Organization Deep Dive
About this site

This is a playthrough

A playthrough is a website you don't read. You play through it. It starts with you doing something about your own organization, reflects your answers back, and only then explains why.

Organization Deep Dive is the first of the Side Quest Projects: small, experimental sites that each take one practical question and explore it in the open. See all projects

It's a cousin of the explorable explanation, the interactive essay format Bret Victor named in 2011. The difference is the subject: an explorable explains an idea, and a playthrough holds up a mirror to how you already work.

Six principles

  1. Act first, read later.The first screen asks you to do something, not to read something.
  2. Every claim is touchable.If the site says something about flow, there's a control that lets you see it happen.
  3. Your answers shape the path.What you choose decides what you see next.
  4. You leave with your own result.Not just the author's conclusion.
  5. Limits are shown, not hidden.Every model, score and chart says what it is and isn't.
  6. Nothing is locked.Any chapter, in any order, at any time.

What this playthrough is, and isn't

Post your results

Share how your organization runs

The image and the post are made in your browser from your answers. Nothing is sent anywhere until you post it.

Your result as a LinkedIn image: the closest model, the match for each of the four models, and the top changes toward Model 3.
1 · Save the image 2 · Copy text and open LinkedIn ↗

  1. Save the image.
  2. Copy the text and open LinkedIn with the button above.
  3. Start a post, paste the text, add the image, and publish. LinkedIn doesn't let other sites fill in a post or attach an image for you, so these two pastes are the only manual part.
Leadership brief

A brief for your leadership team

Made in your browser from your answers: where you are now, the model you chose, what would change, both org charts, a suggested order and questions to discuss. Nothing is sent anywhere.

· The four structures

Same projects,
four structures

Four ways a municipality can organize the same capital program. Same departments, same crews, same council. Only the structure changes, and with it, how the work moves.

Hover a model for its reviewClick to step insideTap a model for its reviewTap again to step inside
The organization behind each flow

Same org chart, four sets of roles

Department heads report to the CAO. Operations is its own department in Models 1 and 3, and a division of Engineering and Public Works in Models 2 and 4. IT is a division of Corporate Services, and policing is contracted to the RCMP. Pick a model, or hover one above, to see who delivers, who sponsors, who supports and who governs.

Delivers projects Sponsors projects Supports Governs and plans Shared crews Contracted service

Who's accountable

RACI by model

Responsible, Accountable, Consulted, Informed. Every activity should have exactly one A. Rows without one are where work stalls and conflicts get settled by whoever pushes hardest.

    AAccountable: owns the outcomeRResponsible: does the workCConsulted at a set pointcConsulted only if someone asksIInformed

    Delivery director means the director of the department delivering the project. In Model 1 that's always Engineering and Public Works. Support departments are Corporate Services, Development Services and HR. IT is a division of Corporate Services: it sponsors projects in Models 1 and 3 and delivers its own in Models 2 and 4. Asset manager means the asset management group in Engineering and Public Works (Models 1 and 3); Models 2 and 4 have none. Operations means the Director of Operations and the operations manager in Models 1 and 3, and the operations manager inside Engineering and Public Works in Models 2 and 4.

    Who runs what

    Who leads which projects

    The same project lands in a different place depending on the structure. Pick a model to see which department leads each kind of work, and what the crews do on it.

    Does Operations do paving?

    Operations crews patch potholes, crack-seal and lay small paving patches as maintenance. The annual paving program needs design, tendering and a contract, so Engineering leads it in every model.

    Operations or Engineering?

    Engineering leads anything on roads and utilities that needs design and a contract: water, sewer, storm, paving and sidewalks. Operations maintains those same assets, does small jobs in-house, and in Models 2 to 4 runs the building and fleet projects.

    Who builds a new tennis court?

    Parks leads it in Models 2 to 4, with Engineering's help on grading, drainage and lighting. In Model 1, Engineering runs it and Parks sponsors it.

    · Five-minute read

    The executive lens

    The study in leadership terms: what it found, how to tell which structure an organization is running, what drift looks like, and the questions worth asking.

