Elephants have the longest gestation period among land mammals, lasting twenty-two months. But even elephants can’t compete with some sales cycles.
One of the most common questions I hear when helping clients with that part of the process is, “How can I possibly stay in touch without being a pest or sounding desperate?” When planning a successful sales strategy, those long-term prospect-to-client opportunities must be nurtured with ongoing communication.
As we discussed in earlier episodes, it’s essential to always know your prospect’s problem and keep it top of mind in all communication. But the long-game sale gives you some flexibility and some opportunities, as long as it all relates to your prospect. Here are ten strategies to stay in touch during a long sales cycle.
1. Send Insightful Content
Sharing relevant articles, white papers, case studies, or industry reports that align with their challenges or are germane to their industry. Position it as “Saw this and thought it might be interesting / help with what we have been discussing / some other ending.”
One of the most straightforward yet often overlooked methods to discover this content is to use Google Alerts. It allows you to enter specific keywords or phrases, and whenever Google indexes new content that matches, it sends you an email alert with links. You can choose how often you want to be notified (daily or weekly), select sources (news, blogs, web, etc.), and even filter by region or language. Setup is simple and puts your sourcing on autopilot.
2. Host or Invite to Webinars/Events
Keep them engaged by inviting them to educational (not sales-oriented) webinars, roundtables, or industry events—especially those that offer opportunities for learning and networking. No sales pitches allowed.
3. Share Customer Success Stories
Provide brief, tailored case studies that show how you solved a similar problem for another client. This keeps the focus on outcomes, not selling. Are you sensing a theme here? You should be. If you keep trying to sell with any of these ten methods, they will turn you off faster than a Cowboys game in the 4th quarter. (Sorry, Dallas fans.)
4. Send Personalized Video Messages
As we pointed out in Episode 9, video makes the world go ‘round. You can always use your mobile phone (hint: keep the microphone close to you), but if you want something more structured, programs like Pirsonal, Idomoo, HippoVideo, Bonjoro, Mindstamp, and Plainly can help. If you’re going to integrate tightly with your CRM, consider Vidyard for its scalability, analytics, and seamless integration.
5. Leverage Social Media Integration
Interact with their LinkedIn posts, share their content, or tag them in something useful. This builds light-touch visibility without engaging in direct outreach (which can seem clingy and desperate if not done well).
6. Offer Exclusive Research or Benchmarking
If you have access to market data or industry benchmarking, share those insights to help them evaluate their position compared to peers. (Key words “their” position). The top five market data and industry benchmarking sites are: Statista, Gartner, FactSet, S&P Compustat, and CB Insights.
7. Set Value-Check Touchpoints
Instead of asking “Are you ready yet?” (a/k/a the annoying “are we there yet?”), Once you recognize that this is a long-term sale, agree with the prospect on a series of quarterly or milestone check-ins, framed around the question, “Has anything changed on your end that we can support?” Then, mark them on your calendar and make sure you don’t miss any. This method helps build credibility by demonstrating you follow through on your commitments – even before the sale is finalized.
8. Provide Tools or Templates
Offer calculators, checklists, or worksheets that simplify their work. Not only does this foster goodwill, but it also positions you as the helpful guide.
9. Send Occasional Personal Touches
A quick note on LinkedIn, such as for someone’s work anniversary, congratulations on a company achievement, or even a thoughtful comment on their challenges, shows that you are paying attention.
Want to stand out? In the age of e-mail, nothing beats a handwritten personal note with a live stamp (not a postage meter) delivered by snail mail. Buy some fold-over notes and keep them handy. Sending a similar “thank you” note immediately after your initial appointment will also make you stand out.
10. Offer Free Consultation/Strategy Sessions
If the cycle is exceptionally long, propose a brief, no-cost strategy session to clarify their needs. It adds value without being a sales trap.
The PMMFI factor
No matter which method(s) you choose, all of them share a subtle trait that will set you apart from others in your field. Early in my career, Bill Wetzel (one of my mentors) told me that everyone you meet is wearing an invisible badge on their chest that says “PMMFI”: Please make me feel important.
Salespeople come and go, but if you make someone feel valued, they will value you. It is in human nature – the way we’re wired. It may take forever to close the sale, but ultimately, your prospect will always do business with someone who provides value before the sale even happens.
Don’t be like most salespeople.
Of course, you could do nothing at all after the initial meeting, which is what 95% of other salespeople do. I can guarantee that taking that route will lead to almost no sales. Why? Because if you do that, you’re on mute.
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