There are some very real challenges with a long sales cycle.

Reps looking to score the kind of commissions that come along with high-price, high-stakes selling know all too well how hard it is to navigate the complex sale. Lead follow up can stretch on for months, or even years, and can be a major burden on your time and resources (and let's pray you close the deal).

But the hardest part about handling a long sales cycle isn't the zen-like patience it requires, it's the uncertainty. Despite the multiple sign-offs and regulatory hurdles, uncertainty is the invisible wall standing between you and your prospect.

Luckily, there's a way to break that wall down, brick by brick. And it can happen faster than you think. Here's why you — and more importantly, your prospects — need a little warming up and some practical advice for how to shorten your sales cycle to get lead nurturing right.

Lead Nurturing 101: Know what's happening in your prospect's head

If uncertainty is the #1 challenge in a long sales cycle, your best chance at closing more deals in less time is to eliminate it at every step in your buyer's journey. But how can you do that on a practical level? After all, there are only 24 hours in a day.

The answer is simple:

Build trust in the sales cycle through automated lead nurturing.

According to a study from Forrester Research, organizations who use lead nurturing can generate 50% more sale-ready leads, at  33% less cost. They also found that marketers see an average of 20% more sales opportunities from nurtured vs. non-nurtured leads.

But in order to build the kind of trust that brings those leads to your door, you need to know what's really happening inside your prospect's head. In other words, you have to apply a little empathy.

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Start by asking yourself these 3 simple questions:

1. What does my prospect stand to gain by working with me?

Don't limit this to hard ROI. Think about what your prospect will gain on an emotional level, too. Will they earn the respect of their peers, idols and family? Will they be their company's biggest hero? What's really in it for them?

2. What does my prospect stand to lose by working with me?

Anytime there are large amounts of cash changing hands, there's a lot at risk, both on a personal and professional level. What if your prospect's team doesn't like or use your product or service? In areas like real estate, your product might literally involve a massive life change. You're asking your leads to make a major leap, it's on you to show them it's a risk worth taking.

3. Who else is involved in the decision?

With a big-ticket product or service, there's never just one person involved in the sale. Your prospect's decision will have a major impact on several other people. Who are those people and what will they gain or lose by working with you? What's their role or level of influence in your prospect's life? How can you answer their questions?

When you take time to uncover your prospect's biggest questions (including the ones they didn't even know to ask), keeping leads engaged starts to feel easy and natural.

At Follow Up Boss, our real estate CRM, we see it all the time: Those who nurture leads close more deals, faster. Debra Beagle is co-owner of the #1 RE/MAX team in the world. For Debra's rockstar team, having the right lead nurture system in place has shortened the buying timeline by up to 75%. “It used to take about 90-120 days for a new agent to write a contract, now with our training and process systems, agents are successfully writing contracts within 30 days."

How to nurture leads in a long sales cycle

A quick caveat before we dive into the nitty-gritty: This "automated" stuff only works when used intentionally.

From getting an email that greets you with, "Hi {{First_Name}}!" to having your name spelled incorrectly on your Starbucks latte, we all know how annoying it is when personalization goes wrong.

Barry Jenkins is the leader of the #1 Better Homes and Gardens Real Estate team in the US. In 2017, he used lead nurturing to almost double his sales volume to 240 deals, while working just 25 hours per week. “We have the automation, but what really matters is that we’re able to wait and apply it relevantly,” says Barry.

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Here's how to set up an automated lead nurture strategy that never annoys:

Step 1. Start by surveying your prospects to find out what info they want most

The best way to find out what your prospects want is to simply ask.

Send out a survey to your current customers or create an online poll for web visitors with a few simple questions about what they're looking for. Open-ended questions like, "What are the 3 biggest challenges?" related to the issue or problem your product solves can bring in a gold mine of info depending on buyer stage.

Tailor your questions to whatever it is you want to know. If you have an inkling your leads are looking at competitors before they come to you go ahead and ask them who they've looked at or what info they haven't been able to find so far. Tools like Typeform and SurveyMonkey make it easy to send, collect and even analyze your surveys.

If you or your internal stakeholders are resistant to sending a marketing survey, you're not alone. Surveying your current customers is hands-down the best way to figure out how to attract more customers, but if you can't make it happen, head to the places your leads hang out and see if you can grab some voice of customer data (basically, fancy marketing speak for the words your prospects are using to describe their challenges).

Online watering holes like review sites, LinkedIn, Facebook and Reddit can be great places to get insights on the convos your prospects are having.

Step 2. Create relevant content based on where leads are in the buyer's journey

Armed with new insights about what your customers really want, now you're ready to create super compelling answers to their questions.

If you're lucky enough to have a rockstar marketing department, now's the time to set any internal rivalries aside and really partner up. With quality information, comes quality leads and you need to be on the same page about what messages your prospects need to see.

If you're a contractor or team leader, try blocking out some time to create a content calendar, and explore these 7 Content Distribution Channels You Aren't Using (But Should).

3. Segment and track your leads

Personalize your follow up based on the core segments that matter. That could be verticle, lead source, buyer behavior, etc. The trick is not to overcomplicate it.

You need just need 3-5 core segments to keep the content personalized enough to feel relevant to your prospects, without burdening your team or process with the logistics that come from multiple email drips.

(Bonus tip: Make sure your CRM is flexible enough to account for leads that jump stages.)

4. Alter your strategy

Once you've got the main systems in place, it's time to test. Alter your lead nurture strategy based on how leads interact with your content.

This is important because, despite the complicated lead scoring metrics that go into most sales cycle systems, the only metric that really matters is behavior. You need to be able to act when your lead acts.

Set your notifications so that you and your team are alerted when a lead takes an important step in the journey, such as downloading a piece of content or replying to a follow-up email. Then, check your performance metrics to see which actions yield the best results and adjust your approach to see if there's anything you can do to shorten the amount of time it takes them to get there.

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Lastly, it's important not to over-automate.

In the earlier stages of the buyer's journey, it's ok to use automation to serve up the relevant content and consistent value-driven follow-ups needed to keep leads moving through the pipeline, but the warmer they get, the more you'll need to include opportunities to keep your lead nurture interactions as personalized as possible. (And trust us, it's great for revenue.)

These steps may feel like a lot of work up front, but remember, no breed of salesperson is more focused, driven and successful, than the one who shows up every day to play the long game — and they've got the recurring revenue to back it up.

When you're ready to get started with lead nurturing, look for a lead tracking system that gives you the right balance between relevant content and scalable automation. Because connecting with more leads, more often is certainly the name of the game — but it won't mean much without that personal touch.

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