Mastering Personalized Outreach Strategies

Have you ever received a cold email that made you stop and go, "Wow, this person really gets me!"?

It happens from time to time, but the overwhelming majority of the cold messages that you have in your inbox probably make cringe. 

That's often the case because of hacky tactics that make a message "overengineered". Suddenly something that's supposed to be personalized ends up sounding super salesy and unnatural.

But, that doesn't mean you shouldn't personalize your messages. You just need to understand what makes some tactics bad and others great. In this article, we'll cover exactly what the difference is and how you can create the types of messages that hit home and start the right kind of conversation.

The Pitfalls of Bad Personalization

The Problem with Repetition

One common mistake in personalization is simply repeating someone's information back to them. This can come across as insincere and lazy, and can quickly turn off potential customers. Just because we have access to data tools doesn't mean we should use them to regurgitate information without adding any value, insights, or extra context.

Back in the early 2000s, getting a cold email with your name on it might have felt great! Clearly, the sender must have spent time researching and truly sending a thoughtful message. 

But these days, just having your name, your company name, or some other data point blasted at you over and over again....does that really feel like someone's spent time and effort trying to speak to you? 

Blind repetition does not make your message more personalized!

The Dangers of False Flattery

Another pitfall in personalization is "false flattery". Sending emails filled with excessive praise and compliments can come across as disingenuous and insincere. It's important to focus on providing value and addressing the specific needs and pain points of your potential customers, rather than trying to win them over with empty flattery.

False flattery often shows up in subject lines or hooks that compliment the reader's job role, personal accomplishments, or a school they attended. Here's a couple of examples from my inbox:

In the last year, I've received over 20 of these false flattery emails that use my university as a hook. 

It's a weak message because the university has nothing to do with the sales conversation they actually want to start. Look at the big jump from the first line to the second - it's an awkward, unnatural transition. 

Secondly, it's a template that many people are using. For me, the reader, it immediately shows up as one of a clump of emails that I don't want to pay any attention to. They feel fake and a little manipulative - not a great way to start a conversation! 

The Problem with Irrelevant Small Talk

While small talk can be an effective way to build rapport in face-to-face conversations, it often falls flat in sales outreach. Bringing up irrelevant topics or generic small talk can make your message seem disconnected from the prospect's needs and can hinder the progress of the conversation.

Like the university examples above, if you're starting conversations with hooks that are "far" from the sales topic you actually want to have, you're setting yourself up for failure.

When you're in person or on the phone, you can get away with a little bit of small talk. You have body language, vocal tone, and multiple communication channels that help create rapport. But, you can't do that with emails or DMs. 

That's why your written messages have to be clear, direct, and as close as possible to the conversation topic you actually want to have!

The Principles of Good Personalization

Principle 1: Specificity

Good personalization is all about being specific. Instead of bombarding your prospects with a laundry list of features or questions, focus on one focused question or pain point that you can address. By honing in on a specific topic, you can demonstrate your understanding of the prospect's needs and eventually offer a targeted solution.

Specificity makes it easy for the prospect to wrap their mind around exactly what the sales rep wants to cover. That makes the message more understandable and more memorable. 

Principle 2: Relevancy

Relevancy is another crucial aspect of good personalization. Make sure that your message is directly related to the prospect's current situation or pain point. Avoid generic statements or irrelevant information that adds unnecessary noise to the conversation.

Like specificity, relevancy shows that you actually understand the prospect and what they're going through. It's a chance to show the prospect that your company is dedicated to helping them and might have the best solution out there. 

Principle 3: Clarity

Clarity is another essential element of personalization. If you can clearly communicate the value you can provide and how it directly addresses the prospect's pain points, you'll set things up for a fruitful conversation. Avoid lengthy emails filled with unnecessary information and jargon. Keep your message concise, straightforward, and easy to understand.

If you can create a message that's Specific, Relevant, and Clear, you'll have something that feels much more personalized than a generic email with a bunch of custom fields and other window dressing. 

The Five Levels of Personalization

There are five levels you can use when personalizing your messages. To be clear, none of these levels are a magic bullet and each one of them can still include poor personalization. But, if you use them right, you'll find strong angles that'll help you create personalized messages. 

Level 1: Company Triggers

Identify specific triggers related to the prospect's company, such as recent news, funding, or industry trends. This is the weakest level and often the one that's easiest to automate. The problem is, everyone else is probably using the same triggers that you'll have access to.

Level 2: Personal Triggers

Personal triggers focus on the individual prospect's news. For example, this could be a new job role, a work anniversary, or something they've shared on social media. 

You might find some good connection points here, but the problem is that not everyone is active on social and not every piece of personal news is close to the sales topic you want to talk about.

Level 3: Common Ground

This is where things start to get a little stronger. Common ground personalization involves finding shared experiences or interests between you and the prospect. This could be attending the same university (this is different than just hitting a prospect with fake flattery about their university), having similar career paths, or being part of the same industry. Highlighting these commonalities helps build rapport and establishes a sense of trust.

The only problem here is that there's a chance for small talk here. The closer your common ground is to the sales conversation you want to start, the better.

Level 4: Straight to the Point

Straight-to-the-point personalization focuses on addressing the prospect's specific problem or pain point directly. Craft a concise and clear message that highlights how your product or solution can solve their problem. Keep the message short, focused, and free of jargon and buzzwords.

This is my favorite level to shoot for because it starts with a strong core message. If you have that, you can always look for some personalization points to add on as needed or as is available. And if you can't find any common ground, you still have a strong message that can be sent out. 

Level 5: Join Their Conversations

If the prospect is active on social media or has a public persona, you can join their conversations to personalize your outreach. Comment on their posts or engage in discussions related to their industry or interests. This shows that you are actively listening and engaged in their world.

The only challenge here is that not everyone is active on LinkedIn or whatever social platform you're using. This is a nice-to-have strategy that you can use if your prospect posts content and engages on social media. 

Just keep in mind that you should do this thoughtfully. These days, automation tools are flooding the comments sections with templated responses. This approach will not create wins for you the same way that manual, thoughtful comments will.

Ready to Get More Personalized?

Personalization is a powerful tool in B2B sales, but it must be done effectively to make a genuine connection with prospects. By following the principles of specificity, relevancy, and clarity, and utilizing the five levels of personalization, you can craft messages that start great conversations and ultimately lead to successful sales outcomes.

Personalization is not about using hacks or tricks, but rather about understanding your prospect's needs and pain points and providing targeted solutions. By personalizing your outreach in a thoughtful and genuine way, you can build trust, establish rapport, and create meaningful connections with your potential customers.

Remember, personalization is not just about repeating someone's information or using false flattery. It's about addressing their specific needs, finding common ground, and offering a solution that genuinely solves their problem. So take the time to understand your prospects, tailor your messages, and start great conversations that lead to successful sales outcomes.

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