5 min read

15 Tips for Better B2B Sales Conversations

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Raise your hand if you’ve heard the word “chatbot” or “bot” recently. Sound familiar? If not, I want you to think about the last time you were on a software company’s website. As you scrolled down or went to the pricing page for information, did a little box pop up in the lower right-hand corner saying “hi” and asking how it can help you? That, dear reader, is a chatbot.

A chatbot – like the ones from Drift and HubSpot, among others – is a piece of technology that is implemented on a website to start up a conversation and, hopefully, direct them to where they want to go or connect the site visitor with a human sales rep or agent who can help nurture that potential B2B sales lead further.

Learn the best way to reach your B2B sales prospects. Read our blog.


How does the chatbot know what to say? Sorry, it’s not sentient and you’re not interacting with Rosie the Robot from “The Jetsons”, although that would be one heck of a name for a bot, wouldn’t it? The flow of each conversation with a chatbot is set up ahead of time by a human, who determines the potential answers the visitor could give along with the if/then statements for the conversation and actions to be taken.

So, if a human is creating a conversational flow for a chatbot, shouldn’t they also be doing so for their own communications? All forms of B2B sales outreach should be conversations instead of just “me, me, me” statements and pitches. Read on to learn how to make all parts of your B2B selling, from live chats to emails, videos to LinkedIn, conversational and showcase your personality.

Live Chats

  • When someone comes to your site, the chat conversation should be entirely about that person and not just a pitch for your product.
  • Show your personality. If you’re funny, make a joke. If you’re not, don’t as it’ll probably go flat.
  • You are not a robot, so don’t act like one asking only the qualifying questions that will determine if that person is a true lead.
  • Make things easy for the site visitor. Are they looking for a demo? Drop your videoconferencing link into chat to have a meeting with them, which will further show that they’re having a conversation with an actual person rather than a robot.
  • When you’re messaging with friends, do you leave them hanging or do you reply almost right away (unless you’re busy)? It’s the same for a live chat window, except that when you’re in that live chat window, you are NOT busy. Your priority is the person on the other end of the chat, so reply to them in less than 30 seconds or they’ll swipe left on your live chat and swipe right on your competitor.

Cold Email

  • When you’re creating the emails for your sales cadence, your goal is to write them in your voice. Be authentic, genuine, and show a sense of humor. I’m all for including gifs or memes. Heck, a political email I received recently got me to donate specifically because they added in a gif of a happy dog saying that would be their reaction if I did so. Worked on me.
  • Personalization is everything in cold emails. Consider the problems the recipient of your cold emails are dealing with, which goes back to knowing who your customers are, and reference those challenges in the email. 
  • Include an embedded video from Vidyard for extra personality. See more tips below about how to make those videos conversational.
  • Add value in every email. DO NOT send a “Hey, just checking in” email. Ever. Just don’t. Think about how you want to be communicated with and what you would delete if you received. I know I’d delete a “Hey, just checking in” email from someone I’ve never talked to before.

Embedded Videos in Email

  • Include a personalized video in your cold emails in your cadence. This should be recorded at your desk, since that’s where you do your work, and should start off with your face and a wave.
  • Are you funny? Quirky? Show that! Some of my favorite videos I’ve received include a rep wearing a chicken suit and one wearing an inflatable dinosaur outfit. That latter one got my interest considering I own a pink inflatable T-rex costume, but that’s a tale for another blog... or a video blog.
  • When you’re making your video, talk in your normal conversational pattern, like you would if you were speaking with the person face to face or over the phone. Don’t just read off a script because it will show in the video that it’s canned and isn’t something you’d typically say.


  • If you’ve connected with a prospect on LinkedIn, engage with their content and have a conversation there as well.
  • When your prospect gets a promotion, or posts about something good that happens to them, don’t just “like” the post. Instead comment on it as you would to any other of your LinkedIn contacts.
  • If they post something that’s asking for feedback or they ask a question, respond—and don’t just respond with “Good post!” Reply with a thoughtful response that is written in your voice and adds to the conversation.

Reach out to us here at ConnectLeader today to see how to help your sales reps, SDRs, and BDRs have more sales conversations through phone, email, video, text, and social with Koncert Cadence and Agent-Assisted Dialer. Simply click here or give us a call at 800-955-5040.

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