Calvin Hollywood’s DM Advice

Hey guys,

interview with

was epic! In it, Calvin dove deep into the Auto DM feature of Skool. I got so much out of it, I decided to synthesize it for you guys below!

𝗔𝘂𝘁𝗼 𝗗𝗠 𝗕𝗲𝘀𝘁 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗲𝘀

𝐀𝐮𝐭𝐨 𝐃𝐌𝐬 𝐚𝐫𝐞 𝐭𝐡𝐞 𝐟𝐢𝐫𝐬𝐭 𝐩𝐨𝐢𝐧𝐭 𝐨𝐟 𝐜𝐨𝐧𝐭𝐚𝐜𝐭 𝐟𝐨𝐫 𝐧𝐞𝐰 𝐦𝐞𝐦𝐛𝐞𝐫𝐬 𝐢𝐧 𝐚 𝐒𝐤𝐨𝐨𝐥 𝐜𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲. 𝗪𝗵𝗲𝗻 𝗱𝗼𝗻𝗲 𝗿𝗶𝗴𝗵𝘁, 𝘁𝗵𝗲𝘆 𝗰𝗮𝗻 𝗯𝘂𝗶𝗹𝗱 𝗿𝗲𝗹𝗮𝘁𝗶𝗼𝗻𝘀𝗵𝗶𝗽𝘀, 𝗳𝗼𝘀𝘁𝗲𝗿 𝗲𝗻𝗴𝗮𝗴𝗲𝗺𝗲𝗻𝘁, 𝗮𝗻𝗱 𝗹𝗲𝗮𝗱 𝘁𝗼 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗶𝗼𝗻𝘀.

𝟭. 𝗖𝗼𝗺𝗺𝗼𝗻 𝗔𝘂𝘁𝗼 𝗗𝗠 𝗠𝗶𝘀𝘁𝗮𝗸𝗲𝘀

𝑨𝒗𝒐𝒊𝒅 𝒕𝒉𝒆𝒔𝒆 𝒑𝒊𝒕𝒇𝒂𝒍𝒍𝒔 𝒕𝒐 𝒎𝒂𝒌𝒆 𝒔𝒖𝒓𝒆 𝒏𝒆𝒘 𝒎𝒆𝒎𝒃𝒆𝒓𝒔 𝒇𝒆𝒆𝒍 𝒘𝒆𝒍𝒄𝒐𝒎𝒆:

• ❌ 𝑺𝒆𝒏𝒅𝒊𝒏𝒈 𝑪𝒐𝒎𝒎𝒂𝒏𝒅𝒔:

Example: “Click here” or “Watch this now.”

Feels too transactional and lacks a warm introduction.

• ❌ 𝑰𝒎𝒑𝒆𝒓𝒔𝒐𝒏𝒂𝒍 𝑴𝒆𝒔𝒔𝒂𝒈𝒆𝒔:

Example: “Welcome to the group!” misses the chance to build a connection.

• ❌ 𝑶𝒗𝒆𝒓𝒍𝒐𝒂𝒅 𝑾𝒊𝒕𝒉 𝑰𝒏𝒇𝒐:

Too many links or instructions overwhelm new members and can push them away.

𝟮. 𝗘𝗳𝗳𝗲𝗰𝘁𝗶𝘃𝗲 𝗔𝘂𝘁𝗼 𝗗𝗠 𝗦𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲

𝑭𝒐𝒄𝒖𝒔 𝒐𝒏 𝒆𝒏𝒈𝒂𝒈𝒊𝒏𝒈, 𝒑𝒆𝒓𝒔𝒐𝒏𝒂𝒍, 𝒂𝒏𝒅 𝒊𝒎𝒑𝒂𝒄𝒕𝒇𝒖𝒍 𝒎𝒆𝒔𝒔𝒂𝒈𝒆𝒔:

1. 🌟 𝐖𝐚𝐫𝐦 𝐖𝐞𝐥𝐜𝐨𝐦𝐞:

• Start with a friendly and personal tone.

• Example:

Hey [Name]! Welcome to [Community Name]—we’re so glad you’re here! 🎉

2. ❓ 𝐀𝐬𝐤 𝐐𝐮𝐞𝐬𝐭𝐢𝐨𝐧𝐬 (𝐒𝐭𝐫𝐚𝐭𝐞𝐠𝐢𝐜𝐚𝐥𝐥𝐲):

• Open Question: For detailed responders.

• Example: “What inspired you to join this community?”

• Closed Question: For shy or short-answer responders.

• Example: “Are you new to Skool? Yes/No.”

