Personalized messaging guide

I've seen a lot of people telling me they are not able to get a response for the email outreach they are doing. I see personalized messaging as an essential and successful method. Questions are why it matters, how rare it is, and how to do it. This guide is a combination of my thoughts and experience of doing it.

The state of outreach fatigue

The rise of marketing automation software was quickly followed by the rise of sales automation/acceleration software. I'm a big fan of these technologies and they have their place in the stack. However, their ease of use has led to laziness from reps, resulting in email & LinkedIn inboxes that are completely inundated with obviously templated messages.

So how do you stand out? How do you rise above the noise and earn the right to give people your value prop? It starts with research.

Make it personal

If your prospect is willing to share things about their personal life via social channels (LinkedIn, Twitter, Facebook, etc.), use it in your messaging! Check out the data below to see the kinds of things that have been proven to majorly increase response rates and meetings booked.

Personalize around these things:

👶🏡 Their childhood home

☄️😲 Their meteoric career arc

📖🎙 Their published work

⚾️🏈 Their sportsball interests

Account-level info is useful too, but it doesn’t move the needle nearly as much.

Check out the data below, courtesy of SalesLoft

The transition to your value prop

One of the most difficult things to learn is how to take the research you've done, and connect the dots between that research and your company's value prop. When done well, the message reads seamlessly and impresses the reader. When done clumsily (or more often, not done at all), it's impossible to forget that this is, after all, a sales email.

How to personalize at scale

Some people make the mistake of thinking that "personalization" means 100% tailoring of each message to each individual. That is false. Because people's inboxes are so flooded, you do have to play the numbers game a bit -- sending a decent quantity of high quality messaging. You can't do this if it takes you 30 minutes to research & write every email.

Here are my thoughts on how to scale your personalization efforts.

Personalize these things:

- Your intros, including the reason you’re reaching out

- The call-outs to the research you’ve done on the person or company

- The synergy between that research & your company’s value prop

Templatize these things:

- Your company’s value prop -- for that persona/industry

- Your call-outs on the individual’s pain points and how your company solves them

- Your CTAs

Reduce, reuse, recycle:

- Make use of the same bit of research multiple times -- just change the phrasing

- Make use of multiple channels (email, LinkedIn, phone, direct mail, video)


Every message does not need to be 100% bespoke for the recipient.

But it should resonate with them and demonstrate that you’ve done your homework.

Some tips for writing solid emails

Now that you're armed with some facts about them or their company, you need to craft the message in a compelling way. The best research in the world falls flat if the message you send reads like a Dostoevsky novel. Keep it short, keep it simple, and pique their interest.

Some rules for writing emails people will read & respond to

- Keep them under 125 words. Way harder than it seems.

- Put each thought on its own line — white space is your friend.

- Write the way you speak. Be professional but not rigidly formal.

Show them you know them. Provide valuable insights/content for their role, company, or industry.

The habit of reading before you hit send

I got into the habit of re-reading my emails early in my career, and go a step further when writing outbound email copy. I truly recommend following the advice below, it's changed the game for myself and many people I know who follow it.

- You’ll realize quickly that your first draft is too long. If you’re boring yourself, you’re boring your audience.

- You’ll notice that you say “I” a lot. This should be about them, not you.

- You’ll remember the message more. This allows you to be consistent in the voicemails you leave & conversations you have with that person.

I hope that you take at least some of this advice and incorporate it into your outbound methodology. I promise it'll be worth the effort.