06 June 2023

Is it ever ok to move a deadline?

1Frameworks

5Insights

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Frameworks in this episode

Strategy5 steps

Decision to Delay Framework

Test whether postponing a deadline will create a stronger customer outcome

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster02:48

Why Hitting Every Deadline Is an Invisible Badge

Jasmine describes how self-imposed deadlines can become symbols of ambition, competence, and team capability even when nobody outside the organization knows they exist. That identity attachment can make changing an arbitrary timeline feel far more consequential than it really is.

Teams create many of the deadlines they later treat as immovable
Leaders can mistake schedule adherence for proof of capability
External customers rarely see the internal badge associated with a deadline
Changing a timeline does not inherently say anything about the leader or business

“But the deadline was something like we made up, like we made up the deadline and nobody with the exception of the team knew about…”
Jasmine Star · 03:49

“Nobody knows this invisible badge of a deadline we wear.”
Jasmine Star · 04:00

#deadlines#identity#leadership#mindset

Story· 1

Story12:23

The CEO's Fear of Disappointing a Hardworking Team

Jasmine recounts worrying that questioning the release date would disappoint people who had worked long hours and were proud of the product. She needed to acknowledge their excitement and capability while remaining equally empathetic to the customers who would experience the platform.

Questioning readiness can feel like questioning the team's competence
Past effort and excitement create emotional pressure to proceed
Leaders should explicitly acknowledge the team's perspective
Customer empathy must remain equal to internal empathy

“I didn't want them to think that I did not trust their capabilities for success.”
Jasmine Star · 12:53

“I had to weigh the desires and excitement from our team against the desires and excitement from our customers.”
Jasmine Star · 13:15

#empathy#leadership#teamwork#customers

Tool· 1

Tool15:58

How Social Curator Used a Staged Rollout to Protect Paying Users

Instead of immediately releasing the rebuilt platform to thousands of existing members, Social Curator tested it first with 130 beta users and then exposed free-trial users to the new experience. The team observed behavior and friction on the backend, using those findings to improve the product before its broad release.

Begin with a bounded group of committed beta testers
Give testers explicit tasks and feedback prompts
Observe actual behavior rather than relying only on stated opinions
Use a lower-risk cohort before exposing the full paying customer base
Fix friction before the broad rollout

“We had did a beta test with 130 users of Social Curator.”
Jasmine Star · 16:14

“But we learned a lot.”
Jasmine Star · 17:48

#beta-testing#product-launch#user-feedback#saas

Takeaway· 2

Takeaway07:51

Open a Difficult Meeting by Stating the Goal, Not Your Opinion

When Jasmine convened stakeholders to discuss the platform release, she began with the meeting's objective instead of announcing her preferred answer. This allowed people from customer success, technology, marketing, and community to contribute evidence from their distinct vantage points.

State the shared objective before offering a personal view
Ask stakeholders to make the case both for and against a proposal
Invite functions that experience the same situation differently
Use competing perspectives to improve the final judgment

“I expressed my concern, but I started the meeting by stating the goal of the meeting.”
Jasmine Star · 07:51

“I believe that getting a room full of differing ideas in people help us come up with the best ideas and opinions.”
Jasmine Star · 08:14

#meetings#leadership#communication#stakeholders

Takeaway13:51

Stop Fighting Each Other and Start Fighting for the Customer

During the discussion, some team members changed their positions after hearing evidence from colleagues. Jasmine frames this humility as recognition that departments are not adversaries: they share an outcome, while contributing different views about how to achieve it.

Changing your position after hearing evidence is a strength
Cross-functional disagreement does not mean teams have opposing goals
A shared customer outcome can unify competing viewpoints
The route to the outcome must account for every relevant perspective

“We're not fighting against each other, we're fighting for our customers. We're on the same team.”
Jasmine Star · 14:04

“We all want the same outcome, but the way that we achieve that outcome must be balanced by every perspective.”
Jasmine Star · 14:17

#teamwork#customers#conflict#perspective