Awkward intros to cringey DMs: 10 networking mistakes experts say you need to avoid

You know networking matters. Everyone says so. But when you're in the moment — sending a connection request, making small talk at an event, or following up after a meeting — it’s easy to second-guess yourself.

Am I coming across as too eager? Too transactional? Should I even reach out at all?

I’ve been there. When I first started networking on LinkedIn, I thought I had to impress people with long, detailed messages. So I sent 500-word InMails, packed with my background, why I admired their work, and exactly how I thought we could collaborate.

I was sure they’d be impressed. Instead? Crickets. No responses.

Over time, I learned what works and what doesn’t, both from experience and from observing people who do it effortlessly. Let’s break down the biggest mistakes and how to do better.

Networking Mistakes to Avoid

Not too long ago, networking mostly happened at conferences, coffee meetings, and industry events. You had to shake hands, make eye contact, and navigate small talk in real time. Now, with LinkedIn, you can connect with anyone, anywhere, at any time.

That’s a huge advantage — but it also means more ways to make a bad first impression.

I contacted my LinkedIn community and asked them to share their biggest networking blunders. I’m also sharing some examples (sent to me and by me).

In this section, you’ll learn the virtual and in-person mistakes that make networking feel awkward, ineffective, or even damaging your professional reputation.

In-Person Networking Mistakes

Conferences, industry meetups, coffee chats — anywhere professionals gather, there’s an opportunity to make helpful connections. But in-person networking comes with its own set of challenges. You’re juggling first impressions, real-time conversations, and the pressure to be memorable, all while trying not to come across as awkward or pushy.

The good news? Most networking mistakes are easy to fix once you know what to look out for. Here are five common missteps to avoid.

1. Showing up without a plan.

If you don’t know why you’re attending an event or who you want to meet, you’ll struggle to make genuine connections. Without a plan, you risk feeling out of place, missing key opportunities, or leaving early without any takeaways.

Harshala Chavan, founder of Merrative, a community of industry and academic experts, experienced this firsthand:

To avoid this, set clear goals before attending. Research attendees or speakers, identify a few people you’d like to connect with, and prepare a couple of conversation starters. Having a plan makes networking feel intentional rather than overwhelming.

2. Mistaking quantity for quality.

I’m naturally social, but at one conference, I cranked it up to another level, talking to as many people as possible and exchanging LinkedIn connections left and right.

The problem? Most of those connections didn’t mean anything. I was so focused on meeting everyone that I barely had any productive conversations.

A week later, I looked at my LinkedIn inbox — dozens of new contacts but barely any replies when I followed up.

Quality connections come from genuine conversations where you learn about someone's challenges, share relevant insights, and establish actual rapport.

One thoughtful 15-minute conversation can be worth more than 20 rushed introductions. Focus on making a few people remember you rather than forgetting dozens yourself.

3. Holding back and missing opportunities.

Networking can be draining, especially if you’re not naturally extroverted. But if you let that discomfort keep you from engaging, you might leave an event without making any new connections.

Saloni Ordia, a B2B SaaS freelancer writer, recalled attending her first big industry event, only to leave regretting that she hadn’t introduced herself to anyone.

Similarly, Kuba Czubajewski, Founder of content agency StoryAngled, admitted:

It’s easy to stick to what feels safe, whether it’s standing on the sidelines or talking only to people you already know. But pushing yourself just a little outside your comfort zone can make all the difference.

Instead of aiming to meet everyone, set a small, achievable goal: introduce yourself to three new people, ask one speaker a question, or join a conversation already in progress. The more you do it, the easier it gets.

4. Oversharing your research.

There’s preparation — and then there’s oversharing.

Before a conference, I had a few leads in mind and did my homework. I checked out their LinkedIn posts, read their articles, and noted discussion points I could bring up. So far, so good.

Then I met them. And in my eagerness to show I was prepared, I blurted out that I had read all of their posts before coming.

Their smile froze, and they nodded awkwardly before quickly shifting the conversation.

Yikes. Stalker-level.

Research is great — it helps you start important conversations — but you don’t need to lay it all out. Instead, use your knowledge naturally. Mention a recent post of theirs if it fits the conversation, but don’t make it sound like you’ve been studying them for weeks.

