The Complete Guide to Using Humor Effectively in Sales Emails

For salespeople flooded with generic professional correspondence daily, it’s tempting to inject humor into emails to connect better. But does comedy actually help convert prospects? Or is it an unnecessary distraction that undermines critical messaging?

In this comprehensive guide, we’ll explore if and when humor has a place alongside serious sales conversations. You’ll discover:

• Real data on how comedy impacts email performance
• Actionable tips for crafting targeted, professional jokes
• Tools to test humor approaches before sending
• Examples of tasteful humor adding value in the sales cycle
• Dangers of inappropriate humor and how to avoid them

If leveraged carefully, humor may provide the edge your sales emails need to engage crowded inboxes. Let’s dive in on when funny works, when it backfires, and how to walk the line successfully.

Why Use Humor in Sales Emails?

Sales emails have become ubiquitous in the modern business world. Studies show that the average office worker receives over 100 emails per day, with sales emails making up a significant portion of that barrage. With inboxes constantly flooded, simply sending more sales emails is no longer enough to engage modern prospects. To truly stand out, you need to get creative and inject some tactical humor into your outreach.

Below are some of the key benefits humor can provide in your sales emails when used strategically:

Make Your Emails More Memorable and Stand Out

Humor is an excellent tool for boosting the memorability of your emails so that they don’t get lost in the endless sea of sales outreach most prospects receive daily. According to psychology research, information paired with humor is significantly more memorable than dry facts alone.

Even if a prospect doesn’t read your entire email right away, a funny subject line or preview text can spark intrigue and entice them to come back to it later. Humor gives your emails the “wait, I want to read this” factor that plain sales correspondence often lacks.

Consider adding some light humor through:

• Amusing subject lines – “Avoid the parking ticket apocalypse!” for outreach regarding city infrastructure projects
• Funny preheaders – “This proposal is a real page turner” for book publishers
• Gifs or images related to the prospect’s interests – a meme about football targeting NFL sponsors

Small touches of unexpected humor like these make your emails stand out from the rest begging for attention in the prospect’s crowded inbox.

Help Build Rapport with Prospects

Many sales experts agree that establishing rapport and trust with prospects is one of the most vital parts of the sales process. Using relevant humor in your outreach helps humanize your brand and makes you more relatable.

According to a study published in the Journal of Computer-Mediated Communication, even exposure to a simple humorous stimuli can increase interpersonal attraction between strangers. Rather than coming across as robotic and all-business, measured uses of humor demonstrate shared interests, values, and mindsets with your prospects.

The beginning stages of the sales cycle are the optimal time to build rapport through humor. Once you have an established relationship, you can take more liberties with inside jokes and direct references tailored to what you know about the prospect’s personality.

Allow You to Connect with Prospects on a More Personal Level

Humor enables you to move beyond the stiff, formal interactions that characterize most sales outreach. By injecting humor, you facilitate meaningful back-and-forth conversations between human beings, rather than pure business transactions.

According to social scientist and humor expert Ifat Maoz, humor can “grease the wheels” of interpersonal communication by fostering intimacy and camaraderie between sender and receiver. As prospects see you more as a relatable person than a faceless sales rep, they’ll be more likely to open up and share information that helps you customize your outreach and offerings.

Make Your Brand Seem More Approachable and Human

Today’s consumers and business buyers gravitate towards brands that exude personality and originality. A study by Brandon Gaille found 72% of participants feel more positive about a company that has humor in its ads vs more serious ads. Humor makes you seem more down-to-earth and accessible.

Your prospects likely feel inundated with hundreds of nearly identical sales emails from faceless corporations every week. Even B2B buyers are consumers who want to engage with brands that share their sensibilities, not sterile robots.

Peppering humor throughout your communications where appropriate portrays your brand as the former. Maintaining a stiff, uber-professional, corporate image at all times can actually hurt more than help in the modern landscape.

Can Pique Interest and Curiosity to Get Opened and Read

Humor’s ability to surprise and delight recipients primes them to want to open and engage with your emails. Marketing experiments by HubSpot found emails with humor in subject lines were opened 10% more than strictly professional subject lines. Humor signals there will be a payoff for the prospect’s attention.

Similarly, sprinkling humor throughout your email body entices the reader to keep going to find out what amusing thing you’ll say next. Rather than dense blocks of dry text, humorous asides and anecdotes give your emails reader momentum.

