What the movies can tell us about planning!

“Unless commitment is made, there are only promises and hopes, but no plans.” ― Peter F. Drucker.

Author: Andre Peters February 2021

Planning is a vital part of life and business. Have you ever wondered why some companies are so bad at planning? We make plans that never work out and are simply unrealistic. Oftentimes, planning is merely done as a tick box exercise. The planning process produces a very smart document which is just ‘’left on the shelf’’.

Not to be referred to again except for performance management purposes at the end of the year. We talk about top down and bottom up planning, but never the two shall meet. How do we go about planning more effectively? This article deals with planning and specifically planning for IT software development and product development. Allow us some creative license, and fun, as we convey our concepts and ideas on planning in terms of well-known Hollywood movie titles. Full feature films may take several years to conceptualise, with plenty of planning before the actual filming starts.


The focus in this article is planning for the shorter term (12 weeks / 3 months) and is sometimes called Programme Increment or ''PI'' planning. Large programmes are typically broken down into increments and planned accordingly. It's a collaborative process between various stakeholders in 'face to face interactions' (taking into account current Covid 19 restrictions). Planning must be more agile. That’s why shorter-term planning is so useful and must be done correctly. Let’s look at some important concepts and principles during planning. We liken these principles to movies and provide some information on the movie and what we can learn from it. 

Principle 1 - Planning needs to be done by the whole team - Saving Private Ryan 

(Film starring Tom Hanks. This movie is set in the 2nd world war with a team of soldiers sent to rescue a fellow soldier after all three of his other brothers are killed in action. The US army not wanting a mother to lose all her sons and a team is deployed to bring her son home). In war, the mission objectives typically come down from the top and there is little debate about what needs to be done. The top brass knows the landscape and has a bird’s eye view of the battlefield. This is also the case with many IT projects. The team is given a mission which they need to achieve. How the team accomplishes the mission is up to them. They are the ''boots on the ground'' and must face the dangers and challenges. The generals provide the mission, context and vision. The planning or operational aspects are left to the team. After all, it's their lives on the line. The ranking officer is responsible for the team, but he would be wise to involve the whole team in planning the operation. A PI planning event requires face to face interaction and involves all in the process. The team may have to change and adapt as their situation demands which often happens in war and business. The team thinks about the risks they may face, as well as the things they are dependent on, and what equipment they will need. The team plans their moves and next steps and breaks down the objective into smaller tasks. Saving Private Ryan ends with the soldier returning home safely, but only after an unexpected battle, which was not part of the original objective. The team had to plan, adapt and prepare on the fly. Failing to plan (by involving the team) is planning to fail.

Principle 2 - Be as detailed as possible in your planning given the knowledge you have at the  time - Ocean's 11 

(Movie about a group of con artists working together to pull off a very elaborate casino heist). The amount of planning done by the team in the movie is astounding given that this group had never worked together previously. This required great leadership and motivation. One of the things this movie illustrates is working together as a team. Each team member brings their own skills and expertise to the table. The same with PI planning. Each person is involved and has to contribute. The team provides input and agrees to the objectives and how to get there. The team looks at the details and must plan accordingly. The only difference between this movie and real life is that real life has more variables and uncertainty. The team can only estimate the tasks and the amount of time and effort required. Planning is not an exact science. The movie ends with a successful heist. In the IT world, we need to hustle at times, but after careful planning and being able to adapt the plan where required. It is also suggested to have pre-PI planning sessions with the team to prepare for the actual PI event. Doing planning upfront, helps the team to be ready for the actual planning event involving all stakeholders.

