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Don’t Be That Guy (or Girl): A Better Way to Sell
The Agency Inner Circle guide to Sales. 0% sleeze. Promise.
Tim Kilroy
11 Apr • Estimated Reading Time: 20 minutes
Table of Contents
Editor’s Note: This is a long email - almost 3500 words. If it’s truncated in your inbox, read it in it’s full glory at Agency Inner Circle #52.
Sales That Don’t Suck (Yes, Really)
Sales usually feels like a necessary evil, right? The awkward outreach, the vague proposals, those “Always Be Closing” high-pressure tactics. OMFG. It’s AWFUL.
Sales doesn't have to be a miserable grind. In fact, it can be surprisingly enjoyable, for both you and your prospect…especially when you're doing it right.
This guide isn’t your typical "10 hacks to close more deals!" sales-bro nonsense. It's a practical, BS-free roadmap to transforming your entire sales process from first contact to "When do we start?" into something clear, compelling, and even a bit of fun.
Buckle up, sports fans, because your sales game is about to get seriously upgraded.
Stage 1: Prospecting - Stop Chasing Shiny Objects
Prospecting is the awkward first date of the sales process: you're trying to impress, they're sizing you up, and everyone's secretly hoping this goes better than last time. But instead of stumbling around with generic pitches, let's get strategic (and maybe skip the “Uh, so what do you like to do on the weekends?” small talk).
Why Most Agencies Get Prospecting Wrong (and How You Won't)
Most agencies treat prospecting like throwing spaghetti at a wall—lots of mess, little accuracy. You end up chasing shiny objects (hello, "anyone with a pulse and a budget"), and before you know it, your sales pipeline looks like a hot mess.
Here's how to clean that up:
Tip #1: Get Obsessive About Your ICP (Ideal Client Profile)
Your ICP isn't just some buzzword to drop in meetings. It's your definition of not too hot, not too cold, juuuust right. Define it clearly, deeply, and obsessively.
Start with winners: Who are your happiest, most profitable clients right now? Find the commonalities→industry, size, pain points, target audiences, etc.
Go deeper than demographics: Sure, "ecommerce businesses" is a start, but what about "ecommerce brands doing $2–10 million who just hired their first dedicated marketer"? Now that’s the stuff you really want..
This isn't just theory…this is sanity preservation. The better you know your targets, the less likely you will sign up a client who makes you insane.
Tip #2: Keep Your Eyes on the Signals
Successful prospecting isn't just about who fits your ICP; it's about who fits it right now. Timing is everything (just ask Blockbuster).
Growth indicators: Watch for businesses hiring aggressively, launching new products, receiving funding, all that stuff. These are green flags waving at you.
Set it and forget it (almost): Set Google Alerts, Sales Navigator triggers, and keep an eye on industry news. Let technology do the stalking for you (but not in a creepy way).
Tip #3: Give Before You Ask
Nobody wants another cold email asking for 15 minutes. Seriously. No-f’ing-body.
Provide legit value first: Share insights, articles, or industry trends relevant specifically to them.
Warm it up: Engage first through social channels. Comment thoughtfully on their LinkedIn posts. Start conversations, don't just jump into inboxes like a digital ninja. You are the intruder. Bring a freakin’ gift, OK?
One Thing You Absolutely, Positively Must Avoid
Generic, spray-and-pray outreach. It's like the cargo shorts of the sales world -sure, convenient, comfortable, but ultimately, it’s embarrassing.
Instead:
Hyper-relevance: Take 5 extra minutes to tailor your message so that it is relevant to the recipient and their needs. Reference their business directly. Be specific. No faux personalization like “Joe, love what you are doing at X!” That stuff is a waste of time.
Quality over quantity: Better to deeply engage 10 perfect prospects than weakly spam 100 random contacts.
Prospecting done right isn't about brute force…it's finesse, focus, and yes, a touch of charm. Stick to these guidelines, and you'll build a pipeline filled with real conversations, genuine opportunities, and fewer awkward "Who are you again?" moments.
Stage 2: Engagement → Moving From "Who?" to "Hell Yeah!"
Engagement is where prospecting goes from swiping right to actually chatting. (Feel free to bust out your best Joey Tribbiani “How you doin’?” here.) This stage isn't about immediately pitching your services. The pitchslap is a terrible scourge on humankind. This part is about opening a conversation that's insightful, relevant, mutually relevant and maybe even a bit charming. (Again, cue your inner Joey…)
Why Engagement Usually Falls Flat (And How You're About to Nail It)
Most agencies mistake engagement for cold pitches masked as conversations. Prospects aren't fooled. They can smell a sales pitch from a mile away. Let's avoid that and focus on genuine interactions.