Varying offers like “Get 300 free hours just for listening to this ridiculous proposal” in your CTAs creates intrigue and a feeling of reciprocity around your offers that compels prospects to engage.

Humor should never compromise the core professionalism and quality of your communications. But used judiciously and thoughtfully, it can be the key ingredient that turns a forgettable sales email into a memorable, relationship-building interaction. Test different variations to find the ideal humor balance that suits your brand voice and resonates with your audience. The payoff from increased rapport, likability, and prospect engagement from humor will be well worth it!

When Should You Use Humor in Sales Emails?

Humor can be a useful tool for boosting engagement and connecting with prospects. But timing and context are everything when it comes to humor – what works well once you have an established rapport may fall completely flat if used prematurely.

Below are some best practices around when humor tends to work best in sales emails:

When You Have an Existing Relationship or Rapport with the Prospect

Once you have a solid foundational relationship with a prospect, that’s when you have the most leeway to inject humor into your communications in a natural way. At this point, you understand the prospect’s personality, interests, and sensibilities enough to tailor humor specifically to them in a way they’ll appreciate.

According to a Stanford study, the more familiar the parties involved are with one another, the more funny they perceive shared humorous experiences together. So humor hits its peak when built upon insider knowledge of the prospect you’ve accumulated through prior interactions.

For example, if you know a prospect is a fan of the TV show The Office, you could sprinkle in GIFs from the show or references to popular jokes that only true fans would recognize. This strengthens your rapport and provides enjoyment for the prospect as you’re sharing something proprietary to your relationship.

When Contacting Less Formal Prospects or Industries

Certain prospects and industries naturally lend themselves better to humor than others given their less rigid professional cultural norms. For instance, humor may play better when reaching out to:

• Startups
• Creative agencies
• Tech companies
• Youth brands
• Entertainment and media
• Consumer goods and services

More straight-laced, conservative prospects in industries like banking, law, government agencies, etc may not be as receptive to unsolicited, unnecessary humor in professional correspondence. Know your audience.

For Follow-Up and Relationship-Building Emails in the Sales Cycle

While you need to be more cautious using humor in initial sales outreach emails, once you’re deeper into the sales cycle follow-ups are a prime opportunity to inject some levity. At this stage, you have hopefully established some rapport and trust already.

Follow-up emails after sales calls or demos are an ideal chance to reinforce something amusing the prospect said or did. This continues building your interpersonal bond. You can also use humorous gifs celebrating milestones like contract signings to your mutual enjoyment.

When Sending Emails to Multiple Recipients at Once

If you’re emailing a group of recipients simultaneously who don’t know each other, self-deprecating humor allows you to get some laughs while also ingratiating yourself to the group.

For example, if giving a sales presentation to the c-suite of a company, you could start with a gif poking fun at overzealous salespeople. This helps relax the group and puts you in the “we’re all in this together” camp vs being an adversarial outsider.

Use Selectively and Sparingly in Initial Outreach Emails

Cold prospecting emails are generally not the best place for humor, as you have not established any rapport yet. There may be exceptions if you have a highly irreverent brand voice that aligns with your target demographic.

But in most cases, humor should be used selectively and thoughtfully. For cold outreach, you’re usually safest sticking to more straightforward subject lines conveying value. You can test injecting some light humor in the preheader or intro paragraph, but the bulk of the email should focus on introducing yourself and your offering clearly.

Overusing cutesy humor from the start can make you seem unserious or undermine the gravity of your value proposition. Get your foot in the door first with a solid, professional initial email, then gradually work humor into follow-ups once you have the prospect’s attention.

Understanding when humor tends to work best in the sales cycle, and when it may backfire, is key to using it effectively. Apply the above best practices around establishing baseline rapport first, warming up more formal prospects slowly over time, and balancing humor with core sales messaging. This will allow you to maximize humor’s potential as a relationship-building tool.

What Types of Humor Work Best?

Humor takes endless forms – slapstick, satire, dad jokes, memes, self-deprecation, and much more. When using humor in sales emails, some varieties tend to work better than others. Below are the top types of humor that generally go over well in sales correspondence when used deliberately and tactfully:

Lighthearted, Inoffensive, and Non-Controversial

This broad category encompasses benign, universally-appealing humor that is appropriate for professional correspondence. Think dad puns, cute animals, amusing work-life observations, laughing at minor everyday mishaps we all experience, etc.

