Welcome to "The Pipeline" — a new weekly column from HubSpot, featuring actionable advice and insight from real sales leaders.
Your relationship with a prospect isn’t the sum of one conversation. It’s also not the sum of your emails. A strong prospect relationship is built from a series of meaningful touchpoints spread out over time.
I’m a firm believer that conversation frequency trumps length. If I have a five-minute conversation today, a 10-minute conversation tomorrow, and a 15-minute conversation next week, my prospect is likely to remember more of what I’ve said than if I schedule a one-hour-long conference call.
But with more touchpoints comes the tendency to substitute email conversations for phone calls. Emails won’t further your relationship with prospects, so save them for answering mundane questions and sharing contracts. Here are a few of the worst questions to ask over email — along with tips on how to get deals back on track and prospects back on the phone.
The Worst Sales Questions to Ask Over Email
1. “Do you prefer to communicate over phone or email?”
One thing I hear a lot from reps is, "But my prospect prefers communicating over email,“ or ”They just won’t get back to me on the phone." No kidding! Do you think prospects want to build a relationship that will make it harder for them to tell you no?
Don’t ask your prospect whether they prefer to communicate over phone or email. Use both forms of communication, but know when to choose one over the other — and when in doubt, use the phone.
I’m not suggesting you get so specific that every third touchpoint is a phone call, but avoid getting over-excited when a prospect says, "When can we get a demo scheduled?" or "I think we’re ready to sign. I just have one question."
When salespeople hear these phrases, we want to move the deal forward immediately — but doing so over email is ambiguous and can harm deals by not giving real interaction enough attention.
Instead of replying, "When would you like to schedule your demo?“ pick up the phone and ask, ”I’m glad to hear you’re ready for a demo! What do you hope to learn from this meeting?" You’ll gain more context, be better able to prepare, and be able to schedule a meeting in real-time. Work a little harder, and get your prospect on the phone.
2. “Can I give you a call?”
Don’t ask for permission to call or meet with your prospect. Close for their cell phone or direct number as early as possible — ideally before you schedule the first meeting or discovery call.
In my experience, asking for a cell phone number prior to the first meeting yields a 60% success rate because prospects don’t want to put their first meeting with you in jeopardy.
If you wait until after a meeting or demo to ask for their number, the success rates plummet to around 15% because they’ve already gotten what they need from you.
Still feeling weird about closing for a cell phone number? Think of it this way. If you call a Porsche dealer and ask to test drive their latest model, the salesperson will say, “Sure, I just need a phone number for you.” Of course, you give to them. It’s an exchange of information. The Porsche dealer gives you a car to test drive, and you give them your phone number.
To break the ice, I offer my cell phone number first. For example, I’ll say, "Great. It looks like we’re all set for Tuesday at 9:00 a.m. My cell number is 123-456-7890, what’s yours?"
You’re giving them your number in exchange for theirs. This conversation tactic also establishes you’re not afraid to ask for what you want — an excellent way to position yourself to a prospect.
3. "When would you like to reschedule?"
If a prospect reschedules, you know the chances of them rescheduling again skyrockets. If your prospect sends a last-minute email asking to push a meeting or trial because they need more time, pick up the phone immediately and say, "We can absolutely reschedule. When’s your next availability?"
Be flexible with their schedule but firm on slotting a new meeting within a week of the original date. You’ll save time, prevent an endless email chain resulting in no rescheduled meeting, and mitigate the risk of your prospect ghosting.
4. "Who is the person you cc’d on your last email?"
If I’m in the middle of an email thread with a prospect and they cc someone new, I pick up the phone immediately. I need to find out who this person is and why they’re important to the conversation.
If I reply all or fail to acknowledge the new addition, I risk not giving this new person the information they need — or worse, offending them.
For example, let’s say a customer sends an email asking, "Is your solution compatible with Platform X?" If I’ve already spoken with them over the phone and this question won’t move the deal forward, I would send my answer over email.
But, if the prospect cc’s someone else on this email, I’d give them a call. Instead of immediately asking who the cc’d individual is, I’d ask the prospect to clarify part of their question. Then, I’d follow their answer with, "By the way, who is Caroline Gilbert? I noticed she was cc’d on our last email."
This gives you more context into the sale and avoids an awkward email thread where you either ignore the new person or ask who they are directly, which can be uncomfortable for all parties.
5. "What did you think of the meeting last week?"
Don’t ask for feedback on your proposal or the meeting you facilitated last week. It’s a weak position. By asking for feedback, you give your prospect an invitation to think about what didn’t go well. Your prospect’s opinion shouldn’t impact your performance. Your performance should already be stellar.
When asking for feedback over email, you’re basically saying, "I’m chasing you to determine what you think of me." If you need feedback, ask for it immediately. If you have a meeting, ask how your prospect thinks it went before you get off the call. This makes you look prepared and confident. But make sure you’re not taking time away from the meeting itself. Instead, schedule five minutes after your presentation to ask for their feedback.
Similarly, if you’re seeking feedback on a proposal, ask your prospect for time to talk it through immediately after you send it.
6. "When would you like me to reach out to start this up again?"
If the customer says they need to delay — say, for example, they move the close out a quarter — don’t ask them when they’d like you to touch base. That comes across as needy and passive-aggressive. Instead, simply say, "Thanks for the update."
Don’t ask for permission to contact them again. You won’t want to wait on their timeline. If something changes on your end, you can reach out sooner rather than later. Call them when it’s right for you.
Use email sparingly — and do this universally. Don’t shift your approach based on the prospect. Making exceptions like, "Well, this person prefers email, so I’ll just do it this time," only makes it easier to fall into the habit of email.
Remember, people with influence usually don’t mind taking calls. It’s non-decision makers who avoid the phone. If you’re faced with a prospect who won’t answer your calls, consider it a warning sign they either don’t have influence or aren’t interested in your offer.