LinkedIn Direct Messaging Triggers: The Ultimate Guide to Strategic Outreach

You will not get clients if you do not reach out. Waiting for people to come to you is a pipedream.

Some people promise that they will teach you how to post and BOOM you will get clients from posting.

What you will get is burned, not clients.

Why? Because clients dont come from posting.

Posting is important but not to get clients.

You get clients for a combination of strategy, assets and action.

Posting alone is just ONE SMALL part.. While its important, I believe that Direct Messaging or DMing is more important than posting.

When someone sends me a DM, I check it.

Most Dms are SPAM because they lack context and they lack an event that makes sense.

I call those events TRIGGERS.

SOOOOO Here are 25 triggers, which are REASONS to direct message people.

Oh, and Im giving you a template for each one!

Remeber that with direct messaging there is a FUNNEL you want to take people through.

Greeting, Feeding and Meeting.

At the end of the day, your goal is to get on a call with a prospect or referral partner.

POSTING > CONNECTION > ENGAGEMENT > MESSAGING > MEETING

Come to our next training session and watch this in action.

BTW, did you know that when you DM someone they are more likely to see your content!

How many connections do you have right now?

Personally I have the MAX 30k, but im happy to remove a few folks and add new ones!

While building an impressive connection count might look good on paper, the real power of LinkedIn lies in the relationships you nurture through strategic, timely communication.

Timely means there is an event.

This is where Direct Messaging Triggers come into play – specific moments and opportunities that create natural, welcome reasons to initiate or deepen professional relationships through LinkedIn's messaging platform.

When leveraged correctly, these triggers transform cold outreach into warm conversations and passive connections into active relationships.

As someone who has built and optimized WORKING LinkedIn strategies for over 1000 clients, I've identified 30 high-impact Direct Messaging Triggers that can systematically strengthen your professional network.

Join our next 2 hour strategy session by getting the bundle www.evyai.com/bundle

I've organized these DM templates and triggers into five strategic categories to help you implement them methodically in your outreach efforts.

Lets break it all down for you.

Category 1: Engagement-Based Triggers

These triggers capitalize on existing engagement, extending conversations that have already begun in some form.

1. Newsletter Subscribers

Why it matters: Your newsletter subscribers have already expressed interest in your insights. Reaching out personally converts them from audience members to actual connections.

Feeding Template: "Hi [Name], I noticed you subscribed to my LinkedIn newsletter on [Topic]. I'm curious – what specific aspects of [Industry/Topic] are you most interested in learning about? I'm planning upcoming content and would value your input."

Greeting Template: "Hi [Name], THANK YOU for subscribing to my LinkedIn newsletter on [Topic]. I appreciate any feedback you might have, feel free to let me know what you think of the articles!"

2. Commenters After Delay (10+ Hours)

Why it matters: Following up privately after public comments shows you value their contribution beyond the initial interaction.

Feeding Template: "Hey [Name], Your comment on my post about [Topic] yesterday really stood out to me. I'd love to hear more about your experience with [Related Point They Made]. Would you be open to sharing a bit more about how you've approached this challenge?"

Greeting Template: "[Name], I noticed your comment on my post about [Topic] yesterday I really appreciate your comment and I wanted to drop a line to say, THANK YOU."

3. Daily New Commenters

Why it matters: First-time commenters have crossed the engagement threshold and are prime candidates for deeper connection.

Feeding Template: "Hi [Name], I noticed and appreciated your first comment on my content today. I'm always looking to connect with professionals who share interests in [Relevant Topic]. What prompted you to engage with that particular post?"

Greeting Template: "[Name], Welcome to my world, thanks for the comment! Looking forward to seeing more of you in my posts! Appreciate the engagement."

4. Content Sharers

Why it matters: People who share your content are actively amplifying your voice – they're already advocates.

Feeding Template: "Hello [Name], I just saw that you shared my post about [Topic]. I really appreciate you extending its reach to your network. What aspect of the content resonated most with you? I'd love to provide more value in that area."

Greeting Template: "[Name], I just saw that you shared my post about [Topic] with your connections. I really appreciate you extending with a REPOST. Thank you for doing that!"

5. Profile Mentions

Why it matters: When someone mentions you publicly, acknowledging it privately adds a personal touch to the professional relationship.

Feeding Template: "Hi [Name], Thanks for mentioning me in your post about [Topic]. I appreciate the recognition and would love to learn more about your work in this area. What projects are you currently focused on?"

Greeting Template: "[Name], Thanks for mentioning me in your post about [Topic]. I loved seeing that I was mentioned, feel free to mention me in the future again. Thanks for the exposure to your network!"

6. Post Reactors

Why it matters: Reactions (especially "insightful" ones) demonstrate specific content resonance worth exploring.

