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How to Do Better Strategic Planning




John Sculley quote future belongs

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.

  • Remember all those services your clients have asked about. Write them down.

  • What questions have you been asked over and over again. Add them to your list.

  • Dust off those random ideas someone on your team had. Your list is really growing now.


  • 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?” 

  • Is this a problem in search of a solution? What would it look like?

  • We don’t have the expertise to do all of the work ourselves. Who can we partner with?

  • How will our customers’ lives be better if we do this?

  • How will doing this change our company?

  • What’s the worst that can happen if we try?

  • What will we give up if we don't try?


  • 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


    Free Strategic Planning Workbook



    If you're ready to dive into the strategic planning details and not sure where to start, this free 67-page workbook will guide you step-by-step.





    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.  

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    How to Create Your Next Strategic Plan Workbook



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    Tags: Business Strategy

    . . .

    Linda Rolf is a lifelong curious learner who believes a knowledge-first approach builds valuable client relationships. She is fueled by discovering the unexpected connections among technology, data, information, people and process. For more than four decades, Linda and Quest Technology Group have been their clients' trusted advisor and strategic partner.

    Linda believes that lasting value and trust are created through continuously listening, sharing knowledge freely, and delivering more than their clients even know they need. As the CIO of their first startup client said, "The value that Quest brings to Cotton States is far greater than the software they develop."



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