Calling Prospects

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Cold-calling is the epitome of everything that scares first-time sales staff. While not face-to-face exactly, it’s a synchronous interaction with the very person who can reject your solution, which, of course, your own personal worth is pretty heavily tied to. Why would I possibly want to put myself in a situation where someone could stomp on my product and, by extension, me? For a lot of reasons, actually—because synchronous verbal communication, miraculously, is a really rich way of communicating and gathering information. It’s almost like it might be one of the linchpins of the last few hundred thousand years of human evolution!

The trick to calling on your prospects, unsurprisingly, is similar to the trick for engendering email responsiveness: make sure that your solution is relevant to their situation, get your point across with clear messaging, and demonstrate that you are concerned about their situation with a customized, prospect-centric approach.

So let’s shed that fear of cold-calling right now. Yes, it will take some getting used to. But remember, you’re calling highly qualified contacts who have the problem you solve, and you’re seeking to help them solve that problem. Who wouldn’t welcome that?

Call Timing

The success of your phone outreach will often be contingent on the times at which you call. Connect rates can vary substantially depending on the day-in, day-out tempo of your prospects, so being in tune with this is helpful. If you’re calling on white-collar office workers (you might be a recruiting or sales solution and are calling on Directors of Sales Operations or VPs of Talent Acquisition), then your better bets are going to be early in the morning, just as people are getting into the office, or at the end of the day. Middle of the day is tougher because people are away from their desks, in meetings, and going to or coming from lunch. Another trick can be particularly late calling. If you want to avoid gatekeepers and get directly to a senior executive, often they are still around at 6 p.m. or 7 p.m., when executive assistants have gone home.

If you’re calling on small businesses, these times may be totally different. If you sell to restaurants, calling in the middle of service is a great way to piss off your potential customer! Figure out when your decision-maker’s day begins (maybe it’s 9 a.m. or 10 a.m. if they serve lunch, or maybe it’s the 2 p.m. or 3 p.m. doldrums between lunch and dinner service). Because all of your customers (assuming they conform to a similar profile) will likely share this cyclicality, when you get to the point of calling against customers in multiple time zones, you can prioritize the ones whose time zone is within the raised connect-rate interval, and follow the proverbial 10 a.m. hour as it moves from eastern to central to mountain to Pacific time. Think about what the right day cycle timing is and target your calling then. Otherwise the proportion of your calls that result in connects will suffer.

Context-Sensitive Timing

As discussed earlier, email instrumentation via Yesware, Tout, Outreach, and others can be particularly helpful in making your calling more effective by showing you which of your prospects have been engaging with your outreach, so you can focus your calling efforts on them.

If a drip-marketing email fires on a Tuesday at 10 a.m., you can prioritize your Wednesday morning calling based on who opened and clicked links in that email. At a minimum, those who opened and clicked will have context for your call, and they will likely be more receptive to your messaging.

Even better are calls and follow-up emails that happen in immediate response to opens and clicks. If you’re at your machine and you see that a prospect just opened your email, give them a quick call. It does wonders for connect rates. This is where mobile sales email tools like Immediately can be especially helpful, in that you can see who has opened your email, even if you’re away from your computer, and call them right away.

Point-of-Contact Discovery

Calling can be particularly useful when it’s not possible to get a hold of the email address of the most relevant point of contact for a given account, or if a specific point of contact wasn’t readily discoverable. (SMBs, like local restaurants, auto repair shops, and so on, often fall into this category.) But when calling on these types of businesses, without a specific point of contact, the first step of your engagement will likely be to locate that decision-maker, as he may not be the one answering the phone. This adds a wrinkle to the messaging in your phone scripting; now you need to sell this intermediary, this gatekeeper, on why it’s a good idea for him to share the name of the decision-maker in question. Your best approach here is to use very, very simple statements of the value of your product, so someone who isn’t necessarily invested with authority can quickly parse them and realize, “Hey, it’s probably a good thing if I let Bob know about this.” (For example, if you’re Groupon, you might say, “Hi there! I’d like to be in touch with the owner, because I’d like to discuss how Groupon can make him twenty thousand dollars in one day. Who’s the right person to talk to?”) The goal is to make it clear to the gatekeeper that by helping you engage with the right person, he will be looked upon as a hero by the eventual decision-maker, likely his superior—and that if he doesn’t, that same superior will be upset to have missed this opportunity.

