The dark arts of interrupting someone

Why speaking up mid-sentence might be the most generous move in the room

“May I ask you a question?”

That’s what Alan Weiss said to me, thirteen seconds into my very first mastermind call.

I mean, I’d barely warmed up.

I wanted to ask him a question but first, I eased into it by giving him some background information.

You know what it’s like; You share a bit of context, a dash of nuance, maybe a side quest or two before landing on the actual question.

When he interrupted me, it was the conversational equivalent of a record scratch.

What the...?

Then Alan added, “Just ask your question. If I need context, I’ll ask.”

It was a little bruising. And completely brilliant.

That was the first time I witnessed what I now call one of the dark arts of hosting a room: the power to interrupt well.

Most people tiptoe around this. It feels taboo. Too pushy. But when done right, interrupting isn’t rude.

It’s actually one of the most generous, room-respecting moves you can make.

If you’re leading meetings, group coaching, masterminds, team huddles or hot-seat sessions, learning this skill puts you in a league of your own.

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Most people think interrupting is impolite.

They’re wrong.

We’re taught that good people don’t talk over others. That it’s better to nod, smile, and endure the ramble than to redirect.

But in high-stakes conversations, especially in group settings, that mindset can destroy value.

Like most dark arts, interrupting comes with risk. Do it badly and you tank the vibe. Do it well and you lift the entire room.

However, if you choose not to interrupt, here’s what happens:

• You create space for unfiltered, irrelevant storytelling.

• The extroverts take over.

• The introverts disengage.

• Time just drags on and on.

• Everyone leaves a little more depleted.

Interrupting resets the dynamic. It lets people know this is a room where attention is respected, and time has value.

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Why we avoid interrupting

Gosh, even though I am now a confinterrupter (confident interrupter), it’s not like I enjoy it. Every time, I still have to muster up the courage to give it a go.

Here are some reasons why we let conversations go loose:

1. We want to be liked
Interrupting feels harsh. It clashes with our inner people-pleaser. Especially in peer-based spaces, we’d rather keep it breezy than step in.

2. We don’t trust ourselves
What if we misjudge the moment? What if we misread their flow? What if they were about to land on something profound?

So we all wait

and wait

and wait………..

…

(and realise, the cymbal crash / epiphany is never coming).

3. We haven’t set expectations
You cannot interrupt confidently if you haven’t given people a clear roadmap. If participants think they have twenty minutes to share their life story, they’ll use it.

If they know upfront they have two minutes, or to simply just ask their question, they’ll self-edit (and it also gives you permission to cut in after a couple mins).

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Interrupting is a public service

Honestly, if you interrupt to set things on course, you are my new hero.

Firstly, it protects the group
Imagine you’re running a Zoom for eight people. Sixty minutes total. Back of napkin math is 7.5 minutes each, max.

One over-talker blows that out. A sharp interruption reins it in. It restores rhythm and makes it more equitable.

Everyone else on that call is sighing with relief and giving you virtual high-fives.

Secondly, it protects the speaker
Most people don’t realise they’re meandering. They think they’re being helpful. But often, they’re drowning in detail. A clear redirect like, “What’s the core challenge here?” pulls them out of the weeds and into clarity.

Thirdly, it protects your reputation
Let the session drag and people will ghost your next one. However, if you become known as someone who runs tight, purposeful rooms then your Work Fame grows. People remember who made their time feel valuable.

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Mastering the dark arts: How to protect the room without killing the vibe

So, how do you create group value without becoming a micromanager?

This is where Michael Bungay Stanier’s concept of stage directions comes into play.

In his book The Advice Trap (btw, if you listen to the audio book, you might hear my commentary!), MBS talks about “sealing the exits.”

In your coaching conversations, you have to gently, confidently bring the room back to purpose.

And the tool for that? A well-placed interruption.

Some powerful redirect phrases include:

• “Let me jump in here”

• “Can I pause you for a second”

• “What’s the real question you’re trying to answer right now”

Tone matters

You can’t just say the right phrase. You have to land it.

Drop your voice. Slow your pace.

Honestly, when I’m on the other side of a call and someone starts monologuing, I feel so much relief when the host jumps in with a redirect.

Be that person for others.

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Set the game plan early

Want to interrupt without shocking people? Lay the groundwork.

Try opening with:

• “We’ve got a lot to cover, so I may jump in to keep us focused”

• “Please keep context to one or two sentences, then ask your question”

• “If I cut in, it’s just to help make the most of our time together”

You can shift the tone of an entire session in your first sixty seconds. Use them.

Work Fame is built on dark art mastery

Most people talk too much. Few know how to interrupt well. Even fewer know how to manage group time in a way that builds trust and sharpens value.

Btw..

It’s not only 100% of the host’s responsibility to reinforce this.

If you need ten minutes to explain your question, you don’t have one. You have a monologue. Save it for your journal (sorry! Too harsh? LMK in the comments).

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Join me daily as I podcast on Leanne on Demand.

This week, I recorded an episode on a morning walk in Dandenong, Victoria reminding you to not trust your morning mood, and my throwback episode chatting to Andy Storch about writing a book in 100 days has been popular, too.

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Join Alan Weiss and me on our next Talk the Walk livestream

Are you chasing opportunities that drain your time, energy, and sanity? In our next Talk the Walk live-stream, we’re unpacking why even the smartest people sometimes look for business in all the wrong places, and how to course-correct fast.

• It’s on Thursday 1 May 5pm ET (Friday 7am AEST Brisbane)

• LinkedIn Live. Click here to RSVP.

We’ll share how to:
- Spot dead-end leads before they waste your time
- How to shift from hustling to magnetising ideal clients

Save your seat + bring your favourite drink (martini or coffee optional).

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🌴

Leanne “Can I jump in…” Hughes

p.s. Did you enjoy my book, The 2-Hour Workshop Blueprint? In three weeks, I’m hosting a once-off virtual masterclass, sharing the scoop/tips/workshop advice I left out of the book. To join, donate $50 to stamp out homelessness, and you’ll get an invite. 100% of workshop proceeds go to St Vincent’s, a charity doing great work in Australia.

p.p.s. If this hits home, tap the ❤️ below, or share your thoughts in the comments.