Road Warrior Prospecting (Ask Jeb)

Kyle, a field sales rep from British Columbia, is struggling with a common prospecting challenge: how to consistently prospect when you’re constantly on the move. Kyle’s situation likely resonates with many of you in outside sales. He described his typical day—starting at job sites at 7:30 AM, running between appointments, sending proposals from his truck, and working from Starbucks in between meetings. Sound familiar? He had read my book, Fanatical Prospecting, where I advocate for dedicated time blocks for prospecting. But Kyle’s reality made traditional time blocking nearly impossible. So what’s a field rep to do? What follows is the advice I gave Kyle, cleaned up and expanded so every field seller, territory manager, and outside sales road warrior can put it to work—right now. Focus on Activity Count, Not Time Blocks If you’re in Kyle’s shoes (or truck), here’s my advice: Stop obsessing over time and start focusing on activity counts. Instead of trying to carve out a rigid one- or two-hour block, set a daily activity goal. For someone in Kyle’s position, committing to 30 quality outbound touches per day is likely sufficient. In my early days, I personally made 100 dials daily, no matter what—but you need to find your number. It’s amazing what you can accomplish in small pockets of time. Got 10 minutes between appointments? You can make 10 dials. These micro-prospecting sessions add up throughout your day. Instead of asking, “How do I find two uninterrupted hours?” ask, “How many outbound touches do I need to hit my pipeline goal?” Reverse-engineer your math. If 30 dials typically create two meetings—and two meetings a day keep your funnel fat—commit to 30 dials, period. Activity over chronology. Whether you burn those calls in one block or in six five-minute bursts between site visits doesn’t matter. Hitting the activity target does. Prospecting is like push-ups: the muscle only cares that you completed the reps, not whether you did them all at once. Practical Fanatical Prospecting Implementation for Field Reps Here’s how to make this work in the field: Set up your list the night before: Don’t waste precious morning energy building your call list. Have everything ready to go when you start your day. A pre-built list eliminates the mental drag of figuring out who to call while you’re juggling mud, invoices, and traffic. Use the gaps: Those small windows between appointments are prospecting gold. Five minutes here, ten minutes there—use them. Capture information efficiently: Most calls will go to voicemail. For the ones who answer, quickly note any important information to input into your CRM later. Don’t try to update your CRM in real-time between every call. Be safe: Obviously, don’t text and drive. Pull over if you need to take notes or send follow-up messages. What Kyle is experiencing is common for outside sales professionals. You can’t prospect the same way as an inside sales rep with a dedicated desk and phone. Your office is your vehicle. Your desk is wherever you can find a flat surface. Your schedule is dictated by customers and job sites. Create a Mobile Prospecting Kit Salesforce is great—when you have stable Wi-Fi and two hands on a keyboard. Field reps need something that works when the LTE bars dip to one. Print or export your list with phone numbers and a skinny note column. Hyperlink mobile numbers in a notes app so a single tap dials the next contact—no scrolling, no fumbling. Use a hands-free auto-dial app (tons exist) if local regulations allow. Safety first; quotas second. Capture notes on paper or dictate voice memos. At day’s end, batch-enter critical intel into your CRM. Perfect data hygiene is optional; capturing deal-moving facts is mandatory. Rule of thumb: Log information, not activity. Managers love call-count metrics, but conversations and follow-up triggers win deals. Prospect in the Micro-Moments I built my career on a simple principle: five dials fit in five minutes. Waiting for the site supervisor? Dial. Stuck at a railroad crossing? Dial. Early for lunch with a GC? Dial. If you rinse and repeat ten times a day, that’s 50 dials—without ever blocking a formal hour. Your smartphone is a Swiss Army knife; flip out the prospecting blade at every lull. Respect the Platinum Hours—But Redefine Them Kyle also asked about “platinum hours” for prospecting in the construction world. This is where understanding your market’s rhythm becomes crucial. Kyle noted that contractors and builders are easier to reach in the morning, while homeowners are more accessible in the afternoon. This creates a “sandwich” with potentially lighter activity in the middle of the day. This midday lull is your opportunity. Use this time to build lists, handle admin work, and prepare proposals. Unlike the evening when you’re exhausted from a full day in the field, these midday hours could be your most productive for planning and organizing your prospecting efforts. Another strategy: dedicate time on Sunday evenings to build your entire week’s prospecting list. Create a master list of 100 names and work through it all week, making adjustments as needed when new leads come in. Creating a Predictable Pipeline Consistent prospecting—even in small chunks—creates a predictable pipeline. For field reps, this approach is actually more sustainable than trying to force traditional time blocks into an already chaotic schedule. When you hit your daily outbound touch goal consistently, you create a steady stream of new opportunities flowing into your pipeline. This prevents the feast-or-famine cycle that plagues so many field sales professionals. Remember, it’s not about how much time you spend prospecting—it’s about how many quality touches you make each day. Set your number, stick to it religiously, and watch your pipeline grow. Prospect the Way Your Territory Demands Kyle’s biggest burden wasn’t time—it was guilt. He felt like a prospecting slacker because he wasn’t doing textbook blocks. Let me settle it: If your role is to be on-site talking to buyers, that is high-value selling time. The goal of prospecting is pipeline, not calendar purity. Flexible, numbers-driven activity beats rigid, time-driven blocks every day of the week. Give yourself permission to sell the way your territory demands. Outside sales is messy, chaotic, and wildly fun. You’ll spill coffee on contracts, burn through playlists, and hunt for cell service in cornfields—but none of that excuses an empty pipeline. If you’re like Kyle—constantly on the move but committed to growth—focus on activity goals rather than time blocks. Your truck becomes your prospecting command center, and those small gaps in your day become opportunities to move your business forward. Keep hustling. Keep prospecting. And at the end of the day, when it is time to go home, always make one more call. Want to set more appointments from the road? Download our FREE guide 25 Ways to Ask For the Appointment on a Cold Call Our Sponsors: