The 4 Best Social Selling Conversation Starters (& 15 Post Ideas), According to Real Sales Leaders

Download Now: 50+ Social Selling Tips
Caroline Forsey
Caroline Forsey


With roughly 930 million members, LinkedIn is undoubtedly one of the most popular, trusted social channels sales professionals have at their disposal — making it one of the (if not the) best platforms for social selling.

salespeople using great social selling conversation starters

But its popularity also makes it a crowded platform to stand out — and sales reps risk sounding overly promotional if they don't compose their messages appropriately.

To understand the elements of an effective social selling conversation starter, I spoke with four sales experts. Let's dive into what they had to say.

Download 37 Tips for Social Selling on LinkedIn

How to Start a Conversation on LinkedIn

Before we dive into more specific expert-backed advice, let's go over a few general best practices when starting a conversation with anyone on LinkedIn.

If you‘re aiming to start a one-on-one conversation, you’ll want to start by connecting with the person and including a brief message explaining why you want to connect.

When reaching out to someone:

  • Don't ask for a favor
  • Don't send a generic “Hi, how are you” greeting
  • Do explain how you know them or why you want to connect
  • Do show personalized interest in their LinkedIn activity

For instance, rather than connecting with someone and saying, “Hey there, I thought it would be good to connect”, try saying something like: “Hey there. I found your recent post on social selling very interesting — It would be great to be in your network to continue sharing content.”

Alternatively, perhaps you send something like this: “Hey [Name]. It looks like we both attended Elon University. Would love to connect, and if there's anyone in my network I can introduce you to, please let me know.”

Additionally, if you‘re hoping to engage with a prospect, it’s likely best to post on your own LinkedIn to attract interested viewers, or comment on a prospect's post before directly messaging them. Forming a meaningful connection with the prospect ahead of cold-pitching them is going to be the most effective strategy.

Expert's Best Social Selling Conversation Starter Tips

1. Leverage video posts.

Alex Wedderburn, a Strategic Account Director & Higher Education Lead at Hootsuite, told me he believes video posts are incredibly effective when starting a conversation on LinkedIn.

As he puts it, "I use LinkedIn to publish video posts to highlight the amazing things I experience while working at Hootsuite from both an individual and company-wide perspective.

"Let's face it — text is the medium and format for everything. It‘s on our phones, our emails, and our presentations. We digest text constantly across multiple digital devices and screens all day long, so when a video comes up, it stands out, it’s different, it's fun and authentic."

Wedderburn says, “Video can offer that genuine, unpolished, true version of yourself that people can relate to — and that often opens conversations on LinkedIn.”

There are a few best practices when using video to sell to prospects, including:

  • Be concise
  • Don't be too scripted
  • Do your research

As an example, take a look at Wedderburn's recent LinkedIn video in which he highlights three things happening at Hootsuite in a quick one-minute rundown:

However, using video can add a personal touch and help you connect more quickly with the prospect on LinkedIn. Plus, it will help you stand out.

Wedderburn adds, “Video provides an opportunity to just be a human—to connect with people in new ways and champion the power of human connection and build something that's real with your audience.”

2. Use hashtags.

Lately's Co-Founder & CEO Kate Bradley Chernis told me her best conversation starter garnered 278 comments — and it was a single sentence containing 73 characters, plus three hashtags (all of them made up spur-of-the-moment) and a 24-second video attached.

Chernis told me, "Why did it work? For one, short always works; everybody's algorithms are set to boost 80 characters or less. Secondly, hashtags that contextualize your message versus try to pile on a trend or work as indexers (the opposite of what any marketer will tell you) crush it every time. For example, my highest performing hashtag is #peeingmypants, which I used when Gary Vee tweeted about!"

Here's the post for reference:

"Certainly, this particular post was of the moment — COVID had basically just happened, which meant everyone was all by themselves; hence, there‘s crowd-sourced sympathy at work here. In addition, there’s enough mystery about what I wrote to most people not utterly immersed in Venture Startup Land that they were curious to ask questions or Google it (why is $1 million ARR remarkable?)."

Chernis adds, "I also commented on the comments, asked my team to comment on the comments and the more play the post got, the more we continued to comment. Fuel the fire once you've started it!

In short: Selling on LinkedIn doesn't have to look like, well, selling. It can look like excitement, joy, passion, or humor as it relates to your brand — which will attract and engage viewers and, ideally, result in new leads and prospects.

3. Inspire and educate with your outreach.

Sprout Social‘s VP of Revenue Operations and Strategy, Dan Summers, reminded me that most buyers are 70% of the way through their buyer’s journey before they engage with sales. So how do you capture the attention of a buyer who isn't already interested?

He told me, "Buyers are busy and focused on accomplishing their own objectives. To capture their attention, it is imperative to inspire and educate them with your outreach. There are many ways to approach this, but I've seen a few that have been incredibly effective."

