This is the third in a series of three posts illustrating some core insights from Slack by Tom DeMarco. The first post is on unhealthy busyness, and the second post is on the white space in the org chart.

TL;DR: Substantial change is hard for people, because it makes them turn from experts to novices. The most important ingredient for successful change is safety. It has to be ok to fail.

In a previous article on Slack by Tom DeMarco, I illustrated the point he makes about middle management and organizational reinvention. An organization must be responsive to change in order to survive in the long run. Teams of middle managers are the most likely group to invent successful schemes to cope with change. It is also them who have to guide their people through the difficult time of adaption to change. How should they do that?

People. Hate. Change.

This cat hates change, too

People mostly hate change in the work environment. It is scary. They have become experts at something, and feel comfortable with the way things are currently done. Now, they are supposed to abandon it just because somebody “up there” says so. They are thrown back to “beginner” level, and that is frustrating. Failure occurs, mistakes happen, and fear and insecurity spread.

DeMarco makes the point that, in life, fear is not always bad. Fear can even motivate us, and increase our performance. A ski jumper or skydiver will be very alert and attentive, because they fear injury or death in case of a mistake. However, while the fear of breaking your neck might have a positive effect and be embraced as part of the game, the fear that is present when people go through a major change is different and unhealthy: It is the fear of mockery, and the fear of embarrassment. If people have reason for this fear, change will not happen:

“If you want to make change in your organization utterly impossible, try mocking people as they struggle with the new, unfamiliar ways you have just urged upon them.” — Tom DeMarco


Feeling safe

As an example, imagine a developer who has always defined herself as a C++ expert, and now you migrate your codebase from C++ to Java or Python. The developer has to go with it, even though it was not her who made that choice. This is a profound change in the way your developer works and thinks. She probably still thinks of herself as a C++ expert, but she cannot show it and prove it every day any more. Years of mastering the language partly go to waste. It is something very personal, like giving up part of her identity. Even if she tries to be open to the change, she will be insecure about it, and not sure yet if she likes it.

If, in this situation, anybody makes fun of her when she builds typical C++ constructs into her Java code, or if she develops overly complex solutions that do not make use of Java’s language features, then her openness might quickly disappear. She will be frustrated and angry, and resist the change. She might even look for a job elsewhere.

If you want your substantial change to proceed and to succeed, you have to create an atmosphere of safety. People need to feel safe whatever they do. It has to be ok to fail, and it has to be ok to make mistakes. Otherwise, they will not embrace, but reject the change. Some might openly resist, others might try to subtly undermine the change, but if people fear something, expect them to reject it.

In summary, DeMarco makes the following, very true statement:

“The single must-be-present ingredient of successful organizational change is safety. […] In an unsafe environment, people are not likely to let themselves be thrust into a position of inexperience.” — Tom DeMarco

Creating such an environment of safety can mean:

  • Tutoring people one-to-one or in small groups
  • Doing pair programming so that nobody fails alone
  • Praising and respecting people for trying out new ways, even if they fail
  • Removing any incentives, and banning any behaviour, that encourage competition
  • Encouraging collaboration instead of competition
  • Allowing enough time for practice, so that real learning can happen

Don’t rush when doing your homework

Slow down during training

The last point is especially important, and often overlooked. A lot of organizational training presents some new method of doing things, and maybe, if you are lucky, contains a couple of exercises. Afterwards, people are supposed to go off and apply the new method autonomously, without further assistance, all the while needing less time for tasks than before. After all, the new method is superior, and we took the time to train people so they would become faster, right?

However, learning something difficult takes time. If you have just started to learn it, you will, of course, not be able to perform it at expert-level speed. Trying to do so will not help you. You have to master it at slow speed first. Anybody who ever learnt to play an instrument or mastered complex martial-arts moves knows that. If you move too fast, and if you are hurried, you will not learn properly. Put differently:

“Any so-called training experience that lacks the slow-down characteristic is an exercise in nonlearning.” — Tom DeMarco

Or, turned around:

“Training = practice by doing a new task much more slowly than an expert would do it.”

Therefore, plan for things to take longer. Reduce the amount of work you take on per sprint, or per whatever unit of time you choose. Avoid pressure. Provide an encouraging learning environment, so that each learner has access to and can communicate with:

  • A facilitator
  • Other learners
  • Learning material

In other words, provide enough coaching time (facilitator), and set teams up and distribute tasks so that people can help each other (other learners). If real-world tasks are still too challenging and difficult to tackle for your learners, then provide learning material in the form of increasingly complex exercises (learning material).

Side note: This is one of the reasons why many first-time managers struggle at the beginning. Their learning environment has no facilitators (unless somebody mentors them), no other learners (because, as a manager, you are supposed to get along on your own), and no relevant learning material that covers anything besides the technical part of the job. If you are a first-time manager, try to find a mentor, and reach out to peer managers if you can.


Real change is hard and takes time. Moreover, you cannot bring about successful change by enforcing it, as DeMarco warns us:

“As a manager, you can’t make proactive change happen; the best you can do is help it to happen.” — Tom DeMarco

If you drive internal competition out, take away fear of failure and embarrassment, and take time for the practice stages of training, you provide the must-haves of a learning organization that can adapt to change. If, additionally, your people see the benefit of the change, or at least its necessity, they will embark on the difficult journey and take the first steps into the future.

Slack series

If you haven’t yet, check out my two other pieces on insights from the book! The first post is on unhealthy busyness, and the second post is on the white space in the org chart.

Time investment

This post took me about 3 hours to write.