Unfortunately, doing decision-maker discovery via calling can be a game of cat and mouse (even if you’re Groupon!), which is why the prospecting approaches we’ve discussed are so helpful in shortening this exercise. And this is why solutions attacking the SMB market (like Groupon, Yelp, FreshBooks, for example), where decision-maker identification (or even account sourcing) can be a challenge, will often rely on inbound marketing approaches of the sort HubSpot has heavily popularized. However, if there are no better ways to do so, you can call into these accounts and seek to piece together who the relevant contact might be by asking who makes decisions about technology investment (even just getting a name is the first step), when she’s typically in the office, and if you can get her email address or direct phone number. You might be wondering who would give out that sort of contact information, but you’d be amazed what you can get by just asking—especially in conjunction with a solid gatekeeper pitch (like the Groupon example above) that convinces the person on the other end that she’ll be a hero for bringing your solution to the fore (or potentially in the doghouse if she doesn’t). No one wants to be responsible for barring a valuable solution, so gatekeepers are often happy passing you off so you can engage directly.

Gatekeepers and Directories

If you make contact with a gatekeeper, and you already know which point of contact you’re seeking to engage, a different set of approaches is required. In this case, you’re likely calling into the main switchboard. If there’s a dial-by-name directory, you may be in luck and able to go straight to the desk line. Of course, there’s a challenge there too: who answers their desk line nowadays? However, if you are able to get to the desk line, you may be able to connect to the target point of contact or, at worst, leave a voicemail. More on this later.

If there isn’t a dial-by-name directory, and a human gatekeeper receives those switchboard calls, he’s likely pretty used to receiving calls from sales professionals. In that case, it’s good to just ask for the point of contact by name: “Hi there! Can you connect me to Frank?” If the organization is small enough that there is only one Frank, using just the first name will sometimes pass muster. “Ah, he knows Frank.” In larger orgs, it may be more of a challenge, as you’d have to specify first and last name, which does away with that approach. That’s fine: if the gatekeeper wants to guard the gate, that’s his prerogative. And honestly, that’s what he’s there for—to make sure that decision-maker time is guarded for things that are actually relevant.

Conveniently, you’re only calling to discuss something that is relevant, so truth is on your side. It’s just a question of making that clear. You’ll likely get, “Is he expecting your call?” Lying won’t benefit you, nor will being unpleasant to gatekeepers. They deal with pushy sales reps (who may have done poor prospecting and are approaching prospects with an irrelevant pitch) all day long, so you can really differentiate yourself by being pleasant, cheerful, and respectful. Plus, it’s good karma. Deliver the gatekeeper the same shortened pitch about why your offering is relevant to Frank—“Twenty thousand in a single day. Sounds great, right? I want to get ten minutes on Frank’s calendar to discuss.”—and why he’ll be a hero for letting you through. If he’s not biting, you can always ask to leave Frank a voicemail, which the gatekeeper will typically be happy to facilitate (he doesn’t like shooting you down, either). If he’s willing to put you through (with or without a pitch), it’s also good to ask for the direct number for future reference: “Hey, can I get Frank’s direct line in case I get disconnected, so I don’t have to bother you again? Thanks!”

Voice Mails

Generally speaking, when you call, you’re probably not going to connect with the person you’re seeking to engage, which can feel pretty inefficient. That’s why calling is often more like verbal email (via voicemail) than anything else. In Early-Stage Sales Materials Basics, we discussed voicemail templates. They’re short and sweet and loaded with personalization related to the research you’ve done on the prospect, the magnitude of business pain you think they have, the potential benefit of talking with you, and the fact that you’re the founder of the company, seeking to learn. Of course you should leave your contact information, though it’s not going to be super common for prospects to return your call. Returning calls is a huge pain compared to just hitting reply in an email, which, again, makes voicemail behave more like audio email than anything else. Speaking of which, it’s more and more common for folks to have their work voicemail set up in a way that forwards an audio message (and maybe even a transcription) to their email. So think about your voicemail being consumed in that format.

