Struggling to spark 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.
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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.
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."
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."
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."
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."
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."
Would you rather close deals remotely or always in person?
💡 Example: "Remote closing is more efficient for me, but in-person feels more rewarding."
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."
Would you rather have one loyal long-term client or many short-term wins?
💡 Example: "Long-term clients build stronger relationships and recurring revenue."
Would you rather master cold calls or become a follow-up email expert?
💡 Example: "Cold calling mastery opens more doors for new business."
Would you rather always meet quota on time or occasionally exceed it by a lot?
💡 Example: "Consistently meeting quota keeps my stress low."
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."
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."
Would you rather pitch to a new industry or stick with what you know?
💡 Example: "New industries keep things exciting and challenging."
Would you rather have a mentor for every deal or unlimited training resources?
💡 Example: "A mentor for every deal would be invaluable for growth."
Would you rather negotiate with a friendly or a tough client?
💡 Example: "Tough clients push me to improve my negotiation skills."
Would you rather get more referrals or have higher conversion rates on cold leads?
💡 Example: "Referrals are warmer and usually close faster."
Would you rather use automation tools or rely on a personal touch for closing?
💡 Example: "Personal touch is key for building trust."
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."
Would you rather be known for your closing skills or your networking ability?
💡 Example: "Closing skills are more measurable and impactful for my role."
Would you rather close a record deal on your birthday or on the last day of the quarter?
💡 Example: "Birthday wins are extra special!"
Would you rather have a smooth negotiation or a fast decision every time?
💡 Example: "Fast decisions reduce the stress of waiting."
Would you rather close deals in a competitive market or a niche market?
💡 Example: "Niche markets allow for more tailored value propositions."
Would you rather close a deal over coffee or via video call?
💡 Example: "Coffee meetings help build rapport."
Would you rather be a product expert or a relationship builder for closing?
💡 Example: "Building relationships leads to repeat business."
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."
Would you rather have a long sales lunch or a quick call to close a deal?
💡 Example: "Quick calls save time for more prospecting."
Would you rather close deals with detailed proposals or simple contracts?
💡 Example: "Simple contracts speed up the closing process."
Would you rather have a flexible closing deadline or a fixed one?
💡 Example: "Fixed deadlines keep everyone accountable."
Would you rather win deals through storytelling or data-driven pitches?
💡 Example: "Storytelling connects emotionally with clients."
Would you rather get sales advice from a legend or learn by trial and error?
💡 Example: "Advice from legends can shortcut years of mistakes."
Would you rather close deals with scripts or improvise every time?
💡 Example: "Improvisation lets me adapt on the fly."
Would you rather have unlimited time to close or unlimited resources for closing?
💡 Example: "Unlimited resources make the process smoother."
Would you rather close a deal that helps a charity or one that breaks a personal record?
💡 Example: "Helping a charity feels more meaningful."
Would you rather get instant feedback after every pitch or a monthly performance review?
💡 Example: "Instant feedback helps me improve faster."
Would you rather close a deal in your favorite city or from your home office?
💡 Example: "Nothing beats the comfort of my home office."
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."
Would you rather have a perfect CRM or a support team that anticipates every need?
💡 Example: "A proactive support team is a game changer."
Would you rather follow up by phone or by creative video message?
💡 Example: "Video messages stand out and grab attention."
Would you rather close a deal with a handshake or with a digital signature?
💡 Example: "Digital signatures are faster and more convenient."
Would you rather learn a new sales technique every month or master one skill deeply?
💡 Example: "Mastering one skill leads to expertise and confidence."
Would you rather always have the perfect pitch or always have the perfect timing?
💡 Example: "Perfect timing gets the best results in my experience."
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.
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.
Post once or twice a week to keep the content fresh and encourage ongoing participation without overwhelming members.
Absolutely. Feel free to tweak the wording or scenarios to better match your company's style, products, or current campaigns.
Include a simple call to action like 'Tell us why you chose your answer' or highlight interesting responses in follow-up posts.
Yes, these questions are designed to work in any size community and can spark engagement regardless of group size.
Track comments, votes, and reaction counts on your posts. Consider running periodic polls to see which types of scenarios resonate best.
Try posting at a different time or tagging a few active members to kick off the conversation. You can also ask for suggestions on future topics.
You can use them in both. They work well in private team spaces for team-building as well as in public communities for broader engagement.