Phase 3 — Outreach & Engagement (Days 6–7)
Day 6 of 14

Send Looms + Direct Outreach

Phase 2 built the arsenal. Phase 3 pulls the trigger. Send personalized Loom messages to every hand-raiser from Day 3 using the 5/5/5 staggered batch method. Track who watches, respond to every reply within 2 hours, and start real conversations.

Time: 2-3 hours Deliverables: 15 Looms sent + responses handled Depends on: Day 5 (Loom + 15 messages drafted) Sprint: Mastery Monetization Lab
Before You Start Day 6
  • Loom Video Live: Your Day 5 Loom URL is working and shareable — tested from a different device
  • 15 Messages Ready: All personalized messages from Day 5 reviewed with fresh eyes this morning
  • Team Review Complete: At least 1 team member signed off on all 15 messages
  • Objection Handlers Loaded: Top 3 micro-Loom objection scripts recorded or scripted
  • Loom Dashboard Open: You can see view analytics in real-time (loom.com → My Videos)
  • Notification Sound ON: LinkedIn/platform notifications enabled so you catch replies fast
Hard Rule: Never Send All 15 at Once

Sending all messages simultaneously means you can't handle all the replies, messages feel batch-sent, and platforms might flag you for spam. Use the 5/5/5 staggered approach. Send 5, wait 30-60 minutes, read responses, adjust messaging if needed, then send the next 5.

Objective
Send Looms + Start Conversations
Output
15 messages sent, 3+ conversations
Key Metric
8-10 Loom viewers by end of day
Quality Gate
Every reply responded to within 2 hours
Jason's Lens: This Is Where It Gets Real

Days 1-5 were preparation. Day 6 is the first day someone sees your work and decides if they care. That's scary. That's the point.

The biggest mistake people make is drafting 15 perfect messages and then never pressing send. They find excuses — "let me re-read one more time," "maybe I should record a better Loom," "I'll send tomorrow when the timing is better." The timing is never better. Send the first 5 right now.

Here's the truth: most people won't respond. That's normal. A 20% response rate means 3 out of 15 reply. If 3 people start real conversations with you today, that's a win. One of those might become a paying customer. You need 3-5 paying customers from this sprint. Today starts the funnel.

The 5/5/5 Staggered Batch Method

5
Batch 1 — Morning
Send your 5 strongest messages first. These are the people who engaged most on Day 3. Monitor for immediate responses.
5
Batch 2 — Midday
Wait 60 minutes after Batch 1. Adjust messaging based on any Batch 1 responses. Send next 5 with refinements.
5
Batch 3 — Afternoon
Final 5. By now you know what's landing. Apply all learnings from Batches 1-2. These should be your sharpest messages.
Hour 1
Send Batch 1 (5 messages) — Your warmest leads first. Log each send in the tracker (Tool 12). Open Loom analytics dashboard.
Hour 2
Monitor + Respond + Send Batch 2 — Check Loom analytics (who watched?). Respond to any Batch 1 replies. Adjust messaging. Send next 5.
Hour 3
Send Batch 3 + Handle All Responses — Final 5 messages. Respond to all outstanding replies. Use objection handlers (Tool 11) if needed. Log everything.
Derek
Send + Respond
  • Send Batch 1 (5 messages) to warmest leads
  • Monitor replies — respond within 2 hours max
  • Adjust messaging based on Batch 1 responses
  • Send Batches 2 and 3 with refinements
  • Check Loom analytics — who viewed? How long?
  • Continue daily: 50 connects + engagement
~120 min
Will
Analytics + Templates
  • Monitor Loom view analytics in real-time
  • Track: who opened, watch %, engagement signals
  • Prepare follow-up templates for different response types
  • Draft end-of-day engagement report
  • Flag hot leads (watched 80%+ of Loom)
~60 min
Jason
Tracker + Automation
  • Deploy Loom send tracker (Tool 12)
  • Build response categorization system
  • Monitor response rates across batches
  • Optional: bulk send helper for Batches 2-3
  • Compile Day 6 metrics for reconciliation prep
~45 min
Critical: Speed of Response = Conversion
  • Respond to every reply within 2 hours — ideally within 30 minutes
  • The faster you respond, the more likely the conversation continues
  • A late reply feels like you don't care — an immediate reply feels like a real conversation
  • Set an alarm every 30 minutes to check for new responses
Block 1 — 30 min
Final Message Review + Batch 1 Send
  • Re-read all 15 messages with fresh eyes
  • Rank them: who's most likely to respond?
  • Top 5 become Batch 1 — send now
  • Log each send: name, platform, time, message variant
  • Open Loom analytics dashboard in a separate tab
Block 2 — 60 min
Monitor + Batch 2 Send
  • Check Loom analytics: who from Batch 1 has viewed?
  • Respond to any early replies immediately
  • For non-viewers: note for follow-up tomorrow
  • Adjust messaging if needed based on Batch 1 signals
  • Send Batch 2 (next 5 messages)
Block 3 — 60 min
Batch 3 + Response Handling
  • Send final 5 messages (Batch 3)
  • Respond to all outstanding replies across all batches
  • For objections: deploy micro-Loom response scripts
  • For interested replies: move to deeper conversation
  • Update tracker with all response data
Block 4 — 30 min
End-of-Day Report
  • Complete Loom Send Tracker (all 15 entries)
  • Loom analytics summary: total views, avg watch %, top viewer
  • Response rate: how many replied out of 15?
  • Conversations started: who's engaged in real back-and-forth?
  • Post Slack debrief with Day 6 metrics
Tool 12 — AI Prompt