Tip #1: Make It Personal (Seriously)
Generic messages are like socks as a birthday present. Forgettable at best, smelly at worst.
Get Specific: Reference something unique about their business. New product launch? Recent award? Mention it. Find common ground.
Show You Care (Even a Little): Demonstrate you've invested time. Drop a note like, "Loved your latest LinkedIn post about the challenges of growing your sales team - really resonated with me because…"
Tip #2: Offer Real Value (Not Your E-Book)
Nothing kills engagement faster than hollow "value-adds." Your goal is to provide something truly useful…no strings attached. Again, you are the suitor…you don’t want to bring highway exit flowers - take a swing by Trader Joe’s at least.
Be Actually Helpful: Offer actionable insights tailored to their industry, vertical, competitive set or recent initiatives. "Saw your latest campaign and had some quick thoughts on amplifying the impact…interested?"
Curate Carefully: Share resources or insights tailored specifically to their current challenges, like industry-specific trends, useful articles, or case studies that are genuinely relevant.
Tip #3: Mix It Up Across Channels
Don't put all your eggs in one inbox. Engage across multiple platforms.
LinkedIn Love: Comment on their posts with thoughtful, genuine reactions. Don't just click "like" - that doesn’t matter.
Strategic Emails: Send personalized follow-ups referencing your social interactions or even more value.
Humanize Your Outreach: If appropriate, pick up the phone, maybe send a quick voice note this shows you're a real person, not a bot (even though we both know automation rocks).
Pitfall to Avoid: Being a Clingy Stage-5 Clinger
Persistent, value-add followup is good. Stalking? Less good.
Give Breathing Room: Don’t flood their inbox. Space out your touches strategically.
Clear & Concise: Keep communications short and direct. Make it easy for them to reply (and make it interesting enough to make them WANT to reply).
Leave Room for Them to Breathe: Remember, engagement is a two-way street, not a maniacal assault.
Engagement done right turns cold leads into warm conversations. Stick to this approach, and you'll not only have prospects eager to chat, you'll have them excited to take next steps.
Stage 3: Discovery Calls: Don’t Settle For Being Captain Obvious
Discovery calls aren't just about filling in the blanks or ticking boxes. They're your opportunity to demonstrate deep insight, genuine curiosity, and position yourself as a strategic partner, not just another vendor. It's time to elevate from "Tell me what's happening now" to "Here's why what you're doing matters and how we can amplify it."
Stop Asking Basic Questions (Because You're Better Than That)
If your discovery calls feel like scripted interviews, it's time for an intervention. The real magic happens when your questions prompt prospects to see their business and their challenges in a fresh, revealing way.
Tip #1: Shift From 'What' to 'Why'
Don't settle for surface-level info. Dive deeper into why certain business decisions were made or how the current strategy connects to their bigger business goals.
Go Deep: Instead of "What are your monthly sales?", ask "What's driving that sales? New products, market conditions, or internal changes?"
Reveal the Real Issues: Move past symptoms ("We aren't getting leads") to root causes ("Why do you think your message isn't resonating?").
Tip #2: Connect the Dots Between Your Service and Their Strategic Goals
You aren't selling SEO or content or PPC. You're selling growth, profitability, or market leadership. You are selling a future transformation. Your questions should reflect this.
Big Picture Thinking: "How does increasing your organic reach impact your strategic goals like customer acquisition costs or market share?"
Challenge Assumptions (Gently): "If we doubled your conversion rate tomorrow, what operational or fulfillment challenges might arise?"
Tip #3: Talk About Impact Beyond KPIs
KPIs matter, but they're just signposts. Show your prospect you're thinking several moves ahead.
Broader Impact Questions: "If we hit your revenue goals, what else would change in your business? Hiring? New markets? Investment?"
Uncover Opportunities and Risks: "How might achieving (or failing to achieve) these marketing goals impact investor confidence or competitive positioning?"
Pitfall to Avoid: Being a Box-Checker
Discovery calls aren't checklists—they're conversations. If you simply march through questions without engaging, you lose credibility and connection.
Listen Actively: Reflect back insights, challenge gently, and be genuinely curious.
Adapt on the Fly: Let their answers guide your next questions, rather than rigidly sticking to your agenda.
Create Space: Allow silences. Often, your prospect's most profound insights come after a thoughtful pause.
Master discovery calls this way, and you'll become the advisor prospects trust, not just another agency chasing the same KPIs.
Stage 4: The Proposal- Make It Impossible to Say 'No'
Proposals aren't a laundry list of tasks. They're your final shot at showcasing why you're uniquely positioned to solve your prospect's deepest pains. A killer proposal doesn't just explain what you'll do. It vividly illustrates how you're aligned with the client's vision, transforming their challenges into opportunities.
