LLenny's Podcast
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CommunicationJessica Hische (Lettering Artist, Author)

Top-Down Design Diagnosis

Before touching any detail, spend days naming the one big-picture reason a design bothers you.

Difficulty
Easy
Time to result
~days to results
Steps
3
Confidence
85%

When something feels off about a logo, people rush to specific complaints ('the way the R is') that may only bother them and miss the real issue. Hische insists on diagnosing the overall problem first — asking broad 'why doesn't this work' questions and tightening only after the big picture is named. It prevents chasing minutia that doesn't move the design.

Origin

Jessica Hische's advice to clients on how to brief a refresh.

Core principles

  • 01Always start super top-level and ask very broad questions about why it's not working
  • 02Big picture before minutia — sometimes people throw detail complaints because they haven't stopped to find the overall issue
  • 03A single detail complaint might bother only you and no one else
  • 04'This could be better' is a legitimate and often sufficient starting brief
  • 05You never get to the real problem if you address detail before the big picture

How to run it

  1. 1

    Sit with it for a couple of days

    Before specifying anything, spend a couple of days asking yourself why the logo isn't where you want it — what is the thing about this that bothers me?

    Pro tip 'It feels like it could be better' is enough to start; you don't need a precise complaint.

  2. 2

    Stay broad — forbid detail

    Deliberately do not get specific ('the way the R is'). Force yourself to articulate the overall reason, the vibe, the big-picture failure.

    Watch out Detail complaints thrown early are usually a symptom of not having found the overall problem.

  3. 3

    Tighten progressively

    Once the big-picture reason is named, go tighter and tighter. Now specific complaints ('this C has always bothered me') are legitimate and can be addressed during the refresh.

In the wild

'It could just be a lot better'

Lenny's entire initial brief was a feeling: 'this could be better.' Hische confirms that's enough for some people, especially when the existing brand already has a clear, cohesive voice — the job then is massaging it into a more consistent, professional place rather than fixing a named defect.

A purely big-picture brief was sufficient to direct a successful refresh.

Common mistakes

Leading with the 'little bugaboo'

Handing the designer a specific detail that bothers you but might not bother anyone else derails the diagnosis of the real, overall issue.

Is it for you?

Best for

Anyone briefing a designer on why their existing brand feels off but who can't yet articulate it

Not ideal for

Purely technical utilitarian fixes where the defect is already objectively known (e.g. a logo that literally misreads)

From the transcript

always think big picture before you think minutia

54:30

you have to just like always start super top level and really ask yourself like very broad questions about why you think it's not working.…

55:00

Like what is the thing about this that bothers me?

54:30

the it feels like it could like my whole feeling was this could be better

55:30

From the episode

How to see like a designer: The hidden power of typography and logos

Jessica Hische (Lettering Artist, Author)