Mistakes to Avoid in Lead Generation

Here's an avoidable mistake I made with inbound leads when I was an AE for The Challenger Sale. I'd get an inbound lead. They'd tell me they were looking at us + 2 of our competitors. I'd ask discovery Qs to understand why they were evaluating solutions and to understand the need. Then, I'd explain our differentiators and why those made us a better option for their needs. Here's where I fell down. I never slowed down to see if there were other priorities and categories of spend I was unknowingly competing against. As a result, I lost a lot of inbound deals to "We've decided to put a sales training investment on hold. Instead, we're going to invest in sales tech / do a re-org, etc.". After losing enough of them, I learned to add a step. Directly ask buyers 2 Qs: 1) "How did the leadership team arrive on X as the right solution to this problem?" - X = the category of spend. In my case, sales training. Listen for "I" vs "we" language. If I'm hearing "I" language - it might be a signal that they don't yet have buying group alignment on this problem or category of spend. 2) "What other investments/priorities were or are the the business considering?" - Language choice is important here. It's not "Were there other...". This is where we lean into assumptive language. Buying is not linear. Buying groups change their mind, back up, and hit restart. Assume this was not the only solution category they were/are considering. If I hear "none!" - that's a red flag. Most importantly, make it easy for them to be honest with us. Don't rush to convince them to prioritize our category of spend, before we deeply understand the others. "Objection handling" erodes buyer trust here.

Look, cold call pick-up rates and landing in spam are NOT the reasons why outbound isn't working for you in 2025. How do I know? We've worked with thousands of reps in the last few years: - I see all the sh*tty emails - Hardly any reps leave voicemails - People are afraid to call cell phones - Leaders are afraid to set call activity targets - Product pitching like crazy So why isn't outbound working for you? Messaging. I know. Messaging isn't a sexy topic. But poor messaging is likely why outbound doesn't work for you. Common messaging mistakes: ⛔️ Creating outbound messaging in a silo Mistake: A lone BDR leader, sales exec, or marketing exec creates all the cold call talk tracks and email sequences by themselves. Impact: Messaging sounds generic and has too much personal bias. ⛔️ Marketing or product creating outbound messaging Mistake: A PMM or marketing leader writes all the outbound messaging Impact: Since they've had little (or zero) conversations with real customers, the messaging is super generic ⛔️ Product voice: feature heavy messaging Mistake: Messaging focuses on how the solution works, specific features, etc. Impact: This might work on a webpage, but not in a cold email. Messaging feels super salesy and isn't appealing to execs. ⛔️ Not "chunking up" to business outcomes Mistake: Messaging addresses all of the pains of the user, not the decision-makers Impact: Reps get delegated down to product users and struggle to start sales conversations at the exec level ⛔️ Not leveraging customer conversations Mistake: Not using recorded customer conversations to inform messaging Impact: Messaging doesn't use the customer's language and feels generic. What to do instead: ✅ Build a messaging team Get no more than 10 of the best people together to build common messaging. This should include a few of the best AEs, marketing, customer success, sales leaders, product specialists, etc. And make sure to assign a single person to own messaging. ✅ Live workshop messaging by persona/vertical Run live workshops to work out messaging together. At a minimum, messaging should be created for each specific persona. For enterprise, messaging should be created by persona AND industry. A healthcare security leader speaks a different language than a SaaS security leader. ✅ Build a messaging matrix This is what the end product should look like: Personas → Priorities → Current Solutions → Problems/Impact → Desired Outcomes Now you have something that can easily be repurposed into talk tracks and emails. ~~~ If 2025 H1 pipeline looks thin—and outbound isn't producing results—get back to the basics and start with great messaging. Marketing should NOT own sales messaging. Sales needs to own sales messaging. And everyone needs to collaborate together for great messaging. Agree or disagree? 

It took me over 10 years to make $15,000,000+ with cold email. Here are 5 mistakes that cost me years: 1. Using Cheap Tools I started using cheap tools because I thought they were a good deal. That turned out to be a HUGE mistake: - Days/Weeks solving issues - Cash spent on other solutions - Figuring out everything myself All for mediocre results anyway. Lesson: If you can afford the best-in class, get it. 2. Ignoring Blacklists I spent a lot of time thinking blacklists didn’t matter. The sad part is, deliverability is easy to get right. Here’s a quick breakdown of how to evade spam: Domains: - Configure DKIM, DMARC, SPF - Buy Using GoDaddy (rDNS) - Ensure 30+ Day Age Mailboxes: - Custom Names & Images - Send Under 50 Cold/day - Warm for 30+ Days Content: - Little/No Custom Code - Remove Spam Words - Sub 6th Grade Level 3. Not Cleaning Lists I was naive enough to think that list data didn’t have to be cleaned because of its source. In reality: ALL leads you get must be cleaned before you send. If you’re bounce rate goes a bit too high, your deliverability sinks. Sending with bad data is worse than not sending at all. 4. Not Giving Value This is actually 2 mistakes in 1: - Not using a value first approach - Not making the “value” good The market is tired of being fed unrealistic offers, and 50 page PDFs. Giving away value (that the market actually wants) is the way to stand out. 5. Low Split Testing This is obvious - but many cold emailers still don’t do it. The reason: It doesn’t immediately give you a big increase in results, just minor. But on a long enough time frame? Split testing is the difference between failure & success. These were the 5 mistakes that cost me years: - Using Cheap Tools - Ignoring Blacklists - Not Cleaning Lists - Not Giving Value - Not Split Testing What has been your biggest lesson from cold email? Drop a comment below!