The key is selecting humor that is:

• Unlikely to offend or upset anyone
• Doesn’t mock or exclude specific groups
• Isn’t controversial or polarizing
• Maintains an overall positive, upbeat tone

You likely can’t go wrong with this safe, mild brand of humor even with more straight-laced prospects. The humor stems from laughing together at life’s foibles in a good-natured way rather than at someone else’s expense.

Some examples of light, positive humor could include:

• A gif of someone spilling their coffee reacting to a client’s unreasonable request
• A meme about Zoom fatigue after having countless video calls
• A joke about getting stuck behind a slow driver when in a rush

This “we’ve all been there” style of humor builds rapport without risk of alienating prospects.

Self-Deprecating or Making Fun of Own Brand Appropriately

Self-deprecating humor where you poke fun at yourself or your own company (within reason) makes you more approachable. According to Harvard University scholars, appropriate self-directed humor puts recipients at ease, builds trust, and communicates empathy.

You come across more humble and down-to-earth when you don’t take yourself too seriously. Limit self-deprecation to minor, non-offensive observations to avoid seeming unprofessional. For example:

• Poking fun at your terrible handwriting on a sales agreement
• Acknowledging when your website crashes under high traffic
• Joking about your team’s dependence on coffee

Be sure any humor targeting your own brand aligns with and doesn’t undermine your core identity and value proposition.

Funny Gifs, Memes, or Images Related to the Industry

Visual humor can instantly convey the tone you want to achieve. Industry-specific reaction gifs and memes demonstrate you share the prospect’s cultural context and in-group perspectives.

A gif celebrating winning a contract with a new client or meme about supply chain disruptions makes light of familiar situations prospects face daily. This helps prospects feel you truly get their world, strengthening affinity.

When using images, ensure they are appropriate and professional given the context. Also include sufficient explanatory text – don’t rely solely on the visuals to convey the joke.

Anecdotes and Stories Prospects Can Relate To

Humorous anecdotes and stories allow you to bond over common experiences and outlooks. However, take care not to overuse this approach, as extensive personal stories can quickly move you away from a professional sales focus.

Sprinkle in the occasional brief, lighthearted story or anecdote that your prospects will find amusing and retain some shared human connection once the laughter passes. For example:

• Redacting embarrassing details of your Zoom bloopers as you adjusted to remote work
• A quick story about getting trapped in a social media vortex before an important meeting
• Playfully recalling the ugly company website you started with

Touch on the universal experiences that bring us together, even in professional settings. But don’t overshare or provide TMI. Keep it short, family-friendly, and tied back to your core messaging.

Absurdity or Irony That Highlights Frustrating Industry Situations

Pointing out the inherent absurdity or irony in frustrating industry practices prospects deal with daily can be cathartic. Exaggerating the ridiculous parts of the sales process you both constantly face allows prospects to vent their shared grievances while also indirectly highlighting the value of your offering.

For example, you could joke about:

• Creating an auto-reply for the deluge of sales requests you receive
• How you need to attach a PDF of your product just so your email gets opened
• Printing sales decks to counter remote meeting burnout

While highlighting frustrations, keep the tone light rather than bitter, and avoid specific companies or people as targets. Ultimately the humor should convey solidarity around widely experienced industry woes.

Inside Jokes or References Tailored to the Prospect

Once you know a prospect well enough, personalized inside jokes or humorous references to previous conversations hit the sweet spot. This could include:

• Calling back something funny the prospect said on a prior sales call
• Quoting banter from your meeting at an industry conference
• Sending a funny meme only someone with their specific taste would enjoy

Leveraging your rapport this way makes the prospect feel special. Humor is no longer generic, but specially crafted just for them based on your relationship. But take care not to overdo inside jokes with prospects you don’t know extremely well.

Don’t Be Mean, Offensive, Racist, Sexist, or Insensitive

This should go without saying, but any humor that belittles or marginalizes others has no place in sales emails. As a rule of thumb, don’t joke about anything you wouldn’t feel comfortable saying publicly in the workplace or to someone’s face.

Err on the side of being extra cautious and tasteful with humor when contacting prospects you don’t have an existing rapport with. While you may have the best of intentions, misunderstandings can easily happen in written communication without tone and context. When in doubt, keep it 100% professional.

Humor can strengthen relationships and personalize sterile sales correspondence when applied strategically. But be selective – not every prospect will appreciate or respond well to humor. Monitor reactions and continuously refine your approach, favoring benign, universally-relatable humor. With the right balance, adding tasteful humor to your sales emails will make your outreach more memorable and human.

