From Teammate to Team Lead:

Earn Respect Without Losing Connection

Join me for a free 45-minute workshop to help new managers confidently

lead a team of their former peers, earn trust, and avoid common mistakes that

cause big problems down the road.

There’s a big challenge in management no one really talks about.

…how to become the boss of your friends.

One day you’re venting about work over lunch...

Next, you’re running their forecast calls, delivering performance feedback, and being asked to hold them accountable.

You want to lead with confidence—but you don’t want to come off as bossy, fake, or like you’ve “changed.”

You’re trying to strike the right balance, but everything feels a little awkward.

Meanwhile, your old teammates are watching your every move,

wondering if you’ll start playing favorites -

or crack under pressure.

If that feels familiar, you’re not alone.

Most new managers are handed a team and a quota… but zero real training on how to lead former peers, earn respect, or set boundaries without damaging trust.

That’s exactly why I’m hosting this event.

What you’ll learn

Learn From an Experienced Leader

Understand the most common mistakes new managers make when leading former peers so you can avoid them
Know How to Handle Their Reactions

How to spot and handle the 4 types of peer reactions to your promotion (like the Over-Familiar Friend, the Quiet Resistor, the Age-Gap Skeptic, and the "We’re Still Cool... Right?" Teammate)
A Simple Framework

to set expectations and build healthy team boundaries without feeling fake or bossy
Team Meeting & 1:1 Scripts

How to handle your first team meeting and 1:1s to earn trust, set boundaries and prevent future problems
Mindset Shifts

that will help you step into your leadership role with confidence—even when imposter syndrome kicks in
Exactly What To Say

Real scripts and prompts for giving feedback, setting expectations, and holding people accountable without micromanaging or damaging relationships

Meet your facilitator

Casey Calkins, PCC

Hi, I’m Casey — Founder of C2it Partners and a former SaaS sales leader turned executive coach and leadership consultant.

After 15 years leading high-performing sales teams across tech, financial services, and professional services—including nearly 7 years at Salesforce—I learned that the hardest part of any leadership journey is often the very beginning: navigating the transition from peer to manager.

Now, I help new and aspiring leaders step into that transition with clarity and confidence—by developing the emotional intelligence and self-awareness it takes to lead authentically. My goal is to help them build high-performing teams without burning themselves out or pretending to be someone they’re not.

Through my work with fast-growing startups and small businesses, I’ve seen that the best-performing leaders aren’t the loudest or the ones with all the answers—they’re the ones who know how to lead with authenticity, emotional intelligence, and clarity.

This webinar is packed with real-world strategies I wish someone had handed me when I first became a manager. If you're navigating awkward team dynamics, trying to earn respect without losing connection, or just want to feel more confident in this new role—you're in the right place.