Struggling with cold intros that don't convert?  My client was too, and it made her lose heart. She could get referrals, but thought she couldn't close because she disliked selling herself. Most advice focuses on perfecting the offer. Wrong place to start. You don't need the best offer to close. I've sold $50M deals at Fortune 100s,  and netted $100K in 100 days solo. These are the 11 common mistakes I learned kill referrals, and the fixes that get closes: ❌Talking data only and overloading the audience ✅Be curious. Ask questions. Let them tell you what they need. 💬”What prompted you to want to meet today?” The goal is 40-60% buyer talk-time. ❌Pitching features instead of belief ✅Check their belief in you as the solution they need. 💬”What do you think delivers the biggest unlock for you?” Winning discussions have 28% more buyer questions. ❌Positioning as a general problem solver ✅Be the 32MM drill bit for the 32MM hole they need. 💬”Here is how and where I have solved this before.” Specialists are 2.9X more likely to command $10 K-plus project fees. ❌Skipping urgency ✅Show a loss-or-gain case. 💬”Would you burn another $160K trying to figure this out on your own.” An urgency cue lifts revenue 27% in studies. ❌Not establishing a decision expectation ✅Be clear about your direction. It is fair to set the agenda. 💬”I will ask for a decision by the end of this call.” Calls with a clear expectation have a 70% higher close rate. ❌Believing what you do is easy ✅Own your expertise was hard won and unique. 💬”I delivered X by doing Y for this client.” Generic social proof drops win rates 22%. ❌Expecting your experience is sufficient ✅Show leverage, talk method. Method > Experience. 💬”I used my 5 step framework to get the same outcomes at 20 clients.” 78% of clients pay a premium when they perceive exceptional, niche expertise. ❌Not demonstrating your impact ✅Quantify and connect outcomes to their needs. 💬”The result of this was a 20% increase in X.” Value-based pricing raises revenue up to 25% over hourly billing. ❌Focusing on your objectives, not theirs ✅First, demonstrate value, then explore mutual fit. 💬”Given your problem, here is how you accelerate. This is my method.” Buyers talk 28% more in calls that close. ❌Coming across as desperate ✅You choose whether you make an offer. 💬”I'm really excited for this opportunity," not "I really need to close to pay my kid’s tuition.” Discounting too early correlates with a 27% drop in win rates. ❌Treating an ask as dirty ✅Believe in yourself and your offer. 💬”If I feel we are a fit, I will tell how I work and ask for a decision at the end of this call.” Fastest sales cycles spend 53% more time clarifying next steps in the first two calls. My client made these easy fixes. Her close rate increased by 50%. Her confidence in herself? Up 100%. Try these easy fixes in your next call. Watch your close rate soar. Which do you believe will make the biggest difference?

It took me 6 years as a commission-only sales rep to make my first $1M in commissions in a single year. If I could go back in time and help my younger self get there faster… I’d tell him to NEVER do these 7 mistakes: 1. Stop being a product pusher You’re not selling the thing You’re selling the results of what your thing does Don’t focus on your product’s features and benefits Focus on the person’s/company's problems and where they want to be. That’s what prospects care about. 2. Sounding needy Sounding desperate will just drive prospects away You don’t want to say things like: “Just tell me what it’s gonna take for you to buy today” (Lowers your status) “If you buy today, we can offer a 20% discount” Etc… 3. Being assumptive too early You don’t want to say things like this too early in a conversation: “When we onboard you, we’ll do XYZ” It will trigger sales resistance with many prospects and cause them to emotionally shut down and throw objections at you. 4. Lowering your status Most salespeople lower their status to “please” the prospect. They build “fake rapport”, say “yes” to everything, and let the prospect have all the “power” You want to do the opposite to come across as the trusted authority, the expert who can solve their problems and get them the results they want. 5. Sounding overly-excited Ever heard “If you’re not excited about what you’re selling, your prospect won’t buy”? That’s a big myth. In fact, there's no data that supports this assertion at all. If you come across as overly-excited and biased, you’ll just trigger sales resistance with many prospects. You want to come across as more neutral, unbiased, collective and detached. 6. Sounding scripted Great salespeople are like great actors/actresses. They know their lines, but they sound natural. You should 100% have a framework/script so you don’t wing it. But you want to understand it so well that everything you say sounds natural. 7. Asking surface-level questions Surface level questions aren’t enough to get your prospect to emotionally open up to you. Don’t ask: “What are your top 3 challenges right now?” Ask: “Off the record, what’s really going on over here that’s caused you to look at possibly changing companies/vendors?” (curious tone)