Feeding Template: "Hello [Name], I noticed you found my post about [Topic] insightful. I'm curious – what elements particularly connected with your experience? I'm developing more content in this area and would value your perspective."

Greeting Template: "[Name], I noticed you found my post about [Topic] insightful. Giving my content a like really helps get it out there. Appreciate your engagement very much. Thanks"

Category 2: Network Expansion Triggers

These triggers help strategically grow your network through timely outreach to people already showing interest.

7. New Profile Viewers

Why it matters: Profile views indicate interest – reaching out captures attention while their curiosity is active.

Template: "Hi [Name], I noticed you viewed my profile recently. I took a look at yours as well and was impressed by your work in [Their Field/Company]. I'd love to connect and learn more about your experience with [Specific Element from Their Profile]."

8. Company Page Followers

Why it matters: These connections already value your company; personalizing the relationship elevates their engagement.

Template: "Hello [Name], I see you're following [Company Name]. As [Your Position], I'm always keen to connect personally with professionals interested in our work. What aspects of [Company Industry/Focus] are you most curious about?"

9. New Connections

Why it matters: Welcome messages establish relationship tone and prevent connections from becoming dormant.

Template: "Hi [Name], Thanks for connecting! I'm interested in learning more about your work in [Their Industry]. What projects or challenges are you currently focused on? I'd be happy to share resources that might be helpful based on my experience with [Your Expertise]."

10. Currently Online Connections

Why it matters: Reaching out when someone is active increases response likelihood and conversation immediacy.

Template: "Hello [Name], I noticed you're online and thought I'd reach out about [Relevant Topic/Opportunity]. Do you have a few minutes to chat about [Specific Question/Idea]? Your perspective would be valuable."

11. Inbound Connection Requests

Why it matters: Following up after accepting requests shows enthusiasm and creates momentum.

Template: "Hi [Name], Thanks for reaching out to connect! I'm curious what prompted you to connect – was it my work in [Your Field], or do we have mutual interests in [Industry Trend]? I'm always looking to build meaningful professional relationships."

12. Content-Posting Industry Peers

Why it matters: Reaching out about specific content they've shared creates natural conversation starters.

Template: "Hello [Name], I just read your post about [Topic] and found your perspective on [Specific Point] particularly interesting. I've been thinking about this from [Your Perspective]. Would you be open to exchanging thoughts on this topic?"

Category 3: Relationship Maintenance Triggers

These triggers help keep your network warm through regular, meaningful touchpoints.

13. Work Anniversaries

Why it matters: Acknowledging professional milestones shows attentiveness and creates natural reconnection points.

Template: "Hi [Name], I noticed it's your [X] anniversary at [Company]. Congratulations on this milestone! I'd love to hear about your journey there – what has been your most significant learning or achievement over this time?"

14. Birthday Celebrations

Why it matters: Personal acknowledgments build genuine connections beyond pure business interests.

Template: "Happy birthday, [Name]! I hope your day brings both joy and a moment to reflect on your accomplishments this past year. Is there anything exciting you're looking forward to in the coming year professionally?"

15. Missed Celebration Opportunities

Why it matters: Following up on missed milestones shows thoughtfulness and can stand out more than day-of greetings.

Template: "Hello [Name], I just realized I missed your [work anniversary/birthday] last week. While belated, my congratulations and good wishes are no less sincere! How have things been developing at [Company/Life] lately?"

16. Job Changes

Why it matters: Career transitions create natural opportunities for reconnection and support.

Template: "Hi [Name], Congratulations on your new role at [Company]! Your experience at [Previous Company] seems like perfect preparation. I'd love to hear about what excites you most about this new chapter in your career."

17. Published Content

Why it matters: Acknowledging their thought leadership creates meaningful engagement based on their expertise.

Template: "Hello [Name], I just read your article on [Topic]. Your point about [Specific Insight] was particularly thought-provoking. I'm curious – what inspired you to explore this subject? I have some related thoughts I'd be happy to share."

18. Notable Achievements

Why it matters: Recognizing accomplishments beyond standard promotions shows genuine interest in their success.

Template: "Hi [Name], I just saw the news about [Their Achievement]. What an impressive accomplishment! I'd love to hear more about the work that led to this success when you have a moment."

Category 4: Event-Based Triggers

These triggers leverage shared experiences to create or strengthen connections.

19. AMA/Live Event Participants

Why it matters: Following up after hosting events converts group interactions to individual connections.

Template: "Hello [Name], Thank you for participating in yesterday's live session on [Topic]. Your question about [Specific Question] was insightful. I'd love to explore that further – did my response address what you were looking for, or would you like to discuss this more deeply?"

20. Fellow Event Attendees

Why it matters: Connecting with peers from events creates bonds based on shared interests and experiences.

Template: "Hi [Name], I noticed we both attended [Event Name]. What did you think of the session on [Topic]? I found the speaker's perspective on [Specific Point] particularly relevant to my work in [Your Field]."

