Note: I like fixing this type of problem. But I also enjoy highlighting the dynamic first…

Management: Why aren’t we getting anything thing done? We need to go faster!

Teams: Debt. Dependencies. Feature bloat. Multi-tasking. “Specials” and silver bullets. Outdated tools. Swamped shared resources. Onboarding new hires. Specialist silos. Rework. Unplanned work. Fragile environments. Employee attrition.

Management: We can’t fix everything at once! No one likes a whiny developer. Legacy code is code you didn’t write. Bring us solutions not problems!

Teams: Here’s a plan to address the debt…

Management: OK. Can you create tickets and estimate them? And run this by compliance? Then put together a deck…keep it simple, top line. We’re going to need to sell this to the higher ups. And try to be realistic, OK? We’ve lost some political capital with the organization so…

Teams: Lost capital? Really? But…

Management: The tickets…

Teams: Here are 300 tickets. If we make the investment now we…

Management: Finally! Thank you. Let’s dedicate 8% time to this, okay? Track your time…

Teams: We’re adding tickets 3x faster than we are completing them. We’re not sure 8% time will cut it. The multi-tasking hit alone is — um — at this rate — 18 years — I’m not sure we can handle it…

Management: Hmmm, I see. You’re not confident in your ability to fix this. Can we outsource it? Actually, we’ve had a consultant look at the problem and they think that might be possible. Would you mind meeting with them?

Teams: A consultant? That guy over there? At the temporary desk?

Management: We have a business to run! And leadership is wondering how we let things get into such a crappy state. They had no idea….

Teams: Did you tell them? This has been brewing for a while…

Management: Of course, sure. We painted the picture. They don’t like to get down in the weeds you know. So how about that 8% time? Schedule a meeting…we’ll tighten up the plans.

Teams: Oh, um, you know, it might be OK for now…

So…how do you break this cycle? Assume for a moment that management is doing their best, and that the teams are doing their best. How does this dynamic lead to dysfunctional behavior over time (from both “sides”)? And how can it be avoided?