What Separates the Best Sellers?

I’ve had the good fortune to be around a lot of very good salespeople throughout my career thus far. Some of them have worked alongside me and others I have hired. What I find fascinating about all of these people is that they were so wonderfully different. While some were very charismatic and outgoing, others were much more modest, quiet, and soft-spoken. Yet there were still a handful of traits that united them all.

1. Relentless Pursuit

The best sellers I have ever worked with engaged in relentless pursuit. But what I mean by relentless pursuit is probably different than what it sounds like at the outset.

What most people probably imagine when I say “relentless pursuit” is hard workers who are very persistent with their prospecting or with their prospects. I actually mean something a little bit different.

What I mean by this phrase is that the best sellers I have ever worked with treated themselves as franchise owners of a business and modeled out their business accordingly. They were relentless in understanding the minutiae of the activities they needed to perform on a daily basis in order to hit their goals. They understood the conversion data of their own pipelines and how they were evolving without needing a sales leader to intervene. They were proactive in diagnosing issues.

Moreover, the best sellers I have ever worked with have also been relentless in pursuit of personal and professional excellence. They tend to be people who are interested in always getting better. They have the growth mindset and seek out criticism and coaching constantly. 

This is what relentless pursuit looks like. It is not nagging people or making three hundred cold calls a day. It’s being meticulous about the details and building out a strategy and staying very close to that strategy. It’s looking to get 1% better every day.

2. Genuine Curiosity

The most important skill to have in sales is listening. I always ask new hires about this on Day 1 and make sure we spend a good chunk of time talking about the importance of listening. And to be sure, a lot of sellers ask good questions and listen.

But here’s a hot take: I would posit that a majority of these sellers who ask a lot of questions and do a lot of listening are not asking those questions for genuine reasons, nor are they genuinely listening. And the reason for that is because they are not genuinely curious.

So what are they doing wrong? Well, when your motivation is to sell your product, naturally you can still follow a script given to you by your sales leader to ask certain questions. And those questions may very well be good ones. And you may very well be capable of sitting back and being patient and listening and not interrupting. But it does not mean that you are truly listening. It just means you are looking to hear what you want to hear, and asking follow up questions that might drive you to that outcome.

The best sellers are completely detached from the outcome. They realize – smartly – that their time is best spent with people who they can truly help. They are not afraid to get to a “no” quickly in their sales conversations. They realize there was life before the prospect and there will be life afterward too. This enables them to ask the right questions, and in doing so, it also enables them to actually hear what the customer is saying.

Trust me when I say this – your prospects can tell the difference. No one likes showing up to a discovery call just to answer a list of questions. People do, however, enjoy feeling like they are partnering with someone who can actually help them.

3. MultiThreading (External)

This one does not really come as a surprise to anyone – we have all heard about the importance of multi-threading lately. In fact, I was interviewed about it a year ago for a podcast. One of the main drivers for this is the revelation that buying committees have gotten bigger and bigger. In the good ‘ole days, a decision funneled up to one individual who had signing authority. Now, there are larger groups making decisions together, which drives the need for multi-threading.

With that being said, I think multithreading has always been very important, and the larger buying committees have merely created more awareness around it. I say this because in any decision, there have always been various people and personas affected irrespective of whether or not they all had decision-making or even influencing capabilities. 

For example, it is often said in the context of the MEDDPICC framework that you might be wasting time with a Coach (not a Champion) or someone else who does not influence a decision. I think that is erroneous. In one of my past jobs, we would interview the actual potential users of our product. These were typically individual contributors who had no say whatsoever in a decision. By interviewing them, we better understood their current workflow and the implications of not solving their pain. We could then gather this feedback and tell it to the leadership team straight from the horse’s mouth. This was time very well spent.

4. MultiThreading (Internal)

The type of multithreading you hear much less about is internal multithreading. To be sure, many sales cycles are very transactional and in those cases, the salespeople are often self-sufficient. In other words, they do not need to rely on internal peers in order to drive their deals across the line.

For the rest, multithreading is essential, and also not often discussed. It is assumed that the sales team has whatever it needs…the collateral, the sales engineers, the answers from product. In some ways, it is the responsibility of a good leader to help ensure that the team has all of these things. But not all teams have great leaders. And sometimes you need to get creative. This means that if the collateral does not exist, you may need to create it, or find someone who can. When there is a customer with very specific integration questions, it means you may need to build an asset that speaks to their questions, or find someone who can help you on a call. It also often means several internal prep calls so that you can align various internal stakeholders about what is happening and what you need from them. Not to mention keeping them motivated to help you out.

Good sellers can do all of the above. It is not an easy task. But the best ones find a way.

5. Paranoia About Risk

This one is my favorite by far. I have sometimes joked in job interviews when asked what I look for in sales hires that I want someone who might suffer from a form Obsessive Compulsive Disorder. The thing is that I am not really kidding. The absolute best salespeople you will ever work with are paranoid about risk in their deals. Let me explain.

Most times you will show up at a forecast meeting and a sales rep will tell you everything that is going well in a deal. I generally find this to be a waste of time for a number of reasons. First, there is an inherent bias for people to be positive about their own work in a group setting. But more importantly, the meeting is not for us to pat each other on the back. It’s to get an objective outlook on the future and to figure out ways to mitigate our risk in achieving that forecast.

What is far more productive to be a top seller is to think about what can go wrong in your deal at all times. Of course, you need to be fair-minded about it and not assume that your decision-maker might get hit by a bus the next day. While that is entirely possible, it is highly unlikely, and we have to keep it all within the realm of possibility.

Sometimes it is really out of your control. I recall one time I was selling to a top bank and just as we were about to start looking at legal agreements, they found out they were being bought out by a private equity firm. The PE firm wanted a hold on all purchasing. Maybe someone can coach me on a way around this, but I never found one.

Usually though the risk is a lot more obvious. It might be that you have not engaged a specific stakeholder, who, despite not being a decision-maker, has the ability to throw enough of a fit that others might cower and decide not to move forward. Perhaps yet another risk is that the people you are speaking with are self-identified as having the ability to take a decision but have not proven to you that they have taken similar decisions in the past.

Whatever it is, get paranoid. Being paranoid is the best way to make sure something you feel good about will not fall apart. A lot of times, your customer is not as paranoid as you need to be. Your champion may not even be aware of the thing that can go wrong when it does go wrong. It is your job to know before them.