The Top 6 Questions to Ask During a Strategy Check-up

If your annual planning process will start soon, you should read this!


Why is it that most companies, regardless of size, go from year to year doing an annual planning process that is not making a difference in the company’s results?

The typical routine is that during last Q3/Q4 the company did a planning exercise by:

  • Setting some tops-down targets for the business based on what the desired financial results were
  • Having the marketing people and business managers grind out some standard powerpoint templates and fill in some spreadsheets from finance
  • Holding a business review to go over it with the leadership team
  • Finalizing it all into budget for next year and some objectives for the managers
  • Presenting it all to the Board for their blessing

This year then turned out to be an incrementally better version of last year, without substantial change or growth.

I believe technology businesses can have a much better and more meaningful process if they pay regular attention to updating their strategies.

These should be living documents, not tucked away in dusty corners of the laptop or bookshelf, but rather active and central pieces of the management mind-set.

Wouldn’t it be great to have a planning process this year that can produce significantly more impact for the business?

By starting out with a quick strategy check-up in Q2/Q3 before doing the annual planning this year, it can happen.

When is the last time you really examined your strategy, in whatever form it exists today?

Quick indicators that you could use a check-up:

  • if it is hard to put your fingers on the strategy document or
  • the strategy is not clear and understandable to an uninformed observer looking at it,

Or more serious indicators:

  • the business is stagnant
  • you are suffering blows from competition or you cannot catch them to become the market leader
  • the Board and owners are not satisfied with the growth and valuation being achieved
  • employees are not motivated
  • customers are not delighted
  • there is a large gap between your business ambitions and your resources to achieve them

If none of the above are the case for your business today, then you are likely good to go until next year with your current strategy.

On the other hand, if any of the above items are true, a strategy check-up is in order.


Here are the 6 questions to ask and work through during a checkup to find the weak spots in your strategy framework:

1) What is your winning intent?

This is the clear focus of your activity, the inspirational direction for your company that employees can rally behind.

2) Where will you play?

You need to be clear on the market where you can achieve this intent and become the market leader.

3) How will you win in that market?

It must be defined clearly how you will beat the competition.

4) What competencies/capabilities must be in place to achieve that and over what timeframe?

This will determine the key investments required by the business over a multi-year timeframe.

5) Do you have a company culture that fosters the innovation needed to delight your customers?

Without this, a technology company will not become the market leader.

6) What management system do you have to insure focused execution of the multi-year plans?

Great plans go nowhere without a clear approach to insure they get implemented and progress gets tracked.


All of the above answers should be clear and unambiguous, written down and kept in a place that can be easily accessed and reviewed at least annually.

This checkup is an area where an objective, third party review by someone not wrapped up in the day to day details and the history of how you got to where you are today can help.

If re-tooling different aspects of the strategy is deemed necessary, a custom plan to do that with your team can be quickly developed and executed as well.

When strategy is re-thought and re-stated such that the answers to the checkup questions are clear to your team, then this year’s planning process to determine how to implement that strategy can be the best one yet for your company.

If you would like to get a FREE strategy check-up this year, click here to get a download of my paper “The Four Steps to Market Leadership” so you can read more about my approach to developing and implementing strategy and get more information on bringing your company to the next level. 

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