We present a domain-grounded framework and benchmark for tool-aware plan generation in contact centers, where answering a query for business insights, our target use case, requires decomposing it into executable steps over structured tools (Text2SQL (T2S)/Snowflake) and unstructured tools (RAG/transcripts) with explicit depends_on for parallelism. Our contributions are threefold: (i) a reference-based plan evaluation framework operating in two modes - a metric-wise evaluator spanning seven dimensions (e.g., tool-prompt alignment, query adherence) and a one-shot evaluator; (ii) a data curation methodology that iteratively refines plans via an evaluator->optimizer loop to produce high-quality plan lineages (ordered plan revisions) while reducing manual effort; and (iii) a large-scale study of 14 LLMs across sizes and families for their ability to decompose queries into step-by-step, executable, and tool-assigned plans, evaluated under prompts with and without lineage. Empirically, LLMs struggle on compound queries and on plans exceeding 4 steps (typically 5-15); the best total metric score reaches 84.8% (Claude-3-7-Sonnet), while the strongest one-shot match rate at the "A+" tier (Extremely Good, Very Good) is only 49.75% (o3-mini). Plan lineage yields mixed gains overall but benefits several top models and improves step executability for many. Our results highlight persistent gaps in tool-understanding, especially in tool-prompt alignment and tool-usage completeness, and show that shorter, simpler plans are markedly easier. The framework and findings provide a reproducible path for assessing and improving agentic planning with tools for answering data-analysis queries in contact-center settings.