There are other sneaky approaches to voicemail, like not actually leaving much context, and instead saying something along the lines of, “Hey, Frank, this is Pete. Call me back. 650-892-4475.” Or even skeezier, “Hey, this is Pete returning your call. Call me back at 650-892-4475.” (That last one is like adding a fake Re: prefix on emails, to trick the prospect into thinking he’s already participating in a back-and-forth). While this sort of thing can be employed by market development staff, it’s a little more advanced than you probably need to implement. Instead, the straightforward voice mail, patterned after your outreach emails, is probably your best bet.

​important​Always use voicemail in conjunction with email; if your voicemail is well formed, and well delivered, it may inspire your prospect to simply hit reply on the email that came in at the same time.

Live Messages

Lastly, there may be occasions when the gatekeeper offers to take down a message for the point of contact, and write down your information and share it with Frank. This is typically not a great idea, in that the transmission of information here will end up looking like a kindergarten game of telephone. Of course, you don’t want to tell the gatekeeper that you have little confidence that he’ll be able to pass along your message appropriately. A good approach is to instead frame it as a benefit to him for you to present the message yourself. Something along the lines of, “That’s so nice of you! It’s kind of involved. Would you be open to sharing Frank’s email address with me so I can just send it to him directly?” If that fails, often the gatekeeper will be willing to share his own email address as an intermediary, which you can then email with an amazing, super personalized first-outreach email (instrumented with Yesware, and so on, so you can see when Frank opens it). Of course, if you have Frank’s email address already, this isn’t necessary; instead, it’s a better idea to ask to be passed along to his voice mail. Or, you can try for the best of both worlds: “You know, it’s kind of involved. How about this: Just note that Pete called and wants to discuss how to make your business twenty thousand dollars in a day—here’s my phone number—and that the details are in his voicemail. And then you can patch me through to his voicemail. That saves you a bunch of scribbling.” Or something to this effect.

Making Contact

Because live-connect rates are so low, it can often come as a surprise when you actually reach your prospect. Like, “Whoa! Why did you pick up the phone?!” In this context, you have about 30 seconds to sell her on an appointment, using the framework you put in place in your phone script. The most important thing to remember is that you’re not selling the product on this call. You’re selling the opportunity to spend a limited amount of time to understand the prospect’s pains better, help her learn something new and valuable, and potentially solve a big issue she has. You would like to get on her calendar for 10–20 minutes in the near future.

If you’ve been doing a good job with your email-based outreach, ideally the person on the other end of the phone has context on who you are and what it is you’re up to. However, by no means can you rely on that to be the case—these folks get a lot of emails, and it’s likely that yours, regardless of how well personalized and excellently and concisely written, have been going straight to their archives.

Once you deliver your scripted pitch, typically the response will fall into one of three buckets: success, outright rejection, and something in the middle, involving various types of objections—not an outright rejection, but not agreement either.

Success

If your excellent prospecting research, coupled with compelling phone messaging, piques the prospect’s interest and she agrees to a follow-up call at a more convenient time, you’ve won. That was the immediate goal, and you did it. High five!

However, in your excitement, don’t forget to get all the info you need before you get off the phone. First and foremost is calendar availability. Don’t rely on scheduling over email; this is a rookie error—being so excited (or scared) that you pull a, “Great, I’ll email you some times that could work!” That turns into email hell, and you just blew that demo you set. Instead, the approach should be:

​important​Make sure that you’re not setting the appointment too far in advance; anything over a week out heavily degrades attendance rates. Usually a good time frame is a couple days out; that raises the likelihood that the prospect will have an opening, but reduces the lag in which excitement can temper, lowering attendance rates.

Beyond calendaring, this is also the opportunity to get an email address, direct phone, mobile phone, or other pieces of contact information that you might need. (This is not the time for full discovery, though. We’ll get into that in Sales Pitches for Startup Founders.) If you didn’t yet have the prospect’s email address, you’ll definitely need it to send a meeting invite, and it’s also useful for sending a reminder email ahead of the meeting. And if the prospect doesn’t make the meeting, you’re going to want to have a direct phone number to call and remind her, or to follow up after the fact and get the meeting back on the calendar.

