the Five Pillars of a Healthy Business :

• Clients : determine who your ideal target market is – and what they need from your business as well as the marketing strategy to make sure they can find you!
• Products/services: design the products/services that will solve their problem and decide what distribution channels you will use.
• Team : they are your biggest asset because they are the face of your business, drivers of growth, client relationships, quality service levels.  We will help you develop a strategy that ensures they are engaged and driving your business.
• Systems & Processes : high performing businesses have internal systems to ensure consistent service standards for clients and a team commitment to maintaining these standards.
• Finances : a strategically healthy business has clear KPIs so it can measure its success.  We also ensure that your finances are structured the right way and that you have enough working capital and cash flow to ensure you can implement your strategies.

Once we know what needs to be done – we prioritise the issues and figure out what resources you need:

• What is the time frame and how much time do you need to dedicate to implementing the plan?
• Who is going to help you and be responsible for which issues – new or existing team members or do you need some external help like a marketing consultant?
• How are you going to fund the things necessary to implement eg working capital or new equipment?

Making it happen!

We help you embed the implementation plan into your day to day operations to ensure it becomes part of your daily routine and you actually make it happen! 

But what is the point of setting a goal and implementing the strategies if you’re not measuring progress to confirm if you are on track or not?

This can be the tricky part. Some business owners get excited by the planning process, and walk away thinking the hard work is done. Doing business is complicated and not everything goes according to plan. So, it is important to develop and monitor KPIs to see what is working and what is not. You then need to tweak as necessary to ensure you stay on track. Regular monitoring and reviewing takes discipline!

This is why we don’t just hand over your business strategy and send you on your merry way. 

DFK Everalls can help. Not only with the development and implementation of your strategic plan, but also the monitoring and refining. 

We can make sure you are measuring the right things so that you can identify progress or problems as soon as possible – and tweak the strategy accordingly.  We can arrange follow up meetings with you to review the progress and ensure you stay on track. 

Need a business strategy? Work with us

Celebrating progress and success is our favourite part! It’s what we go to work for every day – to witness our clients’ growth in action and see them achieve their goals. 

We will be with you each step of the way – because we live to help build better businesses. 

If you want more information about our Strategic Planning Days . contact us and we can walk you through the process.

We would love to help your business grow!

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