Use risk policies and avoid common planning fallacies in software development

Even though most methods tell you otherwise, always use a rule of thumb in software planning.

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Software estimation is every software engineer’s favorite topic. Nobody wants to hack away and just see if it works.

And now the reality.

Planning in software engineering

Planning sessions are experienced by many as a necessary evil. Something you need to do so that the team boss can go to his boss to provide some numbers. These numbers are just there, so the big folks have something to discuss.

Switch. Sometimes, people honestly plan the amount of work that is necessary. Fierce discussions follow, and if there was a team before the workshop, there certainly is none left afterward.

Methods, methods, methods

There is nothing like a good new software planning method, or so they say. Get the Fibonacci number generator ready. We will do some serious planning now. The best plans have a fancy Gant chart and some confidence intervals to account for the insecurity.

Still, many plans are of by weeks, despite the best planning methods. There was just this tiny technical problem that held back delivery for four weeks. And then, testing couldn’t start because the deployment pipeline was not ready.

Missing the forest, for all the trees

Many planning sessions examine every issue for itself. The interplay of the problems, components, or procedures is seldom explored.

Often a guy (hands up if you were in this unlucky of all roles) says, well, you forgot to factor in x, y and omega. That can not work; it did not work the last time we tried it. The comparison of the current work to a similar reference work is called the outside perspective.

Risk policies are the planning’s rule of thumb.

But equally often, planning for this stuff is not even possible. We are all inside our boxes, having the same limited view. What can help here is a risk policy. Like “never buy extended warranties,” you can assume, “Never plan integration testing with less than two days.” These rules of thumb go everywhere where you have experience but face a lot of uncertainty.

You do not know what obstacles you will face, but you know that you will face obstacles.

Risk policies do not work with cutting corners.

There is often immense pressure to fit the work into a tight deadline. “You must make it work, or we can not take this client.” Who wants to be the dealbreaker in this case? The planning will cut many corners, as it is motivated by loss aversion. A risk policy is the exact opposite of this. Imagine you have a variance for the planning from 2 to 5 days, and a critical subtask like testing has the risk policy to take at least two days. This approach can not work.

Stay tuned to learn how you can still deliver value in this case.

The story of Covid and Plato’s cave allegory

Remember the time before Covid? We all went to work and were happy. Despite all the talk, we will never all go back to the office.

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Scenes from the past

Some city before the year 2020: People rush to the metro stations at 8 o’clock in the morning. Up the stairs, down the stairs. They squeeze themselves into the already-closing doors, avoiding stepping on other people’s toes.

You drink your hot coffee in your warm seat while listening to your favorite morning motivation music.
Then you suddenly look left and see all the other drivers looking equally frustrated towards the red traffic light, down the avenue over the thousand other cars in front of you. Dread begins to rise in the back of your mind. The meeting hour is approaching, and you are still in the car.

You work in such a socially advanced company. Once a week, you can work from home. You get a haircut and do the weekly chores when the shops are less busy. The handyman is coming. Or you are just not feeling well, and everybody prefers you take care of your germ zoo at home. Bonus points if you are allowed to leave early to fetch your kids and then continue working.

The present

Nobody wants to go back to the office. And if we do, we expect fun and a good time with our coworkers. Office time is for celebration, networking, and brainstorming. It is something special. But we only need it every second week.

Entitlement to work from home is rooted in human nature

Working from home has become the norm for many in the hot covid phase. It was expected to remain at home and do your eight hours of work there. Everybody experienced it, even though the equipment and comfort differed.

Many experienced advantages they had never heard of. This makes them similar to those who left the cave with the shadow play to see the sun for the first time. Plato’s story describes that we can never return once we have seen another better reality. This shifted the social norm.

Going back with the knowledge of the advantages is like going to the toilet without toilet paper. You are annoyed if it is not as expected.

As the social norm shifted, people now feel entitled to work from home. Even without the best setup now, they expect they will have better equipment.

Removing the entitlement to working from will come with the same conflicts as removing entitlements to healthcare or retirement pensions. It is the current norm; therefore, the population expects it in the future. Everything else is experienced as a decisive loss.

