How to Build Self-Directed Prospecting Skills

Outbound is dead in cyber. Long live AE-owned prospecting. I will die on the hill of "outbound is dead". But it's been misunderstood when I've brought it up here. In cybersecurity, generic mass outreach is dying or it's a zombie waiting to be whacked. Targeted, value-driven prospecting led by Account Executives is thriving. SDR's have a hard time doing this not because they can't, but because the system is not setup for them to do it (i.e. comp plans, org structures, etc.) We know from research that personalized outreach based on deep account knowledge delivers 3x better engagement than templated SDR approaches. Yet we keep trying to build outbound motions with higher volume and worse conversion rates 🤮 Here's my framework for building a repeatable pipeline development program where AEs actually own the process: 👉 *The Value Hypothesis Approach* 1. Narrow the focus dramatically: Your target account list should be small enough that each account gets hours of dedicated research. 2. Make AEs accountable for contact mapping They need to identify key stakeholders and understand the organizational dynamics before any outreach begins. 3. Develop specific value hypotheses This is the game-changer. Each account gets 2 customized value proposition based on their specific situation. 4. Collaborate on hypothesis refinement The best teams involve SE/PreSales, Product Management, and Sales Leadership in critiquing and improving these hypotheses. 5. Execute with precision With this foundation, outreach becomes a targeted conversation rather than a generic pitch. 6. Close the feedback loop: Sales leaders need to document which value hypotheses resonated and which fell flat - this becomes your competitive advantage. The best-performing enterprise sales teams allocate at least 1/3 of AE time to this process. Yes, it's resource-intensive, but the results speak for themselves. 2 hours a day (minimum) every day, every AE, for 3 months. Then come back and tell me 'thank you' Unexpected benefit: When AEs spend 10+ hours weekly on strategic prospecting, your inbound and partner-led conversion rates automatically improve. Why? No AE will let warm leads slip after experiencing how much work cold prospecting takes. Pro-tip? Spend 'Training Thursdays' evaluating value hypothesis together. Double pro-tip, combine Value Hypotheiss with 'Show me You Know Me' on your messaging (follow Samantha McKenna - She crushes SMYKM content) Anyone here that calls value hypothesis something else? I used to call it my 'angle'. Need something more catchy and less scientific-sounding 😆

I wasted years thinking small talk about weather made me good at sales. My process was embarrassingly simple: Pull up their LinkedIn, scan their last email, then wing it with some chitchat about their location or the weather. I assumed "natural rapport" meant improvising my way through calls. And I was wrong. Truth is, I was resisting structure. I believed scripting meant being robotic and proper preparation would kill authentic conversation. So I kept it casual, kept it flowing, and… kept missing opportunities. Then I started working with a sales coach. Every Wednesday at 10am, I'd get on a call to hear exactly why my approach was wrong. It was expensive, uncomfortable, and exactly what I needed. One day, he caught me using my favorite line (among others) while I talked through a sales call: "Any thoughts on that?" His feedback was brutal: "You're swinging between closed-ended questions that shut people down and questions that leave them hanging. What if, instead, you guided the conversation?" Ouch. Mind blown. He was right. In trying to keep things casual and unstructured, I'd been failing to guide meaningful conversations. My resistance to "scripted" questions wasn't just making my calls superficial—it was leaving both me and my prospects without direction. So we changed… direction: Create and rehearse a flow and replace every closed question with an open one. Instead of "Should I walk you through our services?"   → "What’s the goal?" then… “What’s behind that?” Instead of "Any thoughts?"   → "How would this fit into your current process?" Instead of "Does that pricing work for you?"   → "How does this compare to what you were thinking?" The difference was immediate. Prospects started sharing their actual concerns. Their real budgets. Their true decision-making process. All the things they used to hold back when I gave them an easy "no thoughts" escape hatch. Last quarter alone, we added a record in new MRR—twice our typical close rate. Sales cycles that used to drag on for 8 months now wrap up in 4. But the biggest change is that I finally see sales calls for what they *should* be: guided conversations with clear direction and open ended questions, *not* let-me-wing-this-trust-me-I-got-this improv sessions. The beauty of this approach is that it's not in any way manipulative or calculating. When you introduce structure and direction, you're also helping prospects quickly decide if what you have to offer is what they actually need. Everyone wins. P.S.   Try this today: Take your most common closed question and flip it into an open one, directing one. You'll be amazed at what people tell you when you stop giving them permission to say nothing.

Last quarter I watched one of my top clients scramble to hit quota. He was the THIRD highest performer in his company (out of 10 reps). His activity levels were high. His close rate was even better. But something was VERY wrong... When we looked at his calendar, we discovered he only had THREE discovery calls the ENTIRE MONTH. The pipeline was a mirage. Here's the hard truth most sales leaders won't tell you: Activity ≠ Results Another rep I know made 14,000 calls in a month without booking a SINGLE meeting. Elite performers don't just work harder - they work DIFFERENTLY. 👇 THE ELITE PROSPECTING FRAMEWORK 👇 This is the exact system I've used to build a 7-figure sales career and coach hundreds of reps to double their pipeline in 30 days: 1️⃣ BLOCK YOUR CALENDAR RELIGIOUSLY Schedule 8 hours of dedicated prospecting time weekly (2 hours per day, Mon-Thu) Make these blocks SACRED - nothing overrides them Set them early (8-10am) when your energy is highest Put them as recurring meetings in your calendar NOW Label them clearly: "PROSPECTING - DO NOT BOOK" 2️⃣ RESEARCH BEFORE YOU REACH OUT Dedicate a separate full 2-hour block weekly just for research Validate contact data quality (bad data = wasted time) Identify true buying signals (not just basic triggers) Create a targeted list of 50 PERFECT prospects Document 2-3 personalization points for each target Use tools like LinkedIn, company news, and your CRM data 3️⃣ TARGET THE RIGHT ACCOUNTS Quality ALWAYS trumps quantity Focus on 50 perfect-fit accounts, not 500 random ones Build your list based on clear ideal customer criteria Segment your list by industry, pain point, or use case Prioritize accounts showing buying signals Remove any contact with questionable data quality 4️⃣ EXECUTE WITH PRECISION When you sit down to prospect, it's EXECUTION time only No researching, no planning, no "figuring it out" Follow your pre-built list in order of priority Mix methods: calls, emails, LinkedIn, video Track your results meticulously Adjust your approach weekly based on data 5️⃣ LEVERAGE YOUR SDRs Schedule weekly 15-minute alignment sessions Coach them on messaging that's working for you Give specific feedback on recent meetings they've booked Share your target account list with them Create a feedback loop on what's generating responses THE RESULTS SPEAK FOR THEMSELVES! My client implemented this system and went from 3 to 8 Enterprise discovery calls per month. That's 166% more pipeline. That's 166% more potential commission. That's the difference between missing quota and crushing it. The math is simple but brutal: If your prospecting is inconsistent, your results will be too. If your calendar doesn't protect prospecting time, it won't happen. If you're not tracking the right metrics, you can't improve them. Want to prospect better? Start with a great cold email: https://lnkd.in/gKSzmCda