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We’ve all been the recipients of particularly bad prospecting efforts. As a CEO and sales leader, I’ve noticed salespeople make a few common mistakes when reaching out to me. Some prospecting mistakes can be subtle, but there are a few ways to kill a deal before it even takes its first breath. And they are anything but subtle. If your reps make any of these mistakes, it’s your job to coach them through it. As a sales leader, you’re in a unique position to help reps slip into the shoes of their prospect and actually feel how their approach comes across. Building that kind of empathy is key to actually creating meaningful engagement and earning the right to ask for a next step. Make sure your reps start 2016 off on the right foot with these key lessons.

Baron Schwartz is the Founder & CEO of VividCortex, a SaaS product for database performance monitoring that accelerates IT delivery and improves performance.

1. Earn Your Right to Sell

Many sales reps don’t understand that attention is earned, not deserved. When your reps are asking for a first conversation, they need to give before they get. But what about the first few words the rep and the prospect ever exchange? Has there even been an opportunity for the rep to give yet? Yes, there has, in fact. The first words the rep writes or says to the prospect need to demonstrate that prior to the outreach, the rep has gone to considerable lengths to research the prospect. This is why the rep needs to begin by saying “I’ve already given you [my time and effort] and that justifies me asking for your attention for the next few sentences.” It’s easy for reps to forget that each word they say has but one purpose: to earn the right to say the next. A rep recently reached out to me with a cold email, absent any engagement or interest from me, that went like this: “Thank you for your interest with (company).  I look forward to connecting with you. Please provide a couple good days/times you have available this week.” That was pretty much the whole email. There are so many things wrong with that email, I hardly know where to start, except by pointing out that the rep obviously had not earned the right to ask me for a call.

Your rep’s first email or call is trying to sell something simple: the privilege to have a conversation.

Your rep’s first email or call is trying to sell something simple: the privilege to have a conversation. That privilege must be earned. At each step in the selling and buying journey, the rep must lead with a demonstration that what he or she is asking for has been earned. Reps have to earn a call, they have to earn the right to claim they can solve a problem, they have to earn the right to ask for information about the prospect, they have to earn the right to send a proposal. So few of them understand this. If you coach your reps on this, they’ll be miles ahead of the competition.

How can a rep earn the right to ask something from a prospect? In most cases, you earn by giving the gift of attention. The best way is by demonstrating that you have researched and really understand the prospect’s life. When prospects reject sales people, the root reason most of the time is that they fundamentally don’t believe a salesperson will really listen and understand. If your reps don’t understand the lives of the people they’re selling to, you need to help them walk a mile in their prospects’ shoes.

2. Don’t Simulcast or Prospect Groups

Many business leaders belong to multiple email groups in their organization, some of which are necessarily open to inbound email from the Internet. I’m talking about jobs@company.com, info@company.com, sales@company.com and the like. Few things irritate me more than prospectors sending messages to these groups. Similarly, if I see that a prospector has sent messages to me and several others at the same time, I’m highly likely to tell them to go away and not come back. If you use a technology that automates outreach, your reps might be doing this. And it’s not the reps’ fault. They’re just being efficient with the tools you gave them. I coach my reps to do personal outreach to the most likely prospect before setting up automation. When I do personal outreach, for example, I’ll reference 2-5 things I found online, and not just in a superficial way. I won’t just name-drop a blog post–I’ll discuss something you have to scroll down 3 screens to find. And, I won’t just mention it. I’ll actually extend the topic one step further as a conversation. If this initial attempt doesn’t work, automation might be a helpful tool, but it needs to be used judiciously. Reps may resist this because it requires a high level of research. You can only do so many deep research efforts every day because the pressure is on to hit the numbers. Point out to your reps that this research is table stakes for getting a conversation started anyway, and refer to my previous point to justify this claim.

3. Learn How to Read Between the Lines

Research is great and necessary, but if you get too focused, you might miss the forest for the trees. Keep an eye on whether your reps are missing the obvious.

read lines

For example, when we were a team of about 20 people, a sales development rep reached out to me asking who was the “appropriate person” to discuss a technology choice. If that rep had even done a minimal amount of research on LinkedIn or our “about us” page, he’d have seen that there was literally no one else at the company who was even slightly appropriate. I admit that I might have flown off the handle a bit. I wrote back caustically asking him who he thought was the appropriate person in a company of 20, if not the CEO? This type of bull-in-a-china-shop prospecting demonstrates clearly that the rep hasn’t done any research, or isn’t clued in enough to understand what the bare facts imply. Your reps need to be coached on this, on a case-by-case basis, by individually reviewing accounts. Especially when they are new. You have the experience as a sales leader to help them formulate an appropriate outreach strategy. They don’t. There is simply no substitute for one-on-one review of individual accounts and their communication history. One strategy I like is to ask reps to select 5 recent email threads and forward them to me, and I’ll give my unfiltered impression as though I’m the recipient. It’s hard to put yourself into the recipient’s shoes when you wrote the words. But it’s easy for me to play that role and reflect back to them how I’d feel and what my impressions would be if they’d sent the email to me. I have found this to be an easy and effective way to encourage reps to get reps to evolve their communication strategies.

4. Stop Bouncing Accounts Around Without Notes

There are a few companies that I don’t know very well, but I can tell do not have a culture of detailed record-keeping in their sales teams. I know this because every time they churn through a sales rep and a new one replaces a departed one, I get called all over again. Despite the fact that I’ve already explained patiently to three people that the product is not relevant and never will be relevant, the next rep never seems to have a clue that the previous conversations ever happened. This is a sure way to create enough frustration to lose business, but it’s not just burning good leads by treating them badly. It’s also wasting an epic amount of time. If your reps are repeating history again and again, never learning from each other, you really need to institute a culture of information sharing. It doesn’t have to be much. You can use the Predictable Revenue prospecting statuses—Aaron Ross suggests a few types of “avoid” and “poor fit” ones—or you can just put a summary into the account’s notes or description. Anything will work. Anything’s better than nothing.

5. Engage Inbound Leads Instantly

A few months ago I was evaluating a few different sales tools. Tool A offered me a free trial, and directed me to a signup form. After filling out the form, I realized I’d been suckered. There was no instant online access or free trial. All I’d done is fill out a contact-me form that was going to a sales team to schedule a call before the trial. At best, I was going to get a demo or GoToMeeting. It got worse, though. Not only had I not been granted access to a trial, but the Tool A didn’t contact me quickly. An hour went by, then a day, then I got an email to schedule a call, which took place the next week. Let’s think about what happened in the moments before I’d filled out that “free trial” form to begin with. I had this idea of researching a few sales tools on a low-priority to-do list, and something had happened. For whatever reason, I’d taken some time to do something that wasn’t a top priority for me. That very moment was the only time I was willing to devote to this, from an emotional standpoint. When I filled out Tool A’s contact form, I instantly realized that I was no longer in charge of the schedule for evaluating this tool. If I wanted to continue evaluating, I’d have to do it on their sales team’s terms and schedule.

It is hard to overstate what a turnoff this is. Still, it could have worked out okay—if they’d called me immediately. But they didn’t. I ended up giving them a call, reluctantly. And even if the sales call went okay, which it didn’t, my first impressions almost surely would have predicted the kind of customer support I would have gotten from Tool A. At the same time, I filled out a free trial form for Tool B. Unlike Tool A, this one actually created a fully functional online account for me to start using immediately. Within 15 seconds or so I was surfing around Tool B and I was pretty impressed at what I was seeing. I had only clicked a couple of times, though, when my phone rang. “John Smith from Tool B here,” the voice said. “I see you’ve signed up and I wanted to know if I can assist you. Do you have any spreadsheets I can help you import?” I was impressed. Tool B obviously understood that if they’d waited even a few minutes, it might be too late. My next meeting would have started, I would have gone to get a cup of coffee, or started something else. And this lightning-fast response also promised great things about their responsiveness in the future.

There is absolutely no time like the present. In sales, the present moment is golden. Nothing happens in the future or the past, only the present. Are your reps seizing the moment as it happens? There are all kinds of quantitative evidence of how magical the first few minutes are. Anecdotally, I can tell you the quantitative evidence doesn’t even capture the full story. I ended up buying Tool B, which has been so impressive I want to tell you about it: datafox.co. It’s a key tool in our sales team’s toolbox.

In sales, the present moment is golden. Nothing happens in the future or the past, only the present.

These bad behaviors have been repeating patterns that I’ve noticed. I selected them because they’re not only incredibly harmful, but as sales leaders we have at least some ability to influence our teams for the better, and in some cases a little bit of coaching or process change can make a dramatic difference. The key thing for sales leaders to understand is that these damaging practices are easy to miss if you’re not dedicating some time and attention to individual, personal, case-by-case reviews of at least a sample of your reps’ activities. You need to look over their shoulder, listen in on calls, examine notes in Salesforce, and have regular 1:1 coaching sessions to catch these kinds of things. If you do, the payoffs will be worth it. If not, you’ll risk being outrun by your competition who is making simple changes that pay big dividends.

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Baron Schwartz
Baron Schwartz is the Founder & CEO of VividCortex, a SaaS product for database performance monitoring that accelerates IT delivery and improves performance.
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