Email Copywriting Tips for Using Humor

Crafting genuinely funny, on-brand humor for sales emails is an art that requires careful strategy. Below are some top copywriting tips for seamlessly integrating humor into your outreach:

Know Your Prospect and Target Audience Extremely Well

Humor should always stem from a deep understanding of your prospect and their preferences. Invest time upfront learning all you can about their personality, interests, company, role, pains, and industryculture.

Key elements to research include:

• Their sense of humor style based on social media posts or interviews
• Jokes and viral content they have shared publicly
• Personal interests and hobbies
• Pop culture or celebrities they follow
• Major events, milestones, or news related to their company
• Frustrations and challenges in their role
• Preferred communication style – formal vs informal

This allows you to craft tailored humor that resonates and conveys you get where they are coming from. Generic, one-size-fits-all jokes are far less likely to land. Do your homework.

Ensure Relevance by Relating Humor to Industry Pain Points

The surest way for humor attempts to fall flat is when they lack relevance to the prospect. Before adding any humor, clearly identify:

• Core frustrations and problems in the prospect’s industry
• Tedious parts of their job responsibilities
• Pressures of their particular role
• Current events impacting their business

Then use these pain points as foundations to build humorous examples, stories, analogies, and inside references that tightly tie back to their reality. This results in humor that comes across as insightful rather than random.

Test Different Types of Humor and Measure Results

Humor is highly subjective. The only way to know what styles your prospects respond to best is through real-world testing. Try incorporating different varieties of humor across a subset of emails, such as:

• Subject line puns
• Amusing analogies
• Industry-related memes
• Self-deprecating gifs
• Lighthearted anecdotes

Closely track how each humor type impacts open rates, click rates, and most crucially – prospect replies and conversions. This will reveal what approaches should be reused and refined vs discarded. Be sure to A/B test broadly before determining optimal humor strategies.

Don’t Force It if You Are Not Naturally Funny

Forcing bad jokes or insincere humor is a recipe for awkwardness and tune-out. Use humor judiciously and only if it comes naturally to you. There are still benefits in even subtle acts like adding emoji or gifs that convey warmth without requiring stand-up skills.

Experiment to identify humor formats you can pull off naturally without coming across as trying too hard. Don’t exhaust yourself attempting to be a stand-up comic – focus on humor styles that align with your strengths.

Use Humor Subtly – Don’t Make Whole Email Humorous

Interjecting humor is about enhancing your professional messaging, not becoming a joke delivery system. Limit humor use to:

• Subject lines or preview text
• Quick asides between paragraphs
• Image captions
• Closing sign-offs

The majority of your email copy should still focus directly on introducing your value proposition clearly. Avoid overusing so much humor that it becomes distracting rather than accentuating your core content. Let humor be the spice, not the entree.

Have a Clear CTA and Maintain Core Sales Messaging

Some of the worst advice around using humor is that you should avoid “sounding salesy.” But prospects expect and need to clearly understand what you’re offering and the next steps you want them to take. No amount of humor should detract from these fundamentals.

Keep CTAs unambiguous, and summarize your key differentiators and value prop even while integrating humor. Humor should enhance, not ever undermine, your core sales communication. Avoid letting a gag supercede the clarity of your actual ask and substance.

Used strategically and not gratuitously, humor can forge authentic connections with prospects while still advancing the sale. The above tips will help you incorporate humor seamlessly without compromising your professionalism or sales effectiveness. Humor and serious business can not only co-exist – when done deliberately, they can complement one another beautifully.

Ideal Placement for Humor

Where you integrate humor within an email greatly impacts whether it works. Place humor deliberately in locations most likely to achieve your objectives:

Subject Line

The subject line is prime humorous real estate in a sales email and arguably the highest ROI placement. A funny, unusual, or punny subject piques curiosity to get opened, conveys your tone upfront, and starts building rapport right off the bat.

However, take care that any humor used still clearly communicates the core value proposition or topic of your email. Test amusing subject lines, but only if humor enhances rather than obscures the key info prospects need to understand relevance from the subject alone.

Introduction

After a compelling subject line draws them in, humor in your intro paragraph continues establishing rapport while also easing prospects gently into your core messaging.

For example, open with a brief, lighthearted anecdote, joke, or reaction gif before transitioning fluidly into your central value proposition.

The intro sets the frame through which the rest of your email will be interpreted. Humor orientates them positively. But keep the intro concise before conveying substance.