Principle 3 - Break the plan down into smaller parts (tasks or stories)- The Shawshank redemption 

(1994 film about a wrongly accused man sent to jail for life. After planning his escape for decades, he gets out of prison with a brilliant and patiently executed plan. This involved digging a tunnel through the wall in his cell which was done one spoon full of dirt at a time. He had a clear overall objective: to get out of prison. He broke the objectives down into tasks and stages. In PI planning, objectives are discussed and agreed and a detailed plan of how to achieve the mission is required. The objectives must be broken down into sprints (e.g. two-week sprints). It’s no use having objectives without detail. And remember, the plan is an estimate with assumptions made. Many things can, and will, go wrong during the execution. We need to be real about it. The escape plan in the film had many uncertainties, but Tom Hanks’ character forged ahead with what he thought best. In planning, objectives need to be specific, measurable, achievable, realistic (or relevant) and time bound. The main character spent the rest of his life on a beautiful beach after his escape. The outcome of a carefully conceived plan which led to his freedom. Planning is important. It helps the team to be ‘’free’’ in what they need to do by disciplining themselves to plan upfront. Plans can and must be reviewed regularly.

Principle 4 – Keep it real - The Matrix 

(This iconic sci fi movie provides some surprising moments. One in which the main character realises his ‘’world’’ is not real. He exists in an entirely different world and is awakened rudely from his dream state. In this dream state, he is attached to machines tricking his mind into believing his universe is real. One of the most famous scenes in the movie is where Neo (main character) gets given the choice to take two different coloured pills. The one pill will open his mind to his real situation and the other will make him forget his experience and just wake up and carry on with his current, fake reality. Planning often works this way. We make fake plans that do not keep in step with the realities of the customer or organisation. We must keep it real in planning. Can an objective be achieved within this timeframe? Are we making plans that are totally out of our control and will in no way be achieved? We must take the ‘’pill’’ that is genuine and practical. Even when things are not ideal. The Joker (Dark Knight) said: ''You know what I've noticed? Nobody panics when things go "according to plan". Even if the plan is horrifying! Although a bit twisted, the truth is people need some form of planning. 

Principle 5 - Define your RAIDs (risks, assumptions, issues and dependencies) – The Usual Suspects

(Brilliantly crafted movie starring Kevin Spacey about an elaborate and complex story told by a man held in police custody. At the end of the film, the cops realise the whole story is a hoax with the suspect having been released). In planning, you must speak about assumptions. In the movie, the audience believed what the suspect told them and assumed it was the truth to their own embarrassment and surprise. In planning, it's detrimental not to state assumptions.  “It does not do to leave a live dragon out of your calculations, if you live near one.” – J.R.R. Tolkien.   It's important to identify risks (''dragons'') that could impact your planning. State your current issues as they may impact your planning as well. Who and what are you dependent on? Be honest and have a RAIDs section in your planning document and in the playback of the plan. The idea is for management to remove some of the blockers and assist with managing risks, issues and dependencies. 

Principle 6 - obtain data to use in the planning process. MoneyBall 

(Based on a real-life story, a general manager of a team tries to assemble a baseball team on a lean budget by employing computer-generated analysis to acquire new players). The analyst identifies trends by using data and stats. And this makes all the difference. Using data and stats made them successful as team. The whole being bigger than the sum of the parts. Using stats then became the trend in professional sports. In planning, data and measurements are important. We need to reflect on the previous PI and what was accomplished or not. This means we must have measurements in place to track our progress. This includes data like how many tasks were completed, what our velocity was and how many tasks we still need to complete. 

Principle 7. Innovation – The Social Network 

(Biographical drama film about Facebook’s inventor Mark Zuckerberg). Facebook is seen as a social media game changer and speaks of innovation. Innovation is important during planning. What can we do differently and how will that impact our planning? Spend some of your planning on being creative. It may seem strange, but innovation can change your landscape in an instant and companies have literally disappeared because of technological changes that impacted them. You may want to have an innovation day during planning. 