Here are a few tips Summers shared with me when it comes to starting a conversation on LinkedIn:

  • Lead with information the buyer might not have about their industry, competitors, or their brand — start with value, and tailor your approach to their unique needs
  • Share thought leadership on your social channels, which enables you to demonstrate your expertise, increase credibility with buyers, and show you're on top of your industry
  • Share your personal experiences with their brand if you use their own products or services, which conveys authenticity — if you don‘t have personal experiences to share, consider sharing customers’ experiences on social or review platforms that tie to the value your solution provides

“The key theme to focus on is personalization,” Summers says, “Tailoring your message to your buyer's persona and leading with content that is designed to inspire and educate them will improve your chances of starting a meaningful conversation.”

4. Ask a question, try something new, or share a cold-calling war story.

Jed Mahrle, Mailshake's Head of Outbound Sales, provides three strategies for sales reps hoping to use LinkedIn for social selling.

To start a conversation on LinkedIn, Mahrle advises, "First, ask a question. The sales community on LinkedIn loves to share their opinions. If there's something you genuinely want the answer to, ask."

Consider, for instance, how Mahrle once ended one of his posts with a question to his audience:

“Second,” He adds, "Try something new for a week and share the results. Gather new ideas from people like Josh Braun, Founder of Josh Braun Sales Training, or Jason Bay, Chief Prospecting Officer at Blissful Prospecting, as well as podcasts like 30 Minutes to President's Club. Document the results. Then share what you learned."

Finally, he adds, you could share a cold-calling war story.

“Everyone in sales has an interesting cold call. Share the transcript of a recent one (good or bad) and see if there's a lesson to be learned from it.”

Finally, let's dive into 15 social selling post ideas to engage your prospects.

15 Social Selling Post Ideas to Get Buyers Talking

Use Questions to Start Conversations

Posing a thoughtful question is a great way to engage your prospect. And a question is especially useful if the person shared someone else's post (rather than writing it on their own), since it gives them an opportunity to demonstrate their own expertise.

  1. “Fantastic insights, [name]. What advice would you give for someone in [X situation]?”
  2. “I love what you said about [specific point] -- so true, even though most people think [different opinion]. Which experiences led you to that conclusion?”
  3. “[Name], this was a great read. Have you seen the latest news on [topic]? What's your take?”
  4. “I've never considered [idea] from that angle. Do you think it still holds true [under X circumstances]?”
  5. “I've read a couple other posts on this topic, but yours was the most [convincing, thought-provoking, well-researched, well-argued] by far. What do you believe [topic] will look like in five years?”

Use Comments to Forge Relationships

Giving the prospect some praise will make them feel good — which, in turn, will make them like you more. But of course, this strategy only works if you‘re being genuine, so don’t compliment something you don't truly appreciate.

  1. “Well-said, [name]. I especially liked your point on [topic] -- in my experience … ”
  2. “Yes! This article should be required reading for people in [role, industry, position]. Just forwarded it to a couple friends.”
  3. “Spot-on analysis of [subject]. Your explanation of [X], in particular, was fascinating. I'd be eager to read a follow-up post on [X] alone.”
  4. “Thanks for pointing out why we shouldn't do [X]. I'm definitely guilty of doing that in the past -- to stop, I adopted [strategy].”
  5. “Haven't read anything this accurate in a while, [name], awesome job. To add to this, I've found [related idea].”

Use Shares to Boost Egos

Everyone wants more views, so sharing your prospect's post (or share) will almost certainly score you some points.

  1. “Looking for advice on [subject]? @prospect, expert in X, has your back: [link].”
  2. “Are you up-to-date on [topic]? Check out @prospect's comprehensive article: [link].”
  3. “@prospect's latest post on [topic] is definitely worth your time. [Link]”
  4. “Impressed with the solid insights in this post on [topic] from @prospect. [Link]”
  5. “[Short quote from post] - @prospect. [Link]”

If you add your own sample questions, comments, or posts below, we'll give you some ideas on how to make them even better.

Ultimately, conversation starters aren't easy — but the more personalized, authentic, and human you can make them, the more likely you are to see meaningful responses in return.

New Call to action

Topics: Social Selling

Related Articles

HubSpot uses the information you provide to us to contact you about our relevant content, products, and services. HubSpot will share the information you provide to us with the following partners, who will use your information for similar purposes: Surfe. You can unsubscribe from communications from HubSpot at any time. For more information, check out HubSpot's Privacy Policy. To unsubscribe from Surfe's communications, see Surfe's Privacy Policy.

Use this guide to improve your LinkedIn social selling efforts, train your team, and close more deals.

Powerful and easy-to-use sales software that drives productivity, enables customer connection, and supports growing sales orgs