Truly listening to a customer and being funny can help you close more deals

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Mike was 45 minutes into an important sales call with a hot prospect. Confident in his meticulously prepared presentation, he powered through slide after slide highlighting his company’s innovative product features. Suddenly, the prospect held up his hand and frowned, “I appreciate all these fancy charts, but what I really need to understand is how this will impact my production costs.” Mike’s face reddened as he realized he had completely missed the mark.

A salesperson’s worst nightmare is misreading a prospect’s needs. This common pitfall can be avoided by sharpening two key skills: active listening and strategic humor. When deployed effectively, these tools build rapport and likability, leading to more fruitful discussions and closed deals. This article will provide actionable techniques to help salespeople hear what customers say – and don’t say – while using comedy to enhance connections.

Importance of Active Listening in Sales

After over a decade in B2B sales, I’ve seen firsthand how vital active listening is for truly understanding prospects’ needs. Early in my career, I would breeze through discovery calls, pitching prospects left and right without taking a breath. I would end each meeting feeling accomplished, only to rarely hear back from those I spoke with.

It finally clicked for me when a prospect named Sam abruptly ended a call after 15 minutes. He apologized for his directness, but explained he did not feel heard. Sam suggested that I try asking more open-ended questions, really focusing on what he said, and summarizing things back to confirm I understood. I realized in my zeal to close the deal, I had not been practicing active listening.

Since that wake-up call, I make it a point to devote my full attention to prospects, eliminating distractions. Through asking thoughtful questions and concentrated listening, I can better identify pain points like Sam’s increased production costs. When I summarize what I heard and the prospect affirms my understanding, I know we are aligning on goals.

This level of active listening establishes trust and rapport. Prospects feel comfortable opening up about challenges when they sense you are invested in truly helping, not just pushing product features and benefits. They also become more willing to take next steps like scheduling demos when they feel heard and understood.

In my experience, active listening is the cornerstone for fruitful discovery calls and sales relationships. When prospects know you care about their needs first, they will be more receptive to how your solution can address those needs. Listening intently ultimately puts you in a better position to close deals.

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Tips for Improving Active Listening Skills

After seeing the power of active listening firsthand, I made it a priority to refine my approach. Through trial and error, I discovered tactics that enabled me to become a more attentive, engaged listener during sales calls. Here are some best practices I personally follow:

First, I eliminate any distractions before calls. I close extraneous browser tabs, silence my phone, and find a quiet space to talk. Giving the prospect my undivided attention is key. I also jot down thoughts beforehand so I can clear my mind to focus solely on what the other person is saying.

During discussions, I ask open-ended questions that elicit detailed responses beyond yes/no answers. Phrasing questions to start with “what”, “how”, or “why” encourages the prospect to elaborate on their needs and experiences.

Equally important is periodically paraphrasing what I heard. I’ll summarize key details and pain points to confirm my interpretation is accurate. This shows prospects I’m not just hearing them, but carefully processing the information to understand their perspective.

Taking strategic notes is another technique I leverage. I jot down challenges mentioned, keywords or phrases used frequently, and any crucial context. Referring back to these notes helps me recap and show the prospect I captured their vital concerns.

Mastering these listen-first skills transformed my discovery calls. Prospects open up more about motivations knowing I am fully engaged. The insights gained allow me to tailor solutions directly to their needs, moving deals forward. Putting these tips into practice can strengthen listening and in turn, sales success.

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Benefits of Using Humor in Sales Interactions

Early in my B2B sales career, I viewed meetings with prospects as serious, straight-laced affairs. I thought joking around or bringing levity into the conversation would undermine my professionalism. However, I realized that appropriate, strategic humor can actually humanize salespeople and strengthen connections.

Adding humorous moments helped me become more relatable and likable to prospects. One client even mentioned my “witty but not overbearing” sense of humor put him at ease during negotiations. Rather than a robotic pitch bot, I came across as an authentic person genuinely invested in helping.

Humor also proved valuable for reducing tension in challenging talks. When a prospect grew frustrated explaining their pain points, I would crack a self-deprecating joke, like poking fun at my terrible golf skills. This brought a much-needed laugh, lifting the mood. The prospect became more receptive to collaborating.

Moreover, quick-witted, confident humor displayed charisma and gravitas. I noticed prospects responded positively when I peppered in a well-timed quip or amusing anecdote. This aligned with research showing humor boosts perceived competence.

Perhaps most importantly, appropriate comedy made prospects more open to exploring my suggested solutions. Presenting ideas playfully helped them see new perspectives. The sales process transformed from a rigid transaction into a rewarding human connection.

Clearly, when used strategically, humor can add levity, strengthen rapport, and ultimately advance sales. I encourage reps to infuse their authentic wit and charm into meetings. A little laughter can go a long way.

Custom branding
Showcase your brand.
Video narrations
Easily video-narrate sales presentations or proposals when needed (otherwise video is optional). Redo slide if you made a mistake. Use built-in teleprompter to record longer videos.

Data rooms
Attach any supporting files and links. Make it easy for your prospects and clients to find the right information quickly.

Company profiles
Create company profiles with custom banners and info-packages tailored to different industries.
Contact details
Show your contact info easily accessible by your prospects and clients.
Custom CTAs
Add custom CTAs to drive prospects or clients to your calendar, sign up form, etc.
Engagement analytics
See how prospects and clients interact with your PDFs.

