Backward planning with obstacle avoidance

Work backwards from your goals to identify actions, dependencies, and obstacles.

Backward planning flips conventional planning on its head: instead of moving forward step by step from today, you start with the desired end state and work in reverse. This helps uncover dependencies, anticipate obstacles, and design contingencies early, ensuring a smoother path toward organisational objectives. By combining stepwise methodology, templates, and guides, your organisation can progress efficiently and avoid common pitfalls.

Define the desired state

Purpose: Establish a clear vision of the target outcome.

Implementation:

  • Describe success in concrete terms (e.g., operational SIRT, fully integrated SOC, or cross-trained teams).

  • Include metrics, timelines, and qualitative indicators to make the state measurable.

  • Align with organisational strategy, security priorities, and stakeholder expectations.

Outcome: A precise endpoint against which all backward planning steps are aligned.

Identify key milestones and dependencies

Purpose: Break the desired state into critical milestones and identify what must precede each.

Implementation:

  • Work backward to determine preconditions for each milestone.

  • Map dependencies between teams, processes, tools, and policies.

  • Highlight critical path items that are essential for achieving the end state.

Outcome: A clear sequence of dependencies that informs realistic planning and resource allocation.

Map potential obstacles

Purpose: Anticipate risks, blockers, or challenges at each step.

Implementation:

  • List internal and external obstacles — organisational resistance, skill gaps, technical limitations, regulatory requirements, or resource constraints.

  • Consider both likelihood and impact of each obstacle.

  • Identify early warning signs or indicators for each risk.

Outcome: A proactive risk register that informs contingency planning.

Develop contingency actions

Purpose: Prepare alternative strategies to overcome anticipated obstacles. Implementation:

  • Brainstorm mitigation measures for each identified risk.

  • Assign responsibilities and resources to each contingency.

  • Ensure alternatives are flexible and scalable to adapt as circumstances evolve.

Outcome: A robust set of fallback plans, reducing disruption and maintaining momentum toward the desired state.

Work stepwise toward current state

Purpose: Translate the backward map into actionable steps moving forward.

Implementation:

  • Convert the backward sequence into a forward-acting roadmap.

  • Prioritise early actions that unblock dependencies and reduce risk.

  • Integrate into operational planning, sprints, or quarterly objectives.

Outcome: A practical forward plan informed by backward analysis, minimizing surprises and improving execution efficiency.

Review, monitor, and adjust

Purpose: Keep the plan adaptive to changing conditions.

Implementation:

  • Regularly compare progress to milestones and dependencies.

  • Reassess risks and obstacles; update contingencies as needed.

  • Encourage feedback loops from teams to refine actions and timelines.

Outcome: A dynamic planning process that evolves with the organisation and mitigates risks continuously.

Optional tools and templates

  • Stepwise milestone charts

  • Dependency mapping grids

  • Risk/obstacle scoring matrices

  • Contingency planning templates