Countermeasures against adhocracy and three other enterprise problems affecting software development.

When you work with complex organisational structures, you are preparing to fail if you fail to prepare.

Pawel Halicki
Bootcamp

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A colorful, game-like, 3 d view of a corridor filled with shapes and signs represents navigating complexity in an enterprise environment.
Image by Champ Panupong Techawongthawon and DeepMind

Solving big problems with software is very valuable, but the process of getting to a solution can be painful and take forever.

1. Adhocracy: when short-term needs block long-term goals.

The constant change of course in complex projects is dangerous as it leads to a ton of work-in-progress, and it strips the team from the feeling of accomplishment by constantly moving the finish line.

Think of variations ahead, try to break whatever you are working on into smaller pieces, and invest in templates and patterns you can reuse or adjust more easily.

Look for bigger common denominators and try to reframe the problem into a broader context.

Use date and revision count in the file names, as your colleagues’ memory may not be as good as yours, but numbers will speak for themselves.

2. New concepts take forever to familiarise.

Every now and then, you may feel like you’re in a slow-motion loop explaining to subsequent groups of stakeholders some concepts you take for granted.

Organisational understanding of emerging domains or new ways of working takes much longer at an enterprise scale.

Explain what your colleagues are doing with metaphors. Compare outputs to familiar objects like lego bricks for components or microservices, or explain by comparing how a given profession works against another one your stakeholders are already familiar with.

E.g. while graphic designers are like an artist creating new things to make people feel a certain way about something, UX designer is more like a doctor, analysing symptoms to present a diagnosis and offering solutions to solve particular problems.

3. Complexity makes everything harder, so try to be clear, not clever.

Fight for clarity as the first victim of complexity is language. For many people, complexity represents importance, meaning that important things just can’t be simple or have self-explanatory names.

Identify operational complexity; for every system, there’s a certain amount of complexity that cannot be reduced and focus on the value of the outcome.

Prioritise writing over talking for more asynchronous communication. Focus on what you can control and keep the language clear. A clearer language is the fastest thing to spread and the simplest to scale.

Be hopeful. Most things tend to get complex before eventually getting simple.

4. Siloed decision-making, or what happens in a silo, stays in a silo.

If you can’t influence the organisational chart, try to navigate it by making your stakeholders visible to each other in direct communication or in a structured way using stakeholder maps, dependency maps, project charters or RACI matrices.

Making people aware of problems increases your chances of getting things in motion.

Save yourself a lot of time and meetings by offering consensus negotiation tools like prioritisation formulas or scorecard roadmaps so your dispersed stakeholders can discuss priorities without you in the room.

It takes just a few simple steps to get to the top floor but thousands to get into space.

Enterprise projects often feel like a combination of a logic puzzle and a spy movie — while you’re solving riddles, surprises jump at you from every corner, and it’s hard to predict what’s next.

To stay on track, focus on the vision and stay persistent on the outcome but flexible on the output.

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Product sci-fi, next-stop futures, and professional growth for strategic thinkers preparing to lead in the age of AI. Designing M&A social graph at Datasite.