Best Would You Rather Posts for Sales Closing

Best Would You Rather Prompts for Sales Closing Communities

Need help sparking fresh conversations in your sales closing community? Our Would You Rather templates are the perfect solution to encourage creativity and lively discussions. Use these prompts to get members thinking outside the box and sharing their unique perspectives.

Sales Closing 41 Templates

Why This Works

Would You Rather questions tap into members' imaginations and foster a playful environment. By presenting two intriguing choices, you invite participants to reflect, compare, and justify their preferences, which leads to deeper engagement and richer discussions. This format lowers the barrier to participation by making it easy for everyone to join in, regardless of their experience level.

In sales closing communities, these hypothetical scenarios are especially effective because they mirror the decision-making processes reps face daily. Posing lighthearted dilemmas related to closing deals helps members practice creative thinking and develop new perspectives, all while building camaraderie.

41 Ready-to-Use Templates

Would you rather close a huge deal solo or a smaller one as part of a dream team?

💡 Example: "I would rather close a smaller deal with a dream team because collaboration fuels my motivation."

🟡 Medium Engagement Barrier 👤 Average #teamwork #deal size

Would you rather have unlimited leads or a 100 percent close rate on your current pipeline?

💡 Example: "Unlimited leads would be amazing, but a 100 percent close rate is unbeatable for my pipeline."

🔴 High Engagement Barrier 👤 Frequent #leads #conversion

Would you rather win an award for top closer or get a massive bonus for a single deal?

💡 Example: "I would rather get the award because recognition lasts longer than a one-time bonus."

🟡 Medium Engagement Barrier 👤 Average #recognition #compensation

Would you rather have every prospect say yes but at a lower price or close fewer high-value deals?

💡 Example: "I prefer fewer high-value deals because they are more impactful for quotas."

🟡 Medium Engagement Barrier 👤 Average #pricing #volume

Would you rather demo a product you love or sell one you know will close easily?

💡 Example: "Selling a product I love makes my pitch more authentic."

🟢 Low Engagement Barrier 👤 Lurker #demo #product

Would you rather close deals remotely or always in person?

💡 Example: "Remote closing is more efficient for me, but in-person feels more rewarding."

🟡 Medium Engagement Barrier 👤 Irregular #remote #in-person

Would you rather handle objections up front or address them at the end of your pitch?

💡 Example: "I like to tackle objections early so I can tailor my approach."

🟡 Medium Engagement Barrier 👤 Average #objections #timing

Would you rather have one loyal long-term client or many short-term wins?

💡 Example: "Long-term clients build stronger relationships and recurring revenue."

🟡 Medium Engagement Barrier 👤 Average #client retention #short-term

Would you rather master cold calls or become a follow-up email expert?

💡 Example: "Cold calling mastery opens more doors for new business."

🟢 Low Engagement Barrier 👤 Lurker #cold calling #email

Would you rather always meet quota on time or occasionally exceed it by a lot?

💡 Example: "Consistently meeting quota keeps my stress low."

🟡 Medium Engagement Barrier 👤 Average #quota #performance

Would you rather handle a pipeline packed with small deals or a few big ones?

💡 Example: "Few big deals are easier to manage and track."

🟡 Medium Engagement Barrier 👤 Average #pipeline #deal size

Would you rather close a deal with a super short sales cycle or one that took a year?

💡 Example: "Short cycles are satisfying but long ones usually mean bigger wins."

🟡 Medium Engagement Barrier 👤 Frequent #sales cycle #speed

Would you rather pitch to a new industry or stick with what you know?

💡 Example: "New industries keep things exciting and challenging."

🟢 Low Engagement Barrier 👤 Irregular #industry #pitch

Would you rather have a mentor for every deal or unlimited training resources?

💡 Example: "A mentor for every deal would be invaluable for growth."

🟡 Medium Engagement Barrier 👤 Average #mentorship #training

Would you rather negotiate with a friendly or a tough client?

💡 Example: "Tough clients push me to improve my negotiation skills."

🟡 Medium Engagement Barrier 👤 Average #negotiation #clients

Would you rather get more referrals or have higher conversion rates on cold leads?

