Three Clever Brainteasers to Get Your Meeting Off to a Productive Start

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By on November 29, 2012 in Leadership with 0 Comments

The best work meeting I’ve ever attended (admittedly a very low bar) began with an interesting surprise. It was a small thing, but it improved the mood of the group right from the beginning and made us feel relaxed and comfortable. As a result, the meeting generated real progress and great ideas, and it even strengthened the bonds among the team.

The surprise was waiting for us as we walked in. Written on the white board at the front of the conference room was this question:

Which are worth more: 1978 pennies or 1987 pennies?

I’ll get to the answer later (no peeking). But if you have to run meetings, or if you just need to gather a few co-workers for an informal brainstorming session, here’s the key lesson that this brilliant little riddle can offer you.

Your attendees will almost always come to your meeting distracted – thinking about emails they have to answer, tasks they have to complete, calls they have to make, other meetings they have to prepare for.

If you want your group’s full attention, one great idea is to start your meeting with a mental exercise that’s both enjoyable and calls on as much of your attendees’ brainpower as possible.

The more the riddle or brainteaser mentally taxes them, the more your attendees will need to focus on it – rather than that distracting mental to-do list they walk into the room thinking about.

Now for the answer to that brainteaser above:

Answer: 1987 pennies are worth more.

Why? Because those aren’t dates – they’re amounts. One thousand nine hundred eighty-seven pennies are worth more – nine cents more – than one thousand nine hundred seventy-eight pennies.

In addition to helping your attendees set aside the mental distractions they bring into your meeting, starting with a riddle or brainteaser has other benefits:

  1. It lets your attendees stretch their creative muscles and get into the creative process, which will help generate better ideas and insights in the meeting.
  2. It puts every attendee in the room in the same situation. For those few moments while everyone is wrestling with your brainteaser, there is no hierarchy. Anyone in the room could be the one who discovers the answer first, and your junior employees can see that even the most senior-level person doesn’t always have the answers. That’s valuable, because it lets the more junior employees feel comfortable speaking up later in the meeting.
  3. It can help strengthen your team. When everyone is facing the same tough questions, and no one has the answers right away, your attendees will inevitably feel a little closer to each other. And that can be invaluable for your team’s ongoing productivity.

In the meeting I attended with that pennies question, I remember people walking in, spotting the question on the board, staring at it, and then looking around the room at the other attendees and… laughing. It was a hard riddle, and everyone seemed to enjoy trying to solve it. That’s why that meeting was so productive – we were all acting like more of a team than we normally did.

By the way, in addition to offering them at the beginning of your meetings, riddles and brainteasers can also be valuable at other points during a meeting – right after a break, for example, or as you transition from one topic to another. You can even send them to your team in email, if you think they need a creative jumpstart, and offer a prize (or even just recognition and bragging rights) to the first to get the answer right.

Okay, sold on brainteasers? Here are a couple more I’ve seen used in meetings – and both times the meetings that followed were quite productive.

The five-cups brainteaser

Arrange five cups or glasses on a table, three in a vertical line and then two horizontally to the right, forming an L shape.

See the first picture below for the layout of the brainteaser. The second image shows how it’s solved. (No peeking.)

The three cups lined up vertically each have some juice (or any liquid) in them, and the other two are empty.

Five-cups brainteaser – SETUP

5 cups on a table in an 'L' shape

The objective is to rearrange this set so that every other cup has juice. So, from top to bottom, and then from bottom left to right, it should go juice… empty… juice … empty… juice.

And the rule is, you can touch or move only one cup.

Think about it for a few seconds. Now, if you were running a meeting, every attendee would be completely focused on this brainteaser. They’d be looking at each other. Maybe laughing. Maybe shouting out guesses.

Ready for the answer? Look below.

Five-cups brainteaser – SOLVED

Hand pouring liquid from one cup into another


Answer: pick up the filled cup in the middle, and pour it into the empty cup on the far right.

Remember, the riddle says you can touch or move only one cup, so most people think about rearranging the cups in their existing form – filled with juice, or empty. It doesn’t occur to most of us to empty the contents of one cup into another.

Try that one on your staff. They’ll love it!

Here’s one more.

The light-switch brainteaser – SETUP

On a wall are three standard on/off switches, side-by-side-by-side, each switched to the “off” (or down) position.

One (and only one) of these switches controls a light bulb in a closet in the next room. The other two switches do nothing.

The objective: figure out which of the three switches turns on that closet light.

You can open the closet door only once, and you cannot touch or change any switches after you’ve opened the closet door. Damaging or disassembling the door, walls, or switches is also against the rules. And no cheating – assume the closet is light-tight, so you would not be able to see the light from where you’re standing.

Within these constraints, can you determine which switch controls the light bulb?

The light-switch brainteaser – SOLVED

Answer: turn on switch 1, and leave it turned on for about five minutes. Then turn it off and flip on switch 2. Then open the closet door.

If the light is on, obviously it’s switch 2.

If the light is off, touch the light bulb. If it’s hot, then it’s switch 1.

And if the light is off and not hot, then it’s switch 3.

Try these in your next meeting. I promise a much more lively, creative and productive gathering than normal.

And finding more of these is simple. Just google “brainteaser.”

© 2020 Robbie Hyman. All rights reserved. This article may not be reproduced without express written consent from Robbie Hyman.

About the Author

Robbie Hyman is a professional communications and public affairs writer. He has 15 years’ experience writing for nonprofits, small business and multibillion-dollar international organizations and is available as a freelance writer for federal agencies.

Robbie has written thousands of pages of content, including white papers, speeches, published articles, reports, manuals, newsletters, video scripts, advertisements, technical document and other materials. He is also co-founder of, an online course that teaches smart money habits to teenagers.