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Some Difficult, but Vital, Strategic Planning Questions Every Business Owner Should Ask Themselves Each Year

November 12th, 2019

During the last quarter each year, most business owners focus their attention on reeling in the year’s numbers, while also finalizing a plan to build a better, stronger company for the coming year and beyond.

It is no secret that failing to plan is planning to fail.  We also know that many private businesses that do construct a plan often fall short when it comes execution.  Despite these facts, and some relatively long odds against building a consistent, scalable, high-performance company, most private business owners plan poorly (or worse, not at all).  A large percentage of owners consistently choose to devote their attention to urgencies, busy-ness, and much less impactful activities, than to using a simple, time-tested formula for success.  They don’t fall short for lack of effort, they simply focus their attention upon low-value activities and projects, creating the need to work much harder than necessary.

Sometimes planning fails due to a lack of honesty and transparency, and/or a surplus of hope and optimism.  Optimism is great, but the planning process is a time to get very real. 

Finally, private companies tend to take on the behaviors, mindset, strengths, and weaknesses of their owner.  It is therefore not surprising at all to discover that most organizations will reproduce the same successes (and failures) year after year. In other words, change always starts at the top, and most people love to live inside their comfort zone. So, if you don’t choose to change and adopt new, more productive habits, please don’t hold your breath waiting for your employees to change. 

Planning and execution take work, focus, and a bit of time. If we’re going to invest all this energy in creating an effective, executable plan, it seems to make a hell of a lot of sense to do it right, doesn’t it?  There are a number of good planning process protocols available to help your organization develop clear goals, strategies, action plans, KPIs, and more.  Independent of which process you select, you could gain huge additional benefit by asking yourself just a few brutally honest, highly impactful questions.  These questions form the foundation of the difference between planning as an exercise and Planning for Success. Answer them before you begin the planning process, then again near the end of it (if you do, you’ll likely find that your answers will change).

Honestly completing these steps will double the effectiveness of your planning process, significantly increase your ability to execute your plans, and help turn your goals into reality…:  

  • What am I committed to do in 2020 to stop being busy and start being productive? 
  • What percentage of my time do I currently spend working below my pay scale (aka:  Which tasks and responsibilities will I personally commit to delegate, starting today?) 
  • What projects and activities will I stop doing in 2020 to make room for the new initiatives I intend to start doing? 
  • How is groupthink effecting our objectivity, judgment, and planning, and what proactive actions or processes will we implement to eliminate it?
  • What is the most difficult part of achieving our 2020 strategic plan?  Do we really have the people and processes in place to address it, or are we just living in hope? 
  • Should we focus upon becoming a bigger fish, or identifying a smaller pond? 
  • How effective is my Sales Manager at executing my strategies to build a world-class sales machine? 
  • Are we really different and better, or do we just keep telling ourselves that we are? 
  • Am I personally walking my talk? 
  • What processes and people are in place to inject accountability and alignment into my team?  Are they effective, or do they need to be improved? 
  • What commitments will I make to ensure that I remain personally accountable? 
  • Can I benefit from additional coaching? 
  • Can I benefit from more peer learning? 
  • What can make our beautiful plan blow up, and does it make sense to discuss contingencies for this possibility right now? 
  • What commitments will I make today to become a better leader? 
  • Are there any questions I’ve been avoiding asking myself, for fear that I don’t want to face the answer?
  • What is the one thing I can commit to completing this quarter, that will make everything else easier or unnecessary?

Note: After you complete this personal assessment, you may wish to get together with your team and substitute “we” for “I” in most of these questions, but please understand that all of the people in your company are currently behaving the way they do because that is how they choose to behave, and that they are paying close attention to the example you set. Remember, if you expect your employees to change and grow, the change must begin in your office.

The questions listed above have been extracted and compiled by observing the planning processes of hundreds of highly successful business owners.  If you have additional hard-hitting questions you’ve found to make traditional planning processes more effective, I would appreciate if you would share them. 

Thanks and Best Wishes for an Amazing 2020!


Copyright © Joe Zente 2019.  All Rights Reserved.