The 7-Day Conversation Challenge: Kickstart Meaningful LinkedIn DMs

The DM Drought (And How to End It)

Emily had been on LinkedIn for five years. She posted occasionally. She had 1,200 connections. But when she looked at her DMs, it was a ghost town. A few automated InMails from recruiters. Some old conversations from 2022. Nothing recent. Nothing meaningful.

The problem wasn't that people didn't want to talk to her—it was that she wasn't starting conversations. She'd scroll through her feed, see interesting posts, think "I should reach out to them," and then... do nothing. The idea of sending DMs felt awkward. She didn't know what to say. She worried about being pushy or irrelevant.

So she stayed silent. And opportunities passed her by.

Sound familiar? Most professionals don't have a skill problem with LinkedIn DMs. They have a consistency problem. They know, theoretically, what good outreach looks like. But they don't do it. Not because they can't—because they haven't built the habit.

That's what this 7-Day LinkedIn DM Challenge is for. It's not about perfection. It's about momentum. Just 15 minutes a day, for seven days, to kickstart the conversation habits that lead to real opportunities. By the end, you'll have reached out to at least 7 new people, practiced different message types, and built the muscle memory that makes LinkedIn DMs feel natural instead of nerve-wracking.

Ready? Let's go.

How This Challenge Works

Each day focuses on one specific DM skill or scenario. You'll get:

• A daily prompt: What to focus on and why
• A micro-task: One small action that takes 15 minutes or less
• A reflection question: To help you learn and improve as you go

The rules are simple:

1. Commit to 15 minutes a day for 7 days
2. Complete each day's task before moving to the next
3. Focus on quality over volume—one thoughtful message beats ten generic ones
4. Track your progress (we've included a checklist below)
5. Reflect honestly on what's working and what's not

By the end of the week, you'll have sent at least 7 DMs, practiced multiple conversation styles, and built real momentum. Let's dive into the daily breakdown.

Day 1: From Comment to DM

Focus: Turning public engagement into private conversations.

Why it matters: The easiest way to start a DM is by building on an existing interaction. When you've already commented on someone's post, the DM doesn't feel random—it feels like a natural continuation.

Today's Task (15 minutes):

1. Find 3 posts in your feed that genuinely interest you (5 min)
2. Leave thoughtful comments on each post—add insight, ask a question, or share a related experience (5 min)
3. Choose 1 of those posts and send a DM to the author within an hour of commenting (5 min)

DM Template:
"Hey [Name]—just commented on your post about [topic], but I had one more thought I didn't want to clog the comments with: [insight/question]. Curious to hear how you're thinking about [specific aspect]."

Reflection Question:
Did the DM feel easier because you'd already engaged publicly? How did the person respond?

Checklist:

• ☐ Found 3 interesting posts
• ☐ Left thoughtful comments on all 3
• ☐ Sent 1 DM within an hour of commenting

This approach builds on principles from turning comments into conversations—you're creating context before you ever hit send.

Day 2: The Reconnect Message

Focus: Reviving dormant connections without the awkwardness.

Why it matters: Your existing network is full of opportunities—but only if you re-engage. Most people avoid reaching out to old connections because they feel guilty about the gap. Today, you'll get over that.

Today's Task (15 minutes):

1. Scroll through your connections and identify 3 people you haven't spoken to in 6+ months but who you genuinely liked or respected (5 min)
2. Pick 1 person and look at their recent activity—new job, recent post, company update, etc. (5 min)
3. Send a reconnect DM that acknowledges the gap and ties to something current in their world (5 min)

DM Template:
"Hey [Name]—I know it's been a minute, but I saw you [recent update: new role, recent post, etc.] and wanted to reach out. [Specific observation or compliment]. How's [relevant question about their current work]?"

Reflection Question:
Was it as awkward as you thought it would be? What was their response?

Checklist:

• ☐ Identified 3 dormant connections
• ☐ Researched 1 person's recent activity
• ☐ Sent a reconnect DM

For more on this, see the full guide on how to reconnect with old LinkedIn contacts without the guilt.

Day 3: The Value-First Outreach

Focus: Starting conversations by giving, not asking.

