Design Diary: 4-week venture UX

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In preparation for making another Skillshare class, I decided to do a Friday diary of what I do each week. I’m on a four-week UX design project for a new venture; here’s week one (only 2 days, post-vacation).


CONTEXT: New venture in the insurance industry. Opportunities, insights, journey maps, and V1 concepts have been created. Brand strategy is in progress.

BRIEF: 4-week sprint to do the UX for three V2 concepts. With this agency, “UX design” usually includes product strategy, content strategy, low-fidelity wireframes, and high-fidelity mockups.

TEAM: A product manager/strategist, a business researcher/strategist, a brand/visual designer, and me (a product/UX designer/strategist)

Week 1 (2 days)

Prior to start:

  1. Design brief of framing questions I need answered

    • Background (business goals, previous design work)

    • Product audiences (for each: role, goal, current workflow, pain points, preferences)

    • Competitive landscape (threats, opportunities)

    • Project scope (process, deadlines, success metrics)

    • Tech or design constraints (platforms, devices, bandwidth, etc)

Thursday 1/7

  1. Onboarding meeting and reading, to understand past work and specific context

  2. Notion project page of resources for myself

    • Quick Links

    • Competitive Links

    • Meeting Notes

    • Email Notes

    • Jargon Dictionary

    • Design Priorities / Work Plan

  3. Sketchy wireframes of key moments, to make sure I understand jargon and project priorities

  4. Notes on vendor demo, to capture available functionality

  5. Flowchart of current system logic, to identify conditions that would trigger UI

  6. Diagram of objects in system (OOUX model), to feed feature ideas (with nouns and verbs)

Friday 1/8

  1. Content outlines (UI shorthand listing what people SEE and DO at each key moment in the journey), to get confirmation on my ideas for content and functionality

  2. IA research of structural models (list from Designing Interfaces), as possible formats for entire page or individual components

  3. Sketchy wireframe v1 of concept 1 with max dummy content, to develop and test structure

  4. Team review of wires, to refine strategy and content


  • Understanding jargon — made a list in Notion to refer back to

  • Creating content — revisited stakeholder notes for priorities and language, dug into journey map for features and workflows, created object model for nouns/verbs, dug through documents for dummy text

  • Page layout — did content outlines (aka UI shorthand / page description diagrams / information hierarchy / numbered lists) to clarify priorities and content with team


  • Lists are the best tool! UI is often distracting, and not as good for getting SPECIFIC answers on content.\

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Week 2 (4 days)

(4 is my max for this kind of superdense cerebral work)

Monday 1/10

  1. (prep for and do retro of previous project)

  2. Sketchy wireframes v2 (concept 1 states), to stress-test template and define needs and draft content for discussion

  3. SME review of wires, to confirm most valuable features

  4. Flowchart v2 for SME review

Tues 1/11

  1. Desk research to clarify competitive differentiators and find analogous inspo

  2. Brainstorming on new HMW questions, to generate new feature/execution ideas

  3. Content strategy (detailed outline and colored-box wireframes), to clarify the information, functionality, specific language, and priorities, and try different layout variations

  4. Sketchy wireframes v3 (concept 1 details), to deal with the fuller scope of expected content

  5. Product manager review of wires, to confirm alignment with business strategy

Weds 1/12

  1. Sketchy wireframes v4 (concept 1 variations) — 3 different product models expressing 3 different value props, to facilitate discussion and selection of core value prop

  2. Team review of wires, to confirm leading direction and clarify differentiating features

  3. Sketchy wireframes v5 (concept 1 features), including null state for onboarding and microinteraction design for key elements, to prepare for SME review

  4. Brand design review, to see and discuss how the visual design direction is proceeding

Thurs 1/13

  1. SME review of wires, to confirm most valuable features and execution

  2. Clickable prototype (sketchy wireframes v6) of concept 1, for presentation to investors

  3. Product planning meeting to decide concept 2


  • Bike shedding (fixating on the small details instead of the big decisions) — it was hard to find the right level of design and discussion detail between strategic, conceptual thinking and detailed product interaction thinking (which shouldn’t be done until strategy is final); I just kept pausing in reviews to try to make sure we were staying high-level enough to be strategic

