How to Train Sales Reps to Write Sales Emails

Most teams don’t train their reps to write solid sales emails. This guide covers simple strategies you can use to help your team write killer emails.

Introduction

Chances are pretty good that, as part of your onboarding process, sales reps spend at least a few hours practicing cold calls and learning basics like responding to common objections. (Sidenote: If they don’t, then we recommend you work on your cold calling program).

On the flip side, how much time do new reps spend learning to write strong sales emails? In far too many cases, this is a leadership blindspot.

Maybe someone directs them to recommended sequences or cadences or forwards a few “good” emails they’ve sent from their inboxes. However, very few teams have developed a process for teaching sales reps to write killer sales emails. The consequences are obvious and potentially devastating.

A sucky sales email is going to either end up in spam or get virtually no replies with any positive sentiment. If reps go on writing terrible emails for too long, then they’re going to burn through your prospect lists and sink your overall email deliverability. (Not to mention miss quota and probably get canned).

The good news is that you can avoid this by creating training opportunities for sales reps–both fresh to your team and seasoned alike–to learn to write sales emails that convert. Here’s how.

Before you train anyone, make sure you know how to write a good sales email.

Most people who’ve been in sales for a while can look at an email and either say, “yeah, that’s a good email” or “yikes, that’s going to spam.” You probably have this knack, too. 

The trouble is that marketing teams have put tons of hours into analyzing email quality, deliverability, and performance. But most sales teams haven’t, so sales leaders don’t have a lot of data to back up their instincts about how to write a sales email.

Start with a messaging quality audit.

That’s why we suggest that, before you develop a plan for how to train sales reps to write good sales emails, you spend some time analyzing and documenting your best practices.

We start a lot of engagements with messaging quality audits to assess how a sales team’s templates and sequences, or cadences, are performing. Then, based on the data, we make (and then test) educated guesses about why they’re performing that way.

You can conduct your audit in-house or call in reinforcements. Either way, make sure you have a clear understanding of what best practices are emerging or worth testing, and which messages may need to go the way of the dodo.

Confirm your findings with smart A/B testing.

You don’t have to A/B test every email your team ever sends. In fact, that’s counter-productive. You have better things to do, like walking your dog or eating a taco. (If you’re really ambitious, then try both at once).

Instead, take key findings from your messaging quality audit, turn those into hypotheses, and A/B test them in strategic sequences. Don’t worry, it’s not as complicated as it might sound.

If you need help with this step, here’s a piece to help you out.

Make it a habit to monitor metrics and “star” top-performing sales messages.

Whether or not you A/B test a sequence or cadence, you can watch basic performance indicators (open, reply, and conversion rates) and “star” the ones that are setting the world on fire.

This might be through a naming convention, tag, or messaging collection. No matter what method you choose, the point is simple: you need to watch your messaging metrics (or appoint someone on your team to do so) and develop a clear and shared system for highlighting solid examples.

This doesn’t just help training efforts; this is critical to building your sales messaging program.

Once you know what “good” looks like, make it easy to replicate.

If your team’s definition of a good sales email takes nine hours to recreate, then you’ve got a problem. This is very unlikely, however, because sales emails should be short, conversational, and simple.

Nonetheless, it boils down to this: your sales reps should be able to write a good sales email very quickly, so they can reach out to as many prospects as possible without sacrificing quality.

There are several ways to get there. The first is to choose an existing formula or methodology for sales email writing. Experts have already done the heavy lifting, taking their own insights to create a repeatable structure you can take and use with your team.

Alternatively, you can create your own formula. Make sure you cover the critical bases, like your greeting, introduction, value proposition, social proof, call to action, and sign off. You can either create a series of fully-baked examples or rely on an acronym or other memory device to help your team remember the critical pieces.

Create example sequences or cadences, templates, and snippets in your SEP.

Whether reps choose from a fleet of recommended, tested sequences or cadences, or they use examples in the SEP to clone and adjust for their own purposes, you should have a core messaging library to work from.

For instance, store your winning cold outbound formula as a template, and then put that template in a cold outbound sequence or cadence.

This functional documentation practice kills two birds with one stone: you have a working record of what “good” looks like and you have a set of shortcuts for your team to work from. 

When the infrastructure is ready, here’s how to train sales reps to write killer sales emails.

You’ve got a solid definition for what a “good” sales email looks like, and it’s easy to replicate. Your reps feel empowered to say something when a message is… future fabulous. Congratulations, you’re now ready to think about training.

If someone on your team has been assigned responsibility for enablement–or you have a full team dedicated to it–then you’ll want to share these insights with them. If not, then it’s time to designate someone to own this capability as soon as possible.

