Have you ever found yourself conversing with someone who only gives one-word answers or where there’s a lot of awkward silence? 

I had a meeting today in which one of the participants arrived on time, but the others were running five minutes late. There I was, stuck in a virtual conference room with someone I didn’t know very well, and it was difficult to engage him in a conversation until the others arrived.

Sure, we could have gone on mute and continued our work until others arrived. If I had done that, I would have missed a golden opportunity to start building a positive and productive relationship with him.

So, what did I do? I pulled out my Back Pocket Questions.

Back Pocket Questions are pre-prepared, versatile questions you keep ready for moments when the conversation lags. They’re designed to be open-ended, encouraging detailed responses and further discussion.

Having these questions ready can help ease anxiety when conversations stall, enhance engagement to keep people interested in talking with you, and build deeper connections and understanding of each other.

The person in my meeting was clearly having a bad day and didn’t seem too interested in speaking with me (or being in the meeting). However, I was able to turn it around by asking the right questions to get him out of his funk and interacting with me. 

So, I encourage you to develop some back pocket questions to keep handy if you find yourself in a similar situation.

How to Develop Back Pocket Questions

1. Keep it Open-Ended: Aim for questions that require more than a yes or no answer, which encourages sharing thoughts, feelings, and experiences.
2. Make it Relevant but Broad: Choose questions that can be relevant in various contexts but broad enough to apply to different people.
3. Aim for Positivity: Focus on positive questions that make people feel good about their responses, fostering a pleasant and memorable conversation.

Examples to Get You Started

• “What do you think about __________?” Fill in the blank with something relevant and avoid politics, religion, or sensitive issues.
• “What’s one skill you’ve recently started developing, and what inspired you to pursue it?”
• “Outside of work, what are you passionate about?”
• “Can you tell me about a memorable experience you had this past year?”
• “What has been the most rewarding moment in your career so far?”
• “If you had a magic wand, what’s one thing you would change about _______ and why?”
• “What’s one thing you’re looking forward to in the coming months?”
• “What’s an important lesson you learned from a challenge you faced?”

Using Your Questions Effectively

• Listen Actively: Show genuine interest in the answers and use them as a springboard for further discussion.
• Tailor to the Context: Choose your questions based on the setting and how well you know the person.
• Keep it Natural: Integrate questions smoothly into the conversation so they don’t feel forced or out of place.

Like any skill, becoming adept at using “back pocket” questions takes practice. Try them out in different scenarios to see what works best and refine your approach based on what you learn.

Wishing you the best!