How to Avoid Common Sales Mistakes for Growth

Listen up. I’ve coached thousands of sales calls and most reps sabotage their own deals without realizing it. When I started in 2007, I nearly got fired for not understanding how language impacts buyer psychology. Now, after helping teams double revenue in 90 days, I can spot the hidden mistakes instantly. You're probably killing your win rate with these “harmless” phrases. Here are 6 phrases that are absolutely DESTROYING your deals (and what to say instead): 1) "Sorry to bother you..." Starting with an apology tells the prospect, “I’m not worth your time.” You’ve lost before you’ve begun. Top 1% performers NEVER apologize for delivering value. They command attention through absolute certainty. ✅ POWER MOVE: "Hey Alice, Marcus here from Venli. I'm reaching out because we helped Company X increase their pipeline by 37% last quarter, and I noticed your team might be facing similar challenges..." 2) "Just following up..." This lazy phrase screams, “I’ve got nothing to offer, but want your money.” Total momentum killer. Elite reps are wildly precise with their words and always reference specific commitments made in previous conversations. ✅ POWER MOVE: "Alice, you mentioned you were going to discuss our proposal with Charles during your leadership meeting yesterday. I'm curious … what feedback did you receive that we should address?" 3) "I know you're really busy..." Say this, and you’ve just made yourself irrelevant. Game over. Remember: YOUR time matters. Top performers signal status through subtle positioning every time. ✅ POWER MOVE: "I was just wrapping up a strategy session with Lisa, the CEO over at Company X, and wanted to quickly connect about next steps before my afternoon gets packed..." 4) "What are the next steps?" This signals poor process control - no system, no playbook, no real method. The sales machines I build don’t ask for direction - they GIVE it. They own the process. ✅ POWER MOVE: "Based on what we've discussed, here's what typically happens next: First, we'll schedule a technical review with your team for next Tuesday. Then, we'll deliver a customized implementation plan by Friday. How does that sound?" 5) "To be honest..." Wait, Wait... so everything before this wasn’t true? Nothing kills credibility faster. When I turn around failing sales teams, eliminating this phrase is always one of the first habits we break. ✅ POWER MOVE: "That's an excellent question, Alice. Here's exactly how our solution addresses that challenge..." 6) "What do I have to do to get your business?" Is this 1988? This pushy close screams desperation and kills trust instantly. The best reps I've coached understand that closing isn't an event. It's the natural outcome of a well-executed sales process. ✅ POWER MOVE: "It seems like you're hesitating about X. I'm curious … what specific concerns do you have that we haven't fully addressed yet?" Which of these six phrases have YOU been using without realizing it? 

I led sales at Heap from $400K to $10M ARR in ~3 years. 9 out of 10 startups that hit $1M never make it to $10M. Here are my 5 biggest mistakes and how I’m increasing the odds of doing it again at Champify—faster: 1. I was always focused on the next chunky deal Instead, focus on building a pipeline MACHINE. Sam Blond phrases it perfectly, “Usually a company misdiagnoses a sales problem for a demand gen issue.” Religiously track how many new meetings and opps you are creating and constantly find ways to grow this number. This will have a bigger impact than a small increase in win rate. 2. I spent a lot of time searching for unicorn reps with the exact “right” profile Instead, invest time building the systems and frameworks to make any above average rep successful. That way, your success rate will be higher and when you do hire the truly great reps, they can be an order of magnitude more productive than their peers. 3. I over-indexed on the importance of product knowledge I come from a sales engineer background. The reality is that while product knowledge does matter, understanding of the PROBLEMS your persona and target account face is 10x more important than knowing the product inside and out. During training and enablement, think about ways to enable reps on the problems vs the nuance of your product offering. 4. I spent far too much time with reps in a 1-1 capacity and ended up wasting 100s of hours teaching and training on the same topics (without others benefitting) Implement mandatory enablement every 2-3 weeks. Before you have an enablement team, IT IS THE JOB of the sales leaders to own this. Lean on experienced reps and other roles within your org to deliver these training sessions. It’s critical to constantly level up your sales team AND do so in group settings to create space to share learnings, challenge each other, naturally compete, and scale. 5. I did my best to hire smart SDRs and get out of their way Outbound is significantly harder today. Remove as much of the decisions that an SDR needs to make. Determine the accounts and personas they should target, enable them on the problems each person in your buying committee faces, and search for areas you can improve by using data and constantly getting feedback. The outbound world is too hard today for junior reps to figure it out on their own. Takeaway: Scaling from $1M to $10M ARR isn’t about chasing the next deal or finding unicorn hires—it’s about building scalable systems, understanding your buyer’s problems, and constantly enabling your team to succeed at every level. Don’t make these dumb mistakes I did :)

I’ve been CEO of 4 different VC-backed startups, with valuations ranging from $0 to $150M+. Here are the 3 biggest sales mistakes I see at every company (no matter the size or stage): 1. Confusing “best” and “average” Signing a $300k deal with Coca-Cola was a game-changer. They got huge value, and were willing to tell people about it. So we told ourselves, “We just need to find more Coca-colas." Fat chance. This way is thinking is natural for us salespeople. You signed a $300k deal – the next one should be $350k! It’s tempting to think your your best deal is now your new standard. But it doesn't work that way. Don’t create a plan where suddenly every deal is supposed to be $300k. You’ll strike out and burn a ton of time and talent trying. 2. Premature scaling The math seems to make sense: Number of reps x Quota = Target. Hire the reps, make sure rep hits quota, and you’re golden. The problem is: it rarely works that way. New reps struggle to get up to speed. Response rates are lower → less pipeline Conversion rates are lower → fewer deals closed Average selling price is lower → quotas are missed Your reps doing 140% of plan can’t make up for 5 at 30%. It’s past time to throw out that old math. You can’t add reps to hit an aspirational goal. This market demands you match reps to actual demand. You don’t hire when your plan says you need more production. You hire when you have more in-ICP meetings than you can handle. But how do we hit the number we promised we’d hit??? Bad news – you aren’t going to hit it anyway. Signing up for a crazy goal on bad math just puts your head on the chopping block. Instead, reset expectations. Burn less, longer, to build demand. Grow when demand requires it. 3. Insufficient focus on after-the-sale In the olden days, you could sign $1M deals. Customers knew they couldn’t get value until they fully deployed your solution. Not anymore. SaaS has made trial simple. Time to value is faster. Deals start smaller. It’s easier to sell in. But it’s also easier to churn out. Churn is up in this market. Customers are looking to cut costs. Worse, they're looking to simplify tech stacks and cut vendors. Gone are the days when you can sell a deal and run away. But too many still do exactly that. It’s human nature. After all, Comp Plans get a lot less exciting after Closed-Won! The best sales leaders know that next year’s plan relies on keeping and growing this year’s customers. They deploy their time and people accordingly. TAKEAWAY: Each of these mistakes starts with natural thinking. But it doesn’t work. Hard markets demand focus and discipline. Focus your ICP. Celebrate your big wins, but don’t expect to repeat them every time. Don’t grow faster than actual, real, in-ICP demand. Stay connected to customers throughout the year. Renewal matters. Optimism is great. But hopeful planning is a business (and career) killer. Get it right and you can still win in this market.