The sales questions you email your leads should depend on where they are in the buyer’s journey. It may sound obvious to say that cold leads shouldn’t get the same questions as warm leads. But we feel compelled to mention it because there’s still the temptation within many sales teams out there to try and shorten the number of touchpoints needed for vetting leads and getting them to buy.
The pressure to do this can happen for a few reasons. Maybe Marketing and Sales are playing tug-of-war with their email messaging. Sales may be in charge of all prospecting, on top of managing their normal pipeline. Or there could simply be those within Marketing, Sales, and the C-Suite who want email automation to perform more like an order-taking service than a long-term strategy: send an email, get immediate buying interest from decision-makers. (While it’s not impossible for this last strategy to work some of the time, it’s highly unlikely to work most of the time — and it’s usually not sustainable.)
While prospecting functions may vary for your company, we’ll keep it simple by referring to all questions we discuss as sales questions in prospecting emails. With that in mind, let’s talk about good sales questions you can ask that are better at getting your leads to respond.
Navigational Sales Questions
First-touch emails to cold leads work better when they’re navigational. In other words, they ask who the best person is to talk to.
Why would you want to ask a lead if they’re really the right person? There are a few reasons.
First, while you may think that you know the appropriate job titles of the people you want to contact, the responsibilities under those titles can vary between businesses. You can’t assume that the Chief So-and-So at Company A will mirror the responsibilities of the same position at Company B.
Second, the means you use to obtain contact information for your leads may have outdated or inaccurate information. If you found them on a lead list, for instance, they may or may not still have the jobs they were listed under at the time the data was reported (if at all).
Third, most people are more likely to respond to emails from someone they’ve never heard of if that sender is asking them for help, rather than immediately trying to sell to them.
The key to asking the right sales question at this stage is to actually not ask for a sale at all. Instead, it’s about asking who the best person is to talk to about a service at the lead’s company that ties back to products or services that you offer.
Does that sound complicated? Here’s an example.
Pretend that you sell loan automation software. Rather than begin your first email by promoting it, you’ll want to make sure that you’re talking to the person in charge of evaluating technology for approving new lenders — and, ideally, the person who either purchases that technology, or reports to the one who does.
Your question to them might be, “I’d like to learn more about the system you currently use to process new lender applications. Could you tell me who manages this, please?”
If the person you’re emailing is the right person, all the better. If they aren’t, follow up and ask them who is. Email referrals are more powerful than you think.
Invitational Sales Questions
Once you’ve located the right people to talk with, ask them for phone calls. If they need more information to understand who you are and why you’re asking, keep those explanations brief and direct — conversational, not sales pitches.
Then, if they don’t immediately say yes to a call, follow up every couple of days with brief messaging that a) reminds them about what you’d like to discuss, and b) asks them again if they’re open to talk. This isn’t meant to be pushy, so give your leads at least twenty-four hours between each email (preferably forty-eight) for them to decide.
Educational Sales Questions
For those leads who have engaged with your navigational and invitational questions, it’s time to start sending them educational content. These emails are a thought-of-the-day style of marketing that informs your leads about products, services, and market changes that affect them. They may touch on stories from the news, or pain points that leads are experiencing. The goal for content is to focus the conversation on your leads, while demonstrating your knowledge of their industry in order to build trust.
The more they trust you, the more likely they are to check out your website to learn more about who you are and what you offer — and the more likely they are to remember your name when they have a need.
The sales questions you should ask your leads at this stage should be calls to action based on the content of your emails.
Would you like to try a demo?
Are you available for a call to talk about how [pain point] is affecting your services?
Do you need help with [service]? How about a call to talk more about it?
Continue this series of content emails until leads are ready to talk, or they ask to be unsubscribed from your marketing. Those who agree to phone calls can be shared with Sales for further vetting, and to be added to your normal sales cycle.
Follow-Up Sales Questions
Once your sales reps have further qualified them, leads should know who you are and what you offer, and they should be more receptive to direct sales questions asking them for new business. If they aren’t ready to buy immediately, that means you’ll likely keep them on an email list to continue receiving your outreach until the timing is better.