Image Captions

Images showing a frustrated person with text like “Me deleting sales templates and starting from scratch again” can pack humor into otherwise dry sections of an email.

Sprinkle 1-2 images with funny captions throughout your email body to reinforce or build upon humor first introduced in the copy itself. Avoid standalone images with no explanatory text, as purely visual jokes are easily misinterpreted.

Email Sign-Off or Signature

Ending an email on a humorous high note leaves prospects feeling amused, more receptive to future outreach, and more likely to convert. Sign-off with a friendly joke, funny meme, or witty quip to produce a smile and memorable goodbye.

You can also incorporate humor directly into your email signature through amusing job titles or taglines that recipients will see on every email going forward. But ensure these align with your brand identity.

Email sign-offs and signatures containing tasteful humor give your prospects a pleasant send-off while positioning your expertise.

Other Opportunities

Anywhere prospects’ eyes are likely to land offers options for working in humor. Consider:

• Funny preheader text
• Amusing hyperlink text
• Relatable reaction gifs
• Easter egg jokes in footers

Track click rates on hyperlinked text and gifs to optimize humor placement for maximum visibility and engagement.

Strike the ideal balance between humor and professionalism by aligning funny asides closely with critical email content. When used deliberately in optimal locations, humor makes your emails stand out while enhancing their substantive impact.

Real-World Examples of Humorous Sales Emails

It’s one thing to talk about using humor theoretically, but quite another to illustrate successful examples from actual sales emails. Below are some real-world cases showcasing how different humor tactics helped strengthen engagement and increase conversions:

Poking Fun at Industry Frustrations Prospects Experience

Emphasizing humorous solidarity around shared market woes helps you bond with prospects over mutual pains. For example:

• An HR software provider joking about the complex maze of compliance red tape they help navigate

• A supply chain consultant sending a meme about global shipping delays they can alleviate

• A sales automation platform gif celebrating avoiding manually updating hundreds of spreadsheet leads

Laughing together about widely felt industry headaches positions your solution as their relief. But keep the tone upbeat rather than resentful.

Gifs or Images Related to the Prospect’s Interests

Personalized images build rapport by peeking into prospects’ lives outside work in a fun way. If you know a prospect loves:

• College football – Send a gif cheering a win by their alma mater
• Game of Thrones – Include a meme with their favorite character
• Baking – Attach a photo of a lopsided cake to commiserate

Tasteful personalization shows you did your research on them as an individual. Just ensure references remain professional given your relationship.

Intentionally Bad Puns or Over-the-Top Corny Humor

Some prospects find outrageous, almost cringeworthy puns or excessive silliness amusing. If you have a relationship where this stylistically makes sense, go for it.

For example:

• A trucking company with the tagline “We wheelie deliver!”
• An optometrist advertising “eye-deal vision solutions”
• Overabundant emoji in response to a prospect’s joke

Convey through past interactions you’re both in on the gag before going too overboard. These tactics aren’t for every prospect.

Self-Deprecating Humor About Struggles Marketers Face

When done with care, poking fun at your own flops and failures helps prospects relate to you as more human. Potential examples:

• Commiserating on embarrassing conference presentation bloopers
• A gif about repeatedly having to push back product deadlines
• Memorializing your terrible first website design from the 90s

Be measured in how much you share. Use just enough self-deprecating humor to come across authentic without undermining faith in your abilities.

References to Pop Culture – TV Shows, Movies, Memes

Pop culture humor can instantly connect you with prospects who share your tastes. For instance:

• Sending Baby Yoda memes if you both love Star Wars
• Gifs of Jim from The Office for fellow fans
• An Elf on the Shelf photoshopped into relevant holiday promotions Ensure prospects actually know and appreciate the pop culture content first. Obscure references will just confuse them. Vet ideas before assuming shared context.

Used deliberately, these examples demonstrate how humor applied thoughtfully and sparingly helps emails feel more authentic, enjoyable, and ultimately persuasive. Study your prospects, test carefully, and continue refining your email copy humor with an eye toward maximizing relevancy and engagement.

Testing and Measuring Humor in Sales Emails

Do not assume any humor attempts will work as intended. Thoroughly test and optimize use of humor based on prospect response. Ways to measure humor effectiveness include:

A/B Test Different Types of Humor to See What Resonates

Split test humor styles and variants systematically to determine what best achieves your goals. Test factors like:

• Subject line puns vs industry jokes vs pop culture references
• Images vs animated gifs vs emoji vs text-only
• Humor focused on pain points vs off-topic humor
• Humor in intro vs conclusion vs body sections
• Emails with humor vs strictly professional

Compare open rates, click rates, and prospect replies across these email variant groups to have clear data-driven insights on ideal approaches.

