A surprisingly long cycle has just closed for me and I think it’s a good time to share some lessons learned.

I have been collecting these points in the last six months, but none of them popped up recently, they have taken shape over a few years and they include both things I did and that I failed to do.

Most of these points act as a personal reminder as well as a set of suggestions to others; don’t be surprised if some of them read cryptic.

So, here it is. A summary of what I learnt in the last six years :

The productive organization

1. When the plan is foggy, that’s the moment to communicate as broadly as possible. In fact you should not frame it as a plan, you frame it as the situation and the final state you want to achieve. When you have a detailed plan, that’s when you DON’T need to communicate broadly. So, clearly state the situation and clearly state the foggy goal to everyone who will listen.

2. Don’t be prudish. If you fear that people will lose faith in you because of the foggy goals and dire situation statement you are painting yourself in an heroic corner. People just need to hear and share the situation they are into. Having a common understanding will act as bonding among them and with you, which is actually all you need to make them work out the right answers.

3. Don’t assume that a specific communication medium can’t be effective. Mass emails and top-down communication are not taboo: just because most such communications are irrelevant it doesn’t mean yours will be perceived as such.

4. Teams don’t self-organize unless you organize them to do so.

5. Fostering personal initiative in every developer requires showing the vital need for personal initiative. These are birds that mostly don’t fly out of the cage just because you open the door. You must find a way to show them that the cage is burning.

6. People sitting side-by-side can communicate less than people sitting a continent away. Communication is a chemical reaction that requires catalysers, the thing you get by co-locating people is lowering the cost of the catalysers, but no setup creates automatic communication.

7. Within a development organization both good and bad communication exist, but they are not a function of politeness or rudeness, it’s much more a matter of clarity and goals. You need to learn what the good kind of communication looks like, find some examples and use them as a reference for everyone.

8. Fire people whenever you can. There’s often someone to fire, but not many opportunities to do so. When you are given a lot of opportunities to fire people, it is often due to a crisis situation and you’ll likely fire or otherwise lose the wrong people. People appreciate when you fire the right people, so don’t worry about morale. Also, the average quality of people tends to grow more when dismissing than when recruiting.

9. Hire only for good reasons. Being overworked is not a good reason to hire. Instead, hire to be ready to catch opportunities, not to survive the current battles.

10. It’s often better to lose battles than to staff desperately and win desperate battles at all costs (World War I anyone?).

11. Don’t export recruitment, recruitment must be the direct responsibility of everyone in the organization.

12. People must select their future colleagues, there are infinite benefits in this, but it must not become a conclave. Keep the process in the hands of the people who do the work, but make it as transparent as possible.

13. Always favor actual skill testing in recruitment. When you don’t feel that you are directly testing the candidate skills you are either not competent enough in that skill or you have switched to just playing a set piece (I call this The Interview Theatre) and you will ultimately decide on a whim. Not good.

14. Build some of your teams as training and testing grounds for freshmen. Put some of your best people there.

15. Lack of vision is not agile, it is not data-driven, it is not about ‘taking decisions as late as possible’, it is not something that you should paint out in a positive light at all. It’s just lack of vision, and it’s not good.

16. Construction work is not a good metaphor for software/product development. Factory work neither. Allied junior-officer initiatives during the first week after the d-day in WWII is probably a good guideline, but it is still not a good metaphor overall and, anyway, not known enough to base your communication on.

Yourself

17. Train people to do all of the previous points. Including this one.

18. Don’t shy away from leading without doing, it is unavoidable, so just do it. Then do some work to stay pertinent.

19. If you are not able to hire and fire people, leave. Or stay for the retirement fund if you can stomach it.

20. The Sith are right, rage propels. But the Jedi are right, you must not let it control yourself. What nobody tells you is that the rage game is intrinsically tiring and rage will take control as soon as you get too tired, so stop well before.

21. Write down the situation, for your own understanding just as much as for the others’.

22. If you feel like you don’t know what you are doing it’s probably because you don’t know what you are doing and that’s bad. Anyway, until you learn you don’t really have much of an alternative. Just don’t let that feeling of desperation numb your ability to learn. It does.

