How do I avoid rabbit holes?

Two Dummies
5 min readDec 10, 2020

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Photo by Lysander Yuen on Unsplash

Live in Antarctica! Rabbits inhabit every continent except Antarctica. Wait… let me try again. How do I avoid rabbit holes during my meetings?

Rabbit holes have been on my mind a lot recently. I find myself in numerous conversations each week that spiral out of control, veer off topic, or go off on a tangent. During those conversations, inevitably, someone will say something like “Ok, I think we’re going down a rabbit hole” or “Sorry, I didn’t mean to go down that rabbit hole”.

In consulting, I often find myself hearing or using business jargon and buzzword-filled phrases. I’ll sometimes default to an expression rather than speak plainly and directly. Describing someone or something as being “in a rabbit hole’ is a frequent example and I’ve used the phrase for years without knowing the origin. As far as I can find, the phrase was first used in Lewis Carroll’s Alice’s Adventures in Wonderland & Through the Looking-Glass. Chapter 1 is titled “Down the Rabbit-Hole”. The book starts with Alice following a well-dressed rabbit into a hole. Upon entering, she is suddenly falling for an unexpected, abnormal, and extended amount of time before finally reaching the ground, finding herself in a strange world and at the beginning of a literary classic. Carroll’s fantastical rabbit hole drives the meaning of the expression we use today which Oxford Languages defines as “used to refer to a bizarre, confusing, or nonsensical situation or environment, typically one from which it is difficult to extricate oneself.”

At work, I mostly hear the phrase “rabbit hole” said with some disdain and invoking a negative connotation: they are frivolous and something to be avoided. But, under the right circumstances they should be embraced. Rabbit holes can be beautiful, fun, unfettered explorations into a great unknown and useful experiences for immersion into a topic.

It’s important to know when they’re appropriate, and when they’re not. When unwanted and unplanned, rabbit holes are frustrating, disruptive, unproductive, and wasteful. So the question “how do I avoid rabbit holes during my meetings?” should really be, “if I am trying to avoid rabbit holes in my meetings, what should I do?” That is a better question.

Here’s what I do to minimize undesired rabbit holes and guide my conversations more productively and effectively.

1. Set constraints.

To keep a meeting from going in an unintended direction, put constraints on the conversation to limit the possible number of directions. There are a number of go-to constraints Garett and I define when designing collaborative interventions with clients: objectives (the three to five reasons why a session is bringing people together), scope (the range of topics and focus areas to be covered in the session), and givens (the non-negotiable design parameters set in stone by the universe prior to the session).

With constraints clearly articulated, conversation that does not advance the objectives, touches on subjects or themes outside the scope, or doesn’t adhere to the givens could be viewed as rabbit hole territory. It’s easier to avoid something when you can clearly identify when it’s happening.

2. Establish ground rules.

When you have a clear sense of direction for your meeting, you need to establish ground rules to support your direction. Ground rules should be easy to understand, straightforward, and directive. Strong ground rules include:

  • Focus all conversation on the objectives, scope, and givens.
  • If a topic is identified that needs to be discussed but outside the scope of this conversation, we will schedule additional time to discuss it.
  • Off-topic conversations should be interrupted by anyone in the group and guided back to the topics at hand.

I find the third example to be initially contentious because people’s immediate reaction to an interruption is that it is rude. Allay those reactions by framing interruptions that stop a conversation from tumbling down into a rabbit hole as being in service of the conversation rather than a slight against the person being interrupted. Be hard on the work, not on each other.

It’s important for everyone to acknowledge and agree to the ground rules before launching into your meeting.

3. Enforce the rules. If needed, interrupt.

When you hear a conversation headed into a rabbit hole, try to drive the conversation back within the established constraints. Pause and reread the objectives, scope, and givens to the meeting participants. Remind participants of the agreed upon ground rules. Then, if the journey into the rabbit hole continues, interrupt the culprits. Interrupting someone going full force on a tangent is hard to do — I often find myself uncomfortable doing it, even when it’s sanctioned by the ground rules. I’ve found motivation to interrupt in Priya Parker’s, The Art of Gathering in which she explores the importance of sticking to the rules.

A ubiquitous strain of twenty-first-century culture is infecting our gatherings: being chill. The desire to host while being noninvasive. “Chill” is the idea that it’s better to be relaxed and low-key, better not to care, better not to make a big deal… Chill is a miserable attitude when it comes to hosting gatherings… In gatherings, once your guests have chosen to come into your kingdom, they want to be governed — gently, respectfully, and well. When you fail to govern, you may be elevating how you want them to perceive you over how you want them gathering to go for them. Often, chill is you caring about you masquerading as you caring about them… It isn’t enough just to set a purpose, direction, and ground rules. All these things require enforcement. And if you don’t reinforce them, others will step in and enforce their own purposes, directions, and ground rules.

Well-intentioned interrupting is necessary because failure to do so is a disservice to yourself, the meeting, and the others in the meeting.

4. Acknowledge, capture, and schedule more time.

When you interrupt someone going down a rabbit hole, it’s important to immediately acknowledge and thank them for their contribution. Thanking the person will reduce the harshness of an interruption and make it easier to change the direction of the conversation.

One person’s rabbit hole is another person’s much needed discussion. Capture the person’s comment or discussion topic and offer to address it in a future setting. Capture it so that they can see or understand they’ve been heard. For example, if you’re in-person, write their contribution on a whiteboard; if you’re virtual, use a virtual whiteboard or call out that it’s been added to meeting minutes. When a comment is captured, it shows the contributor they have formally been acknowledged and makes them more likely to move on to other topics of conversation. It’s critical to the integrity of your meeting to schedule and have any promised follow up conversations.

Make space for rabbit holes in your conversations, just be careful about haphazardly tripping and clumsily falling into them. And, when you find yourself intentionally jumping into one, enjoy your journey to wonderland.

Curiously Yours — Seb

Sources and Suggested Reading:

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Two Dummies
Two Dummies

Written by Two Dummies

I’m Garett. I’m Seb. We help courageously curious organizations identify and realize bold ambitions through co-creative experiences.