How to Craft an Appropriate Sales Strategy

You have valuable goods and services, and want to sell, people and organizations have needs, and want to buy.  Connecting the two and finding/crafting sales and marketing talent that drives growth is no simple task.  To craft a selling strategy, one must first understand the product.  I like to categorize based on two factors– complexity and price.


There Are Four Kinds of Products:

First are the low price, low complexity products.  Cheeseburgers.  Pens and pencils.  Toilet paper.  Video games.  Water bottles.  Buyers of these products don’t need a lot of help, they aren’t very concerned with the price unless it is perceived to be exorbitant, and they usually aren’t willing to wait long for delivery or implementation.  Selling strategy needs to match these needs.  Marketing needs to offer up enough information for buyers to make a decision quickly and without a lot of help.  Selling generally takes the form of order taking, person to person selling, or being available and accessible to help immediately if a question arises.  Transactions are generally of two types– high volume or high frequency.  giphy (1).gif

The second category are the low price, high complexity products.  Operating systems.  Masseuse services.  Mobile apps.  Bicycles.  Graphing calculators.  Hedge trimmers.  Buyers of these products need some guidance, but also want the information they require to be readily at hand.  They value consumer feedback and customer reviews very highly in their purchasing decisions.  They expect to be able to understand how to use these products almost immediately, and any instructions need to be as close to self-explanatory as possible.  The selling strategy for these kinds of products needs to take the form of guidance.  Marketing is at its best when it tells a narrative of some kind– demonstrating features and value rather than explaining them.  Salespeople for these types of products must have the wherewithal to know when to interject some advice and when to get out of the way.  Good, better, best is often a good product presentation strategy.  Transactions are generally more focused or intentional– less frequent and less volume per transaction, but usually at a slightly higher price each.giphy (2).gif

The third category has relatively high price, low complexity products.  Cars and trucks.  Smartphones.  Tailored suits.  Airplane rides.  Laptop computers.  Live event tickets.  Buyers of these products need to see value, and a lot of it.  Generally the purchasing decision involves more planning and thought than the previous categories.  Buyers will have complex value questions, and need someone to provide intelligent answers.  Selling strategy should be very much value based– not necessarily focusing heavily on price, but providing a buying experience that overflows with benefits.  Marketing should focus on these benefits– and while feature comparisons should be available, they should not be the primary focus.  Salespeople for these kinds of products should be able to offer free trials and have price flexibility to close more deals.  Cross selling and services tied to products of this kind are appropriate.  Skills like handling objections and addressing complaints are much more important to successful growth.  Transactions are much less frequent than the previous two categories, but also much higher in price.

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Finally the fourth category– high price, high complexity.  Technology consulting.  Engineering services.  Municipal infrastructure.  Real estate.  Government/Military contracting.  Buyers of these kinds of products often have a significant knowledge problem.  They have an idea of what they want, but don’t know the process to get where they want to be, or the implications of decisions they make along the way.  Inherent product value is obviously important, but not as important as the value of the expertise offered in the selling process.   Selling strategy should focus on giving the buyer peace of mind at each stage in the buying journey.  Significant, often lifesaving trust is being placed in the seller, and the selling process should offer whatever is necessary to put the buyer at ease.  Marketing should focus on the value of the process AND the success of the end result.  Salespeople need the skills to articulate concepts that will likely challenge the preconceptions the seller has.  There is a fine line to be walked here– establishing trust first and following immediately with well-reasoned, timely advice.  There are likely to be many instances of stress and many pain points to be alleviated ahead of a purchasing decision.  Transactions are very infrequent, and at higher cost than any previous categories.

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Important Notes:

Align your selling strategy with the category your product falls under– even if your competition does not.  Deviating too far in any direction can be detrimental to success– a cheeseburger marketed and sold like a laptop is more likely to confuse and irritate buyers than to successfully demonstrate value.  A bridge marketed and sold like a used car will fail in like manner.  This also applies to pricing and product development.  If you have sales and marketing talent based around the skills required to sell water bottles in great numbers– releasing a product that is significantly more complex or sold at a much higher price will fail without new talent and tactics.


How to Sell Using Benefits (now with extra Milton)

Selling on benefit rather than on features is an art form most understand, but few perfect.  Before you can master the art of benefit selling, we need to define some terms.


Features are aspects and attributes.  Speeds and feeds.  Features are what makes something work, and what it can do.  The differences are important here, so let’s use the venerable Swingline stapler as an example.


