5 Sales Outreach Mistakes to Avoid in 2023

Nov 9, 2023

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min read

Learn more about sales outreach, which channels to consider using for outreach and dive into the 5 biggest mistakes we see salespeople make, with our best practices to fixing those errors and building an high-performing sales outreach process.

‍If you’ve spent more than one week conducting sales outreach then you know the reality of sales: those long days wondering why your cold email open rate is only 5%, or dreading picking up the phone to yet another rude rejection. You wonder how successful salespeople do it and wish you were Alec Baldwin in Glengarry Glen Ross.‍‍

The good news is that you don’t actually need to be superhuman or be born with an innate ability to sell - in fact, you’re likely just not following best practices that have been brought up to 2023’s standards. Do you sit and listen to every telemarketer’s 90s-style pitch? No? Well, why would your prospect listen to yours?

In this article, we’ll cover exactly what sales outreach is, which channels to consider using for outreach and dive into the 5 biggest mistakes we see salespeople make, with our best practices to fixing those errors and building an high-performing sales outreach process.

What is Sales Outreach?

First, let's establish exactly what “Sales Outreach” is. In a nutshell, sales outreach encompasses any method in which you go directly to a prospective customer with a view to building a relationship that results in a sale.

Outreach methods might include sales calling, cold emailing, going door-to-door or more niche methods like attending a trade show or using direct (physical) mail.

Sales outreach is distinct from marketing, where the focus is less on generating 1-2-1 conversations, and more on broadcasting a message to as many prospects as possible with the view of having them eventually come to you as an inbound conversation.

If marketing is akin to planting seeds and waiting for the crops to grow, sales outreach is hunting for tonight’s dinner.

Which Outreach Method Is Best For Sales?

The most important decision when kicking off sales outreach is which method or channel to use for your outreach. Common advice is to use whichever method will work best for your specific target customers.

For example, if you’re trying to reach busy, multinational CEOs then it's unlikely that they’re going to be sitting around at a phone waiting for your call. However, a retailer with a single location or an accountant working from their desk all day might be next to their phone all day.

We would take this one step further and say choose whichever outreach method works best for your personality. If you’re the type of person to stumble over their words on a sales call or you need 30 minutes trying to pluck up the courage to dial in a number, then you’re likely to be a better, more confident and more successful sales person by using cold email to generate warm calls.

Every channel has advantages and disadvantages. It’s harder to reach receptive prospects by phone, but by default you’re having a conversation with them. It’s easier to get in front of prospects with cold email, but much harder to turn that into a conversation. Door-to-door sales and direct mail are more effective, but much more difficult to scale than emails or calls.

Whichever sales outreach channel you choose, here are the 5 key mistakes we see sales leaders and sales newcomers alike making in 2023.

1. You’re “following up” like someone’s crazy ex

If you haven’t made this mistake personally, then you’ve certainly seen others do it: they break up with their ex, then proceed to send them far too many text messages, complete with an unhelpful dose of desperation and topped-off with groveling or drama.

And it never works.

The oft-quoted advice is that you should follow up at least 5-7 times. This can be true, but a “Did you see this?” isn’t likely to pique the interest of a prospect who ignored your first email.

Instead, try adding value to your next email:

Include a fresh case study or testimonial on your offering
Add a new insight or a new take on your original email
Add a demo or a link to further info on your website
Include a personalized video
Ask a different question e.g. “Is X a problem you’re facing right now?”

Common mistakes to avoid include:

Being dramatic e.g. “Since you haven’t replied, I guess you don’t want your business to make more money this year!”
Giving off a hint of desperation e.g. “If I could just have 5 minutes of your time, you’ll see that our offer is fantastic!”
Creating obviously-false scarcity e.g. “Our offer will definitely be sold out by this time next week, reply soon to take advantage!”

There are nuances to all of these common mistakes - a skilled salesperson with confidence and a great script might be able to pull these off. But unlike with your ex, there’s still a chance to close your prospect - so don’t fumble the opportunity by using sales followup tropes which stopped working 5 years ago!

2. You’re pitching first and asking questions later

Picture the scene: the prospect has picked up the phone, they haven’t immediately slammed it down when you introduce yourself and - shock, horror! - they’re open to a conversation. It’s time to start pitching your product, making sure they know about your most competitive features and giving a clever answer to every objection they have. They love it - deal closed!

Yeah, then you woke up.

The reality of sales is that one of the worst things you can start doing is pitching your product up front. If you’re spending most of your time on sales calls answering a prospect’s questions then the chances are you’re not finding out enough about their business or their problems.

The best thing you can do is get the prospect answering questions for you. The more questions they answer, the more you can understand their business, understand whether they’re a good fit for your offering and ultimately tailor the pitch you eventually deliver to them..

Here are some questions you’ll want to know the answer to in every sales conversation:

What problem(s) are they trying to solve in their business right now?
Why is it a problem? What’s the impact on their bottom line?
What have they already tried to solve the problem?
When do they need to solve this problem? Is it urgent? Why?
Is there anyone else at your company who cares about this problem?

Don’t be afraid to ask questions you think you know the answer to, or which seem obvious.

Even if you do know the answer (you probably don’t), having your prospect mention them out loud is a great way to get them riled up, feeling emotional about the problem and feeling that you care about solving it for them.

