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The Planning Plateau

Why planning is overrated and how to build a strong decision making culture for your team and organization.

Jonas Achouri Sihlén
Jonas Achouri Sihlén
10 min read
The Planning Plateau

Let us be honest, when did you really follow a plan lately?

If you did, was the plan leading you to the outcome and result as expected?


Wow, congratulations! That is very unique. You must either be very lucky or you are very good at…following a plan. The success of a project is more complicated than simply relying on a plan though.

Studies show that planning itself doesn’t influence most companies’ strategy. Even worse if it is performed on a less frequent basis by individual units, it is leading to the opposite outcome than you initially wanted.

When the world is getting more unpredictable and things are changing in a rapid pace old ways of planning is simply not fulfilling our true goals as teams and organizations. Rather it creates a false feeling of control.

“Working without a plan may seem scary. But blindly following a plan that has no relationship with reality is even scarier “— Jason Fried, founder of Basecamp

How come planning has become such a central part of how we start and run businesses and projects? Well, my guess is that it is a combination of habits and a sense of control of something unknown. Starting to think and talk about a projects mission creates a feeling as if you already started. So nothing wrong about that.

The problem starts when you use a plan that was made 1 year ago and start executing and making decisions based on current events. That is when gaps occur between expectations and reality.

Planning = Guessing

Planning is guessing, as Jason Fried and David Heinemeier Hansson puts it in their book “Rework”.

As soon as we accept the narrative that the plan will lead us to success we put blinders on ourselves. By not realizing that planning is guessing we also kill the space for creativity and improvisation. We become a collective driven by a plan.

The information and learning you get from the actual work you put in is increasing as you go ahead with your work cycles. So why do we put the pressure on ourselves on making the big decisions before we have started our work cycles? That is the worst time to make a big decision.

When you do the planning it is worth knowing that the information and the empirical data hasn’t been gathered yet. Making a big decision at that time can be devastating…

To spend time thinking of risks and goals for the future is a great exercise. Becoming obsessed about it and to write a long multi-page plan will only increase the chance of having it stored in the archive anyways.

It is not like we want to ditch the whole planning part either. We should approach it for what it is; a guessing game.

The Great Disconnect

There is a disconnection between planning and decision making. Many teams and organizations out there are working with the belief that either the plan they made is bad or they made the wrong decisions, when shit hits the fan. The reality is actually more related to the belief that last years plan is the map for todays decisions.

Michael C. Mankins and Richard Steele published a study in Harvard Business Review where they pointed out that the great disconnect. The strategic planning that was made by executives and their organizations were performed unit by unit (67%), periodically on prescribed times (66%). Meaning, based on the surveyed companies, 66% are planning on a specific time and 67% do the planning within a single business unit. In addition to this; 100% of the surveyed companies are making strategic decisions without any regard to the calendar and 70% of the surveyed companies make decisions issue by issue.

No wonder only a fraction of executives are highly satisfied with the outcome of strategic planning.

Most executives view the traditional planning process as worthless. As Mankins and Steele explains in their study of decision making and planning, the majority of key decisions made in an organization are actually not made thanks to the planning activity but despite it.

I would like to share a personal experience with you: Back in 2018, I took over a software project as a project manager. It was setup with a traditional waterfall approach. The project plan was created and aligned with the steering group and the external stakeholders. Milestones and toll gates were communicated. The new team was on-boarded and everything looked great. We would deliver this solution and it will be rolled out within a year. The expectations were set.

“Amazing, let’s go”!

One “small detail” was missing though. The build wasn’t even started and we didn’t even have the environments setup to commit the code to. But a plan, that is what we had, what could go wrong?

As the team started to set up the environments needed for the product launch and started the build and tests needed to verify the solution, we saw issues that weren’t accounted for in the plan. More and more errors were stacked up. As time passed the plan was adjusted month by month and the launch we committed to earlier was postponed. The confidence in the project was in a decline and the stakeholders started to get impatient.

The project started to be seen as a failure before we have even started to ship the solution to our customers.

“Your first try will be wrong. Budget and design for it” — Aza Raskin, designer at Firefox

The issues that popped up during the year weren’t even thought of in the original plan, lots of surprises popped up when it came to errors and rabbit holes.

We changed the project approach with the ambition to improve the way we communicate and how we set expectations. Both internally and externally to our stakeholders. Simply by using the empirical evidence from the work cycles.

As the cycles started we got a better picture about the reality. They made us more aware of what did work and what didn’t work in the landscape of our complex infrastructure. We switched the whole planning approach to a more iterative way of capturing the ongoing work so we could make the right decisions as we went ahead.

So should we ditch the whole planning approach and go hay-wild with executing our work blindly?

Well, we don’t have to be so dramatic. Looking ahead and thinking about possible risks and goals is a great exercise to do with your team. Let’s see how we can go ahead with that. Some will continue to call it planning and some will call it guessing. Personally I prefer calling it nudging your way through by making the right decisions.

Avoiding Bias Traps & Managing Intuitions

Before we head in to the decision making framework that will shape your team up we have to drill down on the most common pitfalls you can make when you start making decisions: The cognitive bias trap.

As human beings we are mainly driven by two main systems, System One and System Two, which Daniel Kahneman explains in more detail in his book Thinking Fast & Slow.

System One determines most of our thinking and actions and it requires less effort than System Two. An autonomous system that is most active when we do stuff like brushing our teeth or riding the bike. System Two on the other hand requires more energy and is more reflective. It monitors things whereas System One is the one that makes the executive decisions, both of them are on continuously.