Feedback and Reactions
Collect feedback from prospects and clients. Feedback and reactions are not publicly visible.
Share PDFs
Share any existing PDF presentations and documents.
Live links
Share with a single link. Update files even after sharing your link. Get notified when your PDF is viewed. Turn off access anytime.

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Using Humor Effectively in Sales

Once I realized the upsides of strategic humor, I had to learn how to apply comedy skillfully during sales interactions. Through trial and error, I picked up tactics for deploying humor in a way that builds connections without crossing any lines.

First and foremost, I take cues from prospects to assess their sense of humor. If they use sarcasm, witty quips, or tell stories jokingly, I may reciprocate that style. However, with more reserved clients, I keep it straightforward. Adapting to their humor preferences makes comedy feel organic, not forced.

When I do use humor, less is more. I sprinkle in occasional amusing comments or anecdotes rather than trying to be funny nonstop. This prevents prospects from feeling I’m not taking the process seriously. I also avoid humor that may come across as controversial or offensive. Self-deprecating jokes tend to be a safe bet.

Knowing when to laugh at myself has proven valuable for forming bonds. Like when I fumbled around trying to share my screen, I joked about my lackluster tech skills. Being willing to poke fun at my mistakes makes me more human to prospects.

It’s also crucial that I match the overall tone of the conversation. In tense talks, humor lightens the mood. But for straightforward analysis of needs, I keep things focused, adding humor only when appropriate.

Ultimately, humor strengthens connections only when used strategically. I recommend reps carefully tailor comedy to prospects based on observation and listening first. When executed naturally, humor opens doors in sales relationships.

Humor and Active Listening Working Together in Sales

In my experience, active listening and strategic humor complement each other beautifully for sales success. When used in tandem at the right moments, they enable deeper mutual understanding and trust.

Active listening provides insights into a prospect’s sensibilities that inform when and how to use humor. I listen closely for subtle cues about their personality and preferences. Do they frequently chuckle at things? Do they seem to appreciate sarcasm? This understanding guides if and when comedy might resonate.

Once I establish rapport through engaged listening, I may sprinkle in occasional amusing comments or stories. However, I only do so after demonstrating sincere interest in their needs first. Earning trust opens the door for appropriate humor as an additional connection builder.

Finally, humor can subtly diffuse tension that arises during more difficult conversations. When a prospect grows frustrated recounting challenges, lightening the mood with a self-deprecating joke helps release the tension. Laughter restores a positive spirit, allowing us to address issues rationally.

Overall, integrating humor thoughtfully once listening provides a foundation aligns with my sales experience. Prospects do not want comedy forced upon them prematurely. But when used judiciously after establishing relationship, humor enhances sales interactions meaningfully. Listen first, infuse humor next for optimal results.

Conclusion

Throughout my sales career evolution, I’ve learned active listening and strategic humor separate good reps from great ones. These skills were not innate for me. I developed them through concerted effort and practice over time.

Active listening proves one’s sincere interest in customers’ perspectives. When I devote my full attention and focus to understanding prospects’ needs, they sense my authentic priority is helping them, not making a quick sale. This builds the rapport vital for sales success.

Likewise, when used thoughtfully, humor endears salespeople as authentic, confident, and charismatic. Laughter relieves tension while allowing one’s competence, passion, and wit to shine through.

Yet neither skill works in isolation. Thoughtful humor has no place without the relationship nurtured through attentive listening first. And listening loses impact without occasional levity to strengthen the human connection.

Mastering this blend of listen-first empathy and judicious humor has elevated my discovery calls, negotiations, and closings. Prospects consistently provide positive feedback on my personable approach. More importantly, these skills directly convert to increased sales.

For any salesperson seeking to win more deals and retain loyal accounts, I recommend wholeheartedly developing your listening and comedy chops in tandem. Doing so can refresh your process and excel your career. When implemented strategically, these human skills will undoubtedly drive results.

FAQs

Why is active listening important in sales?

Active listening shows prospects you care about understanding their needs first, building trust/rapport that makes them more likely to buy from you. It provides insights so you can tailor solutions.

Eliminate distractions, ask open-ended questions, paraphrase what you hear, take strategic notes, and summarize key points back to show understanding.

Humor makes salespeople seem more charismatic, likeable and relatable. It reduces tension in difficult conversations and makes prospects more receptive to ideas.

Avoid humor if prospects seem reserved. Never use controversial, political, or offensive humor. Don’t let humor diminish perceived competence.

Listen for cues like sarcasm or witty banter to assess if humor may resonate. Adapt your style to the prospect’s sensibilities.

Self-deprecating jokes, amusing anecdotes, and well-timed wit tend to work. Poke fun at yourself, not the prospect. Keep it clean and professional.

No, establish rapport through listening first. Once trust is built, humor can organically strengthen the connection.

Yes, prospect may perceive forced humor as unprofessional or disingenuous. Never laugh at a prospect vs laughing with them.

They build mutually reinforcing rapport. Listening informs appropriate humor, and humor strengthens connections established via listening.

About the Author

Our content team of sales, lead generation, and marketing experts provides industry-leading thought leadership on B2B sales and marketing, lead nurturing, and sales enablement strategies. With decades of combined C-suite and VP-level experience, we deliver actionable B2B sales and marketing content that gives B2B companies a competitive advantage. Our proven insights on lead management, conversion rate and sales optimization, sales productivity, and tech stack empower companies to increase revenue growth and ROI.

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