See If Humor Affects Open, Click-Through, and Reply Rates

At a minimum, track whether emails containing humor versus more serious emails have any positive impact on:

• Open rates – Do humor emails get opened more?
• Click-through rates – Are prospects more likely to click links or CTAs in humor emails?
• Replies – Do humor emails elicit more prospect responses and two-way dialogue?

Evaluate the metrics statistically, not just based on instinct. The data will reveal if humor is helping achieve response goals or not.

Survey Prospects Directly on Examples of Humor

Ask prospects directly for feedback on humor attempts. For example:

• Send two email variants, one with humor and one professional, and ask which they prefer
• Share some potential funny subject lines and ask prospects to choose their top options
• Ask prospects to review a draft email body with humor and suggest changes

Prospect input helps ensure you’re aligned on what landed with them vs what felt tone-deaf or fell flat. Don’t operate in a vacuum.

Monitor Social Media Mentions and Comments

Pay attention to any public social media commentary on your humor attempts, positive or negative. Are prospects:

• Sharing your funny emails positively?
• Making memes or jokes about email content?
• Publicly slamming any email humor as off-base?

Social listening sheds light on prospect reactions that personal feedback may not reveal. Address concerns promptly and improve approaches.

Ensure Humor Aligns with Brand Voice and Persona

Will prospects who loved prior branding perceive new humorous tones as aligned and authentic? Conduct brand voice assessments before and after injecting humor to confirm changes gel.

Humor should elevate, not deviate too far from, your brand identity. Measure perceptions continually to verify consistency.

Evaluate humor holistically across metrics and feedback channels. Allow prospects to guide you on appropriate humor through their actual response patterns. With ongoing refinement and A/B testing, your humor usage will naturally improve and become more targeted over time.

Tools and Resources for Injecting Humor

Humor doesn’t always come naturally, especially in professional contexts. Try incorporating these tools and resources to master injecting appropriate, audience-tailored humor into sales emails:

Databases of Industry-Related Gifs and Memes

Sites like Giphy and Imgflip offer searchable repositories ideal for finding entertaining reaction gifs and memes tailored to almost any industry. Some examples:

• Finance – gifs about market ups and downs, money printing, Wall Street hysteria
• Healthcare – coronavirus memes, gifs about dealing with insurance providers
• Construction – reaction gifs about project delays, overtime, safety mishaps

Drop targeted gifs into emails to add humor conveniently without writing jokes from scratch. But provide sufficient context explaining relevance.

Joke Writing Templates and Laugh Trackers

Leverage templates with fill-in-the blank formulas to easily create varieties of jokes, such as:

• Common joke frameworks – Knock knock jokes, “. walk into a bar” jokes, limericks
• Mad Libs-style templates for crafting situational humor
• Formulaic pun or “dad joke” generators

Laugh trackers like JokeMapper also help methodically plot humor progression to maximize impact. Don’t limit yourself to purely original content – templates bootstrap jokes.

Online Humor and Comedy Writing Courses

Take guidance from experts through online humor writing programs like:

• Udemy courses on humor writing for comics and authors
• edX lessons on humor psychology and funny speechwriting
• Coursera comedy and humor creation skill classes

Learning professional joke craft ranges from the nitty gritty of comedic language use to broader scriptwriting approaches. Invest in building this skill.

Improv Classes Focused on Business Humor

Many mainstream improv schools like Second City offer specialized corporate humor courses helping professionals apply improv techniques in workplace settings. Typical curriculum covers:

• Using “Yes, and…” in emails to build rapport
• Co-creating safe inside jokes with clients
• Acing humorous speeches or storytelling without prep
• Maintaining professionalism while thinking on your feet humorously

Practice cementing humor instincts in lower-stakes environments before client situations.

Popular Comedy TV Shows, Stand-Up Specials

Immerse yourself in current humor culture and trends by studying models like:

• Bingeing sitcoms known for witty banter like The Office
• Breaking down stand-up specials on Netflix for joke patterns
• Listening to comedy podcasts during your commute
• Reading scripts of late night talk show monologues

Consume a range of humor styles and formats to expand your own comedic repertoire.

