Not now doesn’t mean never: Why long sales cycles need a long game system

In B2B, timing is everything. Especially in longer sales cycles like insurance, cyber, or financial services, where deals can take months to close.

Right now, your CRM is likely full of “not now” leads. People who weren’t ready when you first connected, but who could convert in the future with the right follow-up.

Too often, those opportunities are forgotten. Sales reps get busy, follow-ups stall, and the pipeline quietly shrinks. Before you know it, you’re back to chasing new leads from scratch.

In financial advice, timing can make or break client relationships.

Ever sent a follow-up and thought, “Was that too soon?” Or waited so long you wondered if they’d forgotten you existed? It’s a common challenge—and one that can lead to lost opportunities if you don’t get it right.

The truth is, follow-ups aren’t just about staying on someone’s radar, they’re about building trust. And when you get the timing wrong, you risk looking pushy or disengaged.

That’s where the Goldilocks Rule comes in. It’s all about finding that “just right” moment for your outreach, neither too soon nor too late. Backed by psychology and real-world data, this principle helps you balance timing, tone, and personalisation to create follow-ups that work, not annoy.

Let’s break it down.

Timing: When is ‘just right’?

Timing is everything. Too soon, and you risk coming across as pushy. Too late, and your prospect might forget about you altogether.

For financial advisors, this balance is even more critical. Your prospects are making life-changing decisions about their financial futures, they need to feel confident, not pressured.

Here’s how to get it right:

1. First Follow-Up (2–3 days after initial contact): A gentle reminder that keeps you top of mind without being intrusive.

2. Second Follow-Up (5–7 days later): Share a resource or insight that adds value.

3. Ongoing Follow-Ups (10–14 days apart): Space them out to stay consistent without overwhelming.

And here’s why persistence pays off:

1. 80% of sales require 5-12 follow-ups, yet nearly half of salespeople stop after just one. 

2. 21% of responses come from the second follow-up, and 18% from the third. Giving up early could mean missing out on real opportunities.

Pro tip: If a prospect doesn’t respond right away, consider quarterly check-ins. Timing is everything, and what wasn’t relevant last month might be a priority today.

Tone: Helpful beats pushy every time.

Your tone sets the stage for how your follow-ups are received. If your message feels like a demand, it’s likely to be ignored.

Instead, focus on being genuinely helpful. Replace:

1. “Just checking if you’ve had time to review my last email.”

With:

1. “Hi [Name], I came across this [article/resource] about [specific topic] and thought it might be useful as you consider [specific challenge]. Let me know if you’d like to discuss!”

The key is to show that you’re invested in helping them, not just selling to them.

Personalisation: The secret to standing out.

In a world of templated emails and generic outreach, personalisation is your competitive edge. Prospects are more likely to engage when they feel your message was crafted specifically for them.

Here’s how to personalise effectively:

1. Reference their context:
   “Hi [Name], I noticed you specialise in [specific niche]. I’d love to share how we’ve helped other [description of person i.e. ‘professionals’ in [similar niche] overcome [specific challenge].”

2. Share relevant success stories:
   “Hi [Name], many [description of human]’s in [their industry] are focused on [specific challenge] right now. Here’s how we helped a similar client achieve [specific result].”

3. Highlight shared experiences:
   If you share a location, industry, or mutual connection, mention it. For example:
   “As a fellow [Wellingtonian/industry professional], I thought this insight might resonate with you.”

These small touches show you’ve done your homework, building trust from the very first message.

Your follow-up strategy in action

Here’s an example sequence applying the Goldilocks Rule:

1. Day 1: Initial Message
   “Hi [Name], I’m [Your Name]. I noticed [specific detail] and thought it might be a good time to connect. Let me know if you’d like to chat about [specific value].”

2. Day 3: First Follow-Up
   “Hi [Name], I wanted to follow up on my earlier message. I came across this [resource/article] and thought it might be useful. Let me know your thoughts!”

