The Conversation With My Team I Still Regret
The tension every leader faces: projecting confidence while managing the inner storm.
Today’s post supported by my friend Jason Oakley!
Look like a seasoned PMM, even if you’re starting from zero
What if you could skip the "figuring it out" phase of building a product marketing function?
Jason just launched a free toolkit for founding and solo PMMs. You’ll get access to 5 proven templates from his private membership, the PMM Jetpack:
PMM Charter – Define your function with clarity
Customer Insights Tracker – Uncover what customers really think
Positioning Canvas – Nail your unique value proposition
Competitive Battlecard – Build competitive positioning that wins deals
Launch Playbook – Navigate every launch with confidence
Skip the headaches with battle-tested resources used by hundreds of PMMs.
This 3x Founder thought selling his company would be the pinnacle of his entrepreneurial journey.
Instead, he felt like a fraud.
He couldn’t tell his 55-person team the truth.
He sold because he couldn’t do it anymore. He was burned out and scared this might be the only thing he ever did in his life.
But he couldn’t say that. As the leader, he felt pressure to project excitement and enthusiasm - not exhaustion.
Instead, he sold them a rah-rah story about why they should all be excited. That this would be:
A great opportunity
An exciting next chapter
Their next stop on their way "to the moon"
On the outside, he projected a calm confidence. But inside, he was exhausted and overwhelmed.
That duality is what so many leaders wrestle with.
You put on the brave face because your team needs it. Meanwhile, your real feelings (of burnout, fear, self-doubt, etc) pile up in the background.
Years later, Kirk Reynolds remembers the dishonesty more than the exit itself. It forced him to ask the questions every leader eventually has to face:
How do you motivate your team without pretending you have it all together?
When is projecting confidence useful - and when does it cost you?
What happens when your identity is so tied up in the job that you don’t know who you are without it?
This is exactly why so many new leaders struggle.
Nobody trains us how to project confidence while managing the inner storm.
Our full convo dives into three of Kirk's most challenging moments - and what he learned from each.
Catch our full conversation on YouTube:
Or listen on Spotify
Want help growing faster in Q4?
Sign-up for the Growth Operating System
Install the exact plug-and-play system for leading a cross-functional growth team - without becoming the bottleneck. Perfect for first-time growth leads who want faster execution, more wins, and a stronger reputation.
→ Sign up for the Growth Operating System
Book a 1:1 Coaching Spot
I coach a small group of experienced growth operators who want to break through plateaus - mastering growth strategy, operating system, communication, and inner-game - so they’re seen as indispensable by CEOs and exec teams.
→ Learn more about coaching