6 Ways to Make a Bad First Impression During Business Outreach

7 min read

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As an introvert, I’ve spent the majority of my entrepreneurial life mastering the techniques of inbound marketing.


But avoiding outreach forever isn’t sustainable  especially in the early days where SEO is practically non-existent and your social-media followers primarily represent your “friends and family” circle.

Research led by ValueSelling Associates, Inc reports that 48% of sales professionals are afraid of cold calling. The art of making a great first impression in the first 20 to 30 seconds and taking the lead further down the funnel requires practice and resilience, which led to the further development of automated tools, text bots and outreach systems plugging into exported lists of LinkedIn contacts.

Related: Top 3 Strategies to Sell Without ‘Selling’

But every entrepreneur feels for the efforts of a sales representative  or any outreach person (be it in marketing or recruitment). What really draws the line, however, is an inappropriate message that throws the conversation off  and can negatively impact the brand’s perception in the long run.

While receiving 8:40 a.m. cold calls every other Monday isn’t among the best ways to start the week, here is how to get flagged right away (and why you should avoid these common traps).

1. Sell competitive services

I founded my development agency 11 years ago, and I’ve probably received over 10,000 pitches for development services since. Even if I can relate with outsourcing firms leasing talent, any cold outreach attempting to sell a solution we offer straight on our homepage is outright automated and shows zero personalization in researching the prospect.

While working with a product founder in the SEO space, I saw a LinkedIn pitch from a direct competitor offering a white-label license to the other product. Considering that virtually every review website lists down both solutions among the list of top alternatives, it’s one of the best ways to make your business viral on Twitter or across Facebook groups by trying out too hard.

Related: Stop Selling to Gen Z

2. Insist on a meeting right away

Unless you found a cure to a rare disease or had an unlimited supply of masks on the day of the first lockdown in 2020, there is no practical reason an executive (or a senior manager) would welcome a random phone call the day after. Many executives have their week planned ahead of time  some only booking meetings in 15 to 25 business days.

There are different variations of this outreach approach:

  • Suggesting an urgent meeting within 24 hours.
  • Sending two available time slots that fit you best (without considering the other party).
  • Proposing meeting hours late at night or very early in the morning.

Warming up a lead takes time, especially when it comes to cold outreach. Some sales reps try to ease the process by sending Calend.ly links or looping in an automated scheduling bot, but facilitating personalization immediately gets in the way.

Give your leads some breathing room; suggest providing some context or send some brochures over before insisting on urgent calls.

3. Provide zero context

Being secretive isn’t helping out in landing a demo meeting. 

A surprising percentage of the automated follow-up LinkedIn messages I receive include something along the lines of: “I work in IT, let’s book some time next week and explore the best way to help you out.”

And last month, a LinkedIn connection request came in from a medical professional.

“I’m a doctor, we need to jump on a call.”

After inquiring about additional details, she insisted on disclosing more over a call.

Needless to say, I archived this message and moved on. Time is valuable, and having to hop on dozens of cold calls monthly would hardly allow any business professional to complete anything else. 

Be mindful of the prospect and provide succinct yet sufficient information before moving to a meeting request.

4. Butcher someone’s name

Our CTO conducted an experiment and added a random emoji to his LinkedIn name. After assessing the results a month later, he reported that 30% of all outreach messages included the emoji in the initial pitch.

Any seasoned practitioner with access to the internet would immediately realize they have fallen prey to an automated bot. We may be used to receiving robocalls from governmental institutions or a cell provider, but hey, at least they are relevant and personalized.

Some of the corresponding examples include a nickname or an alias used in a forum system instead of the person’s real name. We have all seen this in the context of mass emails among newsletters, but trying to mimic a human message or a LinkedIn outreach deserves a personal touch.

5. Ignore the application requirements

Not every outreach is cold  sometimes there is a legitimate reason to touch base, and that’s great.

But missing out on essential details in an RFP or a social-media post really defeats the purpose of trying to connect with a prospect.

Our hiring posts always disclose location (and the fact that we look for individuals starting full-time employment). At least half of the respondents are business developers or recruitment firms leasing people abroad, completely omitting the details in the post.

This practice is recognized broadly and using freelance networks or job boards often leads to a simple “test” for applicants. An example here is asking applicants to include a random word in the subject line  or pick their favorite color. Application-tracking systems never capture these, and business professionals save time sifting through these ignorant submissions.

6. Offer something irrational

While entire Reddit communities exist solely to mock hilarious spam messages, it’s not uncommon for business professionals to receive an irrelevant outreach proposal that simply does not make any sense.

At least twice a month, I receive a premium InMail offering a low-level job that isn’t fit for my skills (and certainly does not make sense as a serial founder). This includes anything from seasonal jobs for students to entry-level positions in legal or pharmacy.

I have been pitched on trucks in South America, unlimited supplies of integrated chips from Chinese manufacturers, enterprise-grade solutions aimed for Fortune 500 corporations and everything in between.

Related: The Only 9 Things You Need to Know About Selling

Don’t buy an email list and blast every single email right away. While sales outreach is a numbers game, you don’t want to completely demolish the brand value by being intrusive in the wrong circles.

There are different ways to embarrass yourself and harm the reputation of the business during outreach. Trying to contact someone who hasn’t been an employee for years, asking for a random person in the organization you simply found online or mass emailing a series of group emails in a thread (hoping for a single stakeholder) won’t get you anywhere either.

But the bottom line is simple. While the shotgun approach would not disappear overnight, add at least some personalization in your outreach process.

Be mindful of your prospects and spend a few extra minutes confirming that they fit the buyer persona. Check your grammar and construct a simple yet clear message stating the purpose of the outreach. Stay clear of relationships you want to avoid  and make the most out of the remaining list.

Following this simple set of practices will lead to scheduled meetings and slowly grow your pipeline. Just make sure you don’t get busted while taking shortcuts early on.

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