 Principle 8 - Looking back – doing retrospectives. Back to the Future 

(Classic film about a person being sent back to the past in a time machine to change the future). The principle being that by changing the past, you can manipulate or change the future. It’s easy to reflect on something in hindsight. Reflection is very important for planning.  It is a good idea to also have a retro for the planning event itself. What worked and didn’t work? Take one or two points as identified during the retro and formulate some actions out of these to improve future planning sessions. One of the important aspects of PI planning is to show off the software developed over the specific period (Inspect and adapt). Show the product or system that was built. Inspect what was built and adapt where required for the planning going forward. 

To be practical, we suggest a PI planning approach and structure as follows:

  1. Teams need to provide feedback on the previous increment at the start of the planning event. A playback on what was accomplished for the previous period and whether their objectives were achieved or not? The ideal is to show the working software or product / features developed. What were the lessons learnt? The playback is done by all the teams in a joint session.

  2. We give the relevant business stakeholders the opportunity to provide the business context and vision. They share what they see as important and what the business requires from the teams for the next PI to inform their planning.

  3. It is useful to also have an architectural or system view of the applicable landscape. What is envisioned for the future and what are the key considerations and vision from an architectural point of view as this could impact planning.

  4. The leadership team need to explain the PI planning process. What needs to happen during the planning event and what is expected from all teams as an outcome of the planning session? The planning event itself should be held over a two to five-day period. It is recommended to do the PI event in the last week of the current PI period. Teams need to make allowance for planning as these impacts how much they can deliver in the current PI.

  5. Teams then break out and start the actual planning work i.e. objectives, breaking the objectives into smaller parts, RAIDs and providing a confidence level. How confident is the team in their planning estimates? Each objective should have a business value score indicating what business value is per objective e.g. 8 out of 10. The higher the score, the more important the objective and informs the priority of the work.

  6. It is recommended to have check ins during the planning event where key team members report back on how the process is going and to highlight any blockers they may have. Is the planning event going well? 

  7. The teams review the plans and adjust where required based on input from all teams and leadership.

  8. The last day of the planning event should give all teams the opportunity to do a playback of their plans. It’s important at a programme level that all are aligned.

  9. The last item in the process is to do a retrospective of the planning event. What went well and didn’t go well. How can we improve the planning going forward? 

  10. Include an innovation slot. Allow the teams to be creative and innovative during their planning event.

An efficient PI planning event should ensure faster decision making by having all the right stakeholders involved. Risks and dependencies are identified, and objectives are established and planned accordingly. This process allows for quicker feedback to ensure we deliver what the customer requires. The entire team and all relevant stakeholders are involved, and the outcome is a plan to execute in the next few weeks.  Learning and innovation are important. The plan is played back and adjusted where necessary. The plan should align with the business objectives and vision. It's also useful to provide a confidence level i.e. what confidence level does the team have in terms of achieving each objective? 

Let’s close off with one of the most classic movies about victory and perseverance, Rocky (starring Sylvester Stallone about an underdog boxer who beats more experienced and professional opponents. Rocky (boxer) trains hard and has a strategy for beating the odds and winning.

“It Ain’t How Hard You Hit…It’s How Hard You Can Get Hit and Keep Moving Forward. It's About How Much You Can Take And Keep Moving Forward!” ― Sylvester Stallone, Rocky Balboa.


We need to move forward as a team and this requires planning and endurance. We have a plan for the longer term (all the rounds in the boxing match), but we also need a plan for each round. Each round (short term planning exercise) makes a difference and impacts how we achieve our strategic objectives.  We hope these principles for PI planning will make a difference to your planning process and ensure success in the short and long term. Signature Business Solutions can assist you with this process and we would welcome the opportunity to have a chat about agile and planning practices.


·       Program Increment (PI) Planning is a cadence-based, face-to-face event that serves as the heartbeat of the Agile Release Train (ART), aligning all the teams on the ART to a shared mission and Vision. https://www.scaledagileframework.com/pi-planning/

·       https://www.imdb.com/?ref_=nv_home (movie info)

·       https://www.easyagile.com/blog/the-ultimate-guide-to-pi-planning-2020-safe-edition/