We’ve all been there. You’re working with a prospect. Things are coming along nicely. And then they go dark. I found myself in this situation a few years back: The deal had been advancing, my prospect was responsive over email, and I was confident we would close soon. And then … nothing. Weeks passed and I continued sending emails without a response.
Finally, I picked up the phone and called my prospect’s office. It turned out he was no longer with the company, and they hadn’t turned off his email yet. If I had called earlier, I could have saved myself a lot of time and energy.
Email is great for administrative details. Use it to coordinate meetings, set up calls, and confirm next steps — but don’t use it to advance an opportunity. Below are nine conversations you should never have over email. If your prospect approaches any of these topics via email, drop what you’re doing and pick up the phone.
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9 Times You Shouldn't Use Email While Selling
1. Contract Questions
Never comment on a contract or proposal over email. If you’ve sent your prospect a proposal and haven’t heard back, don’t follow up with an ambiguous email asking if they’ve had time to look it over. Call them.
This goes for questions too. If your prospect asks a question about onboarding costs or implementation time, give them a call to answer their questions. Phone calls let you get ahead of questions before they become full-blown concerns — and they can protect you from the “lost in translation” factor that often plagues email communication.
Communicating in real-time, over the phone also gives you a better opportunity to learn the “why” behind your prospect's original question — lending itself to a candid back-and-forth that lets you get at the root of the issue more directly.
If you receive a contract question via email, you can respond with something like, “That's a great question. I'll give you a call, so I can fully address it.”
You can also reply to a question by saying, “Hey, I'd love to discuss this over the phone. I left you a voicemail and will try you again tomorrow.”
Phrases to Avoid in Email
- “I wanted to follow up on the proposal.”
- “Do you have any questions about the contract?”
- “Have you had time to read through the proposal?”
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2. Mid-Stream Introductions
Sometimes you’ll need to introduce yourself to prospects when a deal is already underway. It might be because another rep is handing off the deal, there’s been a territory change, or the deal has closed and an account manager is taking over.
Whatever the reason, early introductions should always be made over the phone or (at the very least) by voicemail. You're entering a new relationship without a connection — you need to set the right tone and start developing the kind of productive trust that will move your deal along.
You don't want to set a precedent where email is your primary mode of communication with your prospect — going that route is impersonal and, in turn, less effective when you try to build rapport.
If a coworker makes an introduction to your prospect over email, follow up by saying "Thanks [coworker]. [Prospect], I’ll give you a call tomorrow to introduce myself." And keep trying until you get through.
Phrases to Avoid in Email
- “I just wanted to introduce myself.”
- “Thanks for the introduction, [coworker]. I’m looking forward to working with you [prospect].”
- “Great to meet you [prospect]! Let me know if you have any questions.”
- “I’ll touch base in a few weeks to see how you’re doing.”
3. Fishing for Answers.
Never nag your prospect for answers over email. I can't stress that enough — don’t do it.
If you ask a prospect "Who else is going to be on the demo next week?" that’s fine. But if your prospect never responds, don’t send another email. If you do, you’ll find yourself in a scenario similar to the one we touched on above — conditioning your prospect to communicate with you only over email.
Deals that happen exclusively online are usually the opportunities that drag on for weeks or months — and that’s not good for anyone’s quota. Keep your communication direct, concise, and friendly. And never badger your prospect via their inbox.
Phrases to Avoid in Email
- “Haven’t heard back from you.”
- “I wanted to confirm you got my last email.”
- “It’s been a while. Just wanted to check in.”
4. Objection Handling
You should welcome objections: They give you a chance to address your prospect’s reservations and reasons not to buy. But don’t handle them over email. You need to gauge how your responses are going over with the buyer — which is tough to do over email.
If a prospect sends an email saying, "I’m not sure I can sell this internally,“ reply with, ”I can help with that — I’ll give you a call and we can discuss." If you try to handle this objection over email, you risk dragging out the deal, losing your prospect’s interest, or even losing the contract.
What if you need to loop in someone else from your company? For example, if a prospect is worried that feature X doesn’t have adequate functionality, you might bring in an engineer to speak about feature X.
It can be tempting to CC your coworker on an existing email thread, but you shouldn't do it. Just like a mid-stream introduction, each party risks losing sight of the original question.
Also, your prospect will have to sort through a rabbit hole of emails in order to piece together an answer or solution to their objection. Save them the confusion and frustration by picking up the phone and getting the right people on the line.