💡 Example: "Referrals are warmer and usually close faster."

🟡 Medium Engagement Barrier 👤 Average #referrals #conversion

Would you rather use automation tools or rely on a personal touch for closing?

💡 Example: "Personal touch is key for building trust."

🟢 Low Engagement Barrier 👤 Lurker #automation #personalization

Would you rather close a deal with little info or have every detail before you start?

💡 Example: "More information helps me tailor my pitch and anticipate objections."

🟡 Medium Engagement Barrier 👤 Average #information #preparation

Would you rather be known for your closing skills or your networking ability?

💡 Example: "Closing skills are more measurable and impactful for my role."

🟡 Medium Engagement Barrier 👤 Average #reputation #skills

Would you rather close a record deal on your birthday or on the last day of the quarter?

💡 Example: "Birthday wins are extra special!"

🟢 Low Engagement Barrier 👤 Irregular #milestones #timing

Would you rather have a smooth negotiation or a fast decision every time?

💡 Example: "Fast decisions reduce the stress of waiting."

🟡 Medium Engagement Barrier 👤 Average #negotiation #decision-making

Would you rather close deals in a competitive market or a niche market?

💡 Example: "Niche markets allow for more tailored value propositions."

🟡 Medium Engagement Barrier 👤 Average #market #competition

Would you rather close a deal over coffee or via video call?

💡 Example: "Coffee meetings help build rapport."

🟢 Low Engagement Barrier 👤 Lurker #meeting #closing

Would you rather be a product expert or a relationship builder for closing?

💡 Example: "Building relationships leads to repeat business."

🟡 Medium Engagement Barrier 👤 Average #expertise #relationships

Would you rather close a difficult deal with a big company or an easy deal with a startup?

💡 Example: "Big company deals are more rewarding and look great on the resume."

🟡 Medium Engagement Barrier 👤 Average #difficulty #client type

Would you rather have a long sales lunch or a quick call to close a deal?

💡 Example: "Quick calls save time for more prospecting."

🟢 Low Engagement Barrier 👤 Lurker #sales lunch #call

Would you rather close deals with detailed proposals or simple contracts?

💡 Example: "Simple contracts speed up the closing process."

🟡 Medium Engagement Barrier 👤 Average #proposals #contracts

Would you rather have a flexible closing deadline or a fixed one?

💡 Example: "Fixed deadlines keep everyone accountable."

🟡 Medium Engagement Barrier 👤 Frequent #deadlines #closing

Would you rather win deals through storytelling or data-driven pitches?

💡 Example: "Storytelling connects emotionally with clients."

🟡 Medium Engagement Barrier 👤 Average #storytelling #data

Would you rather get sales advice from a legend or learn by trial and error?

💡 Example: "Advice from legends can shortcut years of mistakes."

🟢 Low Engagement Barrier 👤 Irregular #advice #learning

Would you rather close deals with scripts or improvise every time?

💡 Example: "Improvisation lets me adapt on the fly."

🟡 Medium Engagement Barrier 👤 Average #scripts #improvisation

Would you rather have unlimited time to close or unlimited resources for closing?

💡 Example: "Unlimited resources make the process smoother."

🟡 Medium Engagement Barrier 👤 Average #resources #time

Would you rather close a deal that helps a charity or one that breaks a personal record?

💡 Example: "Helping a charity feels more meaningful."

🟡 Medium Engagement Barrier 👤 Frequent #impact #achievement

Would you rather get instant feedback after every pitch or a monthly performance review?

💡 Example: "Instant feedback helps me improve faster."

🟡 Medium Engagement Barrier 👤 Average #feedback #reviews

Would you rather close a deal in your favorite city or from your home office?

💡 Example: "Nothing beats the comfort of my home office."

🟢 Low Engagement Barrier 👤 Lurker #location #remote

Would you rather have every meeting start on time or end early with a closed deal?

💡 Example: "Ending early with a closed deal is the dream."

🟡 Medium Engagement Barrier 👤 Average #meetings #efficiency

Would you rather have a perfect CRM or a support team that anticipates every need?