That’s also where sales follow-up emails come into play, as they’re designed to maintain active interest in your potential new customers. It’s important to note that these shouldn’t simply default back to asking your leads if they want to buy. As Sales Hacker explains, your follow-up emails should:
Address an immediate need. This creates urgency for them to respond.
Offer new information and value each time. This keeps your leads engaged.
Keep your content balanced. Offer enough information to grab attention, but not so much that you overwhelm or bore your audience.
Note: At this point in the buyer’s journey, it also doesn’t hurt to connect with leads on LinkedIn, as well as call them directly. Either action outside of your normal email outreach could be the touchpoint needed to encourage them to close the deal.
It’s better if you ask no more than three questions per email, preferably one or two if you can help it. Most people (even those you know) aren’t keen on responding to every question a person asks them, and will likely only answer the last one on your list — so you’ll want to make that one count. Part of deciding what to ask will also depend on whether you want your follow-up questions to be closed or open-ended.
Closed Questions Vs. Open-Ended Questions
Generally speaking, we recommend that any sales questions your leads receive while they’re still in the prospecting phase (i.e., those before sales follow-ups mentioned above) are closed. In other words, they’re easy to answer with a yes, a no, or a short response, similar to examples we’ve already given:
Who’s the best person for this discussion?
Could you tell me more about your [pain point]?
Are you free this week for a call?
We expect that others may disagree with us about this strategy, so here’s our rationale for closed questions. They’re direct and don’t require much effort from your leads to answer, which makes them easier to review and respond to immediately. Considering the sheer number of emails your leads get on a given day, you want them to feel like there’s minimal effort required to help you. (Again, the only caveat to this is to avoid asking too many questions, so that you don’t look like a survey or an interrogation.)
Once a lead joins you for a phone call, it’s time to start using open-ended questions like the following to build on that relationship and drive meaningful conversation:
Tell me more about [service]?
What have you found when you tried [solution]?
How would you like to see your services improve at the end of this program?
In situations like discovery calls, where leads are giving you more of their attention than they would if they were skimming their inbox, your open-ended questions will make them feel like you’re genuinely interested in what they have to say. They’ll also prompt your leads to think about what you’re asking and give you more than one-sentence responses, which benefits you by a) uncovering important information for follow-up questions, and b) building rapport.
Next, let’s talk about how your emails sound.
Tone of Your Questions
How you write your questions is just as important as what you’re asking. In a recent survey, HBR found that people who read questions on a casual-looking website were more open in their answers than those who read them on a site that seemed “official.”
The same applies to the questions themselves. Do yours sound like how a person would say them aloud, or how the actual sender of your emails would ask them in person?
Those that come across like natural conversation are more likely to elicit responses:
I wanted to learn if you’ve been having the same trouble with [service] that we’ve heard from others in the industry. Do you have some time to talk about it?
Thought you might find this information about [service] helpful. Let me know if it’s something you’d like to talk about over a quick call.
Having trouble with [pain point]? We think we’ve found a way to work around it using [solution]. Can we talk about how it can apply to your [services]?
While it’s important to sound natural, don’t try to be funny. Everyone’s sense of humor is different. Because others can’t hear what you’re writing to them, it’s too easy for them to misinterpret a joke and instead become offended. The ideal solution is to remain casual and direct.
Why Are These Good Sales Questions?
We’ve talked about some great sales questions to ask your cold leads, but you may be wondering why these are effective.
HBR has some thoughts on the matter. As one contributor notes, questions are a powerful way to establish “rapport and trust,” while also providing a means to “mitigate business risk by uncovering unforeseen pitfalls and hazards.” While their article specifically addresses questions in relation to coworkers, we’ve seen the same value with lead generation — especially follow-up questions, which provide proof to your leads that “you are listening, care, and want to know more.”
Do You Have Questions About Our Questions?
Whether you have questions about the material we’ve covered, or you’re concerned that the sales questions your reps ask aren’t as good as they could be, we want to hear from you! We’ll review the material you’ve been using, test variations of emails through marketing automation, and identify new leads for you to target. If that sounds like something you’d be interested in, click the link below to schedule your free lead nurturing discussion.