    The thesis

    The structure decides when people talk. When people talk decides how the work flows.

    01The shared crews are the real constraint.Every capital program draws on the same operations crews. Most structures only discover that at construction, when dates are already fixed.
    02Speed and predictability trade off.The fastest structure starts work soonest, then pays for it in overtime, rework, compressed legal review and lost asset records.
    03Ownership and coordination can coexist.Departments can keep their own projects if they're governed as one portfolio, with two early conversations: a capacity review and a support review.
    Self-check

    Which model is your organization running?

    Eight questions. Answer for how capital work actually happens, not how the policy says it should.

    Warning signs · Model 2

    Streams colliding

      Warning signs · Model 4

      Speed-first by drift, not by decision

        Model 4 is a tool, not a default. Used on purpose, it has a trigger, an end date and a review afterward.

        For the next leadership meeting

        Five questions worth asking

        Select a question to see what a well-structured program looks like.

        Side Quest Projects · SQ-01 · A playthrough on municipal capital delivery

        How structure
        shapes flow

        Who does what when a capital project moves from budget request to close-out? Pick a project and walk it through. At each step, choose how your organization does it today.

        At the end you'll see which of four delivery structures you're running, and how the same project would run under the one this research recommends.

        The ten-minute exercise

        Map your organization

        Describe how your municipality is set up. See which of four delivery structures you run, pick the one you want, and get the changes as a brief for your leadership team.

        1. 01Pick the template closest to yours
        2. 02Answer five short steps
        3. 03Plan a change, or post your result
        Step 1 · Choose a projectAbout five minutes each. Nothing is stored or sent.

        Rather warm up first? , or .

        Use ← → to move between chapters

        This work was made with AI assistance. The research combines human and AI input, the website was built with AI, and both were reviewed by people. It may still contain errors, and its accuracy isn't guaranteed. Check it against your own context before relying on it.

        · The sequencing game

        What comes next?

        Ten everyday projects, sixteen tasks each. Put them in the order they should happen. It's the same skill a capital project needs: knowing what has to be true before the next step can start.

        Build the orderTap tasks in the order you'd do them, or drag them on a computer. Use the arrows to fix the order.
        Get scored on dependenciesA task scores when everything it relies on comes before it. More than one order can be right. Safety-critical and costly-to-undo dependencies count double.
        Earn stars95 percent of dependencies in order earns three stars. Hints cost 50 points, and finishing fast adds a bonus.
        03
        100%
        Scroll or pinch to zoomDrag to panClick any stepSwipe for the next modelPinch to zoomTap a step

        Why structure decides flow

        Three ideas from outside municipal government explain most of what the four charts show: how organizations communicate, how queues behave, and how bottlenecks should be managed.

        Best on a bigger screen

        These charts respond to dragging and hovering, so they work best on a computer.

        Email me the link
        01 · Conway's law

        The plan mirrors the conversations

        In 1968 Melvin Conway observed that organizations produce designs that copy their own communication structure.

        A capital program works the same way. The schedule ends up shaped by who talks to whom, and when. The inverse Conway maneuver is to draw the conversations on purpose, so the plan follows.

        Choose a group to see when each model first brings it into the work.

        02 · Queueing

        Busy crews make long queues

        The waiting time for a shared resource doesn't grow in a straight line. It climbs steeply as the resource fills up.

        Drag the slider, or move across the chart, to change how fully the crews are booked, and pick how many crews share the work. The study uses about 75 to 80 percent in peak months as a starting point. It's a rule of thumb to tune with real data, not a standard.

        Overtime doesn't escape the curve. Sustained 50 to 60 hour weeks cut productivity by roughly 10 to 15 percent.

        Modelled as a pool of identical crews (an M/M/c queue). Most capital work is scheduled, not random, but breaks, emergencies and late changes are random, and they feel the queue first. A bigger pool waits less at the same booking level, but every pool climbs steeply near full. Read the curve for its shape, not its exact numbers.