You’ll be surprised at how often a prospect actually thanks you for asking good questions - they want you to deeply understand their problem!

Note: This applies for cold emails too - If you’re pitching your key features in the first email, you’ve already lost!

3. Your outreach isn’t specific enough

One of the most common reasons outreach fails is that you haven’t narrowed down your audience enough.

If your target audience is “marketing teams in the US”, then you’re trying to craft a pitch that will resonate with millions of people all at once. Unless you’re a speechwriter for the President in your spare time, you’re probably not going to succeed at that.

Instead, consider how you can narrow down your lead list to a more specific audience. For example, what about Content Managers working in Marketing Agencies in the US with an annual turnover of >$10m? That’s a much narrower list.

Or maybe you’re trying to target fashion retailers in the US to sell your expensive, $50,000 per year merchandising software solution. What if you could narrow that down to Merchandising Team Leaders in the US with >10 stores? Not only are you reaching the most likely buyers, but you’re also making it more likely that the people you’re pitching to will be at least familiar with the problem you solve, and with over 10 stores they’ll be big enough to afford it too.

Here are some questions to consider when narrowing down your prospect list:

Is your product expensive? Try narrowing down your prospects to people you know will be able to afford it (For example, a large company or a company which recently raised money)
Is your solution designed to be used by a specific job title? Tailor your pitch to different levels of seniority, and the individual view they’re likely to have on the problem (Junior, Senior, Manager, Head of, VP etc)
Does your offering work best for teams rather than individuals? Make sure to target companies with a minimum company size who are likely to have the target team in place
Is there a specific resource that makes your offering more useful? Maybe your prospects already use a certain type of software, work with a certain type of company or use a specific supplier?

And remember, you’re not discarding these prospects! You can always expand your outreach list in the future as you get better at closing customers.

4. You’re trying to sell too early

How many times have you sent a cold email where you’ve pitched your product in the second or third line and ended the email with a “strong” call to action like “Does this sound interesting to you?”

And of course when the prospect doesn’t reply, you either write them off as “not interested” or add them to an endless loop of follow ups for them to also not reply to. Worse yet, the prospect takes the time to reply “no” and you’re left wondering what the problem was - Bad pitch? Bad lead? Bad timing?

These are all examples of shooting your shot too soon!

You’ve effectively pushed the prospect into making a decision there and then about your product and missed your chance to collect more information about the prospect, build a relationship and parlay those things into a future winning pitch.

Instead, try asking for a simple next step or offering a piece of value upfront:

If you’re sending a cold email, don’t ask if they’re interested in a demo.

Instead, suggest a call to run some ideas you have for their business and where you could help them. Use the time before the call to come up with 2-3 ideas of where your offering could be helpful.
If you’re on a cold call, avoid discussing a solution entirely and instead focus on finding out if the prospect has a problem.

Don’t try to pitch there and then; instead set a time to sit down and speak to the prospect at a later date, giving you time to do your research and putting them in the headspace to answer your questions
If you’re sending direct mail to a prospect’s address, it will almost certainly be read - so feel free to discuss the problem and lightly address the solution.

But don’t pitch directly, instead let the recipient know you’ll be following up with a call to discuss at a specific date and time.

One caveat here - Don’t mistake a soft no for an action. A prospect who tells you “I’ll get back to you with a meeting time” is probably a no, another who says “This might be interesting to us in the future” is still a no.

Look for concrete next steps, or push for a hard “no”. If you feel a prospect is shifty, don’t be afraid to address this head on! They’ll appreciate it, and you’ll get to focus your efforts on prospects who do want to buy

5. You’re not using the right tools

It’s 2023 - If you’re only using a CRM, a desktop phone and a notepad, then the 90s would like a word with you.

Your sales pitch and lead list will make the ultimate difference in any sales process, but if you’re not using modern sales tools alongside your modern sales techniques, then you’re leaving money on the table - or worse, losing prospects to your tooled-up competitors who are equipped to move faster than you.

For example, if you’re making sales calls by dialing in your prospects’ telephone numbers one-by-one, hanging on the phone for at least 30 seconds and then spending 60 seconds trying to deliver a convincing voicemail, you’ve already lost several minutes of your life you’re never getting back.

That may sound dramatic, but 10 minutes wasted when calling prospects every hour adds up to hours of lost productivity every single day. Instead, you should be using a parallel dialing system to keep up with the competition and get your prospects on the phone before they do.

A what dialing system?

Essentially, a parallel dialing system will phone multiple prospects at the same time for you, automatically hang up any voicemails (or leave a pre-recorded message you made earlier) and connect you to the first person who picks up the phone.

The best parallel dialers even connect directly to your CRM to pull in your prospects, meaning you can hit the “Ready” button and wait for calls to connect and come straight through to you like a call center, rather than having to manually type in numbers and sort through your CRM.

Pouring more leads into your funnel is great, but using a dialer with the leads you already have is the easiest way to 5x the number of conversations you’re having on a given day.

AI-powered dialers like Nooks take this a step further by recording your calls and making analytics available on them.

Instead of staring in the mirror asking “Is it the leads or is it me” like luddite salespeople of yore, you’ll be fully equipped with all the data you need to find (and plug) the holes in your sales process.

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