Diary of a Leader: When Expectation Ignores Reality - Operational Leadership Insights
- Lindsay Sheldrake
- Nov 13
- 4 min read
Welcome to Diary of a Leader: Real Stories, Leadership Lessons, and Personal Growth
Ah, leadership. It asks us to make things better — to refine, improve, and move forward. But sometimes, in our urgency to fix, we skip the one step that matters most: understanding.
Because improvement without understanding isn’t progress — it’s assumption disguised as action.
Welcome back to Diary of a Leader, where we look behind the scenes at what it truly takes to build alignment, trust, and operational rhythm inside growing businesses.
If last week’s story showed what happens when leaders skip discovery, this week we explore what happens when leaders skip listening.
The Story: When a New Voice Says What Others Won’t
A few days ago, I went for coffee again with the same former colleague I wrote about last week. She had updates — and they were telling.
She recently onboarded someone new into her department. Someone experienced. Someone who’d spent years inside complex systems and understood how supply chain actually works — the dependencies, the constraints, the pacing, the ripple effects.
During training, she walked this new hire through their processes. The approvals. The checks. The steps that, on the surface, might look slow or bureaucratic, but in reality prevent million-dollar mistakes.
After listening carefully, the new hire said something bold:
“You will never be successful doing it this way.”
It wasn’t criticism. It was clarity.
And my colleague asked me:
“What do you think she meant by that?”
What This Story Reveals About Operational Leadership
It wasn’t that the people weren’t talented.
It wasn’t that the department wasn’t trying.
The issue was this:
Leadership had created expectations that operationally could never be met.
Not because the team wasn’t working hard enough.
Not because the system was broken.
But because the expectations were built on assumptions — not operational reality.
Timelines that didn’t match capacity.
Steps skipped that protected the organization.
Dependencies ignored by people who didn’t understand them.
Pressure handed down from above with no room for dialogue.
And here’s the key:
The leaders in this situation didn’t ask questions. Not one.
No curiosity.
No discovery.
No listening.
As we talked through it, we kept coming back to the same truth:
In operational leadership, assumptions are expensive.
They cost time, trust, and engagement.
The Leadership Blind Spot
In many organizations — especially high-growth or high-pressure ones — leaders assume they need to know. They need to decide. They need to define the plan, the timeline, the output.
But here’s the truth:
You don’t need to have the answers.
You need to ask the right questions.
Because the people closest to the work have insight you cannot access through leadership meetings or dashboards.
They understand where timelines bend.
They know which dependencies are rigid.
They see how one misstep can travel through an entire supply chain.
When leaders don’t ask, they never hear this reality.
And when they don’t hear it, they build expectations on fiction.
That’s when teams disengage.
That’s when workarounds multiply.
That’s when “you will never be successful” becomes the only honest thing left to say.
The Opportunity: Trading Answers for Curiosity
Operational leadership isn’t about being the expert in every system.
It’s about being deeply curious about how the system works.
Not curious to validate your assumptions — curious to uncover what you didn’t know you needed to know.
Because in complex environments, the truth lives in the interconnectivity:
the handoffs, the constraints, the dependencies, the hidden impacts.
This is why asking good questions is a leadership skill — not a soft skill.
Without questions, there is no understanding.
Without understanding, there is no alignment.
And without alignment, expectations become pressure instead of possibility.
Reflection Prompts for Leaders
Where am I setting expectations without understanding operational reality?
What assumptions am I making about how work flows?
When was the last time I asked my team to show me the true current state?
Am I listening to learn — or listening to respond?
Wrapping Up: Listening Is a Leadership System
This second conversation reminded me that listening isn’t passive.
It’s operational.
It’s strategic.
It’s foundational.
Operational leadership isn’t about knowing more — it’s about seeing more.
Real improvement doesn’t come from moving faster.
It comes from moving smarter — with clarity, evidence, and shared understanding.
Because you can’t improve what you don’t understand.
And you can’t understand what you don’t take the time to hear.
The work will always tell you what it needs.
But only if you ask.
And only if you’re willing to listen.
Want support building systems grounded in reality, not assumption?
Book a Discovery Call to design processes, capacity, and leadership rhythm that actually work in practice.
Stay tuned for more real-world lessons on leadership, operational clarity, and purposeful growth in the next installment of Diary of a Leader. Because leading teams and managing projects isn’t about doing it all. It’s about focusing on what matters most—and doing it with intention, rhythm, and excellence.