💡 Example: "A proactive support team is a game changer."

🟡 Medium Engagement Barrier 👤 Top #CRM #support

Would you rather follow up by phone or by creative video message?

💡 Example: "Video messages stand out and grab attention."

🟢 Low Engagement Barrier 👤 Irregular #follow-up #communication

Would you rather close a deal with a handshake or with a digital signature?

💡 Example: "Digital signatures are faster and more convenient."

🟢 Low Engagement Barrier 👤 Lurker #closing #signature

Would you rather learn a new sales technique every month or master one skill deeply?

💡 Example: "Mastering one skill leads to expertise and confidence."

🟡 Medium Engagement Barrier 👤 Average #learning #skills

Would you rather always have the perfect pitch or always have the perfect timing?

💡 Example: "Perfect timing gets the best results in my experience."

🟡 Medium Engagement Barrier 👤 Average #pitch #timing

How to Use These Templates

To use these templates, simply copy a question and post it as a new thread or within your community chat. Encourage members to vote or comment with their choice and, if possible, explain their reasoning. Rotate these prompts regularly to keep engagement high and adapt the scenarios to current topics or challenges your team is facing. You can also invite members to submit their own variations for added involvement.

Best Practices

✓ Keep scenarios relevant to real sales closing experiences.
✓ Encourage members to explain their choices for deeper conversation.
✓ Maintain a playful tone to make participation fun and low-pressure.
✓ Rotate questions regularly to avoid repetition.
✓ Monitor responses to identify new discussion themes or pain points.

All Platforms Tips

These Would You Rather templates are designed for all platforms. For forums and Slack, post as a new thread with a clear call for replies. On Facebook or LinkedIn, use as a text post or in Stories with polls. For chat apps like Discord, pin the question for easy access and encourage quick reactions using emojis.

Frequently Asked Questions

How can I craft Would You Rather prompts that highlight advanced closing techniques like the assumptive close versus the summary close?

Focus your prompts on real-life scenarios that force members to choose between closing methods, such as 'Would you rather use the assumptive close or the summary close when a prospect is hesitating on price?' This sparks discussion about the merits and challenges of each technique, encouraging members to share experiences and strategies relevant to high-level sales closing.

Should I include product-specific scenarios, such as B2B SaaS versus enterprise hardware sales, in my Would You Rather posts?

Yes! Tailoring prompts to reflect different product contexts—like 'Would you rather close a six-month SaaS deal with a drawn-out procurement process or a one-call close on high-ticket hardware?'—helps your community relate more closely to the prompts and share nuanced insights based on their sales verticals.

How can I use Would You Rather prompts to address common objections like budget constraints or decision-maker unavailability?

Create prompts that present members with realistic objection-handling dilemmas, such as 'Would you rather face a budget objection at the negotiation table or find out the decision-maker is unavailable after your demo?' This allows members to debate objection-handling strategies and share best practices for overcoming these classic sales closing barriers.

Is it effective to use Would You Rather prompts based on pipeline stages, such as late-stage negotiation versus final paperwork?

Absolutely. For example, ask 'Would you rather handle a stalled deal during late-stage negotiation or push through complex legal paperwork at the final stage?' This helps members discuss pain points unique to each pipeline stage and fosters deeper engagement around the full sales closing cycle.

Can Would You Rather prompts help members explore ethical gray areas in sales closing, like disclosing all pricing options upfront?

Yes, these prompts are a great way to discuss ethical dilemmas. For example, 'Would you rather risk losing a deal by disclosing every pricing tier upfront, or withhold some options until the client asks?' This encourages members to reflect on best ethical practices and share stories about transparency and trust in the closing process.

How do I make Would You Rather prompts resonate with teams using different sales methodologies, such as SPIN Selling versus Challenger Sales?

Design prompts that pit methodologies against each other in practical situations, like 'Would you rather use a SPIN Selling approach for a hesitant client or challenge them with insights as per the Challenger method?' This inspires comparative discussions and helps members evaluate which methods work best for specific closing scenarios.