How to Start Authentic Conversations on LinkedIn and Skip the Sales Pitch

How to Start Authentic Conversations on LinkedIn and Skip the Sales Pitch

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Does it feel like your LinkedIn efforts are disappearing into thin air?

You’re regularly posting, engaging with comments, and reaching out, yet the response is disappointingly quiet.

This struggle is more common than you might think. Many are caught in the cycle of superficial activities that don't translate into meaningful interactions or concrete business results.

LinkedIn is more than a platform for sharp profiles and active feeds; it's a space for making genuine connections that address the needs and solve the problems of your potential clients.

To truly make an impact, you need to rethink your approach. Simply posting and hoping for engagement isn't enough. Deep engagement requires understanding what your audience cares about deeply. It's about moving beyond mere transactional interactions on LinkedIn to build relationships through authentic, value-driven conversations.

The "warming up" phase is critical and often underestimated.

Effective conversation starters involve gradually "warming up" your audience before you send that connection request or message. This process ensures that when you do reach out, you're not just another LinkedIn connection but a thoughtful thought-leader who genuinely understands and can address their specific pain points.

Moreover, it's essential to avoid sounding salesy. The goal is to foster relationships, not just close deals. When you focus on being helpful and providing value without an immediate expectation of something in return, you naturally attract more meaningful and lasting connections.

Here’s how you can shift from a passive to a proactive engagement strategy on LinkedIn, avoiding salesy tactics and initiate real conversations:

1- Focus On Your Audience’s Interests:

To truly drive engagement and generate meaningful business opportunities on LinkedIn, it’s vital to tailor your content to the specific needs and interests of your audience. This approach involves going beyond merely posting educational or entertaining information. Instead, you should create content that demonstrates a clear understanding of the challenges your audience is facing and positions you as a solution provider.

By focusing on their interests, you show that you’re not just another professional on LinkedIn; you’re a valuable resource ready to address their pain points. This not only fosters trust but also naturally initiates conversations that can lead to tangible business relationships. When your audience sees that you genuinely care and have the expertise to help solve their problems, they're more likely to engage with you and consider your services or products as viable solutions.

→ Actionable Tip: Constantly engage with your LinkedIn network by monitoring discussions and identifying pain points within your industry. Use this information to create content—whether it’s a detailed post, a quick tip, or an insightful video—that directly addresses these challenges. This strategy not only positions you as a knowledgeable leader but also as a proactive problem-solver, inviting more meaningful interactions and building trust with your audience.

For instance, if you're in the digital marketing space and notice a lot of discussion about the challenges of adapting to new Google algorithms, use this as a content opportunity.

2- Be a Storyteller, Not a Salesperson:

Whether you're crafting posts, reaching out to connections, or engaging in group discussions on LinkedIn, adopting a storytelling approach can significantly enhance your interactions. Share experiences from your professional journey that highlight how you've tackled challenges, achieved milestones, or learned valuable lessons. This method of storytelling is engaging because it does more than just convey information—it connects on an emotional level, making your content relatable and memorable.

For example, if you're introducing a new product or service, rather than just detailing its features, share the inspiration behind it and the challenges your team overcame during its development. This narrative could be woven into posts, messages, or even comments, providing a richer context that invites engagement.

→ Actionable Point: Next time you achieve something noteworthy or gain a new insight, use this as a foundation for interaction on LinkedIn. Narrate this experience in your posts, weave it into your messages when reaching out to new contacts, or share it during discussions in relevant groups. End with a thought-provoking question like, "Have you faced a similar challenge? What was your takeaway?" This approach not only draws people in but also encourages them to share their stories in response, sparking genuine conversations and deeper connections on the platform.

3- Identify Common Ground Before Reaching Out:

Before you send out a connection request or a message, take the time to understand your potential connection’s interests, challenges, and achievements. Review their profile, recent posts, and shared articles to find topics they care about. This initial effort helps tailor your approach to align with their professional landscape, increasing the likelihood of a positive response.

→ Actionable Point: Use the insights gained to tailor your first message, referencing a piece of content they’ve posted or a mutual interest you’ve identified, to break the ice effectively.

Also read: Top Secrets for Mastering Proactive Outreach on LinkedIn

4- Ask Open-Ended Questions:

Questions are potent tools for initiating and sustaining conversations on LinkedIn. By asking open-ended questions that tap into the expertise or interests of your connections, you demonstrate respect for their knowledge and invite them to engage in a deeper dialogue. This approach not only shows that you value their opinions but also fosters a more meaningful exchange of ideas.

To effectively use this strategy, you can incorporate questions into various interactions on the platform. For instance:

  • In Comments: When someone in your network posts an article or shares an insight, respond with a thoughtful open-ended question that relates to the content. For example, if a connection writes about innovations in technology, you could ask, “How do you see these advancements impacting our day-to-day work in the next five years?”
  • In Posts: When you publish your own content, conclude with an open-ended question to your audience. This invites comments and starts a conversation right on your post. For example, after sharing insights on remote work trends, you might ask, “What strategies have you found most effective for maintaining team cohesion remotely?”
  • During LinkedIn Live: If hosting or participating in a LinkedIn Live session, weave open-ended questions into your dialogue to engage the audience in real-time. This can be particularly effective in Q&A sessions or panel discussions, where live interaction is encouraged.

→ Actionable Point: In your next interaction on LinkedIn, whether it’s a comment, post, or during a live session, ask a question like, "What do you think is the biggest challenge facing our industry today?" This type of question opens up the floor for a detailed response and can lead to a rich exchange of ideas, helping you to start meaningful conversations and build stronger connections.