3. Day 7: Second Follow-Up
   “Hi [Name], I know things get busy, but I wanted to share how we recently helped [similar client] achieve [specific result]. Would you be open to a quick call?”

4. Day 21: Casual Check-In
   “Hi [Name], just wanted to touch base and see if now’s a better time to connect. No rush—let me know what works for you!”

This sequence keeps your outreach proactive, patient, and packed with value.

The benefits of ‘just right’ follow-ups

By following the Goldilocks Rule, you’ll:

1. Boost response rates: Well-timed, personalised messages stand out.

2. Build trust: Helpful follow-ups show that you’re reliable and invested.

3. Maximise ROI: Consistent, thoughtful outreach ensures no lead is wasted.

Final thoughts: Building trust, not pressure.

In financial advice, trust is everything. Mastering the follow-up isn’t about relentless persistence, it’s about showing up consistently, offering value, and respecting your prospect’s time and journey.

By applying the Goldilocks Rule, you’ll transform your follow-ups from forgettable to impactful, opening the door to stronger connections and better results.

At Blackjet Social, we help financial advisors craft outreach strategies that combine smart personalisation with powerful consistency.
Ready to refine your approach? Reach out here.

Many businesses are sitting on untapped revenue, with client databases that haven’t been nurtured or optimised. Every contact in your database holds potential value—whether they’re a current client, a potential referral, or someone who might convert down the road. Ignoring these contacts is like leaving money on the table.

Here’s how to leverage what’s already in front of you and start maximising ROI with practical steps to nurture and activate dormant contacts

1. Organise Your Database
If your contacts are scattered across various spreadsheets, emails, or platforms, it’s time to centralise. Add all your contacts to a CRM (customer relationship management) system, even if you’re starting with a basic platform. This will give you an overview of who you’re connected to and make it easier to nurture each contact intentionally.

2. Segment and Categorise
Not all contacts are the same. Start segmenting your database based on:

• Industry or Sector: Are they in home owners, business owners, or a specific niche?
• Lifecycle Stage: Have they previously engaged in conversations, attended events, or shown any interest in your services?
• Buying Readiness: Are they ‘warm’ and ready to buy, or do they need more nurturing?

This allows you to send targeted content to each group, helping you tailor your messages and focus on the most relevant information.

3. Build Relationships with Valuable Content
Skip the hard sell. Instead, focus on creating content that genuinely adds value. Share insights, industry trends, or tips that address your audience’s pain points and position you as a helpful resource. By giving without asking for a sale, you’re building trust and staying top of mind for when they’re ready to take action.

Example Content Ideas:

• Educational articles relevant to their situation (business owner, home owner).
• Quick tips on overcoming common challenges.

Success stories or case studies that showcase the benefits of your service.

4. Engage on LinkedIn

LinkedIn is a powerful platform for building professional relationships. Connect with contacts in your database, engage with their content, and send personalised messages to show you’re actively thinking about them. This level of interaction not only keeps your brand visible but also builds rapport and trust without being salesy.

5. Monitor and Optimise Your Engagement
Regularly track and analyse your database activities to gauge engagement levels. Look for indicators like:

• Click-Through Rates: Are they clicking on links in your emails?
• Page Views: Have they visited your website or specific landing pages?
• Actions Taken: Have they viewed your calendar link but not yet booked an appointment?

Real-World Impact: Turning a Cold Database Warm
We recently worked with a client to revitalise their cold database, resulting in nine appointments from a single email. For this client, each new customer represents around $30,000 in potential revenue. With nine new prospects, that’s a potential ROI of $270,000—all from nurturing dormant contacts.

Ready to Tap into the Value of Your Database?
If you’re looking to unlock the potential in your existing contacts and create a clear action plan, book a call with us. We’ll discuss how we can help you turn dormant contacts into revenue and maximise the value of every lead.

Let’s explore how we can work together—schedule a chat with us here.