The Seven Ages of Selling

The Seven Ages of SellingA career in selling starts as a shiny, beautiful thing of hope, and then it ends. Hopefully the end is many years, and millions in sales and commissions later. But it ends.

Here’s a look at the arc of a selling career using the Seven Ages of Man Shakespeare made famous in “As You Like It“.

First Age – Infancy

In this stage a salesperson is like a helpless baby – they know very little and ignorance is their flak jacket.


* Tries anything & everything: wastes time & effort
* True “cold” calling to un-targeted, non-customers
* Hopes to avoid doing long-term harm

Deal Making

* Beginner’s luck: blunders into a one-off sale
* “Wow, that wasn’t so tough” – then the zeroes come

Second Age – Childhood

In this stage a salesperson seeks training and becomes a sales process fundamentalist.

The new convert is unwilling to color outside the lines, never varying from the sanctity of their 1-2-3 selling steps.


* Basic by-the-book telemarketing for appointments
* Limited, if any, targeting in a sales plan
* Limited flexibility or opportunistic response

Deal Making

* Some success & increased confidence via baby steps by-the-book
* Appears stiff & robotic with customers until makes learned process their own

Third Age – The Lover

In this age a salesperson can often be remorseful when the “sure thing” isn’t.

This is the beginning of a lifetime’s collection of war stories, and their eventual retelling over drinks with other salespeople.


* Adds LinkedIn participation to go with telemarketing & in-person networking
* Prospecting becomes spotty as more time is spent on deal making
* Begins to develop a small cadre of customers who are friends

Deal Making

* Will ask their bosses for better customer terms to close more deals
* Aware of and appreciates persuasiveness in consultative selling model
* Success comes with a few monster deals, but more frequently with smaller bread-and-butter sales

Fourth Age – The Soldier

In this age the salesperson starts to think less of themselves and more about their customers.

They are now working towards making a reputation for themselves and gaining recognition, however short-lived it may be, even at the cost of more, low profit sales.


* Balance of reaching out to new prospects & customers contacting them
* Larger network of known customers, with growing core of customer-friends
* Prospecting for new business is sporadic

Deal Making

* More emphasis is put on large, flashy, riskier deals
* Past success have given them access above their direct boss & they ask for bigger concessions to close mega-deals
* Almost every deal is a one-off, requiring lots of technical & operational support

Fifth Age – The Justice

In this stage the salesperson has reached their career’s apex.

They’re experienced and knowledgeable, and have gained prosperity and status within their company and industry.

They become very attentive to the look of success; the awards, recognition and finer things of life.


* Referrals are warm & plentiful
* Has a broad social network within the customer base
* Customer-friends help bring deals to fruition

Deal Making

* Insightful about which deals will really close, or work
* Effortlessly leads their firm through complex sales
* It doesn’t get any better than this – and it won’t

Sixth Age – Old Age

And now the salesperson begins to lose their edge. New customers no longer find them as charming, knowledgeable or intelligent as they once believed they were.

Their customers begin to retire, replaced by the new school with generational attitudes and perspectives.

They become the butt of younger customers’ jokes: their style, process and technologies appear old-fashioned and out of place.


* Haven’t actively prospected in years
* Returns to old methods that are now unproductive
* If they have enough juice with their firm, may bring on an intern to prospect using current methods

Deal Making

* Deals, though still large, are fewer & farther between
* Complex sales are more impersonal, impenetrable & Procurement driven
* Sales quotas are hit or miss, dependent on the large deal

Seventh Age – Extreme Old Age

In this age the salesperson has lost their status and become a marginalized, non-entity within their firm.

Their customer-friends are all retired, and new prospects are an unfathomable mystery, speaking a foreign language.


* No one listens
* No one cares
* What’s the point?

Deal Making

* The war stories about the big deals that made this firm are all that’s left
* The gold watch & retirement party are next week

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