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Random Thoughts on Leadership & Technology

Aperitif from the Poisoned Cup or Why You Always Start With Risk

aperitif-from-poisoned-cup

Risk should be your breakfast. Moreover - it should be the appetizer to every meal you have. Drink your aperitif from the poisoned cup.

Beyond avoid, mitigate, transfer, escalate, and accept - the move PMBOK doesn't teach you on how to truly own risk.

It gives you five things to do with a risk - avoid it, mitigate it, transfer it, escalate it, or accept it. It is a tidy list. It is also a list designed for risks that have already arrived - risks you encounter, log, and respond to. It quietly casts the project manager as a triage nurse, sorting incoming threats by severity and shipping them to the appropriate department.

The PMs I respect most refuse to be triage nurses. They are time travelers. When a risk lands on their desk, they don't ask "What do I do with this?" They ask "Where in the project would this have been cheap to solve, and can I still get there?".

This is shift-risk-left. The name is borrowed from DevOps, where shift-left means catching bugs earlier in the development pipeline - closer to the origin, further from the customer and the budget overrun. The principle generalizes far beyond software. In any project, risks get more expensive the later you meet them. A misaligned requirement caught in a Figma file costs an afternoon. The same misalignment caught in production costs a month. The same misalignment caught aver a lifetime of a contract can cost dearly indeed.

The strange thing is that most trainings do not really address this. Avoid, mitigate, transfer, escalate, accept - these are all tactics for risks you are stuck with. They assume the risk has already shown up at your door. Shift-left is different. Shift-left says - I am going to drag this risk backward in time, into a cheaper part of the project, on purpose.

What it looks like in practice

The clearest example is the clickable prototype. Before anyone writes production code, you build a Figma file that pretends to be the app, cutting through the cone of uncertainty. You let real people click through it. Half the risks of the engineering phase - "the workflow doesn't make sense", "the user can't find this button," "executives actually wanted the dashboard to do something else entirely" - get surfaced and resolved while the cost of changing your mind is measured in pixels, not pull requests. You have not avoided the risk. You have not mitigated it. You have moved it from a place where it is expensive to a place where it is cheap.

A second example, newly affordable - AI-validated technical spikes. Used to be that "can we actually build this" was a question you answered by hiring a senior engineer for a month. Now you can sit with an AI agent for an afternoon and have a working sketch of the hardest module before the project has a budget. You are not building the system. You are buying down uncertainty. If the prototype reveals that your favored approach has a fatal flaw - the fancy image recognition fearure is harder that it looks, the data architecture is wrong - you have just spared the project a catastrophic pivot.

A third, less obvious one - overstaffing the early phases. Tuckman's model says every team goes through forming, storming, norming, performing. Storming is expensive - it slows delivery and frays nerves. If you know you'll need to scale down toward milestones, the temptation is to build a small, lean team and add people as needed. This is the wrong move. Each new person triggers another round of storming. Instead - overstaff at the start, run the storming once with everybody in the room, then taper as milestones approach. People are dramatically easier (and better for forecasting and budget predictability - you will know the budget is short for the work at hand earlier) to ramp off than to ramp on. You have shifted the team-formation risk left and consolidated it into a single, manageable disturbance, rather than letting it ambush you four times across the project.

These three share a structure. There is a risk that, traditionally, hits drlivery somewhere in the middle or late stages. There is an early-phase intervention that swaps it out for something smaller and more controllable. Once you start looking, these moves are everywhere.

A field guide

Pre-mortems Before kickoff, gather the team and announce that the project failed catastrophically. Have everyone write down why. The exercise reliably surfaces risks that people felt but didn't feel licensed to raise. It costs an hour. The risks it uncovers would otherwise cost months.

Working-backward documents Amazon's famous practice - write the press release before you build the product. If you can't write a compelling one, you don't have a project - you have a hope. The risk of "we built the wrong thing" gets dragged from launch day to the day the doc is reviewed.

Tabletop launch exercises Walk through launch day in a conference room weeks before it happens. Who pushes the button? What dashboards are watched? Who calls the customer if something breaks? You will discover that nobody owns the rollback plan, that the on-call rotation hasn't been set up, and that the marketing email goes out before the feature flag flips. None of these are technical problems. All of them sink launches.

Vendor proof-of-concepts on your data Vendors demo beautifully on synthetic data. Make them run their solution or do a PoC on a sample of yours, with your edge cases, before you sign. The risk of "this doesn't actually work in our environment" moves from post-purchase - when you are committed and have no leverage - to pre-purchase, when you have all of it.

Front-loaded compliance, legal, and security review Most projects treat these as gates near the end. This guarantees that a portion of projects get torpedoed at the gate, after most of the money has been spent. Bring those reviewers in during planning. Their objections are radically cheaper to absorb when the architecture is still a whiteboard.

Pre-negotiated dependencies If your project needs three things from a partner team, do not assume they will deliver on the timeline you imagine. Get the commitments in writing before you publish your own roadmap. The risk of a dependency slip is shifted from your critical path to their planning meeting.

Staffing for prior scars When you staff a project, prefer people who have lived through one like it before. They bring their lessons pre-loaded. You are not paying them for their hands; you are paying them for the risks they have already shifted left in their heads, on someone else's project.

Decision logs from day one Write down every assumption as it is made. An assumption is a risk in disguise - it is a thing you decided not to verify. A logged assumption can be revisited and tested. An unlogged one becomes the post-mortem.

Cost modeling before commitment. Build the unit economics model at the proposal stage, not after the prototype is built. If the math doesn't work, the project should die at the napkin, not at the demo.

Demo-driven scoping Before defining the scope, make somebody describe the demo. If the demo can't be articulated in three sentences, the scope is wrong. The risk of "we shipped a thing nobody can show off" gets caught before a single line of spec is written.

The deeper move

The pattern under all of these is the same - substitute small, early, controllable encounters with risk for large, late, uncontrollable ones. A pre-mortem is a small encounter with the risk of total failure. A clickable prototype is a small encounter with the risk of building the wrong thing. Overstaffing-then-tapering is a small encounter with team turbulence. Each of them is a tiny, deliberate confrontation that prevents a much larger, accidental one.

This is what high-ownership project management actually looks like. It is not the diligent maintenance of a risk register. It is the active rearrangement of when, where, and how risks meet the project. The risk register is a passive instrument; it tells you what you are afraid of. Shift-left is a verb; it changes when those fears get tested.

A small caution - shift-left is not free. Pre-mortems take time. Prototypes require designers and tokens. Overstaffing costs real money in month one to save heartburn in month four. The discipline is in knowing which risks are worth dragging backward - usually the ones that would be expensive if they arrived late, and cheap to surface early or the risks your team is not familiar with. If a risk is genuinely tail-distributed and unlikely, you can leave it on the register. If it is a near-certainty masquerading as a possibility, drag it left, and drag it now.

The PMBOK list ends with accept. Acceptance is a fine answer for risks you cannot move. But for most of the risks on most projects, acceptance is what you settle for after you have failed to be creative. The first move, before the five PMBOK moves, is to ask - Can this risk live somewhere earlier, where it would cost less and teach more?

More often than people think, the answer is yes. And the projects that consistently succeed are the ones run by people who keep asking that question until it stops being yes.