You are most likely overinsured

Not all insurance cost is transparent, if you are very careful, you forgo good opportunities.

Insurances are a necessary evil of the middle-aged person’s lifestyle. You are old enough to know that you may need it and too young to skip over it.

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What insurances are necessary

Insurance should protect us from a negative outcome, like losing our health or having an expensive lawsuit.

BANG!

You just dropped your phone. While you scramble to the flow, you hope the screen is not broken.

Better buy the insurance and never care again!

On the other side, insurance comes with a cost. Money that you could have spent elsewhere. And unless you are filthy rich, you probably do care. And dirty rich people do not need insurance anyway.

There is no unique strategy to decide whether you need insurance.

A strategy to decide on insurance

What can help is the fourfold pattern. An Eisenhower matrix-like pattern of gains/losses and high/low certainty.

CertaintyGainLoss
certainRisk-averseHope
uncertainGambleInsurance
The fourfold pattern

Suppose you face a potential loss. Think about the probability of the event. How likely is it that you will drop your phone?

Very high? Then factor in the insurance cost to your phone price.

But let’s make things more complicated. Some insurance contracts do not pay in all cases. How likely are these cases to occur? Likely, then hope for the best. You will waste your money on insurance.

This category also applies to cases where no insurance can be bought or is too expensive. Many businesses on the downward path hope to reverse the trend and rise again.

Not all insurance cost is transparent

When there is something to gain, we do not need insurance. Many situations in life are uncertain. Sometimes we lose, and sometimes we win. This is called a gamble.

And sometimes we always win, in any case. There is usually the option to take a save small win and an unsafe big win. Deciding on the potential big win is a gamble.


Take, for example, your latest work project. You probably settled for something less than the maximum solution for the next milestone. This safe decision could have been driven by fear of facing your boss with empty hands if you can not deliver the big solution.

The insurance premium you pay is the value difference between the small and big solutions. In this case, your company paid. But you also paid because the win did not deliver into your account.

You might be overinsured if you are risk-averse and always refuse the gamble.

If you want to know more about the fourfold pattern, check out this article.

There are no losses; just costs for profits

“I sell shit” is a quote from the movie “Triangle of Sadness”.

The guy speaking is a millionaire. And wouldn’t you want to be a millionaire?

The best guide to selling anything, or so they say.

The marketing matters

The way you present your stuff influences how a potential buyer reacts. This is obvious for any shopping window.

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But what about intellectual stuff like ideas and presentations?

This selling of information is also affected by its presentation. Even more, usually, the messenger effect takes place. We trust information more if it comes from a trusted messenger. Few people reject a good offer because they dislike the salesman. Of course, being a likable salesman bears still advantageous.

Bad apples and Watermelons

We often face a situation where the information we want to communicate is negative.
Imagine a sales reporting presentation. If sales are down by 30 %, that is not good.

You can refer to a bad apple selling strategy. From the outside, the apples look good, but from the inside, worms are already calling it their home.

In the business world, this pattern is also known as watermelon reporting. From the outside, all projects are green. Only on the inside are they bright red.

Selling shit the honest way.

There is a better strategy. Everything can be framed in perspective to a reference point.

For the sales reporting: Reporting a 30 % decrease is not as good as reporting that sales are only 70% of last year’s sales. Both mean the same thing, but 70 % sounds better.

If you work on an innovation project and meet with your investors, tell them their investment has not realized any gains, but it is not lost. The investment is still in your company. A winning investment just takes time and some more cost to turn into a profit.

The psychological reason for this approach is the loss of averseness of your emotional brain. If I told you that lost 10000 $ and got a new car, that sounds more negative than your new car cost 10000$.

There are no losses; just costs for profits

As a general approach, try to communicate every lousy outcome as the cost of something, not as a loss.

Plus points if you manage to point out that it is the cost necessary to achieve a formidable gain.

The perfect way that projects will never be planned

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There is a profound difference between selling and planning a project—the order of these two phases matters.

Selling a project

A good presentation is critical when you want to sell a project or product. You want to pitch your solution to investors or internal managers. The presentation should be lively and memorable.

