Admitting that hard problems are hard

In my 14 years in the industry, I watched the technology landscape become more and more complex, with new tools and methodologies emerging and fading away every year. Yet I see “thought leaders” get up on stage every day, promising they can teach you the 3 easy steps to:

  • Achieve full software testability (a subset of the Halting Problem, which is undecidable)
  • Remediate 20 years of legacy code
  • Migrate your entire data center to the cloud
  • Adopt the new architectural pattern that is going to solve all of your problems

Beyond fostering imposter syndrome and burnout, this isn’t good for business. In a room full of people embarrassed to admit that the emperor has no clothes, decisions are made without exploring their full implications. In this talk, we will discuss why we should get better at admitting that hard problems are hard, and how this approach can help us build more resilient companies.



Sasha Rosenbaum

Sasha is a Program Manager on the Azure DevOps engineering team, focused on improving the alignment of the product with open source software. Sasha is a co-organizer of the DevOps Days Chicago ...