Looking to make
your 1:1 meetings
more meaningful?

Book a 30-minute meeting with leadership experts from Hypercontext!

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Jocelyn Brown

Jocelyn Brown
Head of CS & Sales

Leader for 15 years

Brennan McEachran

Brennan McEachran
CEO, Hypercontext
Leader for 10 years

"I had the pleasure of working for Jocelyn for a number of years. She balances a rare leadership quality that allows someone to be both a strategic thinker as well as a strong operator in the business."

Ryan Moon, SVP of Sales

"Brennan has taught me everything I know about leadership and I'm forever grateful. He's the kind of leader you aspire to be: humble, motivating, and above all else, a human."

Hiba Amin, Senior Marketing Manager

Prepare for your session

We believe 1:1s are an invaluable time to build trust, address blockers, talk about career growth, and most importantly, exchange two-way feedback. To get the most out of your session, here are some things to help you prepare:

Write down a list of challenges you're facing

Not sure what to talk about? Here's are some prompts to help you reflect:

  • What's the biggest challenge you're facing as a leader right now?
  • When it comes to 1:1 meetings, what are you struggling with most? (I.e. getting the team to contribute to the agenda, moving beyond status updates, building trust, etc.
  • What keeps you up at night?
  • Psychological safety: Do you have it? How do you create it?
  • How do you balance needing to drive alignment on the team while making time for trust-building on the team?

Prepare some questions

Not sure what to ask? Here are some questions to get you started:

  • What's your approach with 1:1 meetings?
  • What should I talk about during 1:1 meetings?
  • How do you balance having structured conversations with time for "getting to know you" chats?
  • What questions spur the best conversations with your direct reports?
  • How frequently should I be having 1:1 meetings with my team?
  • My 1:1s are starting to feel a bit stale, any ideas?
  • What's the best way to deliver harsh feedback to an underperforming employee?

Level-up your management skills

Book my session