Writing

These are the weekly notes I send as A Thought Worth Keeping.

The Hard Part of Alignment
Rob Speciale Rob Speciale

The Hard Part of Alignment

Alignment sounds simple: clarify goals, agree on priorities, move forward. But when leadership teams enter a new chapter, the real challenge isn’t strategy, it’s identity. Growth asks leaders to evolve, and that shift is often harder than the plan itself.

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The Day I Put the Hammer Down
Rob Speciale Rob Speciale

The Day I Put the Hammer Down

You can feel it coming before it happens. The moment a conversation stretches on, decisions stall, and stepping in feels easier than waiting. This piece explores what happens when a leader resists the urge to fix, and how restraint can shift ownership without everything falling apart.

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When You Realize You're the Problem
Rob Speciale Rob Speciale

When You Realize You're the Problem

Most leaders don’t realize they’ve become the problem because things keep working. Decisions move. Tension gets absorbed. Nothing breaks. Until one day, everything depends on them and limits what’s possible.

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The Leadership Work You'll Never See
Rob Speciale Rob Speciale

The Leadership Work You'll Never See

Some of the most important leadership work never shows up on dashboards. It’s the quiet work of holding pressure so clarity, decisions, and progress can emerge.

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When Authority Is Missing
Rob Speciale Rob Speciale

When Authority Is Missing

Two very different conversations revealed the same leadership pattern. When authority is not clearly named, alignment replaces action, decisions stall, and momentum quietly disappears.

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The Weight People Aren’t Talking About
Rob Speciale Rob Speciale

The Weight People Aren’t Talking About

Many capable, responsible people aren’t struggling on the surface, but their minds are full. The pressure of decisions, expectations, and being relied on adds up quietly. This is a reflection on mental load, clarity, and why doing something with it matters.

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One Goal - Chosen on Purpose
Rob Speciale Rob Speciale

One Goal - Chosen on Purpose

You don’t need a grocery list of goals or the perfect plan for the year ahead. You need honesty. This reflection offers a calm, deliberate way to choose one goal worth protecting, and to build the clarity and focus needed to follow through.

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A Deliberate Look Back
Rob Speciale Rob Speciale

A Deliberate Look Back

As I close the year, I find myself returning to a few simple questions, not to optimize the future, but to honor what unfolded. Before rushing ahead, this is an invitation to pause, reflect, and take a deliberate look back.

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Trying to Get It Right
Rob Speciale Rob Speciale

Trying to Get It Right

A reflective look at the pressure we feel this time of year, closing out commitments, creating meaningful moments, and trying to get it right for the people who matter most.

A reminder that not all pressure is bad, and that sometimes, pressure is a privilege.

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No Surprises
Rob Speciale Rob Speciale

No Surprises

Performance reviews aren’t supposed to be uncomfortable. When leaders provide clear expectations and consistent feedback throughout the year, reviews become a confirmation, not a confrontation. If a performance review comes as a surprise, it’s not a people issue. It’s a leadership one.

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Everyone wants to be heard. Few know how.
Rob Speciale Rob Speciale

Everyone wants to be heard. Few know how.

Most rising leaders feel unheard, not because their ideas lack value, but because they overlook the one skill that builds real influence: listening. This article breaks down why leadership isn’t responding, what you may be missing, and how understanding others’ priorities is the fastest path to having your voice matter.

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Flying with Turkeys?
Rob Speciale Rob Speciale

Flying with Turkeys?

Most people talk about being an eagle, not a turkey, but the real question is who’s in your flock. Are the people around you helping you rise into who you’re becoming, or quietly clipping your wings because they fear you might fly?

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What About March?
Rob Speciale Rob Speciale

What About March?

We’re quick to give thanks on the holiday, but what about in March, when life feels heavy and the grind takes over? Here’s how to stay grounded in gratitude and remember how far you’ve come.

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When Life Gets Messy, Who Shows Up?
Rob Speciale Rob Speciale

When Life Gets Messy, Who Shows Up?

Trust isn’t one thing, it’s layers. From the people who offer small favors to the rare few you’d call at 3 a.m. with a shovel, life has a way of revealing who’s truly in your corner.

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It Could Have Been Worse
Rob Speciale Rob Speciale

It Could Have Been Worse

A string of frustrating moments, a leak, a fire scare, a broken tooth, turned into one of the most grounding lessons I’ve had in a while. Sometimes the things we wish away are actually protecting or preparing us for what’s next.

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We Should…
Rob Speciale Rob Speciale

We Should…

“We should follow up… we should make a plan…” You’ve heard it, or said it. The problem is, “we should” feels collaborative but assigns responsibility to no one. In trying to be polite, we trade clarity for confusion.

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Invisible Effort
Rob Speciale Rob Speciale

Invisible Effort

You’re doing everything right, yet somehow, it’s not enough. Maybe the problem isn’t effort, but visibility. Here’s the quiet truth about being seen.

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How Negotiable Are Your Non-Negotiables?
Rob Speciale Rob Speciale

How Negotiable Are Your Non-Negotiables?

We all say we have non-negotiables, values or boundaries that define who we are and how we lead. But under pressure, many of those lines start to blur. This piece challenges you to examine what truly stands firm in your leadership and where your standards may have quietly drifted.

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Feedback isn’t for them.
Rob Speciale Rob Speciale

Feedback isn’t for them.

Feedback rarely feels like a gift. It’s uncomfortable, inconvenient, and easy to delay. But the moments we avoid are the ones that define our leadership. Feedback isn’t just for others. It’s a mirror, testing our courage, clarity, and willingness to lead with truth.

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Good Intentions. Poor Results.
Rob Speciale Rob Speciale

Good Intentions. Poor Results.

Ambiguity hides in plain sight, in phrases like “take charge” or “own it.” We think we’re being clear, but those words often mean something entirely different to the person hearing them. This post explores why well-intentioned labels create confusion and how clarity of expectation builds stronger leadership and trust.

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