Timely Signals And Decision Space

Happy Sunday Friends!

Here’s one quote I’m musing on this week, two core ideas, three favorite things, and one question to carry with you into the week ahead.

One Quote I’m Musing

“Timing, perseverance, and ten years of trying will eventually make you look like an overnight success.”
| Biz Stone

I vividly recall a key teachable moment early in my career.

I needed help. I had exhausted all my options to overcome a layer of bureaucracy that was beyond my experience or authority to break through. I had tried workarounds, explored alternate routes, and even sat with the problem, trying to game it out.

Finally, late on a Friday evening, I asked my boss for help. I told him exactly where I was in the story, what I’d tried, and what I thought I needed to overcome the blocker.

And he helped. He picked up the phone. One call. Forty-five minutes later, it was solved.

All good, right?

Wrong.

He looked at me—clearly frustrated—and said, “Why didn’t you let me know sooner?”

Years later, being on the receiving end and (even more eye-opening) getting to observe it objectively at the senior executive level, I see the other side of the coin—when team members come too late (and too soon). It’s a delicate balance we all must learn. Knowing when to pull your leader into a problem is a skill that sits at the heart of effective communication, trust, and leadership.

The dilemma of when to bring issues to your leader’s attention isn’t trivial. Engage too early, and you're perceived as complaining or incapable of independently solving problems. Engage too late, and you've stripped your leader of their capacity to influence outcomes effectively.

Engaging at the right moment is akin to catching a wave—too early, and you're merely paddling; too late, and the opportunity has crashed by.

"Never let the future disturb you. You will meet it, if you have to, with the same weapons of reason which today arm you." — Marcus Aurelius

The Cost of Early Engagement: The Whining Trap

When I first started out, I was eager to show my diligence. I brought every small roadblock to my supervisor’s attention, hoping to demonstrate my proactive attitude. Initially, my leader appreciated the updates, but over time, I noticed a subtle shift—my constant early escalations were perceived as a lack of confidence in my own problem-solving abilities.

Constantly raising minor issues drains your leader’s mental bandwidth, shifting your role from capable partner to burdensome messenger. When you escalate too soon, it implies you're unable or unwilling to handle challenges autonomously, potentially eroding trust.

Like Eisenhower, who chose when to act based on preserving momentum, not reacting to noise, your role is to manage perception and input.

The Price of Delayed Escalation: Lost Decision Space

On the flip side are the consequences of waiting too long. Holding back on escalating a significant issue, believing we can resolve it independently. By the time we finally bring it up, the window for a strategic intervention had closed, and we are left scrambling in crisis mode.

When updates reach leaders too late, it restricts their options and forces reactive decisions instead of strategic interventions. Timely intervention redirects outcomes positively, but late information turns potential strategies into crisis management.

And just like that, we close the very decision space we depend on to shape outcomes.

The Sweet Spot: Identifying the Perfect Window

Navigating the sweet spot of escalation requires judgment, intentionality—and a shared language with your leader. It's not just about when to escalate, but how to create an environment where escalation feels like progress, not failure.

The real sweet spot? Developing a culture of flatness and communication.

One way to do this: establish rapport with a rhythm of short updates framed as "I don’t need a decision." These touchpoints allow your leader to track where you are in the story, understand your trajectory, and offer feedback or experience-based insight only if necessary. Sometimes, just hearing your plan is enough for them to spot a hidden blocker before you hit it.

When you do need help, asking isn't giving up, it's refusing to give up. But as the saying goes, we don’t rise to the level of our goals—we fall to the level of our systems.

Here’s a system I use to strike that balance:

🔍 Should I Escalate? Use the EVI Framework

• Emergency: Is time critical?

• Visibility: Would this change leadership posture or resource allocation?

• Impact: Does this materially affect mission, people, or outcomes?

• ✅ Two or more = escalate.

💡 Mini-System: The 2-Attempt Rule
Try twice to resolve an issue independently. If the needle isn’t moving, escalate with one-line context and a proposed solution. (e.g., "Attempted X and Y, still blocked by Z. Recommend A or B. Thoughts?")

Adopting a disciplined timing approach isn’t just tactical; it’s strategic. Your mastery here is a hallmark of professional maturity.

💡 Two Core Insights

1. Preserve Decision Space: Capacity for strategic decision-making is finite. Timely escalation protects and expands strategic options.

2. Strategic Maturity: Mastering escalation timing reflects and reinforces your credibility, enhancing your leadership potential and professional growth.

✨ Three Favorite Things

1. 🎙️Podcast: "Masters of Scale" with Reid Hoffman—excellent insights on the strategic value of timing.

2. 📖Book: "Essentialism" by Greg McKeown—a powerful reminder of focusing attention on what truly matters.

3. 🛠️ Tool: Slack Scheduled Messages—helps manage clear and timely communication without unnecessary disruptions.

Had I known then what I know now, that 45-minute fix would’ve been a 5-minute conversation—days earlier.

❓One Question: A Reflective Call to Action

“This week, try the ‘EVI Framework’ in one meeting. Log what you escalated—or didn’t—and why. Then reflect: did your timing amplify your leader’s impact or reduce it?”

Ask yourself: Are you the kind of professional who solves problems—or accidentally becomes one?

What opportunities might your leader have missed last quarter because you hesitated to speak up?

If someone on your team struggles with timing their escalations, forward this article. It might just save a decision—or a career. And if you’ve learned this lesson the hard way like I have, share it. Your insight could be the turning point for someone else.

Until Sunday My Friends.
Stay adaptable. Stay present.

Think Dangerously.
–e

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