Annual Business Planning: Jamie-Style

If you know me, odds are good that you know about my annual business planning ritual. Every year, I go through a six step process that brings clarity and purpose to my business for the upcoming year.

Because I consistently get questions about what I do during my retreats, how I do it, what I cover, and why, I thought it would be useful for my network, and small business owners everywhere, to gain a little insight into just what these six steps look like for me.

#1. Begin a list of questions.

These can range from general questions like:

  • “What are my top revenue producing products/services this year?”
  • “Are my price points on target for my industry, target and time/effort?”
  • “Are there services I should consider eliminating?”

…to more specific questions, such as:

  • “What one area do I want to focus on growing next year?”
  • “Where is my time being spent and should I invest in finding help?”
  • “What one thing do I need to focus on in Q1?”
  • “What should my email list sign-up incentive be?”

Can’t think of any? These questions are usually ones that have been bouncing around in the back of your head for a while. Trying starting a list now, and saving it in a place that will be easy to access. Maybe you have an online project management system or tool that you can access from your phone, or maybe you have a Daytimer. Once you’ve started the list, begin adding to it over the next few days, weeks or months whenever one of these questions starts bothering you and you’ll have your list ready for planning time.

#2. Begin gathering data and supplies.

table of supplies propelbizworksYou’ll need tools and resources readily available to make the most of your planning session. There is nothing more frustrating than arriving at your retreat destination, 2+ hours away from home, only to find you forgot

If you’re trying to tackle marketing challenges, have marketing data and research ready to go, such as:

  • Social Media profile insights that will tell you what post types are performing best and which days and times seem to be better for posting updates and information.
  • Blog/Website Analytics that will help you identify popular places people are going to on your website, or highly read blog posts that may give you an indication of what your target audience wants from you.
  • Email Marketing statistics like open rates, click-through rates, and days and times you’ve sent blasts or enewsletters.
  • Surveys you’ve sent to your customers or networks.

If you’re deciding on your next new product:

  • Cost spreadsheets will give you bottom line information that will assist in the sales/price point structuring.
  • Prototypes and focus group data
  • Production and sales forecasts may be part of the planning process, or you may already have them ready.
  • Features and benefits

Going over next year’s budget?

  • Print our your Year-to-Date Profit & Loss statements (aka “YTD P&L”)
  • Have your accountant on speed dial
  • Pack your calculator. This is a no brainer, really. 😉
  • Accounting calendars are helpful for planning ahead with cashflow. I have setup a calendar specifically used to remind me when certain bills are due, payroll, annual memberships, tax payments, business registration, rent and utilities. Each year, I simply print out the calendar and dump the info into my budgeting spreadsheet.

snowy night propelbizworksAnd because you never know what may transpire during your planning sessions, I always bring a solid “care box” of planning tools, like:

  • notepads and sticky notes
  • pens, pencils, and highlighters
  • whiteboard and/or flip charts and appropriate markers
  • stapler, tape and paper clips
  • pack your trusty computer (or two)
  • a printer, wifi hotspot, ipad or other tech device you may need to make the job easier
  • food and beverage options of your choice
  • walking clothes and sneakers for exercise breaks, and extra soft sox, just because

#3. Find the perfect spot and decide who’s coming.

Retreat Fireplace propelbizworksIt’s important to find a location where you can focus and be productive, but also a place you can be inspired. If you love solitude and a peaceful place to think, head up to a mountain cabin and crank out some planning amid snow-covered trees, or head to the coast! Of course, there are other options like booking a cool-looking AirBnB in town, renting a conference room for a day, or even locking yourself in the spare bedroom.

Get energy from being around other people? Head to a college library, bustling coffee shop, or co-working space.

You’ll also need to figure out who needs to join you for this planning session. It could be your business partner, team members, significant other, or favorite consultant. Whoever they are, be sure they can help you get things done rather than prove a distraction.

#4. Build an agenda for your time.

Some like to ‘go with the flow’. While I’m becoming known for this approach, nothing can prepare you for the stark realization of the short amount of time you have available to get everything done you want to accomplish. So, create a plan, an agenda, with timeframes for each activity or exercise, then set your alarm and stick to your schedule. If you ever thought working on a deadline was good for you, this will keep you focused!

That said, be willing and prepared to give yourself flex time where you may need more time to sort through hurdles or unforeseen challenges that pop up.

#5. Settle in, set up, and get started!

Business Planning RetreatWhen I arrive at my destination, my first objective is to get familiar with my location, inside and out. Get a feel for your accommodations and decide on the most productive areas for your activities. Usually, I’m rearrange furniture so my table/desk is central to the fireplace. It’s a creature feature I usually require for my retreats.

Once you’ve found your “spot”, get your groceries put away, setup your equipment, grab a glass of water, and get the fire started.

Before you start checking off your list of to-do’s, be sure the smaller, day-to-day problems or emails won’t be a distraction or get in your way. This is your time to figure out important answers and discern the direction of your business for the coming year, so set your out of office responder, turn off your phone’s ringer and then get to work.

Now that you’re setup and ready, begin by reviewing your questions from step one above, and then follow your agenda. Before you know it, you’ll be in the nitty-gritty, running the numbers, analyzing the reports, and making the decisions you need to.

#6. Take a break.

Tea TimeIt may sound like this retreat is going to be all work, but what I’ve learned is that rest and break time is vital to keeping your mind clear and open for inspired thoughts. Be sure to keep your mind engaged and ready to tackle the difficult questions you’re facing head on with regular, refreshing breaks. Give yourself time to ponder, to sit with your thoughts, relax, and open your mind to new ideas. Bring a magazine that inspires you, or talk a long walk or bath in between sessions. And, give yourself permission to go to bed early and sleep a little later than normal each morning. Remember, the brain is similar to a muscle – it gets tired after sprints and needs some rest to be able to perform well again.

By the end of this annual business planning time, you should have answers to at least some of the questions you started with. If you don’t, be sure to make note of the progress you made, any other questions that came up, or anything you found particularly challenging. These notes will be incredibly useful the next time you find yourself doing strategic planning. Most years I find that I need additional strategy sessions to wrap up the final details of the year.

Do you do business planning? What kind of sessions do you have? I’d love to hear your strategies, preparations and planning techniques. Please share below in the comments.

About Jamie Teasdale

Jamie Teasdale founded Propel Businessworks, a small business development company, in 2009. Since then, she has been lending insight and creativity to businesses all over the U.S., giving them the tools they need to plan, promote, and prosper.


  1. BJ Stromme on October 10, 2016 at 9:51 pm

    I love your insights Jamie! Thank you for sharing your hot tips and insider secrets to planning.