How to Do Better Strategic Planning

It’s December, that reflective time of year when we lean back and take a long, deep breath. We smile at all we’ve accomplished. We scowl at the plans that didn’t come together the way we hoped. And then we shrug and plunge headfirst into another year of optimistic planning.

The Same Old Yearly Planning Cycle

If you’re like a lot of us, your annual planning follows a comfortable rinse and repeat cycle.

Last year you targeted x and achieved x plus y. Well done, you say. Next year you’ll go big and shoot for x times y. Our planning is based on what we’ve done before, and we don’t challenge ourselves as often as we should.  

Reality. The way we engage with customers, clients, partners, and employees is continually changing -- and that's not going to stop. We can’t sit patiently on the sidelines waiting to be invited to play in their game. We’ve talked about this a lot – nothing new here.

But there’s a huge gap between knowing and doing. What if next year becomes Your Year of Asking One Question. 

Are you ready to add a new spin to your familiar rinse and repeat goal-setting cycle? This is how it works.

How to Put the Big Strategic Planning Question to Work

Grab a piece of paper and pen. (We’ve all learned that handwriting is more effective than typing or tapping notes into a device.)

At the top of your page in big letters write this question: What if we could?

Now you’re going to create your judgment-free list of possibilities. Don’t get hung up on how, why, or who. You’ll get to the practical thinking in a minute.

Create Your 6-Step Strategic Plan

This is a quick snapshot of the planning process. We won’t get bogged down in the details. Our mission here is to see how what if we could thinking fits into your traditional planning. How will this one unconventional question lead to unexpected outcomes.

Now make a copy of your favorite goal setting and planning outline/template/worksheet. Everyone has the format that works for them. Yours might look something like this. 

Step 1: What do you want your company and your life to look like is ___ years? Use a timeframe that’s relevant to you. This is the easy step.

Step 2: What does your business need to look like to deliver your future life? Still pretty easy, right?

Step 3: What are your 1 year (short term) and 3 year (medium term) goals? These need to be specific, measurable, and align with Step 1 and Step 2. Now you’re getting actionable. 

Step 4: What will you do to get from where you are now to where you want to be? 

Your thinking is more specific and tactical. This is where limited thinking typically kicks in. Pick up your list and for each item ask yourself this upside down question: “What if we could?” 


Step 5: Create your quarterly plan
Include one what if we could project in the first quarter.

Step 6: Create measurable monthly milestones
Build your weekly and daily to do lists 
Review, measure, and adjust weekly

Your Planning Takeaway Is Simply This 

  We all gravitate toward being comfortable, to doing more of what's worked in the past. Uncertainty feels a little irresponsible. But you owe it to yourself and your company to stretch and explore.

Instead of “we can’t because” adopt a curious “what if we could” outlook to exploring unexpected opportunities.