        3.0×

        03 · Theory of Constraints

        Plan around the constraint

        Every system has one resource that limits everything else. In many municipal capital programs, it's the shared operations crews.

        The Theory of Constraints gives five steps for managing that resource. Only one model works through all five.

        This study assumes the crews are the constraint. Confirm it with your own data first: in some organizations it's project manager capacity, design, procurement or council timing.

        Built inPartlyMissing

        Compare the models

        Set what matters to you and see which structure fits. The ratings are the study's qualitative judgments on a 1 to 5 scale, where higher is better.

        Your priorities

        How much does each one matter?

        Pick a preset or set each weight.

        Weighted result

        Best fit

        Against PMI standards

        How each model lines up with standard project management practice

        Practices drawn from PMI's standards for project, program and portfolio management, applied to a capital program. The levels are the study's judgment.

        · Your organization

        Map your organization

        Describe how your municipality is set up: its departments, where the crews and buildings sit, who runs each kind of capital project, and how the program is managed. The site matches it to the closest of the four structures. Then pick the model you want to run, and it lists what would change and builds a brief for your leadership team.

        The match is a prompt for reflection, not an assessment. It reads the structure you describe against the four illustrative models in this study.

        The best method found

        For a standing municipal capital program, one structure stands out. The fastest model still has a place, as a declared emergency mode.

        Recommended

        Model 3: departmental streams, governed as one portfolio, with the crews planned as the system constraint.

        Model 4 is kept as a declared emergency mode inside it.

        • It matches the standards.PMI portfolio capacity management, ISO 55000 alignment and assurance, FCM cross-functional teams and GFOA monitoring, without centralizing delivery.
        • It fixes the flow problem at its source.It adds the two conversations that matter most, early: the capacity review and the support review.
        • It manages the real constraint.It's the only model that names the crews as the shared resource and builds the program around them.
        • It answers what audits keep finding.Standards, governance, prioritization and visibility, for one position and existing software.
        • It keeps what works in Model 2.Departments keep ownership, expertise and speed.
        How to start

        Build control in stages

        Stage 1 · Supportive
        Make the work visibleStand up the tracker, the weekly review and the coordination meeting.
        Stage 2 · Controlling
        Make the reviews requiredAfter a season of data, add the capacity review and the support review as required steps, with published criteria.
        Stage 3 · Asset-led
        Close the loopHire or assign the asset manager and connect close-out to the asset register and next year's ranking.

        Each stage pays for itself on its own, and each makes the next one easier.

        Talking it through

        The first coordination meeting

        An imagined conversation, not a transcript. It's the first coordination meeting of the year at a municipality that has just adopted Model 3. Everyone around the table has lived through Model 2.

        Step through it one line at a time.

        The structure decides when people talk, and when people talk decides how the work flows.

        Sources (37)

        Independent research. Titles are generic, and the four models are illustrative structures rather than a description of any one municipality. Ratings are qualitative judgments drawn from the research.

        · How Model 3 runs

        Tools and comms

        A proposed tracking and communication system built from tools most municipalities already have: Microsoft 365 and a computerized maintenance management system (CMMS), whichever one the municipality already runs. The rule underneath it: every fact is entered once, in one home.

        01 · The stack

        Each tool has one job

        Select a tool to see what lives there, who writes to it and what doesn't belong in it.

        02 · One crew request, end to end

        Follow the data

        How one request for operations crews moves between the tools, from budget approval to close-out. Nobody re-types anything.

        03 · Five lists in one Teams channel

        The tracker

        Lists 1 to 4 come from the study's tracking design. List 5 is new: basic Planner comes with most Microsoft 365 plans, but Gantt charts, dependencies and baselines need a paid premium license, so key dates live in a list. A calendar view of List 5 becomes the one program timeline everyone can see.

        04 · What lives where

        One fact, one home

        05 · The rhythm

        Who looks at what, and when

        06 · Standard practice, built in

        The project management basics Model 3 carries

        07 · Making it stick

        People, agreements and scale

        Rules of the road