Why it matters: The best way to stand out in someone's DMs is to offer value before you ask for anything. Today, you'll practice leading with generosity.

Today's Task (15 minutes):

1. Think of someone you want to connect with but haven't had a reason to reach out to yet (3 min)
2. Find something valuable you can share with them: a relevant article, a resource, an intro to someone in your network, or a quick insight related to their work (7 min)
3. Send a DM that leads with that value—no ask, no pitch, just "thought you'd find this useful" (5 min)

DM Template:
"Hey [Name]—I came across [resource/article/tool] and immediately thought of you based on [something specific about their work]. No agenda here, just thought it might be useful. Hope you're doing well!"

Reflection Question:
How did it feel to reach out without asking for anything in return? Did the person respond differently than you expected?

Checklist:

• ☐ Identified 1 person to reach out to
• ☐ Found something valuable to share
• ☐ Sent a value-first DM with no ask

This mirrors the mindset in building authentic LinkedIn relationships: give first, and opportunities follow.

Day 4: The Micro-Ask Practice

Focus: Making small requests that start big things.

Why it matters: Not every DM should be purely social. Sometimes you need to ask for something. But instead of swinging for a big commitment (like a meeting), today you'll practice the micro-ask—a small request that's easy to say yes to.

Today's Task (15 minutes):

1. Identify someone whose expertise or opinion you value (3 min)
2. Think of a simple, low-effort ask: a quick opinion, a resource recommendation, or a 2-minute piece of advice (5 min)
3. Send a DM that frames the ask as optional and easy (7 min)

DM Template:
"Hey [Name]—quick question if you have 30 seconds: [specific micro-ask]. No pressure if you're swamped, but I value your perspective on this."

Examples of Micro-Asks:

• "Do you have a favorite resource on [topic]?"
• "What's your take on [specific trend/tool]?"
• "If you were in my shoes, would you prioritize [X] or [Y]?"

Reflection Question:
Was it easier to get a response when you made the ask small and low-pressure? How did framing it as optional change the dynamic?

Checklist:

• ☐ Identified someone to ask
• ☐ Crafted a simple, low-effort micro-ask
• ☐ Sent the DM with optional framing

Learn more about this approach in the art of the micro-ask.

Day 5: The Follow-Up (Without the Pushiness)

Focus: Re-engaging someone who didn't respond to your first message.

Why it matters: Most people give up after one DM. But the fortune is in the follow-up. Today, you'll practice reaching out again—but with added value, not just a bump.

Today's Task (15 minutes):

1. Look through your DMs and find 1-2 people who didn't respond to a message you sent in the past 7-14 days (5 min)
2. Think of a new angle: fresh insight, new resource, or updated context that makes the follow-up feel valuable, not desperate (5 min)
3. Send a follow-up DM that references the original message but adds something new (5 min)

DM Template:
"Hey [Name]—I know you're probably swamped, so no worries if this fell off your radar. I just came across [new thing: article, tool, insight] that made me think of [original topic]. Thought I'd share in case it's useful. Either way, hope things are going well!"

Reflection Question:
Did the follow-up feel pushy, or did the added value make it feel natural? Did they respond this time?

Checklist:

• ☐ Found 1-2 unanswered DMs from the past 2 weeks
• ☐ Identified a new angle or added value
• ☐ Sent a follow-up DM

For a full follow-up framework, check out the follow-up playbook.

Day 6: Asking for a Call (The Right Way)

Focus: Transitioning from DMs to a live conversation.

Why it matters: At some point, you need to move offline. But most people ask for calls too early or too vaguely. Today, you'll practice asking at the right moment, with the right framing.

Today's Task (15 minutes):

1. Review your recent DMs and identify 1 conversation that's warm, engaged, and ready for a next step (5 min)
2. Think about what value a call would provide for them, not just you (3 min)
3. Send a DM that proposes a short, specific call with a clear outcome (7 min)

DM Template:
"Hey [Name]—this has been a great conversation. I think a quick 15-minute call might be the easiest way to [specific benefit: compare notes, walk through an idea, dig into this challenge]. I've got a couple of windows this week: [Option 1] or [Option 2]. Either of those work, or should I send a few more options?"

