Strategies for Timing Follow-Up Conversations

Most founders follow up too much. Or not enough. Here's the sweet spot (so you can 3x your response rates) First, 85% of follow-ups fail because of: • Generic "just checking in" DMs • Following up daily (desperate energy) • Copy-pasting the same message • Giving up after 1-2 attempts Most investor DMs get deleted or forgotten after 15 seconds. It’s just the way it is... Follow-up solution: The 3-7-14 method: If your first message gets ghosted, wait 3 days. Then launch this sequence. DAY 3: Share Relevant Industry Insights "Saw this analysis of AI startups' unit economics. Reminded me of (relevant application) ... " No response to that? Bide your time until 7 days after the initial message. DAY 7: Offer Specific Value: "Saw your recent post about enterprise sales. We’ve interviewed 5 CIOs this week. Here are 3 surprising findings..." If you hear crickets after this, don’t stress. Give it another week. Then slide in with an update: DAY 14: Update On Progress: "Since our first message, we've (Specific Outcome Unlocked) and signed XYZ client. Still interested in connecting?" You can use a simple tracking table and create specific follow-up templates in a tool like Notion to track this. No need to go overboard. Tips to run this strategy smoothly: • Add calendar reminders for each follow-up • Track response rates by message type • Follow their social media for conversation starters • Give without asking for anything If you don’t hear back after this, give it two weeks, then circle back with another update. Benefits of the 3-7-14 method: • Non-pushy relationship development • Regular investor feedback loop • Top-of-mind positioning • Stronger network over time Persistence without pestering is an art. The difference between funded and ghosted often comes down to follow-up strategy. Make yours count. ____________________________ Hi, I’m Richard Stroupe, a 3x Entrepreneur, and Venture Capital Investor I help early-stage tech founders turn their startups into VC magnets

Recruiting isn't about closing fast. It's about staying close. But here's the challenge: How do you follow up long-term without annoying the candidate? How do you stay on their radar… without feeling like a telemarketer? You ask for permission, and you earn the right to stay in the conversation. Here's a simple 3-part framework I teach leaders to use: 1. Acknowledge the timing "I totally get that now may not be the right time to make a move." When you acknowledge their current reality, you build trust. 2. Ask for alignment "Would it be okay if I stayed in touch over the next few months, just to keep the conversation open?" This shifts follow-up from "nagging" to agreed-upon access. 3. Set the tone for future value "I'll make sure anything I send your way is relevant to where you're headed, not just where you are today." Now you're not a recruiter. You're a future-focused partner. Bonus tip: Keep it human and low-pressure. Text updates. Quick voice notes. A win your team just had. A leadership thought that made you think of them. The goal isn't to sell. It's to stay worth replying to. Because the best candidates aren't always ready on the first call. But they do remember who stayed connected the right way. Play the long game, with permission, not persistence.

Here's exactly how I structure my follow-ups to stop deals from slipping or ghosting at the last minute. Buyers ask themselves 5 crucial questions before they spend money. So we match our follow ups to each different question of the buying journey. The questions: 1/ "Do we Have a Problem or Goal that we Urgently need help with?" Follow up examples: Thought Leadership emphasizing the size / importance of the problem. Things like articles from Forbes, McKinsey, HBR or an industry specific publication. Screenshots, summations or info-graphics. NOT LINKS. No one reads them. 2/ "What's out there to Solve the Problem? How do Vendors differ?" Follow up examples: Sample RFP templates with pre-filled criteria. Easy to read buying guides. Especially if written by a 3rd party. 3/ "What Exactly do we need this Solution to do? Who do we feel good about?" Follow up examples: 3 bullets of criteria your Buyers commonly use during evaluations (especially differentiators.) Here's example wording I've used at UserGems 💎: "Thought you might find it helpful to see how other companies have evaluated tools to track their past champions. Their criteria are usually: *Data quality & ROI potential *Security (SOC2 type 2 and GDPR) *How easy or hard is it to take action: set up/training, automation, playbooks Cheers!" 4/ "Is the Juice worth the Squeeze - both $$$ & Time?" Follow up examples: Screenshots of emails, texts or DMs from customers talking about easy set up. Love using ones like the Slack pictured here. Feels more organic and authentic than a marketing case study. 5/ "What's next? How will this get done?" Follow up examples: Visual timelines Introductions to the CSM/onboard team Custom/short videos from CSM leadership When we tailor our follow ups to answer the questions our Buyers are asking themselves - Even (especially!) the subconscious ones Our sales cycles can be smoother, faster and easier to forecast. Buyer Experience > Sales Stages What's your best advice for how to follow up? ps - If you liked this breakdown, join 6,000+ other sellers getting value from my newsletter. Details on my website!

Ever had a great first meeting, only to watch the relationship fizzle out? You're not alone. Here are some resources for follow-up success: 1. The 24-Hour Thank-You Blitz Send a personalized note within 24 hours of your meeting. Reference specific points from your conversation to show you were paying attention. Subtly hint at future engagement without being pushy. 2. The Value Bomb (Week 1) Within the first week, share something relevant to their interests. This could be an article, event invitation, or impact story. The key is to prove you listened and care about their passions. No ask here, just pure value. 3. The Engagement Invitation (Weeks 2-3) A few weeks in, invite them to experience your mission firsthand. Think site visits, volunteer opportunities, or exclusive events. The focus should be on involvement, not money. 4. The Impact Showcase (1 Month Mark) At the one-month mark, share a specific story of your work in action. Connect it to the interests they expressed during your meeting. This is your chance to show how supporters like them make real change happen. 5. The "Round Two" Proposition (6 Weeks Post-Meeting) Around six weeks after your first meeting, suggest a follow-up conversation. Frame it as an opportunity to share updates and seek their input. Offer specific meeting options to make it easy for them to say yes. Remember: Every interaction is a chance to deepen the connection. Keep it donor-centric, valuable, and personal. P.S. What was your longest every follow-up attempt that ended in a gift?