Loom Send Tracker

Creates a structured tracking system for all 15 Loom sends. Logs recipient, send time, batch number, platform, response status, Loom view analytics, and conversation temperature. Use this to compile data for Day 7 reconciliation.

You are a sales pipeline tracker. Create a structured tracking sheet for my Loom outreach campaign.

I'm sending 15 personalized Loom video messages in 3 batches of 5.

For each recipient, create a row with these columns:

| # | Name | Platform | Batch | Sent At | Loom Viewed? | Watch % | Replied? | Reply Type | Conversation Temp | Next Action | Notes |

BATCH TRACKING:
- Batch 1 (Morning): Recipients 1-5
- Batch 2 (Midday): Recipients 6-10
- Batch 3 (Afternoon): Recipients 11-15

RESPONSE CATEGORIES (for Reply Type column):
- HOT: Asked a question, expressed interest, or requested more info
- WARM: Acknowledged, said thanks, or gave a positive but vague response
- OBJECTION: Raised a specific concern (price, timing, relevance)
- COLD: No response after 24 hours
- DECLINED: Explicitly said no or not interested

CONVERSATION TEMPERATURE:
- Score 1-5 based on: response speed, question quality, engagement depth
- 5 = ready for next step, 1 = probably not a fit

SUMMARY METRICS (calculate at end of day):
- Total sent: [X]/15
- Total viewed: [X] (from Loom analytics)
- Avg watch %: [X]%
- Response rate: [X]/15 = [X]%
- HOT leads: [count]
- WARM leads: [count]
- Conversations active: [count]

MY RECIPIENTS:
[Paste your 15 names and the message you sent each]

Generate the tracker pre-filled with my recipients, ready to update as data comes in.
  1. Paste your 15 recipients into the prompt before sending Batch 1
  2. After each batch, update the tracker with send times
  3. Check Loom analytics every 30 minutes and update view data
  4. As replies come in, categorize each response
  5. At end of day, calculate summary metrics for Slack debrief
After Using Tool 12: Tracker Ready Check
  • All 15 recipients listed with name and platform
  • Batch assignments clear: who's in Batch 1, 2, and 3
  • Response categories defined and understood by team
  • Loom analytics dashboard is open and accessible
  • Tracker is in a shared location (Google Sheet, Notion, or shared doc)
Tool 13 — AI Prompt

Response Handler

Generates contextual follow-up messages based on how each person responded to your Loom. Different scripts for hot leads, warm acknowledgments, objections, and non-responders.

You are a sales conversation specialist. Generate follow-up messages for different response types to my Loom video outreach.

ABOUT ME:
[Paste your bio/LinkedIn summary here]

MY LOOM VIDEO: [paste Loom URL]
MY WORKSHOP REGISTRATION: [paste URL]

Generate follow-up messages for these 5 response scenarios:

SCENARIO 1 — HOT REPLY (they asked a question or expressed interest):
- Acknowledge their specific question/interest
- Answer directly (no deflection)
- Offer a concrete next step: "Want to hop on a 15-min call this week?" or link to workshop
- Keep it conversational, not salesy

SCENARIO 2 — WARM REPLY (they said "thanks" or "looks cool" but nothing specific):
- Thank them for watching
- Ask ONE specific question to deepen the conversation
- The question should relate to their known pain point
- Give them an easy way to engage further

SCENARIO 3 — OBJECTION: "I'm too busy right now":
- Validate: "Totally get it"
- Reframe: the free workshop is specifically designed for busy people (90 min, one-time)
- Low-pressure: "No rush — here's the link if your schedule opens up"