21. In-Person Meeting Follow-Ups

Why it matters: Promptly transitioning from offline to online reinforces the initial connection.

Template: "Hello [Name], It was great meeting you at [Event] yesterday. I enjoyed our conversation about [Topic You Discussed]. As promised, here's the [Resource/Information] we talked about. I'd love to continue our discussion when you have time."

22. Shared Background Connections

Why it matters: Common history creates instant rapport and mutual understanding.

Template: "Hi [Name], I noticed we both [attended the same university/worked at the same company]. I'd love to connect with a fellow [Alma Mater/Company] alum! What years were you there, and what has your journey been like since?"

Category 5: Strategic Outreach Triggers

These triggers create purpose-driven outreach for specific professional goals.

23. Skill Endorsers

Why it matters: Acknowledging endorsements creates reciprocity while recognizing their support.

Template: "Hello [Name], Thank you for endorsing my skills in [Skill Area]. I appreciate your vote of confidence! I'd be happy to endorse your expertise as well – which areas of your work are you currently most focused on developing?"

24. Multiple Profile Viewers

Why it matters: Repeated views indicate strong interest that they may be hesitant to act on.

Template: "Hi [Name], I've noticed you've visited my profile a few times recently. I'm always open to connecting with professionals interested in [Your Field]. Is there something specific about my background that caught your attention or any way I could be helpful?"

25. Potential Mentors

Why it matters: Approaching leaders with specific questions shows respect for their expertise.

Template: "Hello [Name], I've followed your work in [Their Expertise Area] for some time and particularly admired your approach to [Specific Achievement/Project]. I'm currently working on [Your Related Project] and would value your insight on [Specific Question]. Would you be open to a brief conversation?"

FAQ: LinkedIn Direct Messaging Best Practices and DM Questions

Q1: How many LinkedIn direct messages should I send per day?

A: Quality trumps quantity. Focus on 5-7 highly personalized outreach messages daily rather than mass-sending generic templates. LinkedIn's algorithm may flag accounts sending more than 100 messages daily to non-connections as spam.

Using evyAI templates can make this go very fast. www.evyai.com

Q2: When is the best time to send LinkedIn messages?

A: Tuesday through Thursday, between 8-10am or 1-3pm in the recipient's time zone typically yields the highest open and response rates. However, messaging someone when they're currently active on the platform (green status dot) can increase immediate engagement.

I personally like to send messages on weekends as well as weekdays because people are getting less inbound messages on weekends.

Q3: Should I use voice messages instead of text on LinkedIn?

A: Voice messages can differentiate your outreach and convey authenticity, but use them selectively for contacts with whom you have some familiarity. Keep voice messages under 60 seconds and always provide context at the beginning.

I personally cannot listen to voicenotes while im on the phone so follow up with the context of the note so people know what you said and they could listen to it when they have time.

Q4: Is it appropriate to follow up if someone doesn't respond on LinkedIn?

A: Yes, but limit follow-ups to one or two messages spaced 5-7 days apart. Each follow-up should add new value rather than simply asking for a response. After two follow-ups, respect their implicit communication preference.

Remember that people get busy and RELY on you following up!

Q5: How personalized should my LinkedIn DM messages be?

A: The more personalized, the better. Always reference something specific from their profile, content, or your shared experiences. Avoid using their name multiple times (which signals automation) and never use obvious mail-merge techniques.

Keep things really casual because its a TEXT not a article. lol.

Q6: Should I include calls-to-action in first LinkedIn message?

A: First messages should focus on establishing connection, not driving action. Ask a relevant question to encourage engagement rather than requesting a meeting. Save explicit calls-to-action for after rapport has been established.

Its a funnel not a sales party, do the greeting, feeding and meeting method we teach at evyrgreen.com

Q7: How long should my LinkedIn DM messages be?

A: Aim for 50-150 characters MAX (about 2-3 short sentances). Messages should be scannable on mobile devices, where most professionals check LinkedIn. Longer messages often go unread or are saved for later and forgotten.

I personally send one short sentance... see how it goes and then follow up from there.

Q8: Is it acceptable to message someone I don't know on LinkedIn?

A: Yes, if you have a legitimate reason for connecting and can clearly articulate the value or insight you're offering. Cold outreach works best when it references mutual connections, shared interests, or specific content they've engaged with.

The more context the better.

Q9: Should I use emojis and casual language on LinkedIn?

A: Mirror the communication style of your recipient and industry. Some fields embrace casual, emoji-rich communication while others maintain formal conventions. When in doubt, start slightly more formal and adjust based on their response.

Q10: How can I stand out in a crowded LinkedIn inbox?

A: Timing and relevance are key. Messaging someone after they've just posted content, changed jobs, or achieved something notable dramatically increases your visibility. Focus on being helpful rather than immediately advancing your agenda.