Lastly, this is an opportunity to potentially involve others in the call beyond the individual point of contact you’re addressing. Again, you should be targeting the relevant decision-maker that you sniffed out during prospecting, but oftentimes if you have sufficiently excited the decision-maker you can pull in potential users, or influencers. If you connected with the VP of Sales and she’s excited to learn more, but you know that there’s a Sales Operations Lead and a couple of Sales Managers at the company, you could ask if the decision-maker would like them included in the call. If so, gather their contact information, primarily email, to put them on the meeting invite.

Hot Transfers

In rarer cases, the prospect may actually want to do the demo then and there: “Well, I have time right now. How about now?” If you were surprised to connect to your prospect, this one will probably really knock you off kilter! In sales land, this is known as a hot transfer, and it’s both fairly rare and a double-edged sword. On the one hand, it’s great that the prospect is so interested in what you’re doing and how you’ve described it that she’s open to spending 30 minutes with you then and there, and you certainly don’t want to say no to her on that count! On the other hand, you likely didn’t do all the pre-call planning that you would ahead of a scheduled demo, so your level of personalization and preparation may be wanting. But this doesn’t mean that you should do deep pre-call planning ahead of each cold call, thinking that you might end up in a hot transfer situation. No way! Most of the time you’re not going to connect, so all that prep time would be hugely wasted. Rather, the approach I like here is to proceed with the hot transfer demo, but treat this as a lightweight demo. Use the time to do your relevant discovery, and to offer a preview of what a fuller meeting might be, as a means by which to sell a full demo for which you’re able to better prepare. Set that expectation ahead of time by noting what you would typically do for a full demo (more on that later) and what you’re going to do here. In this manner, you can capitalize on the prospect’s immediate interest and availability, while lessening the impact of the preparation deficit.

Rejection

If you follow the prospecting and messaging instruction we’ve already covered, the amount of out-and-out rejection you encounter shouldn’t be terribly high. Prospects don’t like to completely close the door on something but rather prefer the “not now” approach to forestalling decision-making (even if it’s the tiny decision of putting a meeting on the calendar!).

If you are seeing a bunch of out-and-out rejection, you may not be getting your point across, you may be targeting prospects poorly, or some other issue. In that case, listen for patterns of objection in your interactions that can help you proactively avoid these rejections.

With that said, you will certainly encounter rejection when you catch someone on a bad day and they’re not interested in hearing anything. But there are ways of turning those interactions to your advantage to win the call—make progress in pushing the prospect down the path to becoming a customer, even if it’s the littlest step.

Firstly, don’t take rejections as, “Never,” but rather as, “Not now.” If you think about every massive company out there, the Salesforces, LinkedIns, and others, there were thousands of prospects who rejected initial outreach and eventually became happy customers. When you encounter out-and-out aggressive rejection, treat it as an opportunity to make sure your goal is understood and give the prospect another chance to soften:

This approach achieves a couple things. First, while you acquiesce to the prospect’s request to disengage, you’re doing it on your terms, stating your conviction that this is something that is highly likely to be relevant and helpful to him, and you provide him an out in the event he changes his tune. Further, you’re characterizing this as something that is inevitable, “I’m not going to give up. I believe this is relevant to you, so you’re going to have to evaluate this on the merits rather than dismissing it out of hand.” This characterization of inevitability—“I’ll be back” in the words our friend Arnold—sets the prospect up to be more attuned to your future emails and calls.

