Mailers may be the backbone of your land investing strategy, but they’re far from the only way to connect with, and nurture, your leads.

With the cost of direct mail campaigns and response rates that can feel dishearteningly low, cold calling is an attractive but largely untapped addition to your marketing arsenal – and that creates a big opportunity for those who nail it.

Use these best practices to set yourself up for cold calling success.

Develop resilience and thick skin – Embrace rejection

Let’s start with the obvious: no one loves being told “no” all day.

The reality of cold calling is that you’ll be hearing that a lot. Rejection is part of the process. Embrace it.

Going in with that in mind will ease the pain and make it easier to push through.

And you’ll want to push through because the success rate of turning cold calls into warm leads is ~2%. That’s on par with (or can even be better than) direct mail.

Pebble Tip: Don’t lose the forest for the trees, focus on the big goal of acquiring land, not the number of people who hang up. Set an achievable daily call goal and aim squarely at that.

Techniques for handling rejection:

• Stay curious and keep the conversation moving: Instead of ending the call right away, try a gentle follow-up like, “I understand – could you tell me why selling isn’t a fit right now?” This can often uncover useful information and sometimes even shift the lead’s mindset.

• Detach from the outcome: By focusing more on relationship-building than immediate results, you’ll ease the pressure of each call. Over time, this mindset shift helps you build resilience.

• Reframe the “no” as “not yet”: You’ll be surprised at how often “no” just means “not right now.” Add these leads to a nurture sequence, and follow up periodically, as circumstances can change.

Expert Insight: Alicia Jarrett of Supercharged Offers notes “If someone says they’re not ready to sell, we’ll respond by saying, ‘That’s okay, but what if we put the right offer in front of you?’ It’s all about asking the right questions to turn the lead around. If the lead is rude or dismissive, we politely let them go. We don’t push in those situations, but we do try to ask questions when objections come up to keep the conversation moving forward.”

TCPA compliance and legal considerations

Before you even dive into your first cold call, it’s critical to understand regulations like the Telephone Consumer Protection Act (TCPA), which requires businesses to check numbers against the National Do Not Call (DNC) registry to avoid significant fines.

Maintaining an internal DNC list helps log any requests to avoid future calls.

As Alicia points out, an even better way to do it is using tools that handle that for you.

Expert Insight: “We ensure compliance by running all of our data through a do-not-call list and a litigator’s list. We use a compliant dialer and make sure we follow the specific regulations for each state or region, such as the allowed calling times. We’re very strict about doing everything by the book.”

Start simple and slow

Experience is the best teacher and that goes for cold calling as much as anything else.

Pound the phone on your own when you get started and get a feel for the process, particularly if you plan to hire cold callers to qualify leads for you.

Not only is this the easiest way to get started, but it’s also the cheapest.

Pebble tip: Confirm that cold calling is something you can handle by starting with a cheap and easy approach

Invest in a power dialer

Once you’re sold on cold calling and want to expand your operation into a more efficient and high-volume one, it’s time to get a power dialer.

What’s a power dialer?

A tool that eliminates manual dialing and automatically calls numbers on your list one after another so you can make more calls per hour.

Often these dialers will allow you to make multiple calls at one time; resist the temptation to max out that number.

If all the calls connect, the dialer will drop all but the calls it can connect to you or your employee…creating some annoyed leads.

Pebble Tip: Start with Pebble as your cold calling platform until you get a feel for the process. When you’re ready to take on more, limit your power dialer to make a maximum of 2 calls per agent so you don’t miss any leads

Create a connection and get them talking

Among your best abilities on a call is likability.

People like doing business with people they like and if a seller doesn’t like you, there’s a good chance they’re not giving you the deal.

Land is a people-to-people business and creating rapport is the only thing that matters on the initial calls.

Get them excited and chattering away and you’ll have won the toughest part of the battle.

Pebble tip: Focus on building a relationship and, ideally, don’t talk about money at all on the first 2 calls

Know what you’re going to say

This starter 2-question script has worked wonders for Nicholas:

1. Sorry to bother you, I’m looking for the owner of [describe property]

a.      Do not use their first name. The person you reach may be the spouse, child, friend, etc. of the land owner, not the actual land owner, which may lead to a quick hang-up. You can’t build rapport until you’re talking to the right person.

2.  Have you ever considered selling before?

a.      Asking if they’ve ever wanted to sell as opposed to if they want to sell now has a higher likelihood of getting a yes and creates the opportunity to get a “hesitation lead”.

If they say no?

It’s ok to push back politely with this battle-tested line: “Would you maybe mind taking back my direct phone number, and if anything changes give me a call back?”