3. 🚫 𝐍𝐨 𝐄𝐱𝐭𝐞𝐫𝐧𝐚𝐥 𝐋𝐢𝐧𝐤𝐬:

• Keep the focus on the platform and avoid redirecting new members immediately.

4. 🤝 𝐅𝐨𝐥𝐥𝐨𝐰-𝐔𝐩 𝐄𝐟𝐟𝐞𝐜𝐭𝐢𝐯𝐞𝐥𝐲:

• Acknowledge replies.

• Guide members to specific resources or encourage further interaction.

𝟯. 𝗨𝘀𝗲 𝗔𝘂𝘁𝗼 𝗗𝗠𝘀 𝗮𝘀 𝗟𝗲𝗮𝗱 𝗤𝘂𝗮𝗹𝗶𝗳𝗶𝗰𝗮𝘁𝗶𝗼𝗻 𝗧𝗼𝗼𝗹𝘀

• 🔍 𝐈𝐝𝐞𝐧𝐭𝐢𝐟𝐲 𝐇𝐢𝐠𝐡-𝐕𝐚𝐥𝐮𝐞 𝐌𝐞𝐦𝐛𝐞𝐫𝐬:

• Look for detailed, enthusiastic responses (e.g., “I’m here to scale to $10K/month!”).

• 📊 𝐒𝐞𝐠𝐦𝐞𝐧𝐭 𝐑𝐞𝐬𝐩𝐨𝐧𝐬𝐞𝐬:

• Beginners: Need nurturing and onboarding.

• Advanced Members: High engagement potential and likely to purchase.

• 🚀 𝐅𝐨𝐥𝐥𝐨𝐰 𝐔𝐩 𝐖𝐢𝐭𝐡 𝐏𝐫𝐞𝐜𝐢𝐬𝐢𝐨𝐧:

Respond promptly to every message and guide potential leads toward paid offerings.

𝟰. 𝗞𝗲𝘆 𝗠𝗲𝘁𝗿𝗶𝗰𝘀 𝗳𝗼𝗿 𝗔𝘂𝘁𝗼 𝗗𝗠 𝗦𝘂𝗰𝗰𝗲𝘀𝘀

• 📈 𝐑𝐞𝐬𝐩𝐨𝐧𝐬𝐞 𝐑𝐚𝐭𝐞:

• Goal: 80% of members reply to the initial DM.

• Example: For 10 new members, at least 8 should respond.

• 💰 𝐂𝐨𝐧𝐯𝐞𝐫𝐬𝐢𝐨𝐧 𝐑𝐚𝐭𝐞:

• Goal: 10% conversion from free to paid members.

• Example: For 10 conversations, 1 converts into a paying member.

𝟱. 𝗣𝗿𝗼𝗼𝗳𝗲𝗱 𝗔𝘂𝘁𝗼 𝗗𝗠 𝗦𝗰𝗿𝗶𝗽𝘁𝘀

Initial DM:

Hey [Name]! Welcome to [Community Name]—we’re so excited to have you here! 🎉

Are you new to Skool? (Yes/No)

Also, what brought you to our community? I’d love to hear your goals!

Follow-Up Example for Beginners:

• “That’s awesome! If you’re new, check out our [Welcome Post/Onboarding Section] to get started. Let me know if you have any questions!”

Follow-Up Example for Advanced Members:

• “Wow, you’re already working on [goal]? That’s exciting! If you’re interested, we also have a [paid resource/community]—let me know if you’d like details!”

𝟲. 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗨𝗽𝘀𝗲𝗹𝗹𝘀

• ➡ From Free to Paid:

• Example: “Based on what you shared, I think you’d love [Paid Community Name]. It’s a focused space for [specific benefits]. Want to learn more?”

• 🔥 Highlight Exclusivity:

• Mention perks like limited spots, unique resources, or community-driven benefits to create urgency.

7. 𝗣𝗿𝗼 𝗧𝗶𝗽𝘀

• 🔧 𝐓𝐞𝐬𝐭 𝐚𝐧𝐝 𝐈𝐭𝐞𝐫𝐚𝐭𝐞: Continuously test your Auto DMs to optimize response rates.

• ✂ 𝐊𝐞𝐞𝐩 𝐈𝐭 𝐒𝐡𝐨𝐫𝐭: Avoid overwhelming members with overly lengthy messages.

• 💡 𝐏𝐞𝐫𝐬𝐨𝐧𝐚𝐥𝐢𝐳𝐞: Include details like the user’s name to make the message feel genuine.

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