Phrases to Avoid in Email
- “Let me make sure I understand your concern … ”
- “Here are three reasons why this isn’t a problem for your company.”
- “I’ve CC’d our lead engineer to speak to your concerns.”
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Save time, find new ways to reach out to prospects, and send emails that actually convert.
- First-Touch Emails
- Follow-Up Emails
- Break-Up Emails
- ChatGPT Email Prompts
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5. Negotiations
If a prospect sends an email voicing concern over price or contract terms, answer them by picking up the phone. It’s natural to want to calm them down immediately by saying, "Let me talk to my boss and see what I can do," but if you do, you may be sabotaging yourself and the deal.
It’s difficult to understand the context of their concerns through an email. Before saying anything, jump on the phone and learn why they suddenly don’t have the budget for your product or service or why they need the price to come down by Y amount.
Once you’re on the phone with them, ask questions like "How big of a barrier is this to moving forward with our product?“ or ”What’s changed since the last time we spoke?" Asking these questions allows you to ascertain how much of a deal blocker these concerns really are and where they’re coming from. This ensures you never sell your company or your prospect short.
Phrases to Avoid in Email
- “Let me see if there’s something I can do.”
- “We’d already agreed on X price. I don’t think we can come down.”
- “If we can come down to X price, would you sign today?”
6. Discovery
Don’t ask discovery questions over email. Wait until you can devote your whole attention to asking the right questions and listening for the right answers. It’s important that you’re able to guide the conversation as it’s happening.
Additionally, your prospect might not be comfortable answering certain discovery questions honestly over email. For example, "What are the roadblocks to your company choosing a solution?“ or ”What challenges is your company currently facing?" can be difficult questions for prospects to answer in writing.
Make sure you’re getting honest, accurate answers during this phase of the sales process and you’ll eliminate surprises down the road.
Phrases to avoid in email:
- “Tell me about your goals.”
- “What’s the source of that problem?”
- “Why hasn’t this been addressed before?”
- “Is this a competitive situation?”
7. Rapport Building
Rapport building is crucial in the sales process. While it’s important for your emails to be personable, don’t let that be the only way you build rapport. Get your prospect on a call and guide the conversation as only a salesperson can.
We’re great storytellers, listeners, and conversationalists. It’s part of the job and something we’re both naturally and trained to be good at. If you’re trying to accomplish rapport-building over email, you’re selling yourself and your skills short. The conversation and information will flow freely over the phone.
Set your prospect at ease by beginning the conversation with something like, "I’ve heard of this amazing Italian restaurant near your office. Have you been to Bertelli’s?" You’ll build more of a personal relationship this way, instead of trading pleasantries over email every few days.
Phrases to Avoid in Email
- “How’s the weather over there?”
- “What are your plans for the weekend?”
- “How do you spend your free time?”
8. Breakups
Let me say this right now. I don‘t believe in sending break-up emails to prospects — ever. If you’re in the early stages of reaching out to a new prospect and they haven't responded to your past few messages, stop emailing them.
All you‘re doing by sending a "break-up" email is trying to guilt them into responding. It’s like giving an ultimatum in a relationship. No one benefits, because even if the other party does re-engage, it's because you forced their hand, not because they genuinely want to.
Instead, stop emailing them, wait a few months, and then reach back out.
Phrases to Avoid in Email
- “If I don't hear back from you after this email, I'll stop reaching out.”
- “This will be my last attempt at contacting you.”
- “If I don't hear back, I'll assume you're not interested.”
9. Checking in on New Clients
Good salespeople know that when a deal closes, it‘s not over. When you follow up with new clients to see how they’re settling in, if they‘re happy, and especially when you’re attempting to upsell or cross-sell, pick up the phone.
You want them to feel just as valuable (if not more) as a client as they did as a prospect. Don't send them an automated email every few months to check up on their experience. Be engaged, proactive, and phone forward.
Phrases to Avoid in Email
- “How have your first few weeks been?”
- “How's your experience with our product/service been so far?”
- "You might be interested in our newest Feature X."
To change the sales stage and advance an opportunity, pick up the phone. Keep email as a channel for administrative tasks and communication only. The results will be a faster sales cycle, highly invested prospects, and more deals closed.
50 Free Sales Email Templates
Save time, find new ways to reach out to prospects, and send emails that actually convert.
- First-Touch Emails
- Follow-Up Emails
- Break-Up Emails
- ChatGPT Email Prompts
Download Free
All fields are required.