Some features of the Swingline are as follows:

  • It comes in red (sadly mine is black)
  • It holds precisely 210 1/4″ staples at capacity
  • It’s mechanism delivers staples more reliably than the Boston

While important in the discussion, only below-average salespeople will attempt to close deals based on features alone.  Features force your customer to make two leaps of thinking on their own before they can make a decision.  More on that later.



Advantages are positive properties of a product that its features enable.  They are almost always intangible.  Advantages are what the product lets the consumer do, or the intangibles that it apart from the competition.  Note that each feature will have a corresponding advantage as described below.


Advantages of the Swingline:

  • Color options for every taste, as long as you have a taste for red (or black)
  • More stapling between reloads
  • Doesn’t bind up as much as the Boston

Most salespeople stop their analysis here, and call their advantages benefits.  Yay!  Benefit selling complete!  Don’t make that mistake.  They do themselves and their customers a disservice.  Advantages give a clear picture of the product and what it does, but do little to help ease the pain of decision making.  You want to ease that pain wherever possible.



Benefits are often confused with advantages, so here’s a definition that clearly delineates the two: Benefits are emotions and/or feelings that the advantages of a product help to instill.  They are not related to the features of the product itself, but the experience of using it.  Benefits take some thinking to identify accurately, which is why only the top salespeople sell on benefits.  Note that benefits don’t necessarily have to correspond exactly to a specific advantage, but they can.  In my examples, I make them correlate.  Also important is the formula for describing them, which is: Emotion + Relieved Pain Point.  This lets you identify exactly what emotion will be felt when the associated pain is relieved.  I’ll explain each below for these to help get your thinking on the right path.


Benefits for the venerable Swingline:

  • Feeling of satisfaction from the relieved lack of individuality in an office environment.
    • Office spaces can feel drab and too-uniform.  A shiny red stapler can give an otherwise gray cube a unique piece of flair– making the office worker feel satisfied that they aren’t just a number.
  • Feeling of relief from the extra productivity of not having to interrupt your collating as often to refill staples.
    • If you’re right in the middle of a tricky batch of TPS reports and you have to get up to get staples, you’re going to forget the cover sheet.  Relieving that stress with less trips to the supply closet will get the 15 minutes of real work you do in a week done in 10.
  • Feeling of love/loyalty from the from the removal of the poor comparative performance of the Boston.
    • If you were forced to use a Boston stapler that bound up regularly you would feel frustrated.  That frustration would turn to loyalty and love when presented with a superior Swingline.

Decision Making is Emotional

Salespeople who take their product analysis to the emotional benefit level and adjust their messaging accordingly will reap rewards over those who don’t.  This is because decision making, especially at an organizational level, involves pain.  Pain begets emotion, and even the most logical thinkers appreciate the release of emotional pain.


Stop selling on features and advantages alone.  Analyze your customers and your products and sell on benefits.

Important Notes

Not to go all Uncle Ben on you, but with great power comes great responsibility.  Selling on benefits that don’t actually materialize will alienate customers faster than not responding at all.  Remember– don’t be a scumbag.

I see many amateur attempts to sell on benefits by stating the emotion that will result from a purchase– IE:

“This stapler will make you feel confident!”

This is a mistake.  The stapler won’t do anything of the sort, and you’ll look like an idiot in front of your customers.  Remember: it’s not the product that gives the benefit, it’s the usage.  Rather than “this stapler will…,” build your message intelligently.

“You can comfortably rely on this stapler’s performance– from the first click to the 100,000th.”

They both say the same thing, but the first merely expresses an emotion while the second instills it.  Never express benefits.  Always instill.


Happy Selling.

How to Cold Call: The Definitive Guide (Now with .GIF’s!)

Since the early 80’s, cold calling has been the fastest and easiest way to turn ordinary people into laser-focused selling machines.  Turning technology into dollar signs, this guide will teach you how to cold call like a pro– unflinchingly confident, wildly successful.  First– a bit of history.

Cold Calling Was Born of Technology

When it was born, cold calling was cutting edge.  The status quo for getting new business was through social connection– formal meetings, dinners, drinks, and subtlety.  It was an art form that took years to master, cost inordinate amounts of money to perfect, and often backfired.  Cold calling changed the game.  Rather than putting highly-paid, highly-trained salespeople in front of customers, why not use technology to have the same conversations in an abbreviated fashion over the phone?


