Lenny’s Newsletter · Subscriber post · Execution, roadmaps & process · Communication & influence

How to communicate tradeoffs so leaders will listen

Tactical tips for teeing up critical decisions without pissing leaders off

Lenny RachitskySep 10, 202421 min♥ 171
SourceLenny’s Newsletter
KindSubscriber post
PublishedSep 10, 2024
Readers♥ 171
Originallennysnewsletter.com ↗
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Tara Seshan, a former Stripe and Watershed product leader, shares a playbook for presenting product tradeoffs so leadership actually makes a decision rather than defaulting to "do both." The post covers framing techniques such as public priority stack-ranking, steelmanning requests, anchoring to company goals, projecting long-term outcomes, and recommending an opinionated solution. It also flags common tradeoff traps.

Subscriber post — summary only

01Key takeaways

  • Repeat your priorities and strategy often so that new requests are evaluated against a shared, visible list.
  • Steelman an incoming request before the meeting to uncover blind spots and avoid being surprised by new information.
  • Frame tradeoffs in terms of company goals first, since leadership thinks about company outcomes before team goals.
  • Predict short- and long-term consequences of a decision so leaders can see the full cost of each option.
  • Present a clear, opinionated recommendation with explicit options rather than asking leaders to choose from vague alternatives.
  • Watch for traps like absorbing many small requests, assuming more engineers will solve tradeoffs, and leaning on frameworks without examining specifics.
“repetition doesn't spoil the prayer”Eric Schmidt (as quoted by Tara Seshan) · Lenny’s Newsletter

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.