Five Fatal Assumptions: Why T-Shirt Sizing Systematically Fails for AI Projects
Organizations: Cisco Systems, Inc.
Abstract
Agile estimation techniques, particularly T-shirt sizing, are widely used in software development for their simplicity and utility in scoping work. However, when we apply these methods to artificial intelligence initiatives -- especially those involving large language models (LLMs) and multi-agent systems -- the results can be systematically misleading. This paper shares an evidence-backed analysis of five foundational assumptions we often make during T-shirt sizing. While these assumptions usually hold true for traditional software, they tend to fail in AI contexts: (1) linear effort scaling, (2) repeatability from prior experience, (3) effort-duration fungibility, (4) task decomposability, and (5) deterministic completion criteria. Drawing on recent research into multi-agent system failures, scaling principles, and the inherent unreliability of multi-turn conversations, we show how AI development breaks these rules. We see this through non-linear performance jumps, complex interaction surfaces, and "tight coupling" where a small change in data cascades through the entire stack. To help teams navigate this, we propose Checkpoint Sizing: a more human-centric, iterative approach that uses explicit decision gates where scope and feasibility are reassessed based on what we learn during development, rather than what we assumed at the start. This paper is intended for engineering managers, technical leads, and product owners responsible for planning and delivering AI initiatives.
Figures & tables
| Agent Count | Required Interaction Tests | Complexity Growth |
|---|---|---|
| 2 | 2 | Baseline |
| 3 | 6 | +4 |
| 5 | 20 | +14 |
| 10 | 90 | +70 |
| Combinatorial |
| Principle | Implementation |
|---|---|
| Explicit Decision Gates | Define checkpoints at natural phase boundaries (data readiness, model convergence, safety validation) |
| Evidence-Based Reassessment | Re-estimate scope, timeline, and feasibility at each checkpoint based on empirical observations |
| Uncertainty Acknowledgment | Replace point estimates with confidence intervals that reflect genuine uncertainty |
| Pivot Optionality | Build explicit decision points for scope reduction, pivot, or termination based on checkpoint outcomes |
| Ref | Paper Title | Validates Assumptions | Relevance |
|---|---|---|---|
| [1] | Why Do Multi-Agent LLM Systems Fail? | 4 (Decomposability via inter-agent coupling), 5 (Deterministic completion via verification/termination failures) | 100% |
| [2] | An LLM-based multi-agent framework for agile effort estimation | 2 (Repeatability via subjective inconsistency), 5 (Deterministic completion via estimation instability) | 100% |
| [3] | Towards a Science of Scaling Agent Systems | 1 (Non-linear scaling), 3 (Effort-duration tradeoffs), 4 (Coordination overhead/error amplification) | 100% |
| [4] | LLMs Get Lost In Multi-Turn Conversation | 2 (Repeatability via multi-turn unreliability), 5 (Deterministic completion via non-recovering error trajectories) | 100% |
| [5] | Effort and Size Estimation in Software Projects with Large Language Model-based Intelligent Interfaces | 2 (Repeatability via hidden uncertainty), 5 (Definition of done via evolving spec/AI interface behavior) | 100% |
| Assumption | Primary Support | Secondary Support |
|---|---|---|
| 1. Linear Scaling | [3] | — |
| 2. Repeatability | [2], [4], [5] | — |
| 3. Effort-Duration Trade | [3] | — |
| 4. Decomposability | [1], [3] | — |
| 5. Deterministic Completion | [1], [2], [4], [5] | — |