5 Tips for Planning Season

Robert McLaws
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What time of year is the most hopeful (and, in many ways, the most dreaded) season for businesses that are starting up and scaling?

Next to Board meeting time, the planning season is one of the most important times of year for you as a founder, C-level executive, or sales leader.

This year’s planning season is expected to be especially funky because the impact of the pandemic has changed both business and consumer buying patterns and we still don’t really know what the economy will look like in 2022 and beyond.

Also adding to the complexity of planning now is that many work teams are remote, so gathering your senior leaders to have frank and in-depth conversations about growth, capacity planning, and business needs may need to be done over Zoom and Teams rather than multiple cups of cold brew (or other adult beverage).

What Should You Be Doing NOW to Create the Best Plan Ever?

As you go through these steps, create a tight (but realistic) timeline around when the plan needs to be presented internally and externally. If you’re seeking funding, you’ll need to allow even more time to create a compelling pitch around your plan.

  1. Create your Planning A-Team

Depending on the size of your business, that could be three people or 10 people. Keep the group small but communicate to your entire organization that the process is starting. You want to be sure to have input from your Marketing, Sales, and Finance functions at a minimum. Engaging an advisor from outside your business is a smart move. That objective perspective can temper over-enthusiasm in forecasting and an external professional can raise questions or concerns that your internal team might not think about.

Carving out time for planning is part of the process. Be sure you also have the right technologies and systems in place to allow for “what if” scenarios and tie your marketing and sales spending into your results forecasts.

  1. Do a Deep (and Honest) Dive into the Current Year

Look at your product, your people, your sales structure and approach, and your marketing. What worked? What didn’t? Most importantly, reach out to your current customers and understand what you could be doing better as a business, what new products and features you must develop, and who your current (and future) competition may be.

  1. Understand the World Around You

That may sound cosmic, but what I mean is that buyers have changed radically over the past couple of years. One of the keys to growth is digging deeper into the hearts, minds, and wallets of your prospects.

Time and budget permitting, engage in some qualitative and quantitative research to supplement #2.

Conferences (live, virtual, and hybrid) are starting up again, so make a point of attending at least one event this year that relates to your field.

Be curious about how other organizations -- like yours or those in other industries -- have achieved growth and longevity and apply those best practices to your own business.

4. Create a Growth Plan That Makes Sense...and Then Create Two More Versions

Founders often tend to be overly ambitious and optimistic. If they grew 60 percent in their first years in business, they may assume that that trajectory will simply continue every year. Wrong! At some point (especially with new competitors entering the market and customer needs evolving), that line may begin to flatten out.

So, how are you going to keep it heading in the right direction? Create a human-centric capacity plan that matches your growth needs to your people needs. Wean your CFO and Sales Leader off of Excel spreadsheets before you start this process. Having a cloud-based capacity-planning system enables you to forecast more accurately, make edits on the fly, and encourage team collaboration.

Marketing and Sales should be joined at the hip (or virtual hip) during planning season. The CEO should be sure to step in if the two groups aren’t collaborating well or have radically different perspectives. Create a plan for building your funnel to ensure that leads don’t fizzle out.

Once you’ve created your “comfortable” growth, Sales, and Marketing plan, stretch a little and create a more ambitious forecast and one that reflects a worst-case scenario. You only want to share the first two with your entire company (to maintain a sense of purpose, drive, and optimism), but every prudent (and realistic) leader should do some disaster planning to ensure that they know exactly how and where to belt-tighten if goals aren’t achieved. Make sure you’re always holding some capital in reserve to get you through those tough times.

5. Take a Long and Honest Look at Your Talent

We’ve saved this for last. That’s not because it’s least important. In fact, it’s tied with smart automation as the number one factor that can make or break your business next year.

Assess every member of the team. Although you should have been having conversations with each employee and independent contractor all year long, the end of the year is a great time to be 100% honest with yourself and your team members. The people who helped you launch a business may not be the same people who will help you scale. Consider the diversity of your team too. Set stretch people goals.

I heard of a company that created “baseball cards” with each employee’s profile. They used them during planning season to assess each team member’s strengths and areas for development and then “placed them on the field” in the right positions. Although somewhat cheesy, the philosophy is sound. If you need a strong pitcher and you have way too many cheerleaders and placekickers, you need to reassess your hiring plan.

Tech-enabled capacity planning is a terrific exercise, in that you can combine talent, timing, and type of sales need into one easy-to-share system and then re-forecast as the year progresses, based on your actual results and learning.

Chilling-Out and Planning

Speaking of people, the planning season can be stressful for your team members. They are still working hard to finish the current calendar year strong. A whopping 83 percent of people are already stressed at work, so adding planning responsibilities to their plates can often bring out the worst in people.

If you’re a Founder/CEO, maintain a spirit of levity (especially as we enter the holiday season), give people PTO to decompress, and set an example. Planning season is hardly the most wonderful time of year, but when your plan is done and presented to your Board, your investors, and your team, you should hold a mini-celebration and toast with an early holiday cocktail.

And then, the really hard work begins as you set off (smartly) to achieve your Plan goals!

Treat yourself to a planning gift now! BurnRate will make the process way easier.

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