In the last 60 days, we spent $290,000 on ads. The result? Only $100,000 in bookings. Ouch! Here are the 4 biggest mistakes I made (and how we’re fixing them): 1. Expecting ad spend in historically high-performing channels was scalable We were maximizing our budgets on our highest-performing campaigns in an effort to maximize leads before the holiday lull, and we ended up blowing past the limit of what our campaigns could produce efficiently. The Fix: We are going to scale spend a little each day (instead of all at once) so we can find our point of diminishing marginal returns on our campaigns without waste. This way, we will be more informed about how much spend a specific campaign can take and still be efficient for us. 2. Spending time and money where there wasn’t value While volume was improving and initial traction was made, we found that we had just spent lots of money in places that weren’t entirely driving up-market leads for our sales team. The Fix: we are regularly checking the quality leads that each campaign is getting over a certain time frame. If it is driving quality efficiently, we will give it more love. If not, we need to refactor and it has to earn the budget back in the future. 3. Not aligning on a clear testing framework. We went all-in on a few new campaigns as an experiment and didn’t give ourselves a testing framework. Tens of thousands of dollars were wasted because we didn’t treat this as a proper experiment. The Fix: Now any new channel or campaign will have a testing framework, complete with a hypothesis, execution plan, time frame, and definition of success. 4. Making ad copy with a short shelf life. We used to have ad copy with messaging around “hit your Q3 goals,” or seasonal trends which then would inherently need to be updated every 3 months (sometimes sooner), or else there’s no way it would convert. The Fix: We have shifted to making our copy have a longer shelf life. That way, we can focus on ad delivery metrics to determine ad fatigue, rather than writing ads with a predetermined expiration date. TAKEAWAY: We weren’t being proactive in our paid media planning and spending. We let the urgency of the moment make us reactive, which is a bad place to be as a marketer. Don’t let urgent work get in the way of more important things, particularly with forecasting, analyzing, and testing. P.S. Shout out to 🏔️ Sam Calhoun and Evan Fehler who fixed these issues for us.

Assumptions can lead to costly mistakes. My first SaaS company didn't go anywhere. I thought I was so smart, but going after the wrong people + building for wrong people cost me everything. Lots of hours put in, very little output. Most marketers think they know who their ideal customer is, and they think they know them. But until you validate your assumptions, you’re operating on guesswork—and guesswork is expensive. When I launched the first version of Wynter, I targeted copywriters... after all, who cares more about copy than them? Turns out most of them did not want any messaging validation work ("I don't like people judging my work" lol) + they didn't have any money. There was no pain they felt on their end regarding messaging validation. The pain was all in-house, felt by people hiring the copywriters: will this work? What does my ICP really care about? How can we make this copy stronger? My ICP research work had been lackluster, and I paid the stupid tax (six months of wasted efforts). A strong ICP (ideal customer profile) is built on real insights—validated, actionable, and directly tied to your audience’s needs. Avoid my mistakes and continuously refine your ICP: 1. Interview your customers: Talk to recent buyers or lost deals. Learn why they chose—or didn’t choose—your solution. Focus on the specific triggers that drove their decision and the language they use to describe their needs. 2. Survey your target market: Use target market surveys to dig into pain points, priorities, and decision-making processes. If you're in B2B, Wynter will deliver responses in 48 hrs. 3. Analyze sales conversations: Dive into sales call transcripts using tools like Gong or Chorus. Spot patterns in objections, common themes, and recurring questions your prospects raise. 4. Test your messaging: Use tools like Wynter to test key website pages with a vetted audience that matches your ICP. 5. Study competitor positioning: Analyze competitors’ messaging to uncover what they emphasize and where you can stand out. For example, if their messaging focuses on efficiency, can you carve a niche around customer experience and support? 6. Audit internal data: Review internal resources—support tickets, chat logs, and retention data. Who uses you the most, who gets the most value out of you? 7. Create iterative feedback loops: Insights aren’t static. Use tools like Wynter and Gong regularly get a pulse on your ICPs changing needs and perceptions. Building a strong ICP isn’t about guessing; it’s about listening—through tools, conversations, and data. The payoff? Better targeting, clearer messaging, and avoid paying the stupid tax.

