CIO strategic planning for 2026: insights from Gartner’s “IT executive toolkit for strategic planning”

Executive overview

Late 2025 is when the 2026 IT portfolio is truly set. In practice, boards and CFOs are already locking next year’s priorities, funding envelopes, and risk posture. Gartner’s toolkit responds to that reality by reframing IT planning as an enterprise portfolio discipline: align to business context, sense disruption early, validate execution capacity, and reallocate capital toward measurable impact.

Two structural forces make this shift non-optional. First, growth is required, but capital is constrained; “spend less to create more value” is now a standing planning premise, not a temporary cost cycle. Second, technology is becoming inseparable from workforce design. With most CEOs already integrating human labor and machines, CIO strategy in 2026 is shaped as a hybrid operating model—one that must improve productivity without eroding control, trust, or resilience (p.2).

Planning sequence for 2026

1. Confirm business context and constraints for 1–2–5 year horizons with CEO/CFO/BU leaders (p.2).
2. Run TPESTRE trend sensing and classify implications into footprint vs foothold (p.6).
3. Select and prioritize macro scenarios by impact/likelihood/velocity; define triggers (p.7).
4. Assess capability maturity using Gartner IT Score to surface gaps that will block impact (p.9).
5. Benchmark digital execution with Digital Execution Scorecard™ to validate delivery realism (p.17).
6. Reallocate budgets, set SMART measures, and publish a one-page strategy that is CFO-legible and board-reviewable (pp.11, 17).

This sequence is what turns a 2026 plan into a governable portfolio rather than an internal backlog.

Top 10 strategic insights

1. Start with business context, not IT aspirations. Derive goals directly from enterprise objectives and execution constraints gathered via structured executive interviews (p.2). Implication: Strategy begins in the C-suite. Signal Strength: High.
2. Treat trend-sensing as a formal input using TPESTRE. Apply TPESTRE (Tech, Political, Economic, Social, Trust/Ethics, Regulatory, Environmental) to scan for shocks and opportunities (p.6). Implication: Strategy includes futures, not just forecasts. Signal Strength: High.
3. Separate “footprint” from “foothold.” Gartner distinguishes protecting existing market presence (footprint) from enabling expansion/acquisitions (foothold) (p.6). Implication: The 2026 spend mix must show defense vs growth. Signal Strength: High.
4. Scenario planning needs explicit prioritization. Use impact vs likelihood (plus velocity) to rank scenarios before writing actions (p.7). Implication: Roadmaps become resilient to volatility. Signal Strength: Moderate.
5. Use specific high-impact macro scenarios. Gartner highlights test cases such as retreat of global regulatory order and universal basic income (p.7). Implication: Baseline plans need pre-defined contingencies. Signal Strength: Emerging.
6. Capability maturity is the bridge to execution. Gartner IT Score measures current vs target maturity based on digital ambition (p.9). Implication: Roadmaps should be maturity paths, not wish lists. Signal Strength: High.
7. Budget strategy is portfolio triage. Reallocate from low-return work to initiatives with measurable margin or growth lift (p.2). Implication: Cost decisions must fund impact, not austerity. Signal Strength: High.
8. CFO alignment requires CFO success metrics. The toolkit explicitly lists ROIC, EVA, cash conversion cycle, cost targets, and shareholder value (p.11). Implication: These metrics are the admission price for 2026 approvals. Signal Strength: High.
9. Benchmark execution before scaling innovation. Digital Execution Scorecard™ compares outcomes vs peers and best-in-class priorities (p.17). Implication: Transform based on measured gaps, not optimism. Signal Strength: High.
10. One-page strategy is governance, not simplification. The one-pager forces linkage from objectives to capabilities, actions, risks, KPIs, and timing (p.2). Implication: Clarity accelerates alignment and oversight. Signal Strength: High.

Framework & Tool callouts

Framework: TPESTRE (Trend Scan). A disciplined scan across technology, politics, economics, society, trust/ethics, regulation, and environment. It creates a shared map of external forces that should shape the 2026 portfolio (p.6).

Governance split: Footprint vs Foothold. Footprint investments defend existing revenue and operational resilience; foothold investments enable strategic expansion or acquisition plays. This split makes capital trade-offs explicit for boards and CFOs (p.6).

Tool: Gartner IT score. A maturity assessment of the IT operating model against enterprise digital ambition, used to define current state, target state, and the next capability upgrades your 2026 roadmap must fund (p.9).

Tool: Gartner Digital Execution Scorecard™ . Benchmarks digital outcomes against industry peers and best practices, identifying where delivery capacity lags strategy and where sequencing must change before scaling GenAI or automation (p.17).

Risk radar

Strategy–execution gap (High Impact / Medium Likelihood) Without maturity assessment and benchmarking, plans over-commit relative to delivery reality, leading to chronic delay and loss of executive trust.

Cost cutting masquerading as optimization (High Impact / Medium Likelihood) Savings without cost-to-value mapping weaken differentiating capabilities and create rebound spend.

Metric overload (Medium Impact / High Likelihood) Non-SMART KPI sprawl dilutes signal and slows governance; minimalist measurement protects credibility.

Scenario blindness (High Impact / Low Likelihood) Plans optimized for the base case break under fast regulatory or geopolitical fragmentation.

CFO misalignment (High Impact / Medium Likelihood) Initiatives not expressible in ROIC/EVA/cash terms stall in 2026 capital reviews (p.11).

Executive action checklist

• Run structured business-partner interviews before drafting IT goals.
• Apply TPESTRE scanning and classify investments into footprint vs foothold.
• Stress-test roadmaps against high-impact macro scenarios; pre-plan contingencies.
• Assess capability maturity with Gartner IT Score.
• Benchmark execution gaps with Digital Execution Scorecard™.
• Reallocate budgets via divest-to-invest logic; publish a one-page 2026 strategy.

2026 strategy success criteria

• Portfolio clearly shows footprint/foothold allocation (p.6).
• Every major initiative maps to a CFO success metric (ROIC/EVA/cash cycle) (p.11).
• High-impact scenarios have defined triggers and funded contingencies (p.7).
• Execution gaps are benchmarked before scaling AI or automation (pp.9, 17).
• One-page plan is ready for board review and quarterly tracking (p.2).

Source attribution

Insights based on The IT Executive Toolkit for Strategic Planning (Gartner, 2025). If you experience access issues, contact [email protected].