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LeadershipKatie Dill (Stripe, Airbnb, Lyft)

Come In Listening, Not Swinging

New leader's first move: earn trust before inflicting the change you were hired to make.

Difficulty
Easy
Time to result
~months to results
Steps
5
Confidence
95%

A hard-won protocol for the first 90 days of a leadership role. Dill joined Airbnb having diagnosed the design org's problems during her interview loop, arrived 'swinging', and one month in was ambushed by half her team and an HR partner reading out prepared pages of everything she was doing wrong. The theme underneath every individual complaint was that she had not earned their trust. The correction: still drive the change the org needs, but build it with the team rather than inflicting it on them.

Origin

Katie Dill's own experience at Airbnb in her first month leading experience design, described as the biggest single-moment learning of her leadership career. She has applied it at Lyft and Stripe since.

Core principles

  • 01You can inflict change on people, or you can do it with them — trust is the difference.
  • 02Diagnosing the problem correctly during interviews is not the same as having the standing to fix it.
  • 03When receiving hard feedback, the instinct to explain and justify is exactly the behaviour being complained about.
  • 04Listening first does not mean moving slower — Dill still made fast changes, just with the team behind them.
  • 05The specifics of the feedback matter less than the theme running through them.

How to run it

  1. 1

    Enter listening, even when you already have the diagnosis

    Before making change, hear out what individuals and the team are setting out to do, what they care about, and what motivates them. Your interview-loop diagnosis is a hypothesis, not a mandate.

    Pro tip You can still move fast — Dill made pretty fast changes in the necessary direction, but brought people along with her.

    Watch out Coming in 'ready to go and excited to make change' based on what other leaders told you is the exact failure mode.

  2. 2

    When feedback lands, shut up and take it

    Resist the immediate urge to respond — 'there was a good reason for that', 'that's not how it was'. Listening without rebuttal is the first deposit of trust.

    Pro tip Treat receiving hard feedback like the stages of grief — expect the defensive impulse and plan to override it.

    Watch out Rebutting item-by-item confirms the very complaint that you don't listen.

  3. 3

    Find the theme, not the items

    Look past the individual grievances (which may each be right or wrong) for the systemic message. In Dill's case, every item pointed to the same thing: she had not earned their trust.

  4. 4

    Re-run the change with the team, not at them

    Keep the direction — the org still needed the large operational change — but make the changes together, having established shared goals and demonstrated that you have their interests at heart.

    Pro tip At Lyft, Dill applied this before the org redesign: got to know design, engineering, and product, aligned on shared goals, and then made the change jointly.

  5. 5

    Recognize the value of a team willing to confront you

    A team that organizes to give a new leader hard feedback is showing courage, not insubordination. Dill describes herself as grateful and amazed that they could bring it forward.

In the wild

The Airbnb intervention

One month into leading Airbnb's ~10-person experience design team, Dill found a 90-minute Thursday 8:30 meeting on her calendar with half the team and the HR partner. In a bare white room, five people took turns quietly reading from prepared papers everything she was doing wrong and everything they disliked about her. She listened without rebutting, identified the theme — no trust — and shifted how she operated while keeping the change direction.

A couple of months later the design team had the best engagement scores in the company.

The Lyft door

Arriving at Lyft with the Airbnb lesson learned, Dill needed to break down the literal locked door separating design from engineering and product. Instead of ordering the reorg, she got to know the design, engineering, and product teams, aligned on shared goals first, then made the change with them.

The wall came down with alignment intact, producing faster iteration cycles while preserving a protected creative space.

Common mistakes

Coming in swinging

Arriving with a change agenda built from interviews with other leaders — not with the team you'll actually lead — and executing it before you have standing. Right diagnosis, zero trust, failed change.

Defending yourself when the feedback comes

Explaining your reasons in the feedback moment proves the point being made about you. Listen, then act.

Confusing listening with slowing down

Listening first is not a stall. The change still needs to happen — the only difference is whether the team is behind it or under it.

Is it for you?

Best for

A leader stepping into an existing team — especially one with low engagement scores and known dysfunction — who has already been briefed on 'what's broken' by the leaders above them.

Not ideal for

Genuine emergencies (financial, safety, legal) where the change cannot wait for consensus-building.

From the transcript

hadn't earned their trust so whether you know how right or how wrong what I was doing was

08:00

you can inflict change on people but if you want to do it with them

09:00

instead of coming in swinging you know come in listening

09:30

a couple months later we had the best engagement scores in the company

09:00

From the episode

Building beautiful products with Stripe’s Head of Design

Katie Dill (Stripe, Airbnb, Lyft)