December 21, 2021

There seem to be two camps of entrepreneurs when it comes to strategic planning.

Camp One hears ‘strategic planning’ and thinks stuffy boardrooms, boring charts, and pressure-cooker KPIs. Camp Two hears ‘strategic planning’ and thinks welcome pause, creative visioning, and team bonding. Which camp are you in?

Well, folks, it doesn’t really matter which camp you’re in, because your business needs a plan to keep everyone rowing in the same direction, including you, the founder/CEO. Especially if your business is one of your biggest assets, and you plan to sell it or cash in on its full value someday!

I’m not alone in placing high importance on regular planning. Every business guru will tell you if you fail to plan, you may as well plan to fail.  High-Performance Business Coach Andrea Ivanka agreed with me when she was my guest on the Real Bottom Line podcast. 

So even if you’re in Camp One, read on… Andrea & I came up with a few tips to make sure your Strategic Planning sessions are effective, creative, and empowering. No stuffy boardrooms at our camp!

Lock in that time.

The first thing you’re going to do, Andrea and I agreed, is open that calendar and block off time each quarter to assess (look backward) and plan (look forward). 

This is not an optional, free time appointment, nor something you’re going to squeeze into a ten-minute break. You’re going to schedule and protect regular strategic planning time. If you need to,  have team members or accountability partners check in on you, to ensure you’re taking the time you promised. 

Review and recommit to goals.

Anchor into what you need to accomplish, and how that fits into bigger, broader goals. Recognize the steps you’re taking in the right direction. You may not have reached the goal (which may feel frustrating), but it’s important to recognize when you’re still on track. Andrea offered an interesting perspective:

“I keep the big goal in mind and I don’t attach a time to it. This is counterintuitive to a lot of strategic planning. But if I say I’m taking this company to seven figures, I’m taking this company to seven figures. It doesn’t mean I know exactly how long it’s going to take me to get there. But every quarter I now have strategic initiatives that are going to help get me there (without) the pressure of ‘what if I don’t achieve it this quarter?’… it’s like if I say I’m going to drive to Halifax, I’m driving to Halifax. Even if there’s a detour, even if it rains, even if I have to stop and go to the washroom; I know I’m going to Halifax no matter what.”

Then ask yourself these questions.

Once you clearly know where you’re headed, you can look back over the last quarter(s) and ask yourself…

  • What worked?
  • What didn’t work?
  • What do I want to let go of?
  • What do I want to do more of?
  • And how does this fit with what’s already going on?

My tip to you would be, don’t do what I do and look at something, see that it works and decide to stop doing it immediately! Sometimes we get bored with our own tactics, or we’re too ready to give up on something before we’ve given it enough time to deliver results.  Or we love the idea of something, even though there’s proof that it’s not moving us towards our goal. So be fair and objective in your assessment. 

And be wary of piling tactics on top of tactics:

“None of us is creating from a blank slate, and this is what most people do. They come in and they do their planning –  as if they have nothing else already in the works inside of the business as if they have no other responsibilities outside their business.”

Sure, get creative and brainstorm new ways to reach your goals. But quarterly planning is not about throwing away everything you’re currently doing and starting fresh every 3 months!

Know your numbers.

Andrea gets it: “So much of the work that I do with my clients, they’re all service-based-industry owners, is around pricing and numbers.”

We agreed that everyone has emotional baggage around money and that you’re bound to bump up against it at some point when you’re running a business.

And while I’m not a big fan of bringing budgets into your personal finances, I do believe your business needs a budget. You can’t fly by the seat of your pants. You need to know how much of the money coming in is going straight towards your costs of doing business, and you need to make sure you’re managing all costs, consistently, sustainably, and profitably.

So we start with a goal and figure out the sales we need to make that goal happen. What does our sales cycle look like now, and what marketing activities do we need to add (or subtract) to hit that sales goal? Then we loop back to make sure we’ve set realistic goals within our quarterly time frame. And we look at what resources are required to execute that plan. Those missing resources could be people, IT, tools or upgrades. 

Or they may be scheduled breaks and health checks.

Manage the energy.

“When I look at planning, I’m looking at these two pieces simultaneously: what’s the strategy, and then, what’s the leadership and the mindset and the mental development aspect of it that’s going to be necessary for me to hold these pieces I’m putting in place. It’s really important.” 

As the business owner/entrepreneur/CEO, you’re leading the vision and directing all progress along the path. Andrea is the first to admit, “high pressure and high stress do nothing good for us over the long term.”

Allocate talent and energy as carefully as you allocate funds.  Andrea schedules most of her client work for the start of each month when her energy is high. Her more introspective, planning, quiet work she leaves for the end of the month and sets a day aside to recuperate too. 

“Not all businesses have to look the same way… the better you’re operating from an energy perspective, the more you’re actually going to move the business forward in terms of the things that bring it to that next level.”

Your schedule doesn’t have to match, but we agree on how important it is to block off and lock in time — for planning, for doing, and for recovering. 

Business Value Amplifier - Sept 18
Wendy Brookhouse

Wendy Brookhouse


Wendy has been getting people to their financial goals faster and easier than before for over a decade. She has known what it’s like to control cash flow from childhood, where her first job was raking blueberries for ten cents a pound.