I used to scare clients away (without knowing it). Don't make the same mistakes I did. Trust me, it's not as fun as it sounds. I used to wonder why no one replied to my emails or hired me. Turns out, I was doing everything wrong. Here’s a list of my biggest missteps (and how to avoid them). 1. Never Follow Up One email is enough, right? If they don’t reply, they’re not interested. 2. Target Everyone Don’t bother with “ideal clients.” Pitch to anyone with a pulse. 3. Neglect Your CRM Why organize when chaos is fun? Trust your memory to recall every lead. 4. Avoid Cold Outreach Reaching out is overrated. Wait for clients to magically find you. 5. Take “No” Personally Feedback? No thanks. Let rejection crush your soul. 6. Rely Only on Referrals Who needs a strategy when you’ve got luck? Hope for word-of-mouth to work forever. 7. Chase Likes, Not Leads Focus on going viral. Revenue? That’s a future-you problem. 8. Don’t Create Content Why share value when silence is golden? Let your expertise remain a mystery. 9. Do All the Talking Skip the listening part. Clients love being ignored. 10. Promise More, Deliver Less Overpromise, underdeliver. It’s the perfect recipe for disappointment. 11. Wait for Perfect Conditions Action can wait. Perfection is key (even if it never comes). 12. Ignore Feedback Clients don’t know what they want. Why bother listening to them? 13. Repeat Mistakes Learning is optional. Keep doing what doesn’t work. 14. Focus on Features, Not Benefits List every technical detail. Value? They’ll figure it out. 15. Don’t Ask for Case Studies Why show proof of success? Keep your wins a secret. 16. Ignore Data Decisions don’t need logic. Follow your gut—every time. 17. Copy the Crowd Blend in and expect to stand out. Genius strategy, right? 18. Quit When It Works Find success, then stop. Why bother scaling? If this list feels familiar... Maybe it's time to flip the script. ✨ Pro Tip: Want to actually land clients? Do the OPPOSITE of this list. Seriously. It works. ______________________________ Like the post? Repost ♻️ to help others Follow Arpit Singh tap the 🔔

As I’ve journeyed through the world of lead generation, I’ve stumbled often! Over some common pitfalls that many entrepreneurs face. And trust me, they’re all too easy to fall into. 1. Overlooking your target audience: When I first started, I created content that I thought was engaging. But without a clear understanding of who my audience was, I was essentially shouting into the void. Researching and defining your audience isn’t just important; it’s essential. 2. Ignoring follow-ups: How many times have you sent an email or a message and thought, “That’s done”? I used to do this until I realized that following up is where the magic happens. Often, potential leads need a nudge or two to engage. 3. Focusing solely on quantity: I once aimed for a large email list, thinking the bigger, the better. But I learned that quality trumps quantity. Engaging, interested leads are far more valuable than a long list of disinterested contacts. 4. Not testing and iterating: It’s easy to get stuck in a routine, but if you’re not testing your strategies and learning from the results, you’re missing out. I regularly revisit and refine my approach based on performance data. Remember, Lead generation isn’t a one-size-fits-all process. It requires continuous learning and adaptation. P.S. What lead generation challenges have you encountered? Let’s share👇 #LeadGeneration #Entrepreneurship

How to get lead generation WRONG (and crush your B2B biz in the process): For context, I speak with tech agency owners and SaaS founders every week. Most of them complain about poor results both from their teams and agencies, Yet, lead gen often takes second place in annual budgets or management support. Here's a harsh truth. To fix lead generation in B2B, avoid these mistakes: 1- Outsourcing to agencies: – Why? They often prioritize quantity over quality, burning through your prospects with aggressive outreach. – They aim for short-term gains, not long-term relationship building. 2- Focusing on vanity metrics: – Why? Tracking "meetings booked" instead of SQLs wastes time and harm your reputation. – Agencies won't understand your offer or target market(s) as well as you do. 3- Neglecting relevance + personalization: – Why? Generic, automated messages scream "spam" —and turn off potential clients. – Light lead gen will often push hard on AI and mass outreach as a crutch for poor messaging. __ Instead, double down on these 3 essentials: 1) Make lead generation YOUR priority. → As a business owner, this function is too crucial to outsource. Own the process. 2) Refine your offer through feedback. → Use conversations to shape an offering your buyers actually want. Don't assume, ASK! 3) Learn copywriting & persuasion. → Craft relevant and compelling messages that hit hard with your ideal clients. This skill is worth big $$$. ___ In business, "everything is downstream from lead generation." (Daniel Priestley) If you can fix the lead generation problem, every other problem in your business will go away. PS) What’s your biggest lead-gen challenge?