How to Assess Your Sales Strategy and Execution

Even if a business is well established, the sales strategy should be assessed at least once every six months. A good leader will pause to assess the sales results, then course correct on strategy and execution to ensure the company stays on track to hit its goals. As the old saying goes “if you do what you always did, you will get what you always got”.


  1. Assess the Sales Execution

As a business owner, you can take many approaches when assessing your sales strategy and results.  The approach below starts from sales execution and works its way up to the overarching strategy.

Here are the core questions you should ask related to sales execution…

  • How well do we conduct thorough, professional sales meetings with buyers?
  • How well do we currently navigate our buyers’ decision-making processes?
  • How well do we sell the value of our solutions versus their features?

If your answer to any of the questions above is “not very”, take steps to get your team the resources and education they need allow them to be successful in the sales arena. If your team lacks the skill or knowledgebase to execute, even the best strategy will never work.


  1. Evaluate the Supporting People and Systems

Once you’ve assessed the ability of your team to execute on the strategy then look inward to determine how well the organization has been doing in providing the team the necessary tools to facilitate their selling.

Here are some questions you can ask yourself (on a looking forward basis) about how the organization can support the ongoing sales effort…

  • What new or different marketing support will your sales team need to help them attract buyers that match your ICP (ideal customer profile) and execute on their daily sales activities?
  • What new or different after admin support will your sales team need to free them up to execute on more of their daily sales activities?
  • What new or different products/pricing [if any] will your sales team need to help them improve their results?
  • Will the CRM (customer relationship management software) configuration need to be adjusted to support the sales approach?
  • How will the weekly team and one-on-one sales coaching need to be structured to support sales success?
  • Is the staff compensation plan structured to incentivize the sales behaviours that will act in support of the strategy?
  1. Review the Sales Strategy

Strategy is a broad topic in business. So, to assess your sales strategy start by considering the following questions…


Are our Ideal Customer Profile and Buyer Personas accurate?

It might be that the people the team used to sell to are now in fact the wrong people to sell to. Double check that your team are having conversations with the right buying influences.


Is the business we are winning the business that we want to win?

Sometimes the sales path of least resistance leads sales to say yes to opportunities that are in fact outside of the strategy. Has this been happening to you? Is your team in fact applying sales efforts to the wrong type of prospect client?


How is our profitability?

Sometimes we aim for business of the type we believe we would like, but over time determine that it is problematic business (unprofitable, unwieldy to service, difficult to retain etc).  Such a revelation may in fact take you back to the start of your strategy planning and result in significant course correction interventions. In my experience as a fractional VP sales I’ve seen that companies unwilling to “rip off the Band-Aid” and re-strategize suffer greater in the long run than they would have by addressing the situation in the short run.


Plan-Do-Assess & Course Correct-Repeat

I recommend to business-to-business sellers as well as business to consumer sellers the simple approach of Plan-Do-Assess & Course Correct-Repeat.  The Plan piece is blue sky time and fun. The Do part is exhilarating and rewarding. The Assess & Course Correct component however is the heavy lifting element. The team needs to pause the exhilarating Doing and be ready to face the reality that they may have been marching in the wrong direction or climbing the wrong hill.


  1. Hire a Fractional VP of Sales

As always, there is a great deal nuance in applying the principles I’ve outlined above. And it takes time which not every leader has in abundance. My role as a fractional VP of sales allows me to facilitate this process and much more. I’m happy to speak with you if you would like to learn more [email protected].


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