After disengaging from the call, send a follow-up email. Make it a subtle variation of your initial outreach messaging, crossed with some of the conciliatory messaging you used in your call retreat (templated, of course—Rejected Call Template sounds like a good title to me!). Thank them for their time and characterize why you thought your solution was relevant, with metrics supporting what you think it could do for the organization. Then close with a call to action to get something on the calendar (you’re still selling the demo at this point, even though you retreated from the call), along with a statement echoing that you look forward to being in touch in the future. Following up with the prospect like this gives him an opportunity to marinate on what you spoke about on the phone, and take that out you gave him to actually get something on the calendar. You’d be amazed how many people who seemed hell-bent on getting off the phone change their tune, and decide that they’d like to get on that demo after all, when delivered this sort of follow-up. It’s not luck. It’s that your call cut through the noise, followed by a little bit of footwork to capitalize on the focus you engendered.

Objection Handling

The vast majority of your interactions will fall in between the extremes of success and outright rejection. And typically they will involve objections to setting an appointment. Your job here is to handle those objections—to help the prospect understand why his concern, while valid, is unfounded in this case—and drive to setting the appointment. The last thing you should do in the face of objections is comply, and disengage, as tempting as it may be to get out of an awkward, conflicted situation. This is just where the fun begins! In fact, rather than problematic, objections are great. They mean that your prospect is engaged and at least thinking about the problem you’re addressing. They’re giving you a chance to make a better case. Every time the prospect raises an objection, it’s an opportunity to ask more questions and engage in a better conversation about their situation and where your solution can potentially help.

The problem with preparing you for these objections is that they’re going to be specific to your solution’s space. Sales-productivity solutions will have different objections from recruitment-branding solutions, which will even have different objections from passive-candidate recruiting solutions. So you’ll just have to discover them as you go.

​important​You need to make sure that you are recording the objections you hear and your responses to them. That will ensure that as you encounter them more in the future, you are able to handle them with ease—and later, when you hire staff to help parallelize your efforts, you’ll already have done the hard work for them.

With that said, there are some standard objections that people will use to try to get off the phone with you. If you’re prepared for them, you’ll be better positioned to get that meeting on the calendar.

“Call me later.”

This is typically a gambit to get off the phone without having to actually tell you no. Variants are things like, “Can you call me in a quarter?” The problem with this is that if you comply, when it comes time to call the prospect in a quarter, what do you think his response will be? That’s right. “Call me in a quarter.” You can guess where this ends up. Now extend this across other prospects with this objection. Your end game becomes no demos, ever.

The key to this interaction is a small negotiation trade-off. Instead of getting off the phone immediately, you held out the carrot of never having to hear from you again, which the prospect bought by giving you thirty seconds. And then it’s on you to blow him away with your research and messaging.

“I don’t have budget.”

This is tricky. We talked about demand-characteristic qualification in Early Prospecting, but we haven’t talked about budget qualification yet; we’ll do that more when we discuss discovery questions and pitching. The short of it is that it’s a good thing to know that a prospect has money to spend on a solution and knows what the process is for procuring that solution. If an organization truly has no ability to pay for things, it’s not a good use of time to pitch them, which is why budget is the B in the BANT qualification framework (budget, authority, need, timeline).

With that said, it’s highly unlikely that the speaker of this objection is actually saying, “We don’t spend money on solutions.” Rather, this is a variation of, “Call me later,” and should be heard as, “We may or may not have budget right now, but I’m saying that I don’t have money to spend on the thing you want me to spend it on.”

“Just send me some information.”

This is another version of, “I just want to get off the phone, but I’ll throw you a bone by pretending you can send me information and I’ll read it.” The problem with this, of course, is that there is no commitment to actually consume the information you send. It is very likely it will go in the digital round file.

The right way to approach this, as with the, “Call me in a quarter” objection, is to capitalize on the fact that you’re on the phone right now. Something along the lines of, “I’m totally happy to do that. But if I do, I’m going to do a bang-up job, and it’ll take me thirty minutes to put together something very personalized to you. I don’t want to do that if our solution is not relevant. Can I take thirty seconds to explain what we do, and ask some questions to make sure this is a relevant conversation? That way if it’s not, I won’t be in your inbox chasing you and asking about information that wasn’t even helpful.” Again, you’re trading the prospect time right now for the promise of avoiding pestering later—coupled with a guilt component of, “Do you really want to waste my time? That’s not nice.” If you’ve already explained what you do and how it’s relevant, you’ve qualified the prospect beyond a shadow of a doubt, and they still say, “Just send me some information,” take the approach of selling the demo.

