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.

“Long range planning does not deal with future decisions, but with the future of present decisions.” Peter Drucker

Why planning matters

Planning is what converts a goal from a hope into something that can actually be pursued in an orderly way. Without it, a leader ends up making the same category of decision repeatedly, what to do next, in whatever order problems happen to surface, rather than in the order that would actually get the outcome achieved fastest. The absence of a plan does not mean the absence of effort. It usually means a great deal of effort spent without a clear sense of whether it is moving things forward.

Good planning also buys a leader something that is easy to undervalue until it is missing: the ability to notice early when something has gone off course. A plan creates a reference point, so a gap between where things are and where they were supposed to be becomes visible while there is still time to do something about it. Leaders without a plan often do not find out they are behind until the deadline has already arrived.

The risk on the other side is treating the plan itself as the goal. A plan is a current best guess about how to get somewhere, built with the information available at the time, and the information available at the time is never complete. Leaders who protect the plan more fiercely than they protect the outcome it was built to serve end up executing a sequence of steps that stopped making sense long after the world around it changed.

“Someone’s sitting in the shade today because someone planted a tree a long time ago.” Warren Buffett

What good and bad planning looks like

“The general who wins a battle makes many calculations in his temple before the battle is fought.” Sun Tzu

Barriers to planning

Overconfidence: Leaders who believe their experience is enough to navigate whatever comes up often treat planning as something other people need, not something they do. The gap only becomes visible when a problem arrives that genuinely was not survivable through improvisation, by which point the absence of any earlier structure has already cost real time.
Impatience: A drive for quick results can make the upfront work of planning feel like a delay rather than an investment, so leaders skip or rush it to get to the part that feels like progress. The irony is that skipped planning tends to resurface later as rework, so the time saved at the start is usually spent twice over further down the line.
Rejecting formal structure: Some leaders find processes and systems restrictive, preferring to rely on spontaneity, instinct, or reactive decision making instead. What looks like agility from the inside often looks, to a team trying to coordinate around it, like a leader nobody can plan alongside, since there is nothing stable to plan against.
Avoiding necessary complexity: A preference for the big picture over the specifics can lead leaders to oversimplify a plan just enough to make it comfortable to hold in their head, even when the underlying task genuinely required more detail. The complexity does not disappear when it is left out of the plan. It just resurfaces later, unplanned, usually at a worse time.
Poor time management: Some leaders genuinely intend to plan but never protect the time for it, since planning rarely feels as urgent as whatever is happening today. Without a fixed slot for it, planning consistently loses to the next fire, and the fires that would have been prevented by planning become the reason there is never time to plan.
Lack of foresight: Without the habit of imagining how a current situation is likely to unfold, some leaders do not experience an unplanned future as a risk worth addressing, since they are not picturing it clearly enough to feel concerned. The absence of a vivid enough picture of what could go wrong is often mistaken for genuine confidence that nothing will.
Fear of failure: Planning forces a leader to look directly at what could go wrong, which is uncomfortable in a way that staying vague is not. Avoiding the plan avoids that discomfort in the short term, but it also removes the leader’s best chance of catching the failure while it is still small enough to fix.
Planning only for the happy path: A plan built entirely around the optimistic version of events can look thorough without ever having been tested against a realistic setback. The gap only becomes visible once something predictable, a delay, a departure, a missed dependency, actually happens, and there is no version of the plan that accounted for it.
Treating the plan as a static document rather than a living tool: A plan created once, often under pressure to produce something before a launch or milestone, can quietly become outdated while everyone keeps referring to the original version out of habit. The team ends up coordinating around a document that stopped describing reality some time ago, without anyone having consciously decided to keep using it.
Planning alone and presenting the plan as finished: Leaders who do the planning work in isolation lose the chance for others to catch blind spots while the plan is still easy to change, and the team experiences the finished plan as something handed down rather than something they helped build. A plan nobody helped shape rarely gets the same commitment as one people had a hand in.

