The 5 Mistakes Every Pro Makes When ‘Personalizing’ Outreach

While these 5 mistakes are the most commonly made in personal outreach, at the end of the day, if there is one tip to follow it’s this: Take the time to ensure that what you are saying, doing or sending is relevant, relatable and respectful.
mistakes when trying to be personal in outreach

It is getting harder and harder to connect with your prospects and customers. One of the obvious ways to cut through the noise and spark a conversation is to show an interest in them as a person, but there can be hiccups along the way. Making these 5 mistakes when trying to be being personal in your outreach can really impact results.

At Alyce, we believe in the power of being personal and treating people as people and not a KPI or metric. One of our mottos is: “Don’t blast and harass.”

Connecting with people is about investing time and energy into learning who they are as a person and what is valuable to them. While this is easier said than done, we wanted to share some common traps to avoid while trying to make these personal connections. 

Mistake 1: Personalization is not Personal. 

We say it around here often but personalization and personal are not the same thing.

Subject Line: {First Name}! Here is a gift

Hi {Insert First Name Here},

I hope that this message finds you well. I’m sure the weather in {Insert Location Here} is beautiful this time of year. I’m sending this message to introduce myself as your resource at ACME. I work with small companies in the technology space and I think your company would find value in our ability to help your business grow sales. 

Here is a personalized notebook that I thought you would like. Let me know what time works best to connect. I look forward to talking with you. 


Jane D. 

ACME Inc. 

In this message, the sender is attempting to be personal but it does not come off genuine and misses the mark. Why? Because they are mistaking personalized for personal. 

Buyers are savvier than ever and can spot when they are in a marketing cadence from a mile away. Just putting an {Insert Personal Detail} here placeholder, is not enough to capture someone’s attention anymore.

Mistake 2: Making your Message all about You Instead of Them. 

Taking a second pass at Jane’s email, while she made an attempt at “caring” about the weather where this person is, she immediately began talking about herself and her needs. No one likes to hang out with the person at the party who only talks about themselves all night.

Look through your outreach and count how many times you use the words I or Me. Now, look at how many times you say You or Your. By making the message all about yourself, you miss the opportunity to connect on a personal level with your prospect. 

Highlighting that you took the time to understand their specific pain points, or learned more about their company goes a long way. Before you ask or demand something/time from them (a meeting, a calendar, feedback), demonstrate that you made that investment in them first. 

Mistake 3: Colleges and Universities are not always meaningful personal interests

Sara went to Auburn University, she bleeds orange and blue. She would LOVE to receive something connected to her alma mater. 

George went to Boston University, he did everything he could to graduate as soon as possible and get out of there. Sending him something related to BU would frustrate and annoy him. 

Unless someone is publicly cheering for their alma mater or they are vocal supporters, avoid sending them something from their school. If you are struggling to find something to connect with them on, you can leverage the power of choice and ensure they receive something they are excited about. 

The power of choice empowers your recipient to be in the driver’s seat of the experience. They recognize that you took the time to care about them and did not make a decision for them and have something show up at their door. 

Mistake 4: Forcing what YOU think someone would like on them

Succulents, cupcakes, squish balls oh my… not. 

If your prospect is a plant dad, has a sweet tooth or loves little gadgets, these gift options are great. If they have a black thumb, eat healthily and hate clutter, these are annoying. 

When you send something to a prospect or customer you are trying to elicit a positive reaction and response. Having something show up at your door that you do not want, need or like has the opposite effect. It becomes a burden and is wasteful.

Mistake 5: Using outdated data

More often than not, once someone has done the work, they do not revisit it and then you can fall into the trap of using outdated data. Perhaps they have moved, maybe their job title has changed. Die-hard Tom Brady fans may have now become Buccaneers fans (as a Boston resident that is a questionable decision but so be it). 

Alyce leverages AI technology to surface up publicly available relevant information that helps you make those personal connections with accurate information. This functionality saves me a ton of time and has stopped me from making a silly outdated error. 

Personal is the Better Approach

Being personal requires empathy, but the impact is significant. Let’s take a look at an interaction at the same phase of the sales process, but with a rep who took a personal approach.

Some back story: Colin found out that Lisa loves to cook.  – in the example below, you see how Colin used this insight to connect with Lisa on a personal level. The outcome is more impactful and has a higher probability of capturing her attention and sparking up a genuine conversation. 

Subject Line: Penne for your thoughts?

Hi Lisa,

Saw you’re leading Dunder Mif’s demand generation and that you’re also a master of the kitchen, thought this gift would help you continue to up your cooking game!

Looking forward to hearing about any recipes that you loved and potentially exploring if we can help you cook up some pipeline.

Bon appetit,


While these 5 mistakes are the most commonly made in personal outreach, at the end of the day, if there is one tip to follow it’s this:

Take the time to ensure that what you are saying, doing or sending is relevant, relatable and respectful. 

Before you are asking someone to invest their time and money in you, make sure they are investing your time in them.

Photo by Sarah Kilian on Unsplash.

June 2, 2020
Tori Oellers
Tori Oellers