  • Misunderstanding — doing an insurance product involves a LOT of jargon, so it was extra important to confirm team members were interpreting words or layouts in the same way

  • End-of-week fatigue — my brain was melting so I started the last day by reorganizing some things in my apartment to satisfy my OCD-ness and create some momentum


  • Pauses are good! Working in sprints, it can be hard to stop running and take a breath to make sure you’re doing the right work\


Week 3 (4 days)

Monday 1/17

  1. Clickable prototype v2 (sketchy wireframes v7) to show two more differentiating features for concept 1, also revising and condensing the entire layout for the page

  2. Concept 2 kickoff reviewing the concept’s background and opportunities, to frame the next steps

  3. Concept 2 journey map, to identify the key moments that might be served in a differentiating way

Tuesday 1/18

  1. Analogous research, to refine the journey map and get inspiration for design

  2. Internal review of research, to highlight the insights and how they inspire opportunities on the journey map

  3. Sketchy wires v1 (concept 2 overview), to outline the rough steps in the story

Weds 1/19

  1. Sketchy wires v1 (continued)

  2. Concept 1 prototype review with technology vendor, to confirm mutual interest and capabilities

  3. Branding review of logo designs, to align the product and visual strategies

Thurs 1/20

  1. SME review of concept 2 wires, to gather insights and content

  2. Sketchy wires v2 (concept 2 content), to refine layouts and functionality

  3. Internal review of concept 2 wires, to clarify needed screens and co-create additional content

  4. Project planning, to confirm the final deliverables for next week and ownership of each


  • Fuzzier concepts — a more service-oriented concept implied an entire program design, not just digital product design, so I made sure to keep confirming the scope and priorities for my work

  • Time management — with a lot of different people involved, I was really grateful when people took the initiative to block time and schedule needed meetings, or made themselves available

  • Scoping — since these were early-stage product strategy concepts, not final product designs, I had to show just enough functionality to get the value across without letting myself get too involved or invested in the details


  • Template management is a personal opportunity — I kept visualizing slides or templates from previous projects in my head, but had no easy way to find and reuse them\


Week 4 (4 days)

Monday 1/24

  1. Branding review of logo designs, to make some final decisions

  2. Product roadmap for concept 1, to prepare for handoff to the founding team

  3. SME review of roadmap, to confirm MVP features and longer-term value

  4. Sketchy wires v3 (concept 2 interactions), to polish text and features

  5. Internal review of wires, to gather final content

Tuesday 1/25

  1. Journey map finalization for concept 2, to get all the details polished

  2. Product design principles in the deck, to codify the strategy for the founding team

  3. Top-level product roadmap templates (for all features across concepts), to prepare for a collaborative work session

  4. Visual design review of concept 1 designs, to confirm that all the functionality and insights of the wires were preserved

Weds 1/26

  1. SME review of wires and roadmap for concept 2, to confirm priorities

  2. Product roadmap work session, to organize all the features across all concepts into a timeline for the future team

  3. Sketchy wires v4 (concept 2 details), to refine functionality and content

Thurs 1/27

  1. Hi-fi designs v1 for concept 2 (landing page, onboarding flow, main dashboard)

  2. Visual design review v1 of concept 1 (application), to ensure both groups are staying consistent and to trade ideas back and forth


  • Roadmapping — everyone on the team defines a roadmap in a different way, so it took several options and drafts to hash out the “best” templates to use

  • Visual design — sometimes you just don’t find the right typeface until the week the project is due (but then it’s so much easier to crank)

  • Technical details — early stage products have a LOT of moving pieces to organize, whether licensed or custom built, it was helpful to put extra information on each part in the deck for our own reference, even if it’ll get moved to the appendix later


  • Getting analogous inspiration should be a non-stop process — it’s easy to just pick an obvious solution and stop there, but every time I decided to zoom out and reconsider a piece of the product it got markedly better

Note: The project got extended into a 5th week so we could polish the handoff materials and the visual design

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