Proposals Aren’t Documents. They’re Stories
A great proposal is a narrative that places your client at the center of the story. It clearly articulates their current state, your unique approach, and paints a vivid picture of a future that's genuinely exciting. It is a the story of a journey to a better state for your prospect.
Tip #1: Lead with Insight (It's About Them)
Start by clearly articulating your prospect's key challenges, opportunities, and pain points. Show deep understanding of their challenges and the impact of addressing them.
Be Insightful: Clearly show you've understood the client's issues. Reference specific pain points uncovered during discovery.
Align on the Problem: Demonstrate empathy, aligning yourself as a partner who fully grasps their perspective and goals.
Tip #2: Paint the Future (What's In It For Them?)
Next, vividly depict the transformational outcome your services will deliver. This isn’t about tasks & line item deliverables. It's about outcomes.
Future State Clarity: Show exactly how your prospect's business or life will improve, eg, more leads, increased revenue, reduced costs, or whatever aligns with their strategic goals.
The Delta: Emphasize the difference between their current situation and the exciting future you’ll create together.
Tip #3: Your Unique Process & Proof
Clearly illustrate your unique process and tie each step directly back to client outcomes.
Process Matters: Highlight your proven method, clearly linking your activities to the desired outcomes.
Social Proof: Include relevant case studies, testimonials, or third-party validations that clearly illustrate your credibility and successful track record.
Tip #4: Highlight Your Unique Selling Proposition (USP)
Your proposal must clearly demonstrate why you’re different and better (and better for them).
Stand Out Clearly: Whether it’s your specialized experience, proprietary approach, or unique insights, explicitly connect your USP to direct client benefits.
Client-Centric Benefits: Ensure every "special sauce" element in your proposal directly benefits the client. Remember, awards or processes mean nothing unless translated into tangible client advantages.
Tip #5: Clearly Map Out Next Steps
Don’t leave them guessing.
Procedural Clarity: Clearly lay out next steps including timelines, onboarding, who's involved, reporting cadence, and what you’ll need from them.
Make It Easy to Say Yes: Explicitly spell out what's next, reducing friction and uncertainty.
Tip #6: Price with Purpose
Don’t hide from your pricing. Frame it as an investment in future success, not just a cost.
Value Alignment: Clearly connect your fees with the outcomes and benefits your client will realize.
Investment Mindset: Position pricing not as an expense, but as a strategic investment that pays dividends far beyond the initial engagement.
Pitfall to Avoid: Sending Without Context
Never just "send" a proposal. Ever.
Deliver Personally: Always walk through the proposal live, providing context and answering questions immediately.
Avoid Surprises: Ensure everything in your proposal has already been discussed during discovery. The proposal should reinforce, not introduce, key concepts.
When you treat proposals like the powerful strategic tools they are, you turn hesitant prospects into excited new clients.
Stage 5: The Confident, Comfortable Close
Closing isn't a magical moment where you pressure someone into signing on the dotted line. It's the natural culmination of a thoughtful, value-driven conversation that ends with clarity and confidence on both sides. Your goal? Make saying 'yes' feel like the easiest, smartest decision your prospect has ever made.
Closing is a Conversation, Not a Confrontation
Forget outdated, high-pressure tactics (“Do you hate money, bro?”). Today's buyers are savvy and informed. Your closing approach needs to reflect this reality, guiding prospects smoothly toward agreement rather than backing them into a corner.
Tip #1: Always Lead With Value
You never "sell" at the close. You are reminding your prospect of the value you're bringing.
Reaffirm the Vision: Restate the specific outcomes you've both agreed upon. Remind them of the clear, measurable benefits they'll receive.
Align with Their Goals: Clearly connect your services back to their strategic objectives, making your solution the logical next step.
Tip #2: Handle Objections as Opportunities
Objections are invitations to deeper understanding, not roadblocks.
Listen and Clarify: Genuinely understand the objection. Ask questions to uncover the real concerns beneath the surface.
Respond Thoughtfully: Address objections calmly, factually, and with empathy. Reinforce your solution's value in overcoming their concerns.
Tip #3: Be Clear About Next Steps
Ambiguity kills deals. Your job is to keep everything crystal clear.
Define Exactly What's Next: Clarify onboarding timelines, contracts, meetings, and immediate actions. Make each step explicit.
Create Comfort & Clarity: Your prospect should never wonder what's next or who is involved with what. Confidence comes from clarity.
Tip #4: Stay Detached, Not Desperate
Prospects can smell desperation from miles away. Stay confidently detached. Your job is to guide, not beg.
Maintain Your Posture: Approach every interaction with a spirit of helpfulness and confidence. The right prospects appreciate your value and will move forward without pressure.