SCENARIO 4 — OBJECTION: "I can't afford it / what does it cost?":
- The workshop is FREE — clarify this immediately
- Paid tier exists but start with the free session
- Frame value: "Most people recoup the cost in their first client"

SCENARIO 5 — NO RESPONSE (24+ hours, no reply):
- Short, casual check-in (NOT "just following up")
- Reference one specific insight from the Loom they might find useful
- Give them an easy out: "No worries if the timing isn't right"
- One message only — do NOT send multiple follow-ups

RULES:
- Each follow-up under 3 sentences
- Never sound desperate or pushy
- Always offer the free workshop as the default next step
- Match the tone of their response (casual reply = casual follow-up)
  1. Fill in your bio and URLs
  2. Run the prompt to generate all 5 response templates
  3. When a reply comes in, identify which scenario it matches
  4. Personalize the template for that specific person before sending
  5. Log the follow-up in your tracker (Tool 12)
After Using Tool 13: Response Handler Check
  • All 5 response scenarios have ready-to-use templates
  • Hot lead template includes a specific next step (call booking or workshop link)
  • Objection handlers redirect to the FREE workshop, not the paid tier
  • No-response template is a single message — not a follow-up sequence
  • Every template is under 3 sentences and sounds human
Tool-Level Gates Are Embedded Above

Each tool has its own quality check directly below it. Complete each gate before moving to the next tool. If a gate fails, fix it before stacking more work on top.

Day 6 Big Picture: What Must Be True by Tonight
  • All 15 Loom messages sent via the 5/5/5 staggered batch method
  • Every reply responded to within 2 hours of receiving
  • Loom analytics checked: you know who viewed and for how long
  • 3+ real conversations started (back-and-forth, not just "thanks")
  • Send tracker (Tool 12) is fully populated with all 15 entries
  • End-of-day Slack debrief posted with response rate and hot leads
Common Day 6 Mistakes
WRONG: Sending all 15 messages at once
Result: Can't handle simultaneous replies. Messages feel batch-sent. Platform might flag spam.
RIGHT: 5/5/5 staggered. Send 5, wait 60 min, adjust, send next 5.
WRONG: Waiting 6+ hours to respond to a reply
Result: Conversation dies. They've moved on. Momentum lost.
RIGHT: Respond within 30 minutes if possible, 2 hours maximum. Set a timer.
WRONG: Sending a second follow-up to non-responders on the same day
Result: Feels desperate. Damages the relationship before it starts.
RIGHT: One message today. One follow-up tomorrow if no response. Then stop.
WRONG: Pitching the paid tier when someone says "looks interesting"
Result: Too aggressive. They weren't asking to buy. They were being polite.
RIGHT: Always redirect to the FREE workshop first. Let the workshop sell the paid tier.
What if: Nobody watches the Loom?

SOLUTION: Check that your message is compelling enough to make someone click. If Batch 1 gets 0 views, rewrite the message for Batches 2-3 with a stronger hook. The subject line or first sentence is the problem, not the video.

What if: I get a hostile or negative reply?

SOLUTION: Don't argue. Reply: "Totally fair — appreciate you letting me know. Deleting from my list." Move on. One hostile reply in 15 is normal. It means you're reaching real humans, not just echo chambers.

What if: Someone watches the Loom but doesn't reply?

SOLUTION: This is actually a warm signal. They cared enough to watch. Send a follow-up tomorrow (not today): "Hey, noticed you checked out the walkthrough — any questions about [specific thing from video]?" Loom analytics gives you this data.

What if: I get more than 5 hot replies and can't keep up?

SOLUTION: Great problem to have. Prioritize by conversation temperature (Tool 12). Hot leads get immediate responses. Warm leads get a brief "thanks, more soon" and a response within 4 hours. Will can help draft responses.

What if: I only had 8 hand-raisers from Day 3, not 15?

SOLUTION: Send to all 8. Then expand to Day 4-5 engagers: anyone who liked your posts, commented on your content, or engaged in your Reddit/hijacking threads. Same personalization standard applies — reference what they specifically did.

Day 6 Complete — Outreach Live

Tonight: Check Loom analytics one final time. Note who viewed but didn't reply — they're tomorrow's follow-up list.

Tomorrow (Day 7): Free Workshop Promotion + Mid-Sprint Reconciliation. Announce the workshop across all channels, drive registrations, and run a team data review of everything from Days 1-6.

Key signal: If your response rate is under 10% (less than 2 out of 15), your messaging needs work. Review with the team before Day 7 reconciliation.

If above 20%: You're outperforming average cold outreach. The Loom personalization is working. Double down on what's landing.