It gets a yes over 50% of the time according to Nicholas.

Pebble tip: Do not make an offer without finding out more about the property

Follow up like a pro

Part of the cold calling process is going to be follow-ups because deals are rarely closed on the first call (more on that below). The focus of these calls should be continuing to build a relationship.

Here are some follow-up tips:

• TIP #1: Call in half the amount of time they say. If it’s two months, call back in one, for example.

• TIP #2: Be pleasant and ask questions that both deepen the connection and qualify the lead further

  • How long has this piece of land been in your family?

  • What were you planning to do with the land?

• TIP #3: Don’t talk numbers

• TIP #4: If your VA funnels a warm lead to you, call them back immediately because they’ve shown they’re in the mood to pick up a call from a stranger

Pebble tip: Do not text – if you get too comfortable texting, you’ll be too afraid to call which can make this process longer and lower the success rate

CRM integration for seamless follow-up

Using a CRM system is essential for tracking interactions, managing follow-ups and centralizing lead data, especially in real estate where multiple touchpoints are often necessary.

CRMs like Airtable can make follow-ups easier and more organized. Pebble goes a step further by letting you automate your follow-ups.

Expert Insight: “All of our data is managed in Airtable, where we store scripts, track lead performance, and manage customer data” – Alicia Jarrett

[Pebble follow-up vid]

Qualify leads with these 7 questions

Once you have a warm, toasty lead and you’ve built a friendly relationship, you’ll want to work through at least these questions to properly qualify them.

1. Is there legal road access?

2. Are utilities available?

3. Is the property in a clear or wooded area?

4. Why do you want to sell it?

5. How much do you want to sell it for?

6. Are you open to receiving that total amount in monthly payments?

   1. This lets you know if owner financing is possible

7. Is there a better phone number for you? What’s a good email?

Once you’re ready to make an offer, take time to review all the information and get back to them. Be sure to mention a precise time frame, i.e., within 24 hours.

Pro Tip: Give very clear next steps so they always know what’s happening next.

Have patience: don’t aim for the one-call close

Is it possible to close after a single cold call? Sure.

Will you wreck your chances with a lot of otherwise qualified? 100%.

Striving for the near-mythical one-call close will set you up for huge disappointment and burn more bridges than it’s worth.

The only goal of your first and second call is to have that person fall in love with you.

Your best ability with cold calling is likability.

Pebble tip: Approach cold calling like dating, making your move too soon will only end in heartbreak

Expert tip: “We use a script that we've used a couple of million times, and it works great. The script is simple but effective. It warms up the prospect by letting them know we're interested in properties in their area. We confirm if they still own the property and ask if they’d consider selling directly to a buyer, with no middlemen or realtors involved. We then ask questions about property size, access, utilities, and zoning. We can also customize it to include more personal questions, like their plans for the property when they first purchased it. Our script can end with a warm transfer to an appointment or gathering more detailed information.” – Alicia Jarrett

Understand how to talk money and lead them to the close

Naturally, the goal is to acquire the land you’re after. Throughout our guide here we’ve put a lot of emphasis on not being salesy.

No one likes being pitched and the land space is no different.

Your relationship-based approach should extend through to the end of the deal.

When it comes to closing and talking money, these are the types of questions you should be asking:

• What do you want to do with the money?

  • This gets the owner thinking what’s next after they have the money

• How much money will it take to do what you just say?

  • This allows you to work backward from a very specific desire of theirs and create a compelling offer that factors it in

Develop a voicemail script

Many of the calls you make are going to go to voicemail so it’s important to have a script ready that increases your odds of a callback.

Here are some guidelines for a solid voicemail:

• Be authentic, friendly and high energy

  • Cold calling can be monotonous and boring, don’t let that creep into your voicemails (or conversations)

• Do not sell or make a pitch

• Keep it short, 20 seconds at the absolute maximum, and only relay the most critical info

• Use the land owners first name if you 100% know it and say your name

• Give them a clear action to take without sounding desperate

  • i.e., don’t say something like “call me back whenever”

Pebble Tip: Practice your message. Record and listen to it to ensure it sounds natural and gets all the information you want across.

Cold calling is great for land

The beauty of land investing is that very few people are as attached to a plot of land as they are to a family home, which makes landowners a perfect target for cold calling.

Of course, getting it right and guiding them to a close isn’t as easy as picking up the phone and making an offer though. If it were, we’d all be doing it!

This cold calling guide should equip you with everything you need to make cold calling work for you.

As Alicia puts it, “Cold calling is a great way to test new markets and get leads easily. It helps you assess whether a market is worth going deeper into. It’s a valuable tool for anyone new to land investing.”