Quick Reference
Lessons from the Front
When I first took office as Mayor of Orting, I was stepping into a building where I had just defeated the incumbent. On day one, the tension was thick. Most of the city staff assumed they would be fired.
I knew it would be foolish to come in and wipe the slate clean. I planned to let natural attrition happen over time while we steadily instilled a new culture. But almost immediately, I noticed a massive shift in how information flowed to me compared to my time as a city council member.
The senior executive staff was suddenly positioning themselves to give me the information they thought I wanted.
I have a very open-ended way of leading. I will ask a question to poke at a problem, invite conversation, and build a broader understanding before I ever conclude. But my new staff would get way ahead of me. They would try to anticipate my endgame and deliver a packaged, sanitized answer to please the boss.
This is the Executive Information Bubble. And it is the fastest way to lose control of your organization.
It usually does not happen because your team is malicious. It happens because they want to protect themselves or please you. But when your staff works overtime to sugarcoat bad news, it creates a dangerous temptation. It practically begs you, the executive, to get down into the weeds.
When a complex, failing project (a pothole) gets sanitized into a nice green checkmark on a polished PowerPoint (the pixels), you lose the context. You start jumping in to fix individual problems instead of managing the system.
I see this constantly with the executives I coach. They get pulled into managing individual emails or micromanaging a project because they are reacting to tailored information. But your highest value as an executive is not doing the operational work you used to be good at. Your value is your context, your relationships, your vision, and your ability to build up the next set of executives.
As the leader, you should not be thinking about how to fix a single pothole. You should be figuring out how to mitigate the long-term cost of a thousand potholes.
As the leader, you should not be thinking about how to fix a single pothole. You should be figuring out how to mitigate the long-term cost of a thousand potholes.
If you are operating in the dark, here is the playbook I use to break the bubble, build trust, and keep leaders out of the weeds.
My Playbook to Break the Executive Information Bubble
Prove you work for them (The $1,000 Meeting)
In many old-school organizations, the staff exists to benefit the executive. You must actively reverse that expectation. You must demonstrate that it is your job to help your staff succeed, not their job to help you succeed.
I do this by leading with open-ended questions and enforcing a strict time rule. We do not have meetings just for the sake of meetings. If you put ten people around a table for an hour, you’d better get value out of that $1,000 meeting in lost productivity. The goal of that room is not to stroke the leader's ego. It is to incentivize your team to ask hard questions rather than just trying to hear what I want to hear.
Walk the lines (But leave your tools behind)
In the Marines, we called it "walking the lines." As an executive, you need to walk the floor. But there is a massive trap here.
If you walk the floor, find a problem, and start pointing, picking, and fixing it yourself, you have just jumped over two layers of your own leadership. If you start doing that, your people will either look to you to do it for them next time, or they will view you as a micromanager. You cannot develop good leaders if you are doing their job for them.
You walk the lines to build trust. You engage. You ask about their families. You remember that their kid had baseball practice last week or that they came in on a Saturday. They will eventually give you the unfiltered truth because they trust you. And they trust you because you accept that you do not know their job better than they do.
Eliminate the air gap
When you do walk the floor and discover something broken, you cannot act as a lone wolf. You must bring it straight to your chief of staff, your city administrator, or your operations manager. You are the leader of the organization, and they are the operator. You two must be like peanut butter and jelly. If an air gap exists between the executive and the operations manager, the entire organization will fracture.
Directness, Kindness, and Saved Rounds
When a staff member finally brings you terrible news, thank them.
Coming from a military background, my default response to bad news was often a very direct, "Got it, thank you for the information." But directness can sometimes feel cold to a stressed-out staff member who is dealing with a failure. You must learn where people are coming from and accept bad news in a way that makes them feel supported, not interrogated.
You must remember that as an executive, you do not have unlimited Hollywood power. You operate within the confines of a council or a board. You need your team to bring you the bad news early so you can prepare the board, rather than hiding it until it is unrecoverable.
At the end of my meetings, I always ask, "Are there any saved rounds?" It is a military phrase, but it serves a vital purpose. It is a final, open invitation for the team to share the unfiltered truth before we walk out the door.
Supply the Context (The Forest vs. The Trees)
When bad news finally does make it to your desk, how you process it dictates what happens next. I have been bitten by this over and over again. Very few items are truly unrecoverable. But if a problem is shared without context, your team will hyperfocus on the trees. They will get stuck trying to chop down one specific tree instead of recognizing the bigger strategic picture.
As the executive, you must step back. Your highest value is supplying the missing context. You remind them of the mission, reset the board, and redirect their energy toward managing the entire forest.
Kill the Filler Language
Pay attention to the words your team uses to deliver information. There is a whole corporate buzzword economy that means absolutely nothing.
When someone hands me a phrase packed with buzzwords, I mentally turn the phrase around backward. I ask myself: if this phrase meant the exact opposite, would it still make sense? If the answer is yes, they are using filler language to hide a lack of understanding or to soften a failure.
For example, if a department head says, "Our plan for the new infrastructure bill is to focus on operational excellence," I reverse it. Would anyone ever say, "We plan to focus on operational incompetence"? No. Because "operational excellence" is not a strategy. It is a baseline expectation. The ground truth is that they do not actually have a plan yet, so they are throwing buzzwords at you to buy time.
Or consider the classic excuse: "We are experiencing a temporary realignment of our core deliverables timeline due to unforeseen bandwidth constraints." Turn it around. It is word soup either way. The ground truth is much simpler: "We missed the deadline, and we are out of money."
A highly functional organization built on trust does not need generic corporate speak. Over time, a trusting team will naturally develop its own internal terminology. It might make zero sense to an outsider, but it creates a fast, honest working flow internally.
When you strip away the buzzwords, a high-trust organization develops a shorthand that is blunt, slightly informal, and highly efficient. It tells the executive exactly what is going on in three seconds.
Instead of talking about "synergizing cross-functional approaches," a trusting Public Works director will give it to you straight: "Sir, we can patch that road by Friday, but honestly, we are just painting the grass. It is going to wash out again by November."
Instead of a vague update on "stakeholder alignment," your Chief of Staff will tell you, "That new permit process is stuck in the blender between Legal and Planning."
And at the end of a hard meeting, instead of asking for "final alignment," you ask, "Are there any saved rounds?"
That is what pure honesty sounds like.
Pulling it all together
The longer you sit in the executive chair, the thicker the bubble gets. Your job is not to micromanage the people trying to protect you. Your job is to break the bubble intentionally.
Walk the lines. Ask open-ended questions. Stop solving individual problems and start setting the expectations.
Do not let a sanitized digital report (the pixels) distract you from managing the actual foundation of your organization (the potholes).
Take a hard look at the reports hitting your desk today. Ask yourself what they are leaving out.
If you found this briefing valuable, please forward it to a peer who needs to read it.
Attn: Non-Profit CEOs, Mayors, City Managers & Administrators, Senior Department Directors
Leadership isolation is a real operational threat.
That’s why I’ve created strictly confidential, closed-door Executive Forums for senior leaders.
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