Project Failure Files: Saying Yes to Every Request

In Episode 63 of the Project Failure Files weekly webcast, our focus was “Always Folding at No’,” in which Sharon and I tackle the management trap of saying yes to every request, and how fear of conflict, people-pleasing, and vague expectations invite scope creep, missed deadlines, and burnout. We frame the fix as protecting the project: anchor decisions in a visible plan of record, make trade-offs explicit (time/people/money), and let process—not personalities—govern change.

We then outline cultural fallout when boundaries vanish: resentment toward promise-makers, hero worship that rewards unsustainable all-nighters, and a perpetual “firefighting” mode where retrospectives and celebrations disappear. The antidote is transparent prioritization (e.g., a shared backlog/whiteboard), an intake process that routes requests, and conditional yeses (“yes, if…”), so teams can deliver reliably.

Finally, Sharon and I emphasize empowerment and documentation. Estimation should be owned by the people who do the work; managers must normalize diplomatic “no,” coach assertive communication, and write decisions down (tools from email to Planner/Jira). Do partial deliveries, slice work into MVPs, and invite stakeholders to fund added scope (“pay for play”)—but never at the cost of sustainability.

Enjoy the episode!

Be sure to tune in next Monday, November 3rd at 9am Pacific for a program update on our weekly series. Hope you can join us on our NEW YouTube channel (please subscribe!), or find us on LinkedIn.