5 - Engage Regularly with Their Content:

To effectively initiate conversations on LinkedIn, start by consistently engaging with the content posted by your connections. Before reaching out directly via messaging, make your presence known by thoughtfully commenting on their articles, sharing their posts with your network, or reacting to their updates.

→ Actionable Point: Dedicate a few minutes each day to actively engage with content from your connections. Make a habit of commenting on, sharing, or reacting to a few posts each day. This regular interaction keeps you visible in your network and positions you as an engaged professional. When the time comes to reach out directly, your connection is more likely to recognize you and be open to starting a conversation, thanks to the rapport you've built through consistent engagement.

6- Utilize LinkedIn Stories and Live for Real-Time Engagement:

LinkedIn's Stories and Live features are exceptional tools for sparking real-time conversations and deepening engagement with your network. These interactive formats allow you to share candid moments from your professional life and host live discussions, which can help humanize your presence and make you more relatable to your audience.

For instance, hosting a LinkedIn Live session can be a direct way to engage with your network about current trends or challenges in your industry. This live format encourages viewers to participate actively by asking questions, sharing their viewpoints, or responding to polls, creating a dynamic two-way conversation.

→ Actionable Point: Schedule a LinkedIn Live session to discuss a hot topic or recent development in your industry. Promote the event in advance using LinkedIn posts and Stories, urging your network to join and participate. During the session, actively solicit questions and comments from viewers, and respond in real-time.

7- Comment with Context

Engaging with someone’s LinkedIn post by commenting isn’t just about leaving a remark; it’s about enriching the conversation. When you add your own insights or share relevant experiences, you demonstrate deep engagement and contribute valuable perspectives to the discussion. This approach shows that you're not merely browsing through; instead, you're actively participating and adding substantive content.

For example, if someone posts about challenges in remote team management, share a technique or tool you’ve found effective in your own experience. Not only does this add depth to your comment, but it also positions you as someone knowledgeable and helpful in that area.

→ Actionable Point: When commenting, aim to introduce a point or perspective that hasn’t been brought up yet. This could be an innovative idea, a contrasting viewpoint, or an extension of the original post. By doing this, you show that you’re thoroughly engaged and possess a deep understanding of the topic.

8- Be Responsive and Timely in Your Interactions

Promptness in responding to comments and messages on LinkedIn is crucial for maintaining a lively conversation and demonstrating that you are an engaged and attentive member of your network. When you reply quickly, it shows that you value the interactions and are committed to fostering strong relationships.

For instance, if someone comments on your post or asks a question, responding swiftly not only keeps the discussion active but also encourages others to join in, seeing that you are actively participating. This can lead to more robust interactions and a greater sense of community around your content.

→ Actionable Point: Set a goal to reply to comments and messages within 24 hours. This rapid response rate can significantly increase engagement by showing your connections that you appreciate their input and are eager to engage in dialogue. If possible, tailor your responses to add value, providing further insights or asking follow-up questions to deepen the conversation.


In conclusion, transforming your LinkedIn presence from passive to proactive isn't just about increasing your activity on the platform—it's about strategically fostering genuine relationships through thoughtful, value-driven interactions.

Remember, the key to success on LinkedIn is not in the quantity of your connections, but in the quality of the conversations you initiate.

It’s about understanding the needs of your audience, responding promptly, and maintaining a tone that is helpful, not salesy. This approach ensures that when you reach out, you're seen as a valuable resource rather than just another professional looking for a quick sale.

Reflection Questions:

  • What are the common pain points your connections frequently discuss, and how can you address these in your content?
  • How can you use storytelling to make your interactions on LinkedIn more engaging and memorable?
  • Are you taking the time to listen and respond thoughtfully to the comments and posts of your connections?

If you're looking to dive deeper and truly master the art of initiating real conversations on LinkedIn that lead to tangible business outcomes, I invite you to book a call with me.

To schedule your consultation and learn more about how we can help enhance your LinkedIn strategy, please reach out today.

Let's make your LinkedIn efforts as impactful as possible, transforming potential connections into valuable conversations and clients.

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About Mike Weiss

Introducing Mike Weiss - the LinkedIn maestro and digital marketing strategy guru who turns ordinary profiles into lead-generating powerhouses! Mike's magic touch can transform LinkedIn feeds into thriving digital ecosystems, assisting everyone from thought leaders to sales teams. When not dominating the LinkedIn world, Mike is busy crafting top-notch online education platforms and writing cutting-edge curriculums for digital courses. Catch him collecting digital badges like a Pokémon master and reliving the glory of his 2012 Infusionsoft Internet Marketer of the Year finalist days. With a unique blend of experience, wit, and charm, Mike is your go-to guy for catapulting your LinkedIn presence and digital learning initiatives into the stratosphere!

Book a free call with me, and let’s strategize your LinkedIn success.

??Contact me today to learn more!

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It's interesting that you bring up the challenge of superficial interactions on LinkedIn. We've found that taking a more personalized approach to engagement can make a big difference in building meaningful relationships. What strategies have you found most effective in shifting from passive to proactive engagement without coming across as too sales-focused?

Amanda Hoff

Seeking Opportunities | Ready for the Next Adventure

3 个月

This is such an important topic! Authentic connections are the foundation of building meaningful relationships on LinkedIn.

Put on a blue cap! That looks authentic.

Alistair Chegwidden ??

We help busy founders strategically repurpose & schedule content across platforms to save time and attract new clients. Founder | Coach | Father

3 个月

Great tips, Mike! Authentic conversations are the key to real connections.

Scott Hoffman

I buy profitable, tenured companies as well as consulting with leaders to get their business to the next level.

3 个月

The “warming up” phase is crucial for developing authentic LinkedIn relationships.

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