Either way, here are our top five recommendations:

  1. As part of your onboarding process for new sales reps, hold an interactive, live training (or two or five).
  2. When sales managers identify great examples, from reps who are killing it with personalization or one-off emails, share them with the entire team.
  3. Invite a representative from your content creation committee, or a sales messaging or copywriter, to join sales team meetings once a month to share updates, solicit feedback, and review a different best practice.
  4. Encourage your sales managers to conduct “spot audits” on each sales rep’s emails. Look at templates they’ve personalized within a sequence or cadence, check activity with key accounts for individual emails sent, and evaluate sentiment data to see how prospects are responding to the emails they send. 
  5. Conduct messaging performance audits quarterly (or more frequently, if you’re feeling ambitious) and host team-wide training shortly thereafter to coach on specific issues discovered in the audit.

How to onboard a new sales rep with solid live training(s).

We are huge advocates for live training. It’s an investment of resources, but the ROI on that time will be so much greater than asking a colleague to build a bunch of decks you’re trusting new reps to review on their own. (Hint: They probably won’t).

You can still make a deck, but make sure you present it live and build in many opportunities for interaction. If your “live training” could just as easily be a recording with a Q&A at the end, then you’re doing it wrong.

Make your training(s) as interactive as possible.

Most adult learners need opportunities for direct and immediate application. Build this into your training not only to promote engagement with the material but also to customize the experience to the specific group of learners.

Good educators find a way to connect with their students, and this can’t happen without an ongoing dialogue and plenty of participation. Here are some tips for making this happen, in your onboarding process and training.

  1. Have a structure in place, but allow yourself to “rabbit trail” and cover content they’re interested in or ask about.
    When thinking about how to onboard a new sales rep to your team, remember that you’re not teaching high schoolers to take a standardized test; you’re training adults to get a job done.

    Make sure you cover essential information, but don’t be afraid to speak to their specific needs and curiosities. You want reps who can think for themselves, and who feel empowered to pursue their passions in a way that advances your business.

    For instance, if you have a rep or two who are very interested in email personalization, then camp out here or offer supplementary training later. 

    There is a difficult balance to strike between teaching your sales team to follow a consistent enough process to ensure quality and confident measurement, while also allowing each person to apply their unique skills and talents to get the best results.

    This piece outlines strategies for maintaining this balance in your team’s enablement program.
  1. Deconstruct examples of sales emails.
    Compile a set of examples of the best emails your team has sent, a few stinky ones they have received (or sent, if they are brave enough), and a few “average” emails.

    Mix them up, put each on a slide, and ask the participants to dissect them, pointing out what made each strong or weak.

    You can even have your group vote on whether the email ended up (or would end up) in spam or get a meeting. Don’t be afraid to provoke some debate here. Getting your reps to take a stand for a style or tactic helps them to identify their own “voices.”

    Hint: If used near the beginning of your first training, this can double as an  assessment of  your participants’ baseline familiarity with what you’re going to cover. 
  1. After they’ve seen examples, give them a simple persona or industry and a related value proposition, and then ask them to spontaneously compose a cold outbound email.

    If you did step two, then you can start here with an example the group thought was the best. 

    Alternatively, you can put up a “diagramed” version of a solid sales email. Point out the major elements you want to see in their practice emails.

    Here’s an example of what we mean:
Sales email example, with annotations

As a last step, you can ask each person to share one example. They might not love you for putting them on the spot and asking them to share their emails, but good sales reps put themselves out there all the time. It’s not a profession built on social comfort.

Asking each person to contribute their best practice email is a great way for you to identify any areas where you need to focus further. It’s also a hidden benefit that you’ll see which reps have a knack for email writing.

If you have a content creation committee, or other opportunities for reps to write, these are folks you will want to keep an eye on and consider for these responsibilities.

Thoroughly cover personalization, including clear boundaries and areas where they can be creative.

The term “personalization” is used so often now that it almost doesn’t mean anything. To some sales teams, an email isn’t “personalized” unless 100% of it has been written for that prospect. For others, “personalization” means using a first name variable to use their name in the salutation.

Technically, they’re both right. However, we consider the first “individualization,” and almost never recommend that level of investment. The truth is, if there is a spot in your sequence or cadence for an email, you should have a complete email template plugged in.

Even if it’s a manual step, your reps should never be starting from nothing. It takes much more time (and produces messages that are a lot harder to measure) to start from a blank slate than it does to customize a solid message that’s already been written.

This means your company should have a firm understanding of what “personalization” means to your team, and what levels of investment or personalization are appropriate for specific verticals or industries and personas. 

Make sure your training on personalization covers these things

  1. How much time and investment should be devoted to personalizing emails for specific personas.

    If you don’t give reps clarity here early and often, then they will almost definitely make poor choices with their time and attention. Because being a sales representative is a numbers game, it’s really damaging to their quotas to spend too much time on any one prospect.

