Planning

The ability to structure work, allocate resources, and chart a clear course of action to achieve strategic and operational goals. It involves setting priorities, anticipating risks, organising people and tasks effectively, and ensuring progress is monitored and adjusted as necessary.

“If plan A doesn’t work, the alphabet has 25 more letters – 204 if you’re in Japan.” – Claire Cook

Barriers to planning

Overconfidence: Leaders may believe they possess enough experience or expertise to operate without structured planning, assuming they can navigate challenges as they arise.

Impatience: Some leaders are driven by quick results and may view planning as a slow and tedious process, leading them to skip or rush through it.

Low tolerance for structure: A lack of appreciation for processes and systems can make planning feel restrictive, particularly for leaders who thrive on spontaneity or creativity.

Desire for simplicity: Leaders may oversimplify tasks or goals to avoid complexity, bypassing the detailed planning needed to achieve long-term success.

Poor time management: Some leaders may have the intention to plan but consistently fail to allocate time for it, being caught up in day-to-day urgencies.

Disdain for formal planning: Leaders who are sceptical about the value of planning may reject it altogether, relying instead on reactive decision-making or improvisation.

Lack of foresight: Without the ability to anticipate future challenges or opportunities, some leaders may struggle to see the need for detailed long-term plans.

Fear of failure: Planning involves confronting potential risks and challenges. Leaders who fear failure may avoid planning to evade addressing these difficult aspects.

Limited patience for detail: Planning requires careful attention to detail, and leaders who prefer a broader, more visionary approach may find it difficult to engage in the necessary specifics.

Inconsistent communication: Leaders who struggle with planning often fail to communicate goals and expectations clearly, leaving their teams without a cohesive direction or understanding of the path forward.

“Plans are of little importance, but planning is essential.” – Winston Churchill

Enablers of planning

Explore your roadmaps: Break down your bigger goals into smaller tasks, outlining the steps from start to finish. Consider every resource—time, people, budget—you’ll need, and identify who controls them. Mapping out the entire sequence helps ensure nothing critical is missed and clarifies the journey ahead for yourself and others.

Tool up: Invest in appropriate software or templates for project or task management. Learn how to use these tools effectively to track tasks, manage dependencies, and present clear, organised plans to yourself and your team.

Clarify goals: Define clear, actionable goals for entire tasks or projects. Assign measurable benchmarks to track progress and stay on target. This not only keeps you accountable but also allows you to adjust if timelines or objectives shift.

Simplify complex plans: For large, multi-faceted projects, create a master plan to manage complexity. Break it into manageable segments, ensuring each task or phase has its own mini-plan. This approach helps prevent feeling overwhelmed and keeps you focused.

Maximise resource efficiency: Plan your budget and resources carefully. Track critical elements such as expenditures and time against your plan, and always leave room for unexpected costs.

Match people effectively: Assign tasks based on the strengths and capabilities of your team. Recognise that everyone brings different skills to the table and align tasks accordingly. This way, you’re optimising the potential of your team while ensuring tasks are handled well.

Plan for the unexpected: Think through possible risks and worst-case scenarios. What could go wrong? Develop scenario/contingency plans for each significant risk, especially for areas you have less control over.

Set up reviews & feedback loops: Establish a system to track your plan’s progress in real-time. Regular check-ins, progress reports, and feedback loops keep everyone aligned.

Learn from the best: Observe and learn from colleagues who excel at planning. Compare their methods to yours and identify areas where you can improve. Regularly seek feedback from others (ideally them), especially those who’ve worked close to your projects.

Collaborate more: Planning doesn’t have to be a solo effort. Engage your team early, and invite input from others who might bring valuable perspectives. Delegate the planning process where needed, ensuring the right people are creating detailed steps while you maintain strategic oversight.

“A good plan today is better than a perfect plan tomorrow.” – George S. Patton

Self-reflection questions on planning

Could you break your current project(s) down into clear, manageable steps? How detailed is your current plan? What resources or people will you need at each stage? Are there any critical steps or sequences you might be overlooking?

How do you currently use planning tools: Are you using the right tools to map out tasks and timelines effectively? Could learning a new tool or software make your planning more streamlined? How often do you update or review these tools during a project?

How do you measure progress against your plans: Do you have specific, measurable goals for each phase of the project? What indicators do you rely on to track whether you’re on schedule? How do you adjust when milestones aren’t being met?

How do you simplify complex plans to avoid feeling overwhelmed: Are you able to break large projects into smaller, manageable tasks? What do you do when things feel too complicated? How do you keep focus on both the big picture and the details?

How efficiently are you managing your resources: How carefully are you tracking budget and time? Could you make better use of your team’s time or talents? Are you leaving enough room for unforeseen challenges or costs?

Are you assigning the right tasks to the right people: How well do you understand the strengths of your team members? Could you delegate more effectively based on their skills and experiences? What steps can you take to ensure tasks are matched with the right capabilities?

How prepared are you for unexpected problems: Have you considered the most likely risks or roadblocks? What contingency plans have you developed? How do you stay adaptable when things don’t go as planned?

How do you monitor and adjust your plan in real time: Are you regularly reviewing progress and making adjustments as necessary? What systems do you have in place to receive feedback on your plan’s progress? Could you improve communication to ensure everyone stays aligned?

Could you learn more from others who excel at planning: Who in your network is particularly good at planning? What specific techniques or habits could you adopt from them? How often do you seek feedback from those affected by your plans?

How open are you to collaboration in planning: Do you involve others in the planning process to gain fresh perspectives? Could delegating parts of the plan to others improve the quality of your projects? How do you ensure the team is aligned with the vision and steps of the plan?

“It takes as much energy to wish as it does to plan.” – Eleanor Roosevelt