The best presentations present a simple and emotional story that has concrete details.
They must present something unexpected that invites the reader to continue the story in his head. “Jaws in space” was the memorable slogan that motivated Hollywood producers to fund the film, Alien.

Planning a project

When you want to plan a project properly, you best think of all the eventualities.

Think through every step as best as you can. Avoid planning every step in detail, but all the steps should be clear. Modern techniques to do so include the creation of a feature map.

Think of it as ascending a mountain. You do not precisely know the path or how long it will take you. Yet, you would be foolish not to have a map with you. And like with a good map, you would know in advance if you face obstacles and challenging trails at some point.

In your project, you should know the places of uncertainty as best as possible.

Sold projects are rarely declared a failure.

Usually, projects are first sold and then adequately planned. But now comes the surprise: it should be the other way around.

A project should be first planned and then sold. Why?

A sold project must be completed, no matter the potential risks.
People that sold the project are usually 100 % convinced by its success. They evaluate the project with an inside view. They are no longer open to a new perspective.

The key stakeholders are sold on their own perspective

Once the project starts, new people are hired and tasked with proper planning. They usually have experience with similar projects or tasks. Like engineers do in technical questions.

They can imagine what paths lead to a negative outcome by comparing specific milestones and tasks to their experience. Compared with the stakeholder’s perspective, this is called the outside view. Consultants perform a similar role.

As these people are tasked with planning the project, questioning basic assumptions is not part of the plan. Even if consultants were hired to do that, the outside view is rarely welcome. The

This psychological dilemma poses a challenge for companies and venture capital firms. They will fund winning entrepreneurs with unrealistic plans.

That is why projects would best be planned first and then sold. Unrealistic?

The SAFe confidence vote reveals the state of emotional security in your project

If you have confidence in a plan, there should be a uniform vote for this plan. The question is if your endeavour is predictable.

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The SAFe confidence

In the Scaled Agile Framework (SAFe), a big group planning takes place to organize the next big product cycle, also called the program increment.

All teams come together, discuss features and provide a commitment to a delivery date.
At the end of the meeting, the complete plan is presented to the entire development project, and a confidence vote is held. Vote points range from 1 to 5.

Everything about 2 is ok. Everybody that votes two or less must explain his concerns. The concerns must be resolved for the plan to be valid.

Issues with the power structure

Everybody that has done such planning knows that it is not much fun to stay at the end of the day and resolve any controversial issues.

This procedure brings a psychological load to those that vote with two or fewer. First, they annoy many of their coworkers who want to go home. Second, they can face criticism from the project management, which wants to see the ambitious plan approved. If the head of project management is the boss, few people feel the urge to vote with two or fewer.

What a very low but acceptable score means

With the votes of 2 or less penalized, only votes of at least 3 are an easy way to express everybody’s opinion.

Many people vote three to be left alone. This voting behavior can lead to cases where the average vote is between 3 and 4 and little divergent opinions exist.

The low but uniform confidence means people do not believe in the plan. Nevertheless, they do not feel secure to raise concerns about any issues.

Emotional security is not part of your project, and people do not dare to speak up.

Low Predictability in software programming

Then what should we do if we think a plan is not feasible

Software estimation is always a hot topic. In the agile literature, there is a consensus that estimations should not be commitments. To turn predictions into commitments is a management failure.

Then why are predictions never correct? Is the method wrong? Are the people inexperienced? I presented an idea of how to take care of inexperience in another article.

But the issues are more complex. Kahneman pointed out that “errors of prediction are inevitable because the world is unpredictable.” This can lead to a situation where we have high confidence in experienced people. Trust alone is meaningless for the prediction that can be used as commitment.

“The question is not whether these experts are well trained. It is whether their world is predictable”

And with this, I am off to the next planning round.

Look at your industry’s state and then decide if you want to become an expert

The t-shaped engineer is a human centipede. These modern software engineers are different than traditional experts. Which one is better? And what have foxes to do with it?

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The hedgehog and the fox

In the original essay “The hedgehog and the fox” by Isaiah Berlin, “the author compares two different thinkers.

Hedgehogs know one big thing very well. They have one view of the world. They are reluctant to admit error. A failed prediction is almost always off only on timing or nearly right. They are opinionated and straightforward.

