RUNNING THE BUSINESS
4 Strategies for Managing Long Sales Cycles
Keeping your sales teams motivated, strategic, on-task and successful when the sales cycle stretches on.
BY Troy Harrison
Ivelin Radkov-stock.adobe.com
Have you ever run a marathon? Most people haven’t. But many salespeople run them every day — the long sales cycle. Salespeople love the quick win — that satisfying moment when a prospect becomes a customer in a matter of days or weeks. Sometimes, it’s even the fabled “one call close.” But what about those times where the sales cycle stretches into months or even years? How do you keep your sales teams motivated, strategic, on-task and successful when the finish line seems so far away?
Long sales cycles present unique challenges. They test a salesperson’s patience, strategic thinking and ability to maintain momentum over extended periods. They can also tempt even the most disciplined sales professionals to neglect prospecting, as the gratification of a closed deal feels perpetually out of reach. But here’s the truth: mastering the long sales cycle is not just a skill — it’s an art form. And like any art, it requires dedication, practice and a specific set of techniques. Let’s explore four key strategies that can help you and your team excel in the marathon of long-cycle sales.
1. Never Stop Prospecting
Imagine you’re a farmer (no, not the old, outdated “hunter/farmer” sales term). You know it takes months for your crops to grow, but you also know that if you don’t plant seeds regularly, you’ll eventually have nothing to harvest. The same principle applies to long-cycle sales.
It’s easy to fall into the trap of thinking, “Why start new conversations when I won’t close them for years?” But remember this: you can’t finish a sale unless you start one. Prospecting is the lifeblood of your sales pipeline, regardless of how long it takes to close a deal. A sales funnel that doesn’t consistently fill at the top will run dry at the bottom.
Make prospecting a nonnegotiable part of your weekly routine. Set aside dedicated time each day to reach out to new potential clients. Use a mix of cold calls, emails, social media outreach and networking events to keep your pipeline full. Remember, the seeds you plant today are the deals you’ll close tomorrow — or next year. The best prospecting cadence is to open with a phone call (yes, a genuine, pick up the phone, voice-to-voice call) and attempt to reach your target. If you don’t get an answer (80% to 90% of the time these days), then leave a powerful voicemail and switch to LinkedIn connection. Once connected, slow play the connection using engagement techniques, then ask for the appointment two to three months after connecting.
2. Think Strategically, Act Consistently
Once you’ve initiated a conversation with a prospect, it’s time to shift into strategic mode. This is where the real art of long-cycle selling comes into play.
Start by estimating a realistic timeline for the deal. Is it six months? A year? Two years? This timeline becomes your road map, guiding your interactions and helping you set milestones along the way.
With each contact, your goal should be to move the buyer’s journey forward, even if it’s just by inches. You’re playing the long game, so every interaction should add value and strengthen your position. Basically, you’re positioning yourself to be the dealership of choice at contract time.
Maybe it’s sharing a relevant industry report, offering a fresh perspective on a challenge they’re facing, or simply checking in to maintain the relationship — but offering some new piece of knowledge or expertise every time. The key is consistency. Regular, value-added touchpoints keep you top of mind and position you as a trusted adviser, not just another salesperson.
3. Keep Your Contacts Current
In the span of a long sales cycle, a lot can change. Lifestyles change and priorities shift. Your job is to stay on top of these changes and adapt your strategy accordingly.
Make it a habit to regularly verify and update your contact information. But don’t stop there — strive to expand your network. The more contacts you have, the more resilient your opportunity pipeline becomes. Make sure your potential customers genuinely know you and the value you bring. This approach not only provides you with a more comprehensive understanding of what your customers want and need, but also helps safeguard your opportunity if their lifestyle or priorities change.
4. Be Ready When the Stars Align
Here’s a fundamental truth about sales: a deal happens when need, solution and timing intersect, and the buyer’s journey completes. In a long sales cycle, your job is to be ready when that moment arrives.
Maybe the customer has a poor experience at another dealership, or their finances finally align with their travel dreams. Your consistent presence and value-added interactions have positioned you to capitalize on these moments.
Stay alert to industry trends, and any shifts in your prospect’s needs, and when that window of opportunity opens, be ready to act swiftly and decisively.
Managing long sales cycles is not about passive waiting — it’s about active preparation. It’s about building relationships, demonstrating value and positioning yourself as the obvious choice when the time is right. There are no shortcuts to anyplace worth going.
Winning in long-cycle sales requires a unique blend of patience, persistence and strategic thinking. It demands that we resist getting demoralized due to the lack of quick wins and instead focus on building lasting relationships and delivering consistent value. By maintaining a steady prospecting rhythm, thinking strategically, keeping our contacts current and staying ready for opportunity, we can master the marathon of long sales cycles.
“Mastering the long sales cycle is not just a skill — it’s an art form.”
Troy Harrison is the Sales Navigator, a speaker and the author of “Sell Like You Mean It” and “The Pocket Sales Manager.” He has trained salespeople from 23 different countries who live on three continents and has spoken all over North America and Europe. He helps companies navigate the elements of sales on their journey to success. He offers a free 45-minute sales strategy review. To schedule, please visit royharrison.com/ssr.
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