“Oh, we already use [Competition].”

The great thing about this objection is that the speaker is admitting that she has the problem that your solution addresses, and moreover, that she spends money to solve it. Fantastic! She just partially qualified herself. First, congratulate her on being a student of the game and clued in. Then, all you have to do is succinctly demonstrate why it’s worth the time to look at your solution as a substantially better way to solve her problem.

“Do you have [X, Y, or Z feature]?”

In this situation, the prospect starts to get deep into features and what your product has or doesn’t have. This is actually a really great place to be, if you handle it correctly. It’s not that the prospect is objecting to your solution, per se, it’s just that he’s blocking your ability to get a formal appointment on the calendar. This is kind of like an abortive hot transfer as discussed above, where instead of hearing the whole pitch, having his mental model set correctly, and going through proper discovery questions, the prospect is attempting to have a demo by a thousand cuts.

The best way to handle this is to assumptively close on setting the appointment, as he’s partially admitted his interest in and familiarity with the problem and solution.

“How much does it cost?”

The good thing about prospects asking about cost is that they are admitting that they have the problem, understand to some extent how your solution fits in, and are trying to get a sense of whether the cost fits the pain. The problem, though, is that there’s still a huge information asymmetry here: you don’t yet clearly know the magnitude of the prospect’s pain (because you haven’t asked your discovery questions), and the prospect isn’t anywhere close to understanding all the ways in which your solution can help address this pain. So if you immediately jump to pricing—say, ~$10K a year—she has very little information with which to make a judgment about whether the value the solution provides is worth more (ideally far more) than the price. So you can end up in situations where the prospect responds, “Whoa, that’s way too much.”

The best way to avoid this is to not fall into that trap to begin with. Instead, parry the question and drive to a demo with something like, “While the solution does have a cost, it’s really contingent on a variety of factors, associated with how much value a given customer would get out of it. Typically people find it most effective to schedule a twenty-minute demo so we can get a better sense of whether the solution is relevant and how helpful it could be to your business. Do you have twenty minutes this Thursday or Friday for that conversation?”

“I can’t make that decision.”

This objection can indicate one of two things, and it’s important to resolve which. Is this person actually the relevant point of contact, and trying to dismiss you? Or is she truly not the relevant contact, and you need to find the correct one (and potentially refactor how you’re doing prospecting if you’re calling on the wrong people)? The challenge is that these two things can look the same if you don’t ask the right questions.

The way to sort this out is to assume that the account does have the pain you’re solving but that this person could indeed be the wrong point of contact. Drive to sorting out who you should be talking to:

You can potentially refer to the person’s supposed manager—if you’re Immediately, the sales-first mobile email and CRM client, and you’re talking to a Director of Sales Operations, you might refer to the VP of Sales, to whom the contact you’re talking to likely reports. Or potentially the CFO. Or shoot, maybe even the CEO. This tactic helps indicate where you’re going to go next if they don’t tell you, so they might as well be straight. If that person is indeed the right point of contact, and you sound like you’re going to show up on the CEO’s doorstep saying, “Jeff said that he’s not the right one to discuss this, so I’m here to talk to you,” that’s probably not going to look great for Jeff. So he might as well own up that he’s the right point of contact. And now you’re in the same situation as the “I don’t have budget” objection, where it’s less an issue of, “Not possible” and more a question of, “Is the timing right?”

If it’s the second case, and you’re actually targeting the wrong person, the contact you’re talking to doesn’t have much reason to obscure who the relevant contact would be. And, again, by indicating who you’ll be targeting next, you create a poor best alternative to him giving you the correct name— if you show up on the CEO’s or CFO’s or VP of Sales’ doorstep indicating that Jeff sent you, and she’s not the right person, well, the CEO, CFO, or VP of Sales will probably not be too stoked. So better for Jeff to just be straight with you and point you in the right direction. At this point, Jeff is acting like a gatekeeper, and you should simply employ the tactics described above to help him understand how beneficial passing you along to the right point of contact will be. Make Jeff look like a hero for bringing your solution to the fore!