Lessons from Great Sales Reps

Why do the best sales people think they are losing the deal until the day they win?

An observation that I have repeatedly made over my career is that the best sales reps think they are losing the deal until the day the win. Conversely, the less successful reps often think they are in the lead right up until they get the call that they have lost. Why is this?

There is a phrase that I first heard 25 years ago: "He got his happy ears on". It is easy to fall into the trap of being overly optimistic and overestimate the good news indicators that you hear. The buying process within a company is often a complex. It usually involves many stakeholders with varying levels of influence and control of the final decision. It is also subject to the ambiguities and politics of a decision-making process in an organization, especially in larger companies.

Great sales people cover every base possible. They recognize that there are multiple stakeholders and that solution needs to either meet the needs of the majority (the most powerful majority) while neutralizing the dissent in those stakeholder groups that they can't win over. To do this, they need to understand the prospective customer's organization, people, personalities and politics to determine where are the power bases, who are the influencers and how are decisions really made. Great sales people often have a better understanding of how to drive a decision through an organization than many of the people who work for that organization.

Great sales people also recognize that the buying decision is complex, fluid and constantly changing. This means they must always be in front of their prospect so they can stay on top of the subtle shifts as they happen. They follow the old adage that "if the prospect isn't talking with you, then they are probably spending time with the competitor ", so they strive to always be present.

If you are a start-up, what does this mean to you?

Many of the lessons that you can learn from great sales people apply to founders. Founders often suffer from "having their happy ears on". By nature, they are driven to want to make their "thing" successful. After all, they conceived, gestated and gave birth to their company. The need for their solution is often intuitive to them and their passion for their company drives them.

Unfortunately, the rest of the world doesn't intuitively see what they see. They are looking at the landscape through a different set of lens. All of them have a common equation that they are considering: Risk versus Value.

Investors and prospective advisors see your start-up as one of many trying to establish a share within a market and are speculating on whether the market is large enough and who will be successful. Your prospective customers are considering your viability; ability to execute and deliver; the value of your solution; and the options available from other sources. Your prospective employees are considering the challenges they will face, the experience they will gain, the attractiveness of your culture and rewards they will reap.

Great founders, like great sales people, also cover every base. They assume the investment deal won't happen right up until the money is in the bank and work multiple options at once. They cover every aspect of the investors' needs to ensure they come out on top of the investment selection. With prospective customers, they seek out the innovators and risk takers who have a need or pre-disposition to be an early adopter and develop depth relationship with these key advocates. With employees, they recruit those that thrive on the energy and controlled chaos of a start-up and they weave them into the web that drives their passion.

Raising money, selling early customers, and finding great employees is hard. Don't underestimate it. Invest the time to develop relationships with prospective investors, customers and employees. Make sure every angle is covered. But most importantly, harness your productive paranoia and assume that you are always losing, right up until the day you win.