5 questions, 10 answers that should leave CEOs concerned about their sales strategy

by Mark Savinson

It’s obvious that CEOs are busy people who don’t often have the bandwidth to be able to look above the parapet to ask fundamental questions. Here, we’ve collated a comprehensive list of questions to help aid structured self-reflection, alongside some answers which we believe could be red flags.

If you recognise your own business strategy in the answers below, then it might be time for a rethink.

  1. Who are our sales people talking to?

Operational-level contacts:

“Why should you care? The deal value is likely to be lower and the solution more tactical than strategic.”

Strategic-level solutions that support your customer’s business outcomes will form lasting, referenceable partnerships which will be harder for your competition to challenge or overturn. It also ensures that the solutions you implement will be significant, rather than trivial, helping to forge a lasting impact.

Anyone who will buy our products:

“Why should you care? Your salespeople are leading with product – rather than adding value to the customer – which will reduce the sales to a price point negotiation eroding margin.”

This attitude will lead to a race to the bottom in terms of quality and value, ensuring the solution provided to the customer is half-baked, and potentially something unworthy of your reputation.

  1. What are our people selling?

Our products:

“Why should you care? They may be selling only the products they’re comfortable with, making it difficult for them to sell new solutions to new customer types. Are they selling our vision, or simply what’s in the kit bag?”

Whatever I can persuade the customer to buy:

“Why should you care? Bespoke solutions are often not scalable, supportable long-term, and are rarely replicable, so today’s revenue may be hiding a future problem.”

Both of the responses above demonstrate a lack of strategic, long-term vision, or a willingness to do the hard work. But we know that putting in the additional effort could be greatly rewarded. Does your CRO understand the value proposition of the business or are they simply lazy?

  1. What is our share of wallet within our customers?

I think we have all the business possible in our accounts:

“Why should you care? They said ‘I think’ not that they ‘know’.”

In this instance, we need to be able to quantify actual spend vs. potential spend to help us understand clearly whether your CRO’s statement is accurate. Once determined, we can allocate time and resources appropriately on whether to retain or grow an account.

I’ve been growing this account year-on-year:

“Why should you care? Sounds positive to me. As long as the numbers continue to go up, who cares?”

This is a short-termist attitude which will lead to a reduction over time. Do we actually know whether the client is spending more money and if the growth reflects the increased spend? Or, proportionately, are they spending more elsewhere, equalling a reduced share-of-wallet?

  1. How many times have you restructured sales in the last 10 years?

Every time the CRO changes:

If this is your answer, you are simply moving the deck chairs based upon the whims of your new hire.

Every time our competitors change, we change. e.g., we heard our competition is expanding its inside sales function therefore we are:

This reactionary sales strategy is equivalent to ‘keeping up with the Joneses’. Whilst you might perceive that you are direct in competition, you are unlikely to be identical. Forge your own way forwards – innovation got you here, not copying everyone else.

  1. Can we define what an effective sales function looks like?

Yes, we have one:

This answer is only valid if every salesperson achieves or exceeds quota, and all revenue and profit targets are met; it has nothing to do with a change in behaviour which will allow you to achieve the outcomes you need.

Yes, we’ve invested in a full sales enablement suite, and its AI tells me that everything is trending the right way:

Data is fantastic but it’s also historical. Meanwhile, your business strategy is evolving, so you need forward-looking indicators to move the dial in the right direction. Machine learning based upon six months of practices that haven’t worked will not help you, it will perpetuate the same performance as before. A new standard model is required.