Know When to Say No: Sometimes the best close is recognizing that it's not the right fit. If it isn’t a fit, maintaining integrity will always pay off long-term.
Pitfall to Avoid: High-Pressure Tactics
Aggressive closing methods damage trust and credibility.
Avoid Rushed Decisions: Allow space for thoughtful consideration if needed, offering structured follow-up rather than immediate pressure.
Stay Authentic: Ensure your closing style aligns with your brand and personal values. Authenticity wins trust every time.
When closing is approached thoughtfully and confidently, your prospects feel valued, respected, and eager to move forward.
Stage 6: Sales-to-Delivery Handoff: From Promise to Performance ASAP
The sales-to-delivery handoff isn't about repeating discovery. It's about handing off an object in motion. You are transferring momentum. Your kickoff meeting should never be a redundant recap; it should feel like stepping on the gas pedal, quickly moving from the sales promise to results driven action.
The Handoff is an Acceleration Point
Think of the handoff as passing the baton in a relay race. You want the next runner (your delivery team) to take off at full speed, not pause to figure out where they're headed. A smooth handoff ensures immediate alignment and rapid acceleration toward client outcomes. This is matters so much in helping your team deliver a successful engagement and get the best client lifetime value possible.
Tip #1: Document Clearly, Transfer Completely
Detailed, accessible documentation is critical for a seamless handoff.
Centralized Information: Create a shared, easily accessible repository of key insights from sales conversations. Highlight the players, their goals, concerns, promises made to them, and next steps.
Clarity of Context: Ensure the delivery team fully understands the strategic context…what the client bought, why the client bought, what outcomes they're expecting, and the timeline for success.
Tip #2: Prep Your Delivery Team to Impress
Make sure your service team walks into the kickoff fully informed and ready to take action…not ask basic questions.
Internal Pre-Kickoff Briefing: Have a focused internal meeting beforehand to review essential details and context, ensuring the entire delivery team enters the kickoff with confidence and clarity.
Immediate Value Delivery: Structure the kickoff to focus on proactive recommendations, actionable next steps, and early momentum-building activities, not basic discovery rehash.
Tip #3: Set Clear, Immediate Expectations
Your kickoff meeting should explicitly map the path forward.
Detailed 30-60-90 Day Plan: Present a structured action plan, demonstrating immediate progress and future milestones. Make it tangible and actionable.
Roles & Responsibilities (RACI): Clearly outline who is doing what, when, and how accountability will be managed. Clarity breeds confidence and rapid execution.
Tip #4: Empower Immediate Client Action
Your client should leave the kickoff meeting with clear next steps.
Clear Client Commitments: Explicitly state what the client needs to do next, eg, provide data, access, introductions, etc. Make participation easy and clearly beneficial.
Immediate Wins: Identify quick-win opportunities or low-hanging fruit that provide early successes, reinforcing their decision to engage with you.
Pitfall to Avoid: Rehashing Discovery
Kickoff meetings should never revisit old ground.
Stay Forward-Focused: Redirect immediately if discussions veer into past discovery territory. Your job here is to accelerate action, not re-establish foundations.
Minimize Redundancy: Structure your kickoff agenda strictly around forward-looking actions and immediate strategic alignment, ensuring maximum productivity from minute one.
When the handoff is executed correctly, your client feels immediate confidence and sees rapid progress, setting the stage for long-term trust and partnership success.
Wrap-Up: From "Who the Heck Are You?" to "When Can We Start?!"
Congratulations. You've officially mastered the sales journey from awkward introductions to irresistible handoffs. But here's the kicker: none of this is rocket science (unless you're actually selling rocket science…in that case, kudos).
Here's the straight skinny - sales isn't about slick lines or used car salesman tactics. It's about clarity, connection, and consistently delivering value at every single stage. You’re not just closing deals. You are opening relationships, building trust, and driving genuine success.
Remember:
Prospecting isn't about chasing everyone—it's about being ruthlessly specific.
Engagement isn't just a fancy email—it's thoughtful conversations that matter.
Discovery calls aren't surveys—they're insightful dialogues that create clarity.
Proposals aren't documents—they’re stories your prospects want to believe in.
Closing isn't pressure—it’s confidently guiding decisions.
Hand-offs aren't paperwork—they're turbo boosts into immediate action.
If you follow these steps, your sales process stops being something you dread and starts becoming something you dominate. Less guesswork, less friction, and way more “LFG”.
Now go forth and sell brilliantly.
You've got this. Go crush.
Some Sales Resources For You
20 Sales Resources For Agency Owners: Hand-selected resources (books, software, etc) for agency sales folks.
Fire Yourself From Sales: Want to install a sales function in your agency? Check out FYFS.
Free Sales Call Review: Drop a sales call recording transcript and you’ll get free feedback.
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