Keep it casual, and they’ll appreciate the interest without feeling like they need a restraining order.

5. Making the conversation one-sided.

Networking is about building relationships, not delivering a monologue. But in the moment, especially when you’re trying to make a strong impression, it’s easy to fall into the trap of only talking about yourself — your work, your projects, your goals.

The problem? People remember how you make them feel, not just what you say. And if the conversation feels like a one-person TED Talk, they’ll tune out fast.

A good conversation leaves the other person feeling valued and heard.

Try the 70/30 rule: spend 70% of your time listening and asking thoughtful questions like “How did you get into this industry?” or “What’s the most exciting project you’re working on?” and only 30% talking about yourself.

LinkedIn Networking Mistakes

Consider this my version of LinkedIn Lunatics. I’ve seen it all — and I’ve got receipts.

LinkedIn, at its best, is an incredible place to build meaningful professional relationships. But at its worst? It’s a playground for networking missteps that range from mildly awkward to outright cringe.

As Sara Stella Lattanzio, Head of Marketing at professional services firm Stryber says, bad networking happens more often than we’d like to admit.

We’ve all been on the receiving end of bad LinkedIn networking, but let’s be honest — most of us have probably made a few of these mistakes ourselves.

So here are five of the biggest virtual networking missteps you’ll want to avoid.

1. Messing up the follow-up.

Following up is good. Following up badly is a fast way to burn a bridge.

Our 2024 State of Sales Report highlights how 36% of sales managers say that follow-ups sent to high-quality leads are the most important tracking metric. That means follow-ups are a key factor in whether a conversation turns into an opportunity.

Freelance copywriter Laura Ilioaei learned this the hard way:

A good follow-up is polite, thoughtful, and adds value. A bad one is pushy, impatient, or too informal for the situation. Instead of a one-word nudge, try re-engaging with something useful:

“Hi [Name], I know you’re busy, but I wanted to follow up on my message. No rush at all—just wanted to see if you might have time to connect when it works for you.”

Timing and frequency matter just as much as content. That follow-up email you're itching to send 24 hours after your initial message? Hold off.

Give busy professionals at least a week before your first follow-up, then space additional attempts 2-3 weeks apart.

And know when to take the hint; after two or three unanswered messages, it‘s time to move on. The professional world runs on mutual respect, and part of that is recognizing when someone isn’t interested in connecting right now.

2. Asking for too much right away.

Networking isn’t a shortcut to free coaching. But some people treat it that way, skipping the relationship-building part and jumping straight to big asks.

I get countless DMs from other freelancers who want advice, referrals, or a full breakdown of my client strategy — without ever engaging with me before. Here’s one I received:

No introduction. No effort to build a connection. Just an immediate request for insider knowledge.

Instead of cold DMs asking for a favor, try warm pitching. Engage with their content, comment thoughtfully, and offer value first. For example, if you admire someone’s work, share how it’s helped you.

Build genuine rapport, and when the time comes to ask for advice, they’ll actually want to help.

3. Coming across as desperate.

There’s no way to sugarcoat this: desperation is a networking killer.

For example, you might think offering an incentive makes your request more appealing, but in reality, it can backfire. Sam Wright, Head of Operations and Partnerships at AI resume builder platform Huntr, shared his experience:

Another cringey way you can approach connections is by oversharing personal struggles to get a favor.

I’ve received many messages from people saying they’re struggling to find jobs and support their families. It puts me in a tough position. I understand the struggle, but when a complete stranger frames their request this way, it feels less like networking and more like emotional pressure.

Instead, create mutual value. Show genuine interest in the other person‘s work or expertise. Ask specific, thoughtful questions that demonstrate you’ve done your homework.

Or better yet, offer something helpful first — share an article relevant to their recent post or introduce them to someone in your network who might be valuable to them.

4. Leave AI-generated comments on their posts.

Now, this is something new … and painfully obvious when it happens.

You’ve probably seen them — bland, generic LinkedIn comments that sound robotic and offer zero value. Something like:

Or worse, AI-generated comments that repeat the post almost word for word.

