Being trusted with a role, even one backed by real confidence, doesn’t mean the role itself is well defined. I learned quickly that trust and clarity rarely arrive together.
Often, the work started before boundaries, ownership, or success criteria were fully settled. Waiting for certainty wasn’t an option. Progress was expected, and momentum mattered, even while the shape of the role was still emerging.
In those situations, the challenge wasn’t effort or intent. It was judgment.
It meant deciding what to move forward, what to slow down, and which risks were acceptable when information was incomplete and consequences weren’t mine alone.
Over time, I learned that this kind of work doesn’t reward perfection or preparedness nearly as much as it rewards what’s often called a bias for action. Much can be forgiven if you’re making calls, adjusting quickly, and staying accountable as the ground continues to shift.
Learning While Doing
When I moved into executive communications, I didn’t arrive with a communications background or formal training. On paper, I wasn’t an obvious fit. What I had instead was responsibility that arrived fully formed on day one and expectations that didn’t wait for me to feel ready.
The work was consequential. Narratives needed to be shaped, messages developed, and materials produced on timelines that reflected the pace of executive decision making. Often overnight, sometimes in response to issues already circulating far beyond the room.
I was learning the craft while already accountable for the output. Drafts went out. Feedback came, but rarely on my timeline. Feedback followed the principal’s priorities, not the project’s. A keynote scheduled for the following week might wait while executive decisions and commitments due this week took precedence. Then, the night before something had to go live, it often had his full attention.
The signal wasn’t subtle. Some instincts translated well; others didn’t. Every minute I had with the principal during the lead‑up to a deliverable had to be mined for the insight that would shape the outcome. What mattered wasn’t having certainty upfront, but being willing to make calls, name assumptions clearly, and correct course without losing momentum.
Over time, I learned to operate differently in those conditions. I moved with provisional confidence, paid close attention to where friction showed up, and treated every iteration as both delivery and discovery. Trust wasn’t a static thing I’d been given. It had to hold up continuously, in motion.
That role never came with a finished playbook. It unfolded in real time, under scrutiny, with limited rewind. The work progressed not because clarity arrived first, but because judgment was exercised before it did. That experience wasn’t unique, but it clarified something I’ve seen repeatedly in unfinished roles: judgment matters most when information is incomplete and decisions still must be made.
Judgment Amid Incomplete Information
In several roles, the work itself began before the role was fully defined. Scope was still forming, stakeholders weren’t aligned, and success criteria shifted while momentum was already expected.
I was often figuring these things out while already accountable for outcomes. Most of my real learning happened in that context: needing to act without yet knowing enough. Not in preparation, but in the friction of getting things wrong and adjusting before the consequences compounded.
In practice, that meant doing a lot of my own research and self-guided learning. I would dig for primary sources rather than relying on second‑hand explanations. All the while still having to make calls, revise assumptions, and absorb feedback quickly when momentum slowed. I wanted knowledge I could stand behind, not someone else’s best guess passed along as fact. Books, documentation, and source material. Anything I could work through at my own pace and verify for myself.
Most formal instruction I’ve encountered moves more slowly than situations like this allow. The exceptions stood out precisely because the rigor matched the stakes. More often, learning happened in parallel with delivery, not before it.
Trust wasn’t static; it formed in real time based on whether progress continued as expectations evolved. More often than not, I was brought into roles with no established playbook, where success depended less on prior specialization and more on judgment exercised in motion. Scope evolved, stakeholder experience varied, and prioritization and follow‑through became the real differentiators.
In practice, that meant there usually wasn’t a playbook waiting. The expectation was to help define one—while still delivering results along the way.
Working Without a Pause Button
Over time, I became more comfortable acting without full certainty—not because acting felt safe, but because waiting often carried its own cost. In unfinished roles, the conditions rarely paused long enough for perfect clarity to arrive.
Decisions had to be made with the system already in use. You learned what mattered by engaging with real constraints, adjusting course as new information surfaced, and accepting that some understanding only comes after movement has begun. That habit—making decisions in context, without the luxury of a reset—has shaped how I operate when clarity arrives late, or not at all.
What This Shaped Over Time
Working this way changed how I paid attention. I became more attuned to where decisions actually moved, where work stalled, and which constraints mattered before issues surfaced. Rather than waiting for clarity to arrive, I learned to work toward it by closing gaps in public, following through across handoffs, and earning credibility less through titles than through whether the work kept moving.
Over time, that carried over in ways I didn’t expect.
In the late 1990s, my wife and I started skydiving. It was a vivid lesson in working without a pause button. Once you exit the aircraft, you’re committed to every decision that follows. There is no pause, no reset, and no way back into the plane.
That experience often comes to mind when I think about the first All Hands event I worked on in executive communications, for a division of over 20K people. My manager, who had hired me, confessed backstage that she was a bundle of nerves, while I seemed calm by comparison. At the time, it didn’t feel like calm so much as acceptance. The event was already underway. I could no more change its trajectory in the moment than I could reverse a skydive mid‑descent.
I stayed alert and ready to act if something faltered. That readiness wasn’t accidental. It reflected time spent in advance thinking through contingencies: what could fail, where the work was most exposed, and which decisions I’d need to make without hesitation if things went sideways.
Photo by stephan hinni on Unsplash