Quality humor arises from honing the craft daily across tools, resources, and examples. Set aside time to actively build this skill, not just expect occasional inspiration. With practice, injecting the right humor at the right time in sales emails will progressively feel more natural.

Risks and Dangers of Using Humor in Sales Emails

When used carelessly or excessively, humor in sales emails can backfire and damage your brand and relationships. Be aware of these hazards to avoid:

Prospect May Not Find It Funny or Understand References

Humor is inherently hit or miss based on personal tastes. You may crack yourself up crafting an email, but the prospect could find it confusing or weird if the humor doesn’t land. Obscure inside jokes or niche cultural references will fly over most people’s heads.

Err on the conservative side until you have a strong grasp of what types of humor a specific prospect responds to positively. Personalization minimizes misfired humor.

Can Come Across as Unprofessional If Done Poorly

Mediocre, forced, or inappropriate humor easily makes you seem immature versus business-savvy. Corny puns, outright offensive jokes, or slapstick gags have limited places in professional correspondence.

Stick to your natural humor strengths and keep quality high. Don’t sacrifice your reputation as an expert to make lame jokes.

Dark, Offensive, or Inappropriate Humor Is Damaging

This should be common sense, but avoid any humor normalizing or making light of:

• Racism, sexism, homophobia, or discrimination
• Vulgarity, explicit sexual references, or gross-out gags
• Mental illness, disability, or socioeconomic status
• Religion, politics, tragedies, or other deeply held beliefs

Straying into this territory, even unintentionally, hurts people and justifiably incites outrage. Never worth the risk. Vet ideas extensively beforehand.

Dilutes Core Sales Messaging and Seriousness of Offer

Taken too far, humor can undermine your core value proposition or make an offer seem unserious. Keep humor brief and isolated rather than saturating the entire email.

Prospects still expect concise, benefit-driven explanations of what you’re offering. Don’t let being funny eclipse tangible substance.

Carefully Vet Humor for Appropriateness Beforehand

Every humor attempt should pass an ethical smell test first:

• Would I still find this funny if I was the target rather than sender?
• How might marginalized groups experience or interpret this?
• Does this align with my brand values and the tone I want to project?
• Is this completely professional subject matter?
• Would I be comfortable if this humor went public?

If in doubt, avoid gray area humor not central to your message. Apply a safety-first filter to humor attempts.

Don’t Make Entire Email Humorous – Use Sparingly

Avoid letting humor hijack entire emails into a standup monologue. Sprinkle concise bites of humor selectively around key messaging about your offering and value.

Give the prospect’s eye places to rest from humor so main points retain clarity and calls-to-action don’t get lost in the comedy shuffle.

Test Humor Extensively Before Sending at Scale

Before humor email templates are distributed en masse:

• Pilot them with a small friendly test segment and collect feedback
• Assess whether humor works cross-culturally across global clients
• Share internally to spot potential misinterpretations you may be blind to
• Fix bugs based on initial response data from A/B tests and surveys

Humor nuances are hard to predict across different audiences. Small scale trials ensure large scale launches land.

With careful and respectful usage, humor can succeed as an email enhancement. But reckless humor or taking it too far risks catastrophically backfiring. Keep humor professional, tightly targeted, and in moderation. Mastering humor safely and responsibly takes practice – expect gradual refinement rather than instant expertise.

Wrapping Up and Key Takeaways

Humor can be a powerful tool for boosting sales emails beyond generic professional correspondence. But it must be applied delicately and strategically. Key principles to remember include:

Use Humor Sparingly and Only If Appropriate for Prospect

Humor works best when used selectively and thoughtfully, not gratuitously. Before determining if humor has a place in an email, consider factors like:

• The prospect’s personality type and industry
• Existing rapport you’ve built with them
• Previous reactions to your humor attempts
• Their general receptiveness to informal communication

Avoid forcing humor or guessing if you lack clear insights into what resonates with a specific prospect. Personal relevance is crucial.

Ensure Relevance by Tailoring Humor to Industry or Interests

Generic humor often flops. Ideal humor directly relates to:

• The prospect’s specific company, role, or initiatives
• Frustrations or events in their particular industry
• Known personality traits and non-work interests

Prospects want to feel you get their unique world if you’re joking about it. Do your homework to tailor humor to what matters most in their professional and personal lives.

