Beyond 'How To Win Friends'

Pete Caputa, Vice President of Sales for HubSpot

Many of you may have heard of Dale Carnegie’s ever-famous “How to Win Friends and Influence People,”a collection of rock-solid, tried-and-true life and business advice that has helped thousands of people become successful in their personal and professional lives. For years, it has been touted as the best resource for salespeople to grow their careers – but there’s so much more out there.

I’ve assembled a list of eight superb sales books that I’ve used not only to improve my own sales career, but that I recommend to my colleagues on nearly a daily basis. In sales, any new insight or edge can be a competitive advantage, so while some of these takeaways may seem like common sense, I consider it my responsibility to ensure that I’m educating myself and my sales team and pushing our organization to new levels.

“Baseline Selling: How to Become a Sales Superstar by Using What You Already Know About The Game of Baseball” by Dave Kurlan
The first sales book I ever read was Dave Kurlan’s book, “Baseline Selling,” which equates the sales process to a baseball path – you can’t run to second base without tagging first. It taught me the biggest lesson of my then-early sales career: sales is not about selling; it is about helping people overcome their challenges. By taking the necessary steps leading up to the inevitable pitch, you are much more likely to close a deal. As a salesperson, you should focus more of your energy on finding people that have the challenges that you can solve and be more willing to walk away from people who aren’t qualified or interested in your help. It is important to put more time into prospecting and get better at disqualifying people you cannot help, while properly identifying the people who you can.

“SNAP Selling: Speed Up Sales and Win More Businesses with Today’s Frazzled Customers” by Jill Konrath
This is one of my favorite books. The author is amazing at creating frameworks for training and coaching salespeople. In “SNAP Selling,” she explains the three distinct decisions prospects make before deciding to buy (or not buy) your product or service. The three things prospect do are:

  1. Evaluate your approach to see if it’s worth their time to meet with you
  2. Determine if making the change is worth all of the disruption it will certainly cause
  3. Select the best option for your company

She also provides practical advice which we employ in our sales process heavily for helping prospects with that second decision: This advice is to get commitment from your prospect to co-develop a plan with them. By co-creating a plan to help prospects achieve their goals and overcome their challenges, salespeople can get buy-in as they are creating it and thoroughly establish that their solution is the best solution to the challenges. Also, since the salesperson is creating the plan, they can guide the plan toward their solution, proactively address any concerns or potential obstacles that might prevent the prospect from being successful.

“Sales Shift: How Inbound Marketing Has Turned Sales Upside Down Making It More Difficult And More Lucrative At The Same Time” by Frank Belzer
This book addresses one of the most important changes occurring in the sales process: how buyers are tuning out every message from salespeople. Even when leads are inbound, salespeople must first strive to be helpful. They have to serve as an advisor, a guide in the sales process. Belzer’s book has great stories and tips on how to prospect and then connect with people in a meaningful way. We apply many of these approaches in our sales process. We’re always asking our salespeople, “Do they need our help? Do they want our help? Can we help them?” “Sales Shift” provides a thoughtful argument about why this approach is right for both the prospect and the salesperson.

“The Challenger Sale: Taking Control of the Customer Conversation” by Matthew Dixon
Dixon makes a strong argument that a sales manager’s primary role is to collaboratively work with salespeople to innovate at the deal level, and to unstick stuck deals. In complex sales, like ours, where different prospects have different (and multiple) problems and operate within different constraints and resources, moving deals forward creatively is absolutely critical. Arming your sales managers with the energy and insight to serve as catalysts for the deals their reps are working on it paramount, and “The Challenger Sale” provides unique perspective on how to infuse this objective into your processes, training, and systems for sales managers.

“New Sales. Simplified.: The Essential Handbook for Prospecting and New Business” by Mike Weinberg
Weinberg outlines how you can make sure that your sales pipeline is balanced, breaking prospects down into “hot, active, and target buckets.” As our database has grown, we’ve had to get more disciplined about which opportunities we invest more time and effort into, so, we’re applying this principle to our sales methodology. One other big takeaway you can use in your everyday calls are what Weinberg calls “power statements” – a way to get prospects to share their challenges early in the sales process. You introduce your unique differentiators, introduce challenges you’ve helped similar companies overcome, and ask an open-ended question to start a dialog. By introducing the challenges, outcomes, goals, pain points, opportunities that you’ve helped other companies address, prospects may better relate and be more comfortable opening up.

Good books alone won’t create great salespeople, but taking the time to improve on your strategies, techniques and approach every day certainly does. These books have provided insight that has informed the HubSpot sales approach, shaped my career and helped many of my colleagues and team members become stellar sales reps and managers.

Pete Caputa is Vice President of Sales for HubSpot, developers of all-in-one marketing software helps more than 10,000 companies in 56 countries attract leads and convert them into customers.