Foxes are complex thinkers. There is no single big driver in human history. Reality emerges from the interaction of many agents and forces, including luck. While they do not possess a magical crystal ball, they are slightly better at predicting events.

The software specialist

There are usually many technologies if you work on a medium to a large software project. Some of these technologies are so complex that it takes several years to achieve mastery. An expert in this field has put in 10000 hours.

These experts often have issues dealing with problems that touch the periphery of their knowledge. They are not used to make predictions based on best guesses.

They have seen many applications, and they assume that are only a few right ways to apply their technology. Such behavior makes them like hedgehogs. They are clear in their prescription of a solution that requires implementation. If surprisingly, the solution fails, they will declare that it has almost worked and only a minor technical fault needs fixing in the future.

The T-Shaped engineer

We all only have a certain amount of time in our life. In addition, we should not spend more than 40 to 60 hours a week on our work life.

However, the way we spend these hours is up to everyone on his own. You can decide to learn a lot about the hot technologies in embedded software, internet software, aerospace, or automotive. You can be knowledgeable in many of the applied technologies in your industry.

Similar to the expert, you will also spend 10000 hours.

You will always have an opinion on every technology, yet you often fail to explain how something works completely. You will never be the expert. You are like the fox.

Advantage of the foxes

Problems usually arise on the borders of domains. Many new technologies are created by applying two old technologies.

The amount of uncertainty in these problems makes initial failure very likely.
Enter the fox. His knowledge in all related domains puts him in the best seat to spot potential failures early.

Should we all become foxes? I am not sure. Ultimately the fox requires the advice of several hedgehogs. Without the hedgehogs, the fox will identify the problem but could fail to find a solution.

When to be a fox

My suggestion: treat the issue as a question of the maturity level in your field.

  • When you are new in the field, be a fox.
  • When the field is stable, be a hedgehog.
  • When the field declines, be a fox to find new adjacent areas that offer innovative solutions.

I am off to the fox den.

Trust me; I am an expert

The issue is not whether you are an excellent expert, but expert knowledge can not be trusted in an irregular environment.

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Have you ever been fooled by an expert? The car dealer sold you a bad car? Your doctor prescribed the wrong treatment?

Experts do the work

Do you know the famous expert videos? Seeing these videos, almost nobody wants the role of the expert. Yet our society runs and is advanced mainly on expert knowledge.

Experts are so valued that Ph.D. is a valuable sign of expertise that people use to promote their products. A slightly less impressive expert badge is the white doctor’s coat in the hospital. These badges are there to assure us that we can trust the experts.

Faking expertise

Often people want to appear more proficient than they are. They do so to acquire our trust and, with this, the potential for favors and better deals.

I do not want to talk about these fake experts; I have done so in another article.

Real experts that can be trusted

Instead, let’s examine when we should trust real experts.
An expert can be trusted, if

  • he works in an environment that is sufficiently regular to be predictable,
  • he has an opportunity to learn these regularities through prolonged practice

These preconditions result in skilled intuitions, that is, mental shortcuts, which can be trusted.

Experts in mechanical skills can observe immediate feedback. Many doctors that cure common illnesses receive quick feedback from their patients.

Real experts that can not be trusted

Irregular environments and light exposure create untrustworthy intuitions.

Doctors that treat rare cases do not have enough experience to make reliable and intuitive judgments.

The same applies to many creative experts, like software developers. Many situations are so new that the lack of feedback makes it difficult to make intuitive judgments.

Even worse is the situation for business managers. Cases are rarely comparable, and there is always a new detail.

These experts often replace their lack of experience with confidence in their decisions. That, however, is a dangerous path.
Kahneman pointed out, “Judgments that answer the wrong question can also be made with high confidence.”


Confidence in the own judgment is not a good diagnostic of accuracy. Next time your doctor tells you he is confident in your treatment, ask him how many patients with similar symptoms he had.

You should go back to the office, to help your boss understand you

Shadows are lurking behind your working-from-home chair. There is one big one big disadvantage egoistic developers fail to see.

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Pro and Contra

Some studies try to analyze what kind of person can successfully work from home. Remote work is the future.

