Care Deeply, Challenge Directly — The Feedback Script
Three moves that let hard feedback land as care instead of criticism
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 4
- Confidence
- 92%
Tan resolves the false choice between caring about people and driving impact with a concrete three-part script for hard feedback: state your intention out loud, offer your own help, and keep the content on the work (observation, impact, alternative) rather than the person. The reason to give the feedback at all is that you believe they can do it differently.
Origin
The 'care personally, challenge directly' principle is Kim Scott's, from Radical Candor. Tan overlapped with Scott at Dropbox for three months — Scott was on her interview panel and workshopped the book with her team before publication. The three-move delivery script is Tan's own operationalization.
Core principles
- 01Caring about people and driving results are not mutually exclusive
- 02Directness is the expression of belief, not the absence of care
- 03Avoiding the uncomfortable conversation is the unkind option
- 04Feedback content stays on the work: observation, impact, alternative
- 05A results-oriented culture is itself a form of care — people want to know how they'll be measured
How to run it
- 1
Make measurement explicit first
Before any hard feedback exists, create a results-oriented culture where goals are clear, broken into individual levers, and every person knows how their success will be measured. People appreciate knowing the bar.
Watch out Without this, hard feedback lands as a moving goalpost.
- 2
State your intention out loud
Open by naming why you're having the conversation: 'my intention is to set you up for success' / 'I'm sharing this because I believe you can do all these things.' Restating intention converts the same words from attack to investment.
- 3
Offer concrete support
Say you're there to help and name the form it can take — 'let me know what I can do to support you', 'we can jam on it together if it's helpful.'
- 4
Keep the content on the work
Deliver the substance as: here is what I observed, here is the impact it had, here is a different way. Never finger-point or criticize the person.
Watch out Any sentence that describes who they are rather than what happened has left the script.
In the wild
Two or three weeks after a hire joined, Tan judged they weren't moving quickly enough. She pulled them aside and said the team needed to move much faster, laid out where they needed to get to and by when, why (a growth team needs early proven wins), and how — a roadmap, a list of problems, hypotheses that don't have to be right — plus how success would be measured. She framed the whole thing as setting them up for success.
→ The person went on a tear. A year later they told her unprompted how grateful they were that she had that conversation early.
Common mistakes
Avoiding the uncomfortable conversation
Managers duck early hard feedback to stay liked. Tan's case shows the opposite: the direct, early conversation is what the report ends up grateful for, because it was delivered as belief.
Treating care and results as a trade-off
Tan runs an unambiguously results-oriented, measurable culture and is known for caring about people. Clarity on how someone is measured is a thing team members actively appreciate.
Is it for you?
Best for
New or conflict-averse managers who keep postponing performance conversations with people they like
Not ideal for
Situations that are already a formal performance-management or exit process, where HR process governs
From the transcript
“restating your intention and why you are having that conversation to sharing that you are there to support them and offering your your own help…”
“It's really just hey, this is what I observed. This is the impact that it had and here is like a different way”
“care deeply, but challenge directly”
“I think sometimes as a manager, it can maybe, you know, you want to avoid the uncomfortable conversations.”
From the episode
Building high-performing teams
Melissa Tan (Webflow, Dropbox, Canva)