I get asked often for recommendations on books to read in order to prepare as a new sales manager.  I've probably read more than most on the topic, and so it was a challenge to narrow my list, but here was the question that I used as my frame for these suggestions:

"If I could only read five books on this topic, which ones would you recommend?"

Note: This would be my list of recommendations for someone who is focused primarily on sales management, and not building a sales organization from scratch. My recommendations here will help you: a) understand the principles of sales, b) build a basic foundational knowledge of how the sales machine works, c) provide insight into how an executive leadership team is thinking about the sales function, and d) provide tactical and practical advice for new managers on coaching, and prioritization.

On Selling Principles: The Win Without Pitching Manifesto

Hands down my favourite sales book of all time is The Win Without Pitching Manifesto by Blair Enns.  If I were to write a book on sales, it would look more like this than a lot of the other “how to pitch”, and “how to get your way” books out there.  While this book is written mainly for creative professionals looking to scale their businesses, the principles apply to any and all students of sales.  A must read.

On How the Sales Machine Works: The Sales Acceleration Formula

A common overused phrase used to describe sales is “more art than science”.  What I think people are referring to as art, they actually mean “personalization”, or taking the principles of selling and making them your own.  But I would argue that the “scientific” element of breaking down a revenue goal into it’s component parts, and then applying a metrics-driven, process-oriented lens can be learned and studied.  In this book, Mark Roberge shares his lessons learned in building a $100M business at Hubspot using these methodologies.

On How to View Sales Strategically: Blueprints for a SAAS Sales Organization

If you’re running a SAAS sales organization specifically, the team at Winning by Design have build an incredible resource in this book.  It’s less of a playbook for what to do, and more of a primer in what great looks like, and an overview of the SAAS selling landscape.  Caveat emptor however, it can be overwhelming to see how the sausage is made if you’re just getting started.‍

On Coaching: The Coaching Habit

If there were one book that I wish I read way earlier in my coaching and sales leadership career, this is it.  I don’t think I knew what a good coaching session looked like until I hired my first executive coaching my 30’s, and I quickly realized that I’d been doing it all wrong.  If you read no other book about being a great coach, and manager, read this one.

On Prioritization: Measure What Matters

Few things are worse than running in the wrong direction enthusiastically.  While John Doerr doesn’t mention the word “sales” in the text, the principles of how to focus on what actually matters, and how set up a process to measure progress, and keep a team accountable are priceless.  It reminds me of a lesson I learned from Janet Bannister:  “Business isn’t really that hard: you just have to figure out what the most important things are, and then focus on those things.  That’s it.”  Simple, not easy.