If you are training to become a project manager, one of the most important skills you will develop is not writing plans, but facilitating planning sessions. Most delivery problems don’t come from a lack of tools or frameworks. They come from poorly run planning. Either the wrong people were in the room, the conversation stayed too abstract, or the output looked structured but did not reflect reality.

Over the years, working across product launches, regulatory programmes, iGaming platforms, and data and AI implementations, I have seen the same pattern repeat. A well-run planning session can save weeks of confusion later. A poorly run planning creates a plan that looks organised but never quite works in practice.

Start with the purpose of the planning session

Before choosing a format, you need to understand what kind of planning you are running. Not all planning sessions are the same, even if they use similar tools.

• A strategy planning session is about direction and priorities at a high level.
• A project planning session is about turning that direction into deliverable work.
• A quarterly planning session focuses on sequencing and capacity.
• Roadmap planning sits somewhere between strategy and delivery.
• Sprint planning is focused on short-term execution.

The mistake many new project managers make is using the same format for all of these. For example, trying to run a strategic discussion using a detailed task board, or trying to plan delivery using vague high-level themes. Before you design the session, ask yourself what decisions need to come out of it. That will shape everything else.

Strategy planning: creating direction without getting lost in detail

Strategy planning sessions are often the most difficult to facilitate because they can easily become unfocused.

I was once involved in a leadership session for a digital business where the goal was to define strategic priorities for the next year. The conversation quickly drifted into operational detail. People started discussing specific features, tools, and internal issues. After several hours, there was a lot of discussion but no clear direction. The issue was not the people in the room. It was the lack of structure.

In strategy planning, your role is to keep the conversation at the right level. A useful technique here is to organise discussion around three layers:

• objectives, what the business is trying to achieve
• priorities, what areas matter most to achieve those objectives
• constraints, what will limit or shape the approach

You can use simple frameworks such as OKRs (Objectives and Key Results) or even just structured prompts. The key is to prevent the session from collapsing into task-level thinking too early. A good output from a strategy session is not a detailed plan but more a small number of clear priorities that can later be translated into delivery work.

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Project planning: turning ideas into structured delivery

Project planning is where things move from abstract to concrete. This is where many planning sessions fail because they jump straight into tasks without establishing structure. People start listing activities, but there is no clear sequencing, ownership, or dependency awareness.

In a regulatory compliance programme I worked on, the initial planning session produced a long list of actions. It looked comprehensive, but when we tried to execute it, teams quickly ran into blockers because dependencies had not been considered.

A more effective approach is to structure the session around:

• deliverables, what needs to be produced
• workstreams, how the work is grouped
• dependencies, what relies on what
• sequencing, what needs to happen first

A useful technique here is backward planning. Start from the end goal and work backwards to identify what must be completed before that point. This helps expose dependencies early and is something I rely on very frequently. It works very well especially on projects with strict deadlines. see Project Planning and Delivery Tools.

Another practical method is using sticky notes or digital boards where each item represents a deliverable rather than a task. This keeps the conversation at the right level before breaking things down further.

Quarterly planning: balancing ambition with capacity

Quarterly planning introduces a different challenge. You are not just deciding what should be done, but what can realistically be done within a fixed period.

I have facilitated quarterly planning sessions in one of the largest investment banks in the world, where teams came in with dozens of ideas and priorities. Everything sounded important. Without structure, the session would have resulted in overcommitment and inevitable delays. A good technique that works well here is capacity-based planning.

Instead of asking “what do we want to do this quarter”, you ask “given our current capacity, what can we realistically deliver”. You can introduce simple constraints such as:

• limiting the number of major initiatives per team
• grouping work into high, medium, and low priority
• forcing trade-off discussions

Another useful method is MoSCoW prioritisation:

• Must have – meaning if we don’t do this, something will break and there’s no workaround
• Should have – meaning this is very important and needed but there’s currently a manual workaround
• Could have – meaning we would love to do it if we have spare capacity
• Won’t have – meaning we chose not to do this work

This helps teams move away from treating everything as equally important. Quarterly planning works best when it produces a focused set of commitments rather than an exhaustive list of intentions. Find more information on Agile Business Consortium’s MoSCoW guide.

Roadmap planning: connecting strategy to delivery

Roadmap planning sits between strategy and execution. It is about showing how priorities will unfold over time. In a product environment I worked in, the roadmap initially looked impressive. It covered multiple quarters and included a wide range of initiatives. The problem was that it was not grounded in delivery reality. As a result, it became a communication tool rather than a planning tool. To make roadmap planning effective, you need to anchor it in both strategic intent and delivery constraints. A useful technique is to structure the roadmap in layers:

• themes or initiatives at the top
• key milestones or outcomes beneath
• indicative timelines

Avoid the temptation to over-detail the roadmap. It should provide direction and sequencing, not a full delivery plan. Another helpful approach is timeboxing. Instead of committing to exact dates too early, group work into time periods such as quarters or phases. This keeps the roadmap flexible while still providing structure.

Sprint planning: making short-term work executable

Sprint planning, often used in Agile Scrum environments, is where planning becomes very concrete. This is where teams decide what they will deliver in a short time frame, usually one or two weeks. The challenge here is not lack of detail, but managing scope and focus.

In one Scrum team I worked with in a large investment bank, sprint planning sessions regularly resulted in overcommitment. The team would take on too much work, and by the end of the sprint, several items remained incomplete. This created a cycle of carryover and reduced confidence. The spillovers became a norm and overloading the sprints with enormous amounts of work was regular, and even expected, practice.

A better approach is to focus on:

• clarity of work items
• realistic estimation
• team capacity
• clear definition of done

Techniques such as story pointing or t-shirt sizing can help teams estimate effort without getting lost in precision. Another important aspect is ensuring that work items are well-defined before the session. Sprint planning should not be used to clarify vague requirements. That work should happen beforehand through backlog refinement.

Techniques that work across different planning sessions

While each type of planning has its own focus, there are a few techniques that are consistently useful.

Silent brainstorming can help avoid dominant voices taking over the session. Participants write ideas individually before sharing them.

Affinity mapping allows you to group related ideas and identify patterns. This is especially useful in early stage planning.

Dot voting helps prioritise quickly when there are many options. Each participant gets a limited number of votes to allocate.

Parking lots are essential for keeping sessions on track. When conversations drift, capture the topic and return to it later rather than letting it derail the session.

Pre-work is one of the most underrated techniques. Asking participants to prepare inputs in advance significantly improves the quality of discussion.

The role of the project manager in planning sessions

As a project manager, your role is not to provide all the answers. Your role is to design the session so that the right conversations happen and lead to usable outcomes. This means:

• keeping the discussion at the appropriate level
• ensuring the right people are involved
• making dependencies and constraints visible
• challenging unrealistic assumptions
• guiding the group towards decisions

In many cases, the most valuable contribution you can make is to ask the right question at the right time. In a complex data initiative I worked on among a large group of super-smart data scientists and engineers, a single question during planning changed the direction of the project. We asked, “what happens if this dependency is delayed by two weeks?” That exposed a chain of assumptions that had not been considered, and we adjusted the plan before execution began.

In summary, planning sessions are where projects are either set up for success or quietly set up for difficulty. The goal is not to create the perfect plan. It is to create a shared understanding of what needs to happen, in what order, and with what constraints. Different types of planning require different approaches, but the underlying principle remains the same. Good planning reduces uncertainty and aligns people around a realistic path forward. If you can learn to run planning sessions that produce clarity rather than confusion, you will be doing one of the most valuable parts of the project manager’s role.