On the other hand, some CEOs say working from home is for slackers. And it might not be good for your career.

For companies, one of the key benefits is the enlargement of the talent pool, which is no longer restricted to geographical locations. This can lead to a salary decrease/stagnation in today’s hotspots.

Why you should consider returning to office even if you think it is a bad idea

Engineers are selfish

As an engineer, it is often preferable to think about one’s own needs. What works best for you? How do you get your work done? We prefer tranquil workplaces with a focused daily work schedule. The software developers’ work hell is a noisy environment with lots of spontaneous communication and interruptions.

Manager vs. Maker

Some articles try to explain why the management prefers working in the office and makers prefer to work from home, the maker vs. manager schedule. It comes down to schedule management and unplanned interruptions. This point is much more related to the current office culture and design.

Were we all to have our private spaces and proper meeting planning, then there is little difference between the two schedule types.

Management is not the problem.

The manager’s schedule only partly explains the manager’s preference for working in an office. After all, many project managers face distributed teams and external collaborators. They spent their day almost entirely on the phone. A more structured day with fewer interruptions is better in this setting.

People management methods

However, this neglects one thing. Most of today’s organizations are still power structures. Hierarchy is still predominant. Even flat hierachies are hierachies. Someone pulls the shots, and the majority has to play up.

This also includes performance evaluation.

Managers need to gauge the performance of their associates. During the extended working-from-home periods, many managers saw their effectiveness decrease.

With Covid less threatening than before, they prefer to have everybody working in an office. But this is merely saying my trusted method does not work in a new situation; I want to return to the old position.

Why classic supervision fails

The traditional evaluation methods fail due to availability bias. We only can judge things we are aware of. Humans tend to think of less visible people as less important.

Everybody knows this mind trick: Failing to recall an instance of success means there is no success. Does it? This is why personal contribution always feels much more significant than it is in reality. We all are the best engineer of the team.

We like what we know

This psychological bias always has been at play in office politics. It is one of the cornerstones of successfully managing your boss. Talk more to the boss, and his perception of yourself will be more present in his consciousness.

Even more, this process is self-reinforcing. If you always talk to the same person, you have a specific preference for this person’s success. Compared with other people, you will expect your favorite to succeed better.

Preventing such fallacies requires training and intensive reflection.

Before the massive working-from-home period, the brain was busy treating the mental load of daily office work. Reflection is usually the first thing to be abandoned.

Only as the in-office interactions dried up did most supervisors realize that they were left apart from what was happening and were less effective in doing their job.

Naturally, the easiest thing to do is to go back to the office.

The wise engineer is seen and known.

So as an engineer, it would be best if you went back to the office to give your supervisor a chance to evaluate your performance with his old methods.

As a supervisor, the task is much greater. You need to rise above yourself and overcome your biases and prejudices toward your employees. Give training and reflection the essential place that they deserve. Figure out how to effectively monitor performance during remote work.

Use mental anchors to determine the start position of high-stakes discussions

The next time you find yourself in a tricky situation, try to influence the discussion by anchoring at another reference point.

Time-dependent algorithms usually have one major issue. The starting value heavily decides the outcome. The same applies to your mind’s thinking process.

Anchoring our thinking process

Time-dependent algorithms usually depend on the starting value of a specific variable. Depending on the starting rate, the result can be completely different.

The same is true for your mind. A different starting value can lead to another perception.

This concept is also called anchoring

Anchoring the perception

If you enter a bazaar and the seller starts with a price, he has anchored the price discussion on a specific value. The standard advice is to make a counteroffer with an equally offending low price.

Kahneman suggests that the best approach is not to start with an opposing low number. The contrast principle will lead to a higher price on your part, as the seller has anchored the price. Even if you know the contrast principle as a sales strategy, you will bear the psychological load: you will experience your position as unjustified and amorally.

Resist anchoring by breaking the pattern

Instead, Kahnemann suggests that you should abort any interaction. Make a scene and storm out. You will emotionally brand the initial offer as outlandishly high and attach a negative emotion to it.

When you come back to the store, the emotional charge is on the seller to offer a lower price.