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Sara Osterholzer

5 Big Mistakes Undermining Your Outbound Sales - and How to Fix Them

Outbound sales often feels like trying to hit a bullseye while blindfolded. You’re making the calls, sending the emails, and following up on LinkedIn, but the results aren’t there. What gives? The truth is, even the most hardworking salespeople can fall victim to common mistakes that sabotage their efforts.


Here’s the good news: these mistakes aren’t just avoidable - they’re fixable. Whether you’re new to outbound sales or a seasoned pro looking to refine your approach, this guide will help you identify what’s going wrong and how to put it right. Let’s dive into the five biggest outbound sales blunders and the simple, actionable fixes you can start using today.


1. Shotgun Targeting: Selling to Everyone (and Reaching No One)


If your outbound sales strategy involves reaching out to “anyone who might be interested,” it’s time for a rethink. Casting your net too wide often means your message doesn’t resonate with anyone. It’s like trying to advertise a luxury spa day at a football match - wrong audience, wrong moment, wrong results.


💡 Actionable Fix: Start with your Ideal Customer Profile (ICP). This is your North Star for outbound sales, so take the time to define it properly. Consider factors like industry, company size, location, and decision-maker roles. The more specific you get, the better. Think of it as building a prospect list that’s tailored to your solution - not just throwing darts at a board and hoping something sticks.


Pro tip: Test your ICP regularly. Industries evolve, decision-maker priorities shift, and your targeting should adapt accordingly.


2. Over-Reliance on Automation


Automation is a lifesaver for handling repetitive tasks at scale, but relying on it too heavily can backfire. There’s nothing more off-putting than receiving an email that screams, “I have no idea who you are, but here’s my generic pitch.” Automation without personalisation creates a transactional experience, and nobody wants to feel like just another number in your sequence.


💡 Actionable Fix: Use automation to streamline the admin side of things - like scheduling follow-ups or managing your pipeline - but personalise every prospect interaction. Before sending an email or making a call, take a moment to research. What’s their company been up to? Have they shared any recent posts or announcements? By weaving in these details, you’re showing that you’ve done your homework and genuinely want to help solve their problems.


When you balance efficiency with authenticity, your outreach stops feeling robotic and starts feeling meaningful.


3. One-Size-Fits-All Messaging


If your emails or calls sound like they could be sent to anyone, chances are they’ll resonate with no one. Generic messaging is the quickest way to be ignored - or worse, marked as spam. Think about it: would you respond to an email that starts with “Dear Valued Customer” or “We’d like to talk to you about an exciting opportunity”? Probably not.


💡 Actionable Fix: Personalisation is the antidote to generic outreach. Tailor your messaging to the individual prospect by referencing their company’s recent news, industry trends, or challenges they’re likely facing. For example, if their company just launched a new product, congratulate them and tie it to how your solution can support their growth.


Yes, it takes more time and effort, but personalised outreach consistently delivers better response rates and builds stronger connections. In the long run, it’s worth it.



4. Inconsistent Follow-Up: Giving Up Too Soon


Here’s a sobering statistic: it takes an average of 8–12 touchpoints to engage a prospect. Yet, most sales reps give up after two or three attempts. That’s like planting seeds and walking away before they’ve had a chance to sprout. Follow-up is where deals are won or lost, and inconsistency is one of the biggest reasons why so many leads slip through the cracks.


💡 Actionable Fix: Create a structured follow-up plan, also known as an outreach cadence. This should include a mix of channels (e.g., email, phone, LinkedIn) and be spread over 2–3 weeks. Each touchpoint should add value - whether it’s sharing a relevant case study, a helpful resource, or an industry insight they can actually use.


Remember, follow-up isn’t about pestering your prospect. It’s about keeping the conversation going in a way that’s helpful and relevant. When done right, it shows persistence and professionalism.


5. No Clear Process: Winging It


If your sales process isn’t documented, you’re relying on guesswork - and guesswork rarely scales. Without a clear strategy, it’s easy to waste time on unqualified leads, send mixed messages, or lose track of follow-ups.


💡 Actionable Fix: Map out your outbound sales workflow step by step. Start with your ICP, define how you’ll craft and personalise your messaging, and establish a follow-up cadence. Once your process is in place, track key metrics like response rates, meeting conversions, and closed deals.


Why? Because data-driven adjustments are the secret to continuous improvement. If something’s not working, the numbers will tell you - and you can refine your approach accordingly.


Key Takeaways: Stop Guessing, Start Selling


Outbound sales doesn’t have to feel like you’re shouting into the void. By addressing these five common mistakes, you can transform your approach into one that’s focused, consistent, and effective.


Here’s a quick summary of what to do next:


  • Refine Your ICP: Spend time identifying and targeting the prospects who are most likely to benefit from your solution.

  • Keep It Personal: Make your outreach feel human by referencing specific details about your prospect.

  • Be Persistent: Follow up consistently across multiple channels without being pushy.

  • Document Everything: Create a clear process and track your performance to ensure you’re always improving.


Outbound sales isn’t rocket science - it’s about connecting with the right people, at the right time, in the right way. When you focus on quality over quantity and build a strategy that’s both scalable and authentic, you’re setting yourself up for long-term success.

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