One of the clearest patterns I see in my work with senior tech leaders is this:
The great ones are always upgrading.
They’re not stuck. They’re not stagnant.
They’re learning how to operate at new scales, adapt to evolving team structures, leverage AI, and stay relevant in companies that are evolving fast.
If you think your role is supposed to stabilize over time—you’re in the wrong job.
Leadership is not a destination. It’s a never-ending journey.
Never in Stasis
Even when it feels like you’re “doing the same job,” you’re not.
A VP of Engineering at 10 people and a VP of Engineering at 50 people are two different roles—same title, wildly different skill sets.
Which is why I often say: leaders don’t need to merely grow—they need to accelerate.
And that acceleration needs to be tangible.
Because if it’s not visible, it might as well not be happening.
I’ve had more conversations than I can count where a CEO confided, “I’m starting to worry our VPE isn’t growing fast enough.” Not that they’re failing. Not that they’re underperforming. Just that they’re not keeping up.
And that’s enough to create serious doubt.
Tangible Growth
The best safeguard? Set personal growth goals. Regularly. And with actual deadlines.
Not fluffy “be better at strategy” goals, but real ones:
- Learn to manage a more senior leadership team
- Get ahead on AI-native ways of working
- Move upstream in your role to have more leverage
- Introduce a culture of habitual innovation
Then, every 2 months, ask yourself:
Am I meaningfully better than I was?
If the answer is no two cycles in a row, you’re stagnating. And that’s a problem. These short review cycles work. Because they’re short enough to be honest. You might fake your way through annual self-evaluations, but when we discuss short-term goals, waving your hands won’t do.
Stay Ahead of the Org
Here’s another yardstick I use with clients:
You should be growing faster than your company.
If your org is evolving and you’re not, you’re now the bottleneck.
That’s when roles get quietly questioned. That’s when reorgs start “for alignment.”
That’s how careers stall—without a single major failure.
And staying ahead means being proactive, not reactive.
You need time to zoom out. Rebuild. Think long-term. That’s why I talk about having leadership blocks for maximal efficacy.
It’s also why you need to develop a clear Vision for where things are headed—and where you need to be to lead them there.
One of my running jokes with friends is that Tim Cook probably uses wild internal Apple builds years ahead of public release. So when he grabs a regular iPhone, he’s like, “Wait, this one can’t teleport?”
That’s the mindset. Your job is to be working with the internal build of your future self. Always be two versions ahead.