We notice when comments feel inauthentic. And if your first impression on someone is an AI-generated reply, you’ve already signaled that you’re not invested in the conversation.

Content strategist and writer Tanaaz Khan summarizes the problem with AI-generated comments perfectly:

Instead, take a few extra seconds to add a real thought. React to something specific in the post, share a quick related experience, or ask a follow-up question. Thoughtful comments start honest conversations — copy-paste ones get ignored.

5. Sending mysteriously empty messages.

I recently received this complete LinkedIn message:

That's it. Nothing else. No context, no introduction, no question, no call to action — just those two words floating alone in my inbox.

What exactly am I supposed to do with “Hi, ma'am”? Reply with an equally vague “Hello”? Guess what they might want? Play a digital version of 20 questions to extract their actual purpose?

This lazy networking puts the entire burden of interaction on the recipient.

The strangest part is that the sender likely believes they‘ve initiated a conversation when, in reality, they’ve created a dead end. Without substance, there's simply nowhere for the conversation to go.

If you're reaching out, include your purpose, a specific question, or, at minimum, a complete thought. Your message should give the recipient something concrete to respond to, not a communication riddle to solve.

3 Tips to Get Networking Right

Networking doesn’t have to feel forced. At its core, it’s just about having genuine conversations and building relationships over time.

The problem? A lot of people either overthink it or rush into it without a concrete strategy.

If you want to network in a way that actually leads to opportunities (without feeling awkward or desperate), here are three key things to keep in mind.

1. Read and respond to conversational cues.

Iryna Kutnyak, Director of Operations at content agency Quoleady, shares a relatable moment many of us have experienced:

Iryna's story highlights a crucial networking skill: the ability to read conversational cues and pivot accordingly.

People give off subtle signals about their comfort level, interest, and familiarity in networking situations. Picking up on these cues — confused expressions, hesitant responses, or enthusiastic engagement — lets you adjust your approach in real time.

When someone seems uncertain or uncomfortable, create space with open-ended questions. When they show excitement about a topic, dig deeper. And when you sense they don't remember you (or vice versa), offer context without making it awkward.

This adaptive approach keeps conversations flowing naturally and helps build genuine connections, even in potentially uncomfortable situations.

2. Use small talk as a gateway to deeper conversations.

A simple “How are you?” might seem like just a polite opener, but it’s an opportunity to steer the conversation in a constructive direction.

As content strategist Lara Eviota shared:

Instead of defaulting to a one-word answer, use “How are you?” as a chance to introduce something interesting about yourself.

Try: “Good! Just wrapped up a project on [topic]—it made me rethink how [related insight]. What about you?” This gives the other person something to latch onto, making it easier to spark a real, engaging conversation.

3. Don’t be too transactional.

The transactional networker's mindset is obvious: they appear when they need something and disappear until their next request. They treat relationships as purely utilitarian, focused solely on what others can do for them.

I get it — we‘re all in it for professional growth. But it shouldn’t be limited to just your own.

Networking is about genuinely connecting with others. Our data shows that 82% of sales professionals say building strong relationships is the most crucial and rewarding aspect of the sales process.

That applies beyond sales. Strong professional relationships open doors to referrals, collaborations, and unexpected opportunities, not just one-off transactions.

I regularly share insights on LinkedIn, things like actionable advice, workflow improvements, or lessons learned. I also actively connect people with opportunities, whether that’s recommending a freelancer or introducing someone to a potential mentor.

Building genuine professional relationships means staying connected even when you don't need anything. For example:

• Share resources that might help people in your network
• Congratulate connections on their achievements without expecting anything in return
• Introduce people who could benefit from knowing each other

These small acts of generosity create a foundation of goodwill that transforms networking from a series of transactions into an ecosystem of mutual support. When you consistently show up for others, they're naturally more inclined to help when you eventually do need something.

Good Networking Doesn’t Feel Like Networking

Whether in-person or online, small changes in how you approach conversations can make all the difference.

Avoid the common mistakes, focus on genuine engagement, and remember: the best networking doesn’t feel like networking at all. It feels like connecting with people who share your interests and goals.

Do that consistently, and opportunities will follow naturally.