The strategy turned the business world on its head, and was wildly successful.  Organizations that invested the time and resources in the technology and people who could effectively use it succeeded, while those who clung to the rigid ways of the past slowly faded into obscurity.  The idea was genius, the timing perfect, and the execution flawless.

Customer Confidence

Initially, cold calls worked.  People answered the phone because the person on the other end usually had something important to say.  Getting phone calls from important businessmen was thrilling, like getting a thousand likes on your Instagram pic in the first 5 minutes.  Quickly, however, the luster began to fade.  Turns out when you don’t have to look a person in the eye, you can lie to them with much greater effectiveness.


Salespeople from increasingly dubious organizations picked up (pun intended) on the practice, finding an easy way to mass produce their swindle attempts.  Soon, even legitimate cold calling found hit rates in the single digit percentages.  What was once a way customers wanted to be contacted was now a nuisance.

The Safe Bet

Despite the declining effectiveness, detrimental branding, and increasing cost– cold calling was so successful initially that over time it became (and still is) a ‘safe’ bet.  Risk-averse organizations had a tried and true formula for generating new sales.


Put bodies on phones, tell bodies things to say, repeat as much as possible.  It became an integral part of a salesperson’s repertoire known infamously as– the ‘hustle,’ playing the ‘numbers game,’ or ‘putting in the work.’  As with all things, what was once cutting edge became widely used, and what was widely used became standard practice.  While the smart players moved on to other means (email, then social media, then inbound content), safe-betters could still see success.

The Problem

Today, cold-calling is still widely used.  C-suite professionals can expect their public-facing phone numbers to ring continuously every day as increasingly desperate and burned out salespeople try to reach “decision makers” to peddle their goods.  Organizations still report wild success with cold calling, but a problem in each lies just beneath the surface.  Cost.


Let’s look at some of the numbers, with percentages taken from actual results of a successful Minneapolis SaaS company that relies heavily on cold calling:

Sales Dev Group A makes 1000 calls/day.  Their list is good and their strategy sound, so of those calls, they get 300 people on the phone.  Of that group, the highly skilled SDR’s find 50 that are relevant or convinced enough to agree to a follow-up of some kind.  A very solid 5%.

Through an above-average qualification process, 30% of those follow-ups have the need, ability, interest, and time to investigate the solution and are passed off to inside sales and account executives.  30% of 50 is 15, so there are now 15 qualified leads to work.

Those 15 leads get worked, and a highly trained, highly capable team of reps does a great job and generates 7 qualified opportunities from the 15 leads.

Those 7 opportunities are worked diligently, bringing in engineering resources, doing demos, everything needed to close the business– which is successful on 4 of them.  Overall, 4 wins out of 1000 contacts, or 0.4% success.

I think everyone would agree that those numbers, while somewhat sustainable, are far from ideal.  The problem is this:  Cold calling costs too much.  It sucks money from everywhere– marketing, product development, leadership… everywhere.  The opportunity cost of continuing to blast cold calls outweighs the benefit.

How to Cold Call

So.  You came here for a guide on how to cold call, and here it is:  Don’t.  Real success in sales doesn’t come from what was cutting edge 40 years ago.  You wouldn’t allow IT to give everyone Apple II’s, so there’s no reason you should allow your sales department to live that far in the past either.  Success in sales process comes from the same question that spawned cold calling in the first place:  how can we reach more prospects where/how they want to listen with less effort?  Go back to the beginning, and find where your prospects want you to be.  Learn what gets them excited to interact.  Steer that interaction to your business needs.  Find a way to do it en masse, and for goodness sake put down the phone.





Increase Sales Credibility with High Value Touches

*Ring Ring* -pickup-

“Company G, Frank speaking.”

“Hi Frank, this is Christian from HowToSales- I just wanted to check in to see how you were doing.  Is there anything I can do to help out?

“Nope, we’re good.”

“Ok, great.  Thanks!”


What a waste of time- for both of us.  Low value touches like this are all-too-prevalent among average, quota-missing salespeople.  Instead, learn to use sales touches to increase your chances of success by taking a high-value approach.

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How to Find the Best Sales Jobs (for you!)

Whether you’re just starting to look for a career or are a seasoned pro looking for a change- knowing where and how to find your next sales job requires a unique set of skills.

First: Preparation

Going into a job hunt like Officer John McClane vacations around the holidays is a good way to end up underutilized, underpaid, and unhappy.
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On the other hand, a little planning and preparation really goes a long way- especially when looking for a new sales position.  Here are a few steps to plan like a pro:

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