Structures, Processes, Vendors
Definitions
Goals
Questions to Ask
If the answer involves weeks of waiting and 5+ signatures for a minor change, your process is the bottleneck, not the technology.
Async communication is great for work, but sync meetings are necessary for decisions. Endless email threads/committees avoid decision-making responsibility.
Usually because the funding/approval process is so painful, teams try to bundle everything into one massive request. This increases risk of failure. Iterative funding is safer.
Digitizing a bad process just gives you a fast bad process. You must fix the workflow before you build the software.
Manual onboarding kills momentum. If it takes 2 weeks to get a laptop and access rights, you have wasted 2 weeks of salary.
Many vendors/teams claim to be 'Agile' but just do 'Waterfall in Sprints'. If they can't define velocity or give examples of pivoting based on feedback, it's fake Agile.
This is a key metric for 'Lead Time'. If onboarding takes weeks due to manual approvals or provisioning, you cannot be agile.
Alarm Bells
Policies are meant to serve outcomes. If a policy prevents a logical solution or a good user outcome, the policy (or its interpretation) should be challenged, not blindly followed.
This is HiPPO-driven development. Leadership provides direction, but implementation must solve a verified user problem. Blind execution often leads to expensive white elephants.
This is 'Not Invented Here' syndrome. You are trading the reliability of a proven market solution for the burden of maintaining a custom tool forever, usually just to satisfy a desire for 'control'.
They are going to milk you like a cash cow via Change Requests. If you are the only client asking for this feature, you are now maintaining a fork of their software.
Bureaucracy has crept in. If you need a committee to change a typo, your governance structure is broken.
The most dangerous phrase in business. It ignores technological advancements and changing user needs.
Over-classifying data forces you into expensive, cumbersome compliance architectures that kill agility without reducing real-world risk.
This is 'Legacy on Arrival'. Choosing a framework that peaked over a decade ago for a greenfield project signals that the team has not upskilled. You are creating technical debt before the first line of code is even written.
Microservices introduce massive operational complexity (network latency, distributed tracing, consistency). Unless you have the scale of Netflix or Google, a 'Monolith' is usually faster, cheaper, and easier to maintain.
Dealbreakers
Aimless execution.
Process-driven panic.
Waiver culture.
Hostage situation.