Reflection Question:
Did framing the call around their benefit (not your need) make the ask feel more natural? How did they respond?

Checklist:

• ☐ Identified 1 warm conversation ready for a call
• ☐ Defined the value of the call for them
• ☐ Sent a call request with specific time options

For deeper tactics, see how to ask for a call on LinkedIn and get a yes.

Day 7: Reflection & Building Momentum

Focus: Reviewing what worked, what didn't, and how to keep going.

Why it matters: The challenge doesn't end today—it's just the beginning. Today is about locking in the habits and insights that will keep your LinkedIn DMs active long after this week is over.

Today's Task (15 minutes):

1. Review all the DMs you've sent this week—which ones got responses? Which ones didn't? (5 min)
2. Identify patterns: What tone, timing, or approach worked best? (5 min)
3. Commit to a weekly DM habit going forward: How many DMs will you send per week? What scenarios will you prioritize? (5 min)

Reflection Questions:

• What was the biggest surprise this week?
• What felt uncomfortable at first but got easier?
• What's one DM skill you want to keep practicing?
• How will you maintain this momentum going forward?

Checklist:

• ☐ Reviewed all DMs from the week
• ☐ Identified patterns and insights
• ☐ Set a weekly DM goal going forward

Your 7-Day Challenge Checklist

Track your progress here:

• ☐ Day 1: Sent a DM after commenting on a post
• ☐ Day 2: Reconnected with a dormant contact
• ☐ Day 3: Sent a value-first DM with no ask
• ☐ Day 4: Made a micro-ask
• ☐ Day 5: Followed up with added value
• ☐ Day 6: Asked for a call with specific options
• ☐ Day 7: Reflected and set a weekly DM habit

Tips for Staying Consistent

Set a Daily Reminder

Block 15 minutes on your calendar at the same time each day. Treat it like a meeting with yourself. Consistency builds the habit faster than sporadic effort.

Don't Overthink It

Your first DM doesn't have to be perfect. In fact, slightly imperfect messages often perform better because they feel more human. Hit send and learn as you go.

Celebrate Small Wins

Got a response? Great. Didn't get a response but sent the message anyway? Also great. The goal is momentum, not perfection.

Keep Learning

After the challenge, keep refining your approach. Study what works. Experiment with tone and timing. LinkedIn DMs are a skill—and like any skill, they improve with practice.

What Happens After the Challenge?

The real magic isn't in the 7 days—it's in what comes next. Here's how to keep the momentum going:

• Set a weekly goal: Commit to sending 3-5 DMs per week, even after the challenge ends
• Mix up your approaches: Rotate between value-first messages, micro-asks, follow-ups, and call requests
• Track your results: Keep a simple log of who you reach out to, when, and what happens. Patterns will emerge.
• Refine your templates: Save the messages that work and build your own library of go-to frameworks

And if you want to scale this without losing the personal touch, tools like ANDI can help you manage conversations, set reminders, and keep your outreach organized—so you're building relationships, not just sending messages.

Frequently Asked Questions

What if I don't get responses during the challenge?

That's normal. LinkedIn response rates vary, but 20-40% is typical for thoughtful, personalized DMs. The goal of this challenge is to build the habit, not to get 100% response rates. Focus on improving your approach, not immediate outcomes.

Can I do multiple days in one sitting if I'm busy?

You can, but it's less effective. The challenge is designed to build muscle memory over time. Spacing out the tasks gives you time to reflect, adjust, and internalize each skill. If you must compress it, try to leave at least a few hours between tasks.

What if I'm nervous about reaching out to people I don't know well?

Start with Day 1 (comment to DM) or Day 2 (reconnect message)—both involve people you already have some connection to. As you get more comfortable, you can tackle cold outreach. Remember: the worst thing that happens is they don't respond. That's not rejection—it's just noise.

How do I know if my DMs are working?

Look for engagement: replies, questions back, expressions of interest, or meetings booked. But also track softer signals: profile views, follow-backs, or people engaging with your content after you DM them. Not all wins are immediate or obvious.

Next step: Turn the 7-day challenge into a lasting habit — Try ANDI Free.