Join Our 5-Day Mastering 1:1 Meetings Challenge
Most leaders are massively underutilizing this simple meeting. Are you?
One-on-Ones Were My Boss’s Secret Sauce
My old team leader once told me that his secret to successful leadership was simple: consistent 1:1 check-ins with his team. We worked mostly async, so these were casual chats done via messenger rather than formal, scheduled meetings.
But regardless of the format, those 1:1s allowed him to build real, meaningful connections with his team – even though we all worked remotely and had never met in person.
He always had a pulse on how we were feeling about work, and even what was happening in our personal lives that might affect how we showed up. In turn, we felt safe bringing him issues or concerns, knowing we could have honest, open conversations.
Because of that, our all-team meetings felt more productive and far less performative. We weren’t just sharing updates – we were actually aligned.
Done right, a 1:1 isn’t just a box to check. It can transform how your entire team works together.
Yet most leaders are massively underutilizing this meeting.
Join our new 5-Day Mastering 1:1 Meetings Challenge
Learn how to fully leverage 1:1 chats to build better working relationships with team members.
What a Great 1:1 Accomplishes
When it’s done well, a 1:1 meeting does three things at once that no other meeting on your calendar can pull off.
It gives you a window into how your team member is actually doing – not the filtered version they bring to group settings.
It gives team members space to surface the things that don’t fit anywhere else – blockers, ambitions, frustrations, questions they’ve been sitting on.
And it steadily builds the kind of trust and alignment that make every other part of your working relationship easier.
A good 1:1 isn’t always a status update or a performance review, it can be more like a friendly chat with a bit of an agenda.
Why This Meeting Gets Hard
When I became a content team lead, I suddenly had my own direct reports. I wanted to learn from my boss and use his 1:1 technique to build a strong connection with my team in this new capacity.
Yet I quickly realized that there is an art to the 1:1 that I underestimated.
“What am I even doing?” would run through my head every time I tried to have a 1:1 chat. Along with:
What questions should I ask?
What if I’m overstepping?
What if I can’t help?
Is this just wasted time?
Luckily, I had my old boss to bounce my thoughts off of. Otherwise, there was a very real risk that this 1:1 chat would have ended up feeling more like a status update or, worse, quietly disappeared from my calendar altogether.
If you can relate to that, good news – this month’s challenge will help make 1:1 meetings feel both manageable and productive.
Introducing the 5-Day Mastering 1:1 Meetings Challenge
This month, we’re walking through the pain points leaders run into most often with their 1:1s – one per day, for five days.
Each day, we’ll take one sticking point, unpack what’s actually going on underneath it, and walk through what to do instead.
By the end of the five days, you’ll have a much clearer sense of how to show up to these meetings, what to say when the conversation stalls, and how to walk out of a 1:1 feeling like it was worth the time – for both of you.
The challenge starts Monday, May 4th. Be sure you’re subscribed to participate!
What Comes After the Challenge
Once we’ve covered the fundamentals, we’re going to layer in something that makes all of this a lot more specific: personality.
Because how you run a great 1:1 looks a little different depending on who you are as a leader – and who’s on the other side of the table.
After the challenge, we’ll be rolling out a series of personality-specific 1:1 guides, going deep on how each of the four personality Roles – Analysts, Diplomats, Sentinels, and Explorers – tends to experience these meetings on both sides of the conversation.
How to Join This Challenge
If you’re a paying subscriber, you’re already in – the challenge will land in your inbox automatically starting Monday, May 4th.
Free subscribers will get access to Day 1 and previews of the rest. To unlock the full challenge and personality-specific content, you’ll need to upgrade your subscription.
Still a free subscriber? Claim your welcome discount to save 30% on an annual subscription.
Upgrading will give you access to this Mastering 1:1 Meetings series plus our complete leadership development archive, which covers topics like:
Leading multigenerational teams
Leading well as an Introvert
The top 5 leadership challenges each personality type faces
Leading through uncertain times
Managing stress at work
Leading remote (or hybrid) teams
Managing up to your boss
We Start on Monday
Here’s what I want for you by the end of this challenge:
You walk into your next 1:1 with a clear sense of how you want it to go. You ask better questions and get real answers. You know how your team is doing – how they’re really doing. You catch the things that used to catch you off-guard. You feel closer to the people you lead, and more aligned with them on where you’re all headed.
That’s the version of leadership these meetings are supposed to unlock. That’s what we’re working toward together.
Can’t wait to dig into this with you.
P.S. Keep an eye on your inbox – we have a little something extra dropping tomorrow before the challenge kicks off. If you’ve ever struggled with delivering hard feedback to your team members, you’ll want to see what it is!