“Plans are worthless, but planning is everything.” Dwight D. Eisenhower

Enablers of planning

Structure the sequence, not just the task list: Break a large goal into smaller tasks, but do not stop at listing them. Work out what depends on what, and for genuinely complex projects, build a master plan with a mini plan for each phase, so the sequence itself, not just the collection of tasks, is what gets managed.
Tool up: Invest in project or task management software or templates, and actually learn to use them properly rather than defaulting to a spreadsheet out of habit. The right tool makes dependencies and progress visible to the whole team, not just to the person holding the plan in their head.
Clarify goals: Define specific, measurable goals for each phase of a project rather than a single vague outcome at the end. Clear benchmarks let you tell the difference between a plan that is slightly behind and one that has quietly gone off course.
Maximise resource efficiency: Plan your budget, time, and people deliberately, and track them against the plan as you go rather than only at the end. Leave a genuine margin for the unexpected costs that every plan eventually meets, so they do not derail the whole timeline when they arrive.
Match people effectively: Assign tasks based on who is actually best suited to them, not just who happens to be available. Recognising the different strengths on a team and planning around them, rather than around convenience, tends to produce a plan that is both faster and less fragile.
Plan for the unexpected: Ask what could realistically go wrong, especially in the areas you have the least control over, and build a specific response for each significant risk before it happens. A contingency thought through in advance gets executed in minutes. One improvised under pressure usually costs hours.
Set up reviews and feedback loops: Build regular check ins and progress reviews into the plan itself, not as an afterthought once something looks off. A plan that is only ever reviewed when there is a problem will always be reviewed too late to prevent one.
Learn from the best: Study how colleagues who plan well actually do it, and be specific about what you borrow, not just that they are good at it. Ask them directly for feedback on your own plans, especially people who have worked close enough to your projects to see where the gaps usually are.
Collaborate more: Bring your team into the planning process early rather than only sharing the finished version. Delegating parts of the detailed planning to the people who will execute it, while you hold the overall direction, tends to produce both a better plan and a team more committed to carrying it out.
Build a kill switch into the plan: Decide in advance what evidence, partway through, would mean the plan itself needs to change, not just the timeline. Without a predetermined trigger for reconsidering it, most plans get quietly extended past the point where continuing was still the right call, simply because no moment was ever built in for asking.

“A good plan violently executed now is better than a perfect plan next week.” George S. Patton

Reflection questions on planning

1. Could you break your current project down into a clear sequence, not just a list of tasks? Are you able to simplify complex, multi phase work into manageable segments without losing sight of how the pieces connect? What critical dependencies might you be overlooking?
2. 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?
3. 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 are on schedule? How do you adjust when milestones are not being met?
4. 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?
5. 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 experience? What steps could you take to ensure tasks are matched with the right capabilities?
6. 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 do not go as planned?
7. 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?
8. 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?
9. 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 plan’s vision and steps?
10. Do you know, for your current major plan, what specific evidence would tell you the plan itself needs to change, not just the timeline? Have you decided this in advance, or would you only find out under pressure, partway through? How might deciding this now change how tightly you are holding onto the current approach?

“Expect the best, prepare for the worst, and capitalize on what comes.” Zig Ziglar

Micro practices for planning

1. Map dependencies before you map tasks: Before listing what needs to happen, write down what has to happen before what. A task list without sequence hides the one dependency that will actually determine your timeline.
2. Set the review date before you start, not after you slip: When you finalise a plan, immediately book the first progress check into the calendar. A review that only gets scheduled once something looks wrong is already too late to catch it early.
3. Ask what would have to go wrong for this plan to fail: Before committing to a plan, spend ten minutes listing the three most likely ways it could fail, and write one sentence on what you would do about each. A plan that has never been asked this question has only ever been tested against the version of events where everything goes right.
4. Share the draft before it feels ready: Send the plan to at least one person who will have to execute it while it is still a draft, not once it is finished. The earlier a blind spot is caught, the cheaper it is to fix.
5. Name your kill switch: For any plan running longer than a few weeks, write down in advance what specific evidence partway through would mean the plan itself needs to change, not just the deadline. Decide this before you are emotionally invested in the plan you already built.
6. Revisit one active plan this week and ask if it is still right: Pick a plan you are currently running, and ask, honestly, whether the situation it was built for is still the situation you are actually in. If it is not, update the plan before updating the timeline.
7. Match one task to the right person, not the available person: Before assigning your next task, pause and ask who is actually best suited to it, even if it means more coordination than simply giving it to whoever is free. Small mismatches compound over the life of a plan.

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

Explore related leadership resources

To further develop this capability, examine how it intersects with other core leadership dimensions across the libraries:

Leadership library:

• Sensemaking: Use environmental scanning to understand the why and what of a situation before drafting a plan, ensuring your strategy is grounded in reality.
• Decision Making Quality: Enhance your planning by weighing different options and risks, leading to more robust and defensible courses of action.
• Decision Making Velocity: Balance thorough preparation with the need for speed, ensuring that the planning process does not become a bottleneck to execution.
• Vision and Purpose (Managing): Align your tactical plans with the organisation’s long term direction, ensuring every task contributes to a meaningful long-term goal.

Supporting libraries:

• Objective thinking (Traits): Leverage your ability to view facts without emotional bias, allowing for a more accurate assessment of the resources and time required.
• Process focus (Traits): Draw on your natural inclination for structure to design repeatable, efficient workflows that sustain progress throughout the project lifecycle.
• Realistic thinking (Traits): Temper your ambitions with a grounded assessment of what is actually achievable, preventing team burnout and planning failures.
• Risk orientation (Traits): Proactively identify potential failure points within your plan, allowing you to build in contingencies and navigate uncertainty with confidence.

Continue exploring: Return to the Leadership Library to view the full directory of competencies and resources.