Experiment With Placement and Type of Humor That Works

Every prospect has different humor preferences. The only way to pinpoint what styles work is through continual testing and refinement. Try different approaches to humor, including:

• Dry wit vs slapstick vs hyperbole
• Visual memes vs written jokes
• Pop culture references vs workplace situational humor
• Self-deprecating vs observational humor
• Humor in email intros vs conclusions

Adapt and optimize based on empirical prospect reactions rather than assumptions.

Closely Monitor Results of Humor Through Testing

Apply metrics-based discipline in evaluating humor effectiveness. Specifically track whether emails containing certain types of humor influence:

• Open rates
• Click-through rates
• Prospect reply rates
• Qualified lead conversion rates
• Sales revenue generation

If specified humor tactics don’t positively impact key performance indicators, don’t force them. Follow the data.

Humor Can Help Emails Stand Out and Connect When Done Well

Used strategically, humor makes you more memorable, humanizes your brand, builds rapport, and keeps prospects engaged from subject line to sign-off. But mindful targeting and testing is required to unlock humor’s potential value.

But Don’t Let Humor Dilute Core Sales Messaging and CTA

At the end of the day, prospects want clear details on what you’re offering and what you want them to do next. Don’t allow humor to distract or detract from these fundamentals. Use it to enhance the critical details – not replace them.

With care, creativity and emotional intelligence, humor can help sales emails cut through noise and truly connect with recipients. But like any powerful tool, it requires practice to handle safely and skillfully. Master the balancing act with your prospects’ needs and preferences as the top priority at all times.

Summary on Using Humor Effectively in Sales Emails

Humor can be a valuable tool for enhancing sales emails when applied deliberately, but also risks backfiring if used carelessly. Keep these best practices in mind:

• Tailor humor extremely precisely to each prospect’s personality, interests, and industry pain points. Generic humor often falls flat or confuses.
• Ensure humor remains strictly professional and in no way offensive. Extensively vet jokes through an ethical lens first.
• Use humor sparingly as a complement to core sales messaging, not in excess. Avoid diluting serious details prospects need.
• Test humor extensively through surveys, A/B tests, and performance metrics. Refine approaches based on empirical prospect feedback.
• Place humor strategically in short bursts – subject lines, introductions, images, sign-offs work best. Don’t allow humor to hijack professionalism.
• Humor builds rapport and makes emails memorable when executed thoughtfully. But it can damage your brand if done clumsily or in poor taste.
• Master the humor balancing act with careful targeting, testing, and putting prospect needs first. Humor should enhance, not undermine, your outreach.

Add tasteful humor calibrated to each prospect, but keep core professionalism intact. With practice and emotional intelligence, humor can help sales emails stand out in crowded inboxes.

Frequently Asked Questions

Q: What are some examples of harmless, professional humor I could try in sales emails?

A: Lighthearted gifs poking fun at minor annoyances, amusing industry observations prospects relate to, and soft inside jokes leveraging existing rapport are generally safe starting points.

Q: How much humor should I aim to inject into sales emails?

A: Use humor sparingly, ideally no more than 1-2 instances per email maximum. You want to accentuate your professional messaging, not replace it with comedy. Think seasoning rather than main course.

Q: What metrics should I track to determine if my email humor attempts are working?

A: At minimum, monitor prospect open rates, click-through rates, and reply rates. Positive trends on these indicators suggest your humor is engaging rather than off-putting.

Q: How can I refine my email humor skills?

A: Take improv classes focused on workplace humor, study expert comedic writers, maintain joke idea lists, and continuously A/B test new humor attempts based on prospect feedback.

Q: Is self-deprecating humor about my company ok in sales emails?

A: In moderation, light self-deprecation can make you seem more down-to-earth and approachable. But take care not to excessively undermine perceptions of your competence and expertise.

Q: Should I avoid all politics, religion, ethnicity related humor?

A: Yes, stay far away from any subjects, opinions, or humor that could be perceived as controversial or alienating to entire groups of people. Avoid anything related to marginalized groups or deeply held beliefs.

Q: Is humor appropriate in initial cold outbound sales emails?

A: Use very sparingly and selectively in first interactions where no relationship exists yet. Focus first emails on clear value propositions before gradually injecting humor once rapport is established.

Q: If a prospect doesn’t respond well to my humor attempts, what should I do?

A: Never force humor that a specific prospect obviously doesn’t appreciate. Adapt your style to their personal preferences, even if that means avoiding humor altogether with that person.

Handle humor carefully, tailor it extensively, test it continuously, and keep prospect needs first. Email humor done thoughtfully strengthens connections but carries risks if misused.