Join Our 5-Day New Leader Challenge
The new-leader guide you wish you’d had on Day 1 – with a personality lens.
I can still remember my first day as a new manager. I sat down at my desk, opened my laptop, and just…stared at it.
As an individual contributor, every Monday had been simple. Look at my task list, review where I’d left off on Friday, and get back to work.
But as a manager, my day looked different.
My job was no longer solely focused on my own deliverables, but on leading a team to deliver a product.
That morning is the one I think about whenever someone tells me they’re stepping into their first management role.
Because what I really wish someone had told me, in clear and unhedged terms, is this:
Becoming a leader is a different job than the one you got promoted out of.
The rules underneath the work have changed – and the version of you that was great at being a contributor isn’t automatically the version of you that will be great at leading contributors.
That gap – between who you were and who the role is now asking you to be – is what this month’s challenge is about.
Join our 5-Day New Leader Challenge
To celebrate this new series, we’re offering 35% off an annual subscription.
Plus, you’ll get instant access to a brand-new resource: 27 Questions Every Leader Wishes They’d Asked Sooner. This practical guide is packed with the questions I wish I’d known when I was leading my first team and stepping into management.
But don’t wait – after Friday (May 29th), both the bonus and special rate disappear.
New Leader Doubts
I almost quit two weeks into my first leadership role. I craved the consistency, the simplicity of being an individual contributor and kept feeling plagued with doubts.
“What am I even doing here?” was a near constant question. Along with an internal monologue that went something like this:
What am I supposed to do with my time now?
How do I tell someone their work isn’t good enough without ruining the friendship we had as peers?
What if I’m not the right person for this role, and everyone’s about to find out?
What if I never feel ready?
Every new leader I’ve talked to has some version of this list of questions and doubts.
And the hard part is, you can’t really Google your way out of it – there’s no Wikipedia page for “how to become you, but in charge.”
If any of that sounds familiar, this is exactly the challenge for you.
Introducing the 5-Day New Leader Challenge
This month, we’re walking through five of the biggest sticking points new leaders run into – with a personality spin on everything, of course!
Each day, we’ll take one part of the new-leader transition, unpack what’s actually going on underneath it, and walk through what to do with it.
By the end of the five days, you’ll have a much clearer sense of:
Who you are as a leader
What you’re being asked to trade to step into the role
How to handle the harder conversations that come with leading people
Where to find your footing when confidence won’t quite show up on cue
What your team needs from you on the other side
We’ll kick off on Monday, June 1st. Be sure you’re subscribed so the challenge lands in your inbox.
What Comes After the Challenge
After the challenge, we’ll be rolling out a series of personality-specific guides on one of the trickiest parts of becoming a leader: the shift from being someone’s peer to being their leader (or watching a former peer step into that role over you).
We’ll go Role by Role – Analysts, Diplomats, Sentinels, and Explorers – covering what each Role tends to wrestle with on both sides of that shift.
Finally, we’ll close out the month with a look at one of the trickiest leadership dynamics out there: leading people who are older or more experienced than you.
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, June 1st.
Free subscribers will get access to Days 1 and 2, 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? Take advantage of our limited-time challenge promo to save 35% on an annual subscription.
Upgrading will give you access to this New Leader series plus our complete leadership development library, which covers topics like:
Mastering 1:1 meetings
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
Five days from now, if this challenge does what I want it to do, here’s how you’ll feel:
A little clearer on who you are in the role. A little better at seeing how your personality shows up in your leadership, and deciding when to lean into it and when to adjust. A little more grounded in the harder conversations. A little less alone with the doubt that creeps in at the end of a long day. And a lot more interested in the humans on your team – curious about who they are, what they need, and how to lead each one of them well.
That’s what June can do for you. And five days is enough to start.
Can’t wait to dig into this with you.
P.S. Not a new leader? Even if you’ve been leading for years, I think you’ll find plenty to take away from this series – especially if you’re newer to personality-driven leadership, or if you mentor people who are stepping into their first management role.