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We all need a "lollipop" that opens real conversations.
by Drew Robbins
3 min read
Invest In Relationships
A simple, unexpected prompt can cut through busyness and help people drop their guard, turning rushed exchanges into real conversations that build trust and connection.
This morning I asked my daughter if she was looking forward to school, expecting a playful "of course not." Instead she lit up. Today homeroom meant time with close friends, and in second period her English class handed out lollipops. I asked if she had a favorite flavor. "Not really, but that's not important. The lollipop gives me an opening to have a conversation with kids in the next period." She had found a simple, repeatable icebreaker that turned small talk into connection. It stopped me in my tracks.
We all need a lollipop. At work, small, unexpected prompts can cut through busyness and help people drop their guard. A vivid question about what someone is learning right now, a comment about a shared moment in the meeting, or a quick appreciation with a follow up, these moves create openings for trust and genuine conversation. People respond because it feels human, specific, and unhurried.
Work gets better when we move beyond status updates and into real conversation. When someone asks a surprising, generous question, others lean in. Meetings feel lighter, cross-team work gets easier, and collaboration speeds up. This is not networking for leverage. It is practical generosity that compounds into resilience, opportunity, and a culture where people want to contribute.
Relationships are the safety net beneath our risks and the multipliers of our impact.
— When No One's Keeping Score
What could be your "lollipop" this week, a simple, unexpected prompt that turns a rushed exchange into a real conversation?
Try This
Open your next chat with a concrete, human question such as 'What are you excited to learn this month?' or 'What surprised you in that meeting?'
Notice What Happens
Watch for smiles, longer answers, and follow up questions that signal trust.
Share or Reflect
Post one 'lollipop question' you plan to use, or share a moment when an unexpected prompt opened a door.
Keep Going
Build a short list of go to prompts, use one daily, and let generosity be your default.
If this resonates, share with your network to help others invest in relationships that truly matter.
