Based in Sydney, Australia, the selling business is a blog by Tony hackett and His posts explore modern strategic selling research, methods and practices.

How to Avoid Bowling a Prospecting Gutter Ball



Are you about to sit down and build out a sharp prospecting letter? You might have read up on the latest in copyrighting or headline creation techniques?

If so, don’t scrap that work but I do have something of consequence to share that can fundamentally focus your future business communication.

The Bumper Rails

I have two guides for my business communication and they come from books that are standout favorites of mine:

  1. Crossing the Chasm; and
  2. Selling to VITO (The Very Important Top Officer).

I was introduced to both of these books around 15 years ago as I joined a Venture Capital funded start-up, having previously worked as an account manager with major global tech companies.

As a confession and for a level of context, when I joined the start-up I thought I had it worked out by way of sales methodology and how to go about the business of strategic selling.

In one sense I did, as measured by deals sold. By most other measures, as I was soon to find out, I barely had any idea.

A significant barrier I needed to overcome mentally, was moving from a sales environment where I had a level of incumbency on most occasions to an environment where I had zero incumbency. As a multiplier, I was selling eBilling which was in its absolute infancy and executives at large companies were not getting up each morning hoping to find what I had to sell.

What I Learnt

I am tempted to speak to each book separately but the truth may be that the real learning is from the blended value.

Both books speak to identifying the selling and buying environment and “the chasm” is where the selling really starts. This is due to the self-motivated buyer having already bought your solution and implemented which, on balance, only leaves those that need to be convinced of your worth.

                   From “Crossing the Chasm”

                   From “Crossing the Chasm”

The chasm also presents a powerful qualifier - for you as a seller especially. This is because the onus is now on you to move fully into the mind, pressures and language of the buyer and their industry. It is in this moment that you need to determine how vested you are in the sales opportunity because you are about to move across your own chasm to a point of in-depth research including the competitive environment and financials that govern success for your prospect.

Which is where “Selling to VITO” enters your process. This book lays out a number of steps, processes and approaches that illustrate ways and means of accessing VITO. It is to be noted that VITO isn’t necessarily the most senior person in your prospects org chart, but as stated, the person who is important to solving the problems that you can solve.

One template covered in detail in the book is the VITO letter/email/phone call. It is thorough and it takes time to get right because you need to find a small number of irrefutable reasons that the problems you can solve exist and are worth solving.

…Note: I am happy to share one of my templates, just message me…

The only way you can construct a successful VITO communication is to investigate VITO’s company and competitors. You need to compare their financials and find a discrepancy that is causing pain to VITO. 

An example would be the financial ratio, Days Sales Outstanding (DSOs). The first step is for you to find the DSOs for your prospect’s company which might be 65 days as an example. Next step is to compare this with peer competitors and the market average. If you find that DSOs for competitors is closer to 45 days then you have the basis to calculate a business benefit and competitive research to make an approach to the relevant executive. You now have a problem worth solving.

Also, if your prospect isn’t a listed company you can still use the financials of listed companies in the same industry to build your pitch and trigger VITO’s interest.

Focused Communication

You can only distill your understanding of the problem and your ability to solve the problem through mindful research. If you think broad and loose will win - I guarantee it will not. You might land a punch now and then, but you will not sustain successful, targeted pipeline development.

This “Chasm & VITO” approach will provide you with a repeatable process and framework that will serve:

  • Territory segmentation.
  • Account prioritisation.
  • Opportunity qualification.
  • Calculating your business value to your prospects.
  • Proposal construction.

I am confident that this approach can become a powerful path in your prospecting and business development.

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