23. There’s more and more good content to read and absorb on effective organizations. Don’t despair and don’t stop reading.

24. Don’t let entropy get at your daily routine. Avoid entropy-driven work.

25. Ask questions to people in order to make sure they understand. Trust people who do the same to you. “Do you understand?” is NOT a valid question.

26. Avoid having people waiting on you. Don’t create direct dependencies on your work or decisions, make sure people feel that they can take decisions and still stay true to the vision without referring to you (hence the importance of point 1).

27. Take the time to coach people in depth. Really, spend time with the people who are or have the potential to be great professionals in the organisation.

28. The time you spend with the people you see most potential in is endorsement enough. Avoid any other kind of endorsement of individuals. Unless you are leaving.

The Entropic Organization

29. An organization populated by a majority of incompetents has less than zero net-worth : it is able to destroy other adjacent organizations that are not similarly populated.

30. Incompetence is fiercely gregarious while knowledge is often fractious; the reason for this is that raw ideas transfer more easily through untrained minds than refined ideas transfer through trained minds. There’s a reason why large organisations focus so much on simple messages, pity that difficult problems often have simple solutions that don’t work.

31. Entropy self-selects. Hierarchical and other kinds of entropic organizations always favor solutions that survive within entropic organizations. Thus they will favor easy over simple, complex over difficult, responsibility-dilution over empowerment, accountability over learning, shock-therapy over culture-nurturing. This is the reinforcing loop that brings ever-increasing entropy in the system : entropy generates easy decisions with complex and broken implementations, which in turn generate more entropy. An example of easy decision with a complexity-inducing implementation: this scenario “our company does not have a coherent strategy, as such many projects tend to deliver results that are not coherent, hampering the organic growth of our capabilities.” will be answered by the most classic knee-jerk decision-making pattern “we don’t know how to do X, so let’s overlay a new Y to enforce X”, in this case :”Group together strategic projects into a big strategic program that will ensure coherence”. The difficult but simple option will not even be entertained : “let’s discover our real strategy and shape the organization around it.”

32. Delivery dates have often irrelevant but very simple to understand impacts. Good and bad solutions have dramatic but very difficult to understand impacts. The Entropic Organization will thus tend to make date-based decisions. The Entropic Organization will always worry about the development organization ability to deliver by a given date, never about the ability to find the right solution. There are some very rare cases where delivery date is more important than what you are delivering, but modern management seems to delight in generalizing this unusual occurrence to every situation. People do get promoted for having been able to deliver completely broken, useless and damaging solutions on time. If that’s the measure of project success you can expect dates to rule (even when they continuously slide). After all, if you are not a trained surgeon, and the only thing you are told is that a given surgery should last no more than X hours, guess what will be the one criterium for all your actions during the operation. This showcases the direct link between the constituents incompetence and the establishment of classic Entropic Organization decision-making.

33. Having a strategy will only go so far when you face the Entropic Organization, since it will be only able to appropriate that strategy at the level of energy (understanding) they can attain, which, being entropic, is very low. This results in something that does not look like a strategy at all : ever seen a two-years old play air-traffic control? He got the basic understanding of “talking to planes”, but that’s it.

34. Partially isolating the Development Organization to stay effective does not work. Adapting your organization to be accepted by an incompetent background does not work either. What is left in the scope of alternatives is radical isolation supported by the attempt to radical results and crossing fingers for top-management recognition (also known as `Deus-ex-machina for the worthy’) and the top-down sales-pitch (or POC) to the CEO (also known as “He who has the ear of the King…”). But don’t forget : Nemo propheta in patria, so, act and look like an outsider as long as you can.

35. Growth-shrink symmetry. When an organization grows unhealthily (too fast, for bad reasons or through bad recruitment) it will also shrink unhealthily. When it grows it’s bold and confused, when it shrinks it’s scared and nasty.

36. Most of the ideas that will pop up naturally from the Entropic Organization are bad in the context of modern knowledge-based work, but possess a superficial layer of common-sense to slide through. Exercise extreme prejudice.