Books for
Sales Reps

The best books for sales reps are The Challenger Sale by Matthew Dixon and Brent Adamson, SPIN Selling by Neil Rackham, Gap Selling by Keenan, You Are Capable of More by Chris Sund, Fanatical Prospecting by Jeb Blount, and Influence by Robert Cialdini. Rackham is the foundation and Dixon is the one most likely to change how you run a call.

A category that needs filtering

Sales has more books written about it than almost any other job, and most of them are somebody’s personal system dressed up as a universal law. Every one on this list is here because it rests on either real research or a genuine operating record, and I left off several famous names for exactly that reason.

The other thing worth saying is that technique is usually not the binding constraint. I have run sales organizations for fifteen years, and the reps who struggle are rarely the ones who do not know how to ask a discovery question. They are the ones who stopped making calls in week two of a bad quarter, or who took a lost deal personally enough that it cost them the next three.

So this list has two halves. Four books about how selling actually works, and three about the part that is harder, which is doing it again after it did not go well, and doing it in a job where your number returns to zero every quarter for as long as you stay.

SPIN Selling by Neil Rackham

The foundation, and still the most rigorous thing in the category. Rackham’s team observed thousands of actual sales calls and compared what worked in small transactions against what worked in large ones, and the finding was that they are close to opposites. Classic closing techniques help in small sales and actively hurt in large ones.

The framework, situation, problem, implication and need-payoff questions, is the ancestor of most discovery methodology sold today. It is dry and it was published in 1988 and it is still the book I would put in a new rep’s hands first.

The Challenger Sale by Matthew Dixon and Brent Adamson

The most useful modern research in the field. Dixon and Adamson profiled thousands of reps and found that the relationship builder, the profile most sales cultures were selecting for, was the weakest performer in complex sales, while the challenger, who teaches the customer something about their own business, was the strongest.

The finding has held up better than the training industry that grew around it. What aged badly is the workshop version where challenging turns into lecturing, which is not what the research described at all. Read the book rather than the deck somebody made about it.

Gap Selling by Keenan

Smaller and less polished than the two above, and more immediately usable than either. The core argument is that you are not selling a product, you are selling the distance between where the customer is now and where they want to be, and that if you have not established that gap in concrete terms then there is nothing for your product to attach to.

It is blunt to the point of abrasive and it will make you uncomfortable about your own discovery calls, which is the point. Good for a rep who knows the theory and keeps losing to no decision.

Fanatical Prospecting by Jeb Blount

Expect to dislike this one. Blount’s position is that there is no clever technique that removes the requirement to fill a pipeline, and that most reps in a slump have an activity problem they have quietly reframed as a skill problem so it feels more solvable.

He is right about that, which is why the book keeps selling despite being repetitive and occasionally preachy. The most useful chapter is on the thirty day rule, which is that the work you do this month lands sixty to ninety days out, so an empty week does not hurt today, it hurts in the quarter you had already stopped worrying about.

Influence by Robert Cialdini

The academic foundation under most persuasion writing, from a psychologist who spent years studying how compliance professionals actually operate. Reciprocity, commitment and consistency, social proof, authority, liking, and scarcity.

Read it for two reasons. It explains why some of what you already do works, which lets you do it deliberately rather than by accident. And it makes you much harder to manipulate yourself, which matters in a profession where your own vendors and managers are using the same principles on you.

The Qualified Sales Leader by John McMahon

The book for the fork, when a strong rep gets offered a management role. McMahon ran sales organizations at several enterprise software companies, and this is written from operating rather than from theory.

He is specific about the failure everybody makes, which is continuing to sell the deals yourself because you are still the best closer in the room, instead of building reps who can. Very enterprise-flavored, so translate if your market is smaller, and the diagnosis holds regardless of deal size.

Which one to pick

If you want one, read SPIN Selling. If you have already read it, read The Challenger Sale, and if you have read both and are still missing quota, the problem is probably in Blount rather than in technique.

Common questions