Whereas System One is the most influential system when it comes to making decisions for us on a daily basis it also has an ability to filter away alternative stories and narratives. System One conceptualize all our inputs from daily experiences into distilled narratives that we sooner or later may end up off target.

We have beliefs because mostly we believe in some people, and we trust them. We adopt their beliefs. We don’t reach our beliefs by clear thinking, unless you’re a scientist or doing something like that. — Daniel Kahneman.

The risk of relying too much on your intuitive and individual decision making skill is that your System One can lead you away from the objective truth.

Before we have helpful artificial intelligence that will present most of our possible options, it is worth training our ability to avoid biases and manage our intuitions as human beings.

We will now explore how to create a solid decision making process for your team.

A Disciplined Process > Individual Geniuses

By moving from the individual to the collective we can realize that it is not about hiring and staffing your team based on individual geniuses, rather creating a robust decision making culture that is nurtured by the team itself.

Very quickly you form an impression, and then you spend most of your time confirming it instead of collecting evidence. — Daniel Kahneman

By creating and developing a strong decision making culture in your organization you will be less dependent and stressed out for trying to hire the exceptional talents and geniuses. You can enable, train and develop them for success instead.

You will also ease the pressure from the individual biases and group thinking that is so easily boosting their own bubbles without having to rely on one specific person.

By applying the following three main principles across your team and organization you can nurture a strong decision making culture that will shape up your team:

Principle 1 — Apply The Right Mindset

By encouraging disagreements over compliance to bureaucratic processes you can develop a strong mindset among your team-mates. When you build any decision making framework you need to ‘open up the doors’ so that multiple perspectives and insights can be gathered. You do not want to create yet another isolated assessment unit.

In the project from 2018 mentioned above we created a habit of gathering all the members in the project on a regular basis, in retrospective sessions (looking back), planning events (gazing forward) and other recurring ceremonies. Developers, architects, product managers, operations staff, customer reps. and senior executives were represented in these sessions where everyone was able to take part of the same information and raise their opinions, feedback and questions on a regular basis; i.e bi-monthly, bi-weekly and when needed.

Principle 2 — Rotate The People In Charge

Rotating people in charge, instead of relying on one single ‘quality-police’, can be crucial for your teams success. Many organizations assign, formal or informal, ‘quality assurance specialists’ whose primary job is to critique others. Those quickly loose their influence in the organization. We can mitigate this by enabling a framework for all the accountable team members to play along with. Same rules for everyone by trusting the process.

In our development teams we have the tradition of rotating the role of the scrum master. Even though it is up to all the team members to question, analyze and improve the ways of working for the team it is comforting to have some main guardrails for how the team is working. This is made possible by having one person at the time who drives and follows the process whereas everyone knows it’s not about the single person but the process itself that enables them.

Principle 3 — Diversify The Views And Mix The Skills

By injecting new insights from other teams in the organization or even by involving external teams to review and critique the scope and strategic outline can be really beneficial for progression. You can build competitive advantage by boosting the whole process when you invite for the outside-in perspective.

The research from Michael Mankins and Richard Steeles study shows that almost all of the non-productive strategic planning sessions were made in individual business units. Meaning they were not integrating the various perspectives from the organization. It can really be devastating to not open up the doors and sometimes demand an outside-in perspective and mix of perspectives.

Last But Not Least

Fool-proof the process with this 12-question checklist to make your decision making framework more robust and reliable.

Being a bit paranoid and questioning the decisions continuously can really make you stronger. Once you get to too comfortable and when things feel too good to be true, it usually is…

Conclusion: Start Shaping, Make Decisions And Adapt

Before we truly can trust future technology to make the un-biased decisions for our projects there is a protocol we can follow to make more human decisions, a protocol to train ourselves being better decision makers.

So how can we foster a culture where we make the biased traps and rabbit holes visible?

Going back to the project I lead back in 2018: As mentioned, we switched the approach for the project and started to introduce more iterative ways of nudging our way through. The less frequent planning events were replaced with more continuous operational meetings where we gathered executives, product managers, customer reps, development teams as well as operations teams in order to cover the diverse landscape of our organization.

Planning is good in terms of getting your mind focused on the project, don’t create so much emphasis that a good plan will solve everything for you. What makes a difference is the people you have on board and what decision making framework you are adhering to. Here are the main lessons learned we made in our project shifting from waterfall to a more nimble approach.

  1. Promises are cheap, actual work is hard and expensive. It was easier to make up a theoretical plan and make promises then simply identifying the right work and getting work done. The easy way became very costly.
  2. Get started and get going. Adapt along the way. Ditching the plan completely is not the way either, rather switching the mindset away from thinking “we will stick to this no matter what”. To not use the outcome from the work-cycles as empirical data on what, how and when things are achievable, can be devastating.
  3. Alignment and transparency dialogues. Having the right people in place for a focused discussion on how the project is doing and what we would need to focus on is key. Creating and ambience for a great dialogue between developers, product managers, architects, executives and customer reps is key.
  4. Commitment > consensus. By being transparent with the data on how things are going, present a clear vision statement and a sense of urgency for the team can create strong commitment by itself. With strong and present leadership commitment is enforced and will drive your project forward, rather than spending time and effort trying to create consensus across the whole organization. Strong commitment can also be contagious and create positive ripples in the team.

Going forward it is worth knowing that even competent and well-intentioned leaders out there can make mistakes. That is something we all must be aware and mindful of.

It is by trusting the process of how we make strategic decisions in the organization, not by simply hiring individual geniuses, that will setup your team for success.