People only care about what is in it for them. THINK ABOUT IT THAT WAY!

Want AI to create all these messages for you?

Here is a PROMPT you can use to generate all these messages at ONCE for yourself and then save them into evyAI.

Custom LinkedIn Direct Message Generator

CONTEXT
I need to create personalized LinkedIn direct messages for 25 specific outreach scenarios (triggers) that align with my company's voice, offerings, and unique value proposition.

MY COMPANY
[Describe your business in 3-5 sentences. Include your industry, primary services/products, target audience, and what makes your approach unique]

BRAND VOICE
My brand voice is: [Choose 3-5 descriptors: e.g., "authoritative yet approachable," "data-driven but warm," "innovative and slightly playful," etc.]

PRIMARY GOAL FOR LINKEDIN OUTREACH
[Specify your main objective: lead generation, thought leadership, recruitment, partnership development, etc.]

MESSAGE PARAMETERS

Length: Keep each message between 300-500 characters (2-3 mobile-viewable paragraphs)
Structure: Opening line (personalized hook) → Value statement → Single question to encourage response
CTA: [Specify if you want specific calls-to-action included or if you prefer focusing on conversation initiation]
Links: [Indicate if/when you want to include links to content, calendars, etc.]

FOR EACH SCENARIO, PLEASE CREATE:

A subject line (if applicable)
A personalized message template with clear [PLACEHOLDERS] for customization
A follow-up message for non-responders (optional)

SCENARIOS TO COVER:
[List of the 25 LinkedIn Direct Messaging Triggers, organized by category]
ENGAGEMENT-BASED

Newsletter Subscribers
Delayed Commenters (10+ hours)
First-time Commenters
Content Sharers
Profile Mentions
Post Reactors (especially "insightful" reactions)

NETWORK EXPANSION

New Profile Viewers
Company Page Followers
New Connections
Currently Online Connections
Inbound Connection Requests
Content-Posting Industry Peers

RELATIONSHIP MAINTENANCE

Work Anniversary Congratulations
Birthday Wishes
Missed Celebration Follow-ups
Job Change Congratulations
Published Content Acknowledgment
Notable Achievement Recognition

EVENT-BASED

After Hosting Webinars/Live Events
Fellow Event Attendees
In-Person Meeting Follow-ups
Shared Background Connections (alumni, former coworkers)

STRATEGIC OUTREACH

Skill Endorsers
Multiple Profile Viewers
Potential Mentors/Industry Leaders

PERSONALIZATION INSTRUCTIONS
For each scenario, include specific instructions on:

What research I should conduct before sending (e.g., "Review their last 3 posts" or "Note something specific from their work history")
How to authentically connect their situation to my offering without being pushy
What question would most naturally continue the conversation

SPECIAL REQUIREMENTS
[Include any special considerations, such as regulatory requirements for your industry, content you absolutely want to avoid, or specific branding elements to incorporate]        

So, when should you message people? Lets look at this decision matrix

Want to learn more about LinkedIn? Read this article that breaks down everything you need to know to get up to speed on LinkedIn. We cover 10 different themes and answer over 100 common questions that people typically ask.

https://www.linkedin.com/pulse/top-linkedin-questions-ask-beginners-joe-apfelbaum-bed8e/

Its a must read for anyone that wants to learn LinkedIn even if you never used the platform.

Once you are done reading the article, test your knowlege by visiting this knowlege test here https://strategy.evyai.com/linkedin-101-test Enjoy.

Here are 64 LinkedIn content ideas in an article that you can enjoy so you never run out of ideas for what to post.

https://www.linkedin.com/feed/update/urn:li:activity:7319066587280396289/

Here are the three biggest mistakes people make when they post on LinkedIn. Hope you enjoy it.

https://www.linkedin.com/feed/update/urn:li:activity:7316812768051957760/

In this article I discuss the 18 biggest mistakes people make on Linkedin and what to do instead.

https://www.linkedin.com/pulse/18-critical-linkedin-mistakes-hurting-your-brand-how-fix-apfelbaum-jjnve/

Test your knowlege of the biggest LinkedIn mistakes with this quick quiz https://strategy.evyai.com/linkedin-mistakes-quiz

Here is our last class on how to use Linkedin to get clients.

Here are the details of what is available with the evyAI bundle.

When you are ready you can get started at http://www.evyai.com/bundle

Want to find emails from ANY target market? Use the evyAI pro Target Market Search tool and enjoy. https://strategy.evyai.com/targetmarketsearch

With evyAI you have a Sales Assistant that will help you GENERATE IDEAS, write POSTS and even save LinkedIn profiles into lists so you can strategically follow up with specific LinkedIn connections. Try evyAI now and see why so many people are loving our technology. http://www.evyai.com