    On the other hand, if they don’t personalize an email to a high-value account, and a prospect receives something that feels too generic, they’re leaving a lot of value on the table.

    A great way to provide clear guidance is to create “levels” or “tiers” of prospects, based on persona and/or industry, and to specify levels of investment that are appropriate to each. Many teams bake this direction into their sales messaging playbooks, for ongoing reference.
  1. What makes personalization cringy?

    You’ve probably gotten a personalized email that has taken things way too far. Maybe the rep looked you up on a social network that isn’t business-related and referenced something pretty personal.

    Or, maybe they’ve tried to make a “personal connection” based on a shared connection, and it just falls flat.

    This is a great spot to share direct examples of what to do and what to avoid. For instance, have your sales reps seen a lot of success personalizing emails to company updates and public posts on LinkedIn? But, maybe you recommend against things like alma mater, city of origin, and other more personal or demographical content?
  1. How to do research quickly.

    This is a learned skill but, if your general guideline is to personalize 20% – 25% of an email template, then this translates to a sentence or two. You don’t need someone’s entire life story; you just need one hook.

    What are some best practices your more seasoned sales team members pursue for success, mining that one LinkedIn post or fact about the company? How have they searched for facts or updates which relate to a value proposition?

    And perhaps most importantly, how much time do they spend on this? If they just can’t find something worth using to personalize to the individual, when do they fall back on a persona or industry-based fact that works for creating general rapport?

Give them a “tour” of everything that’s available in your company’s SEP.

Once you’ve covered the fundamentals of good email writing, make sure you set aside at least one training session (and ongoing Q&A opportunities) to give new sales reps a “tour” of all of the sequences, cadences, templates, and snippets in your SEP.

They should not only know what’s in there, but when to use it. If you have a good content organization system in place, then tagging, collections, or naming conventions should be like signposts pointing them to sequences or cadences to use for certain tiers or priority levels, personas, and industries.

Additionally, a clear organization system for standalone templates and accompanying snippets will make their jobs a lot faster. As we’ve already mentioned, you very rarely want to put reps in the position of writing an entire email from scratch.

Imitation is a great teacher, and one of the best ways they will learn is by starting with excellent templates. As they get more and more comfortable, they can innovate and add more of their own flair. However, at least at first, you want them to be very skilled at taking advantage of the resources you’ve already provided. 

Host follow-up training and Q&A sessions as frequently as resources allow.

Even after your reps are no longer in the “onboarding” phases, building in a cadence of Q&A sessions, refreshers, and topical training sessions benefits everyone on your team.

Make sure you’re revisiting best practices with personalization, introducing new sequences or cadences created for specific audiences, informing your sales team of new resources marketing has created for them (case studies, customer stories, white papers, etc.), and addressing problem areas you’re finding in audits.

And, as you’re creating the curriculum for ongoing training sessions, be sure you’re directly addressing questions or concerns that are bubbling up through your open feedback channels. If reps are telling you they don’t like something, or they just don’t understand why you have made certain strategic choices as a company, then it’s time to address it in a training or Q&A session.

Once you’ve developed a training structure, it’s time to make sure your documentation practices are solid.

If you haven’t taken the time to document the brilliant information you’ve discovered and shared in creating your training program, then you’re going to wish you had.

Each time you have to search to find that piece of information or retype that email to the sales rep with a question you’ve heard many times, you’re wasting time.

The best way to make the most of your company’s resources is to have a solid documentation process in place to capture best practices, record them in accessible locations, and revisit those best practices to make sure the information stays current.

Because we’re talking specifically about sales emails, though it’s important to document every key strategy and learning that your sales team needs to know and pass along, our highest-priority recommendation is to create a sales messaging playbook

Even if your sales reps are not creating sequences or cadences, a playbook is critical for guiding the people on your team who are. Furthermore, as we mentioned earlier, it’s important for reps to understand the why behind your messaging. If they don’t, then they’ll accidentally misuse it or abandon it altogether.

That’s why everyone on your sales team should have access to your sales messaging playbook, which captures all of your team’s best practices, guidelines, and strategies behind sales emails and the sales plays they populate.

If you’re not sure about how to create this, or who should own it, then a great place to start is creating a sales messaging program. From there, you can document each step as you build the program.

You know how to train sales reps to write killer emails, so now it’s time to go do it.

If you don’t have time to invest anywhere else, your team should establish how to write a good sales email and then share as many examples as you can. 

With the right culture, which encourages questions and feedback, your reps can build from this foundation and help you co-create an enablement structure that teaches the reps coming up behind them.

With more resources, you can add depth and structure until you have covered every one of these bases. However, don’t be discouraged if you can’t get there tomorrow. 
We’re here to help teams of all sizes maximize their training or enablement resources, encouraging sales reps to be the best possible salespeople. If we can support your team, then reach out to our consultants.

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