Tailored hypotheses + questions

Hi—thanks for taking 20 minutes. I’m researching how hybrid knowledge workers plan their day when the calendar is already packed and priorities shift. I’m not selling anything today; I’m trying to understand your current workflow and what breaks.

Quick context: I’m exploring a calendar-first day planner that turns tasks into realistic time blocks using transparent assumptions (estimates, buffers, rules) so your schedule stays current without constant manual rescheduling.

I’d love to learn: (1) how you plan a typical day/week, (2) where things fall apart, (3) what you’ve tried, and (4) what a ‘better’ solution would need to do to earn daily use. If it’s okay, I’ll ask a few detailed questions and I may share a couple of concept prompts near the end to get your reaction.

Before we start: what’s your role, what tools are in your stack (Google Calendar/Gmail, task tools), and what does a ‘busy week’ look like for you?

Subject: Quick research chat on daily planning in Google Calendar (15–20 min)

Hi {{FirstName}},

I’m doing user research with hybrid knowledge workers at {{Company}}-type teams who live in Google Calendar/Gmail and juggle shifting priorities.

I’m exploring a calendar-first day planner that converts task lists into realistic time-blocked days using transparent assumptions (estimates, buffers, rules) so schedules stay current without constant manual rescheduling.

Would you be open to a 15–20 minute call to share how you currently plan your day and what’s frustrating about it? I’m not selling anything—just trying to understand workflows and pain points.

If yes, what does your availability look like this week? I can also send a couple of time options.

Thanks,
{{YourName}}
{{Title/Org}}
{{LinkedIn or website (optional)}}

Hi {{FirstName}}—I’m researching how hybrid knowledge workers plan day-by-day when Google Calendar is packed and priorities shift. I’m exploring a calendar-first planner that time-blocks tasks with transparent rules (not opaque auto-rescheduling). Would you be open to a 15–20 min chat to share your current workflow and what breaks? Not selling—pure research.

Participant
- Name:
- Title/Function:
- Company/Industry:
- Company size (50–500?):
- Work mode (hybrid/remote/on-site):
- Primary tools (Google Calendar/Gmail + task tools):
- Meeting load (hrs/day or % of week):
- Tasks/week (estimate):

1) Current workflow (day-by-day)
- How do they capture tasks? (email, chat, meetings, docs)
- Where do tasks live? (Asana/Trello/Jira/Sheets/Todoist/etc.)
- How do they plan the day? (morning, night before, weekly)
- Do they time-block? How often?
- What triggers replanning? (new meetings, urgent requests, client changes)

2) Pain + impact
- Top 3 frustrations:
- Recent example of a day that went off the rails:
- Consequences: missed priorities, late deliverables, stress, after-hours work:
- Who else is impacted? (manager/team/clients)

3) Existing solutions tried
- Tools used now and why:
- What’s ‘good enough’ today:
- What’s missing:
- Experience with Notion-style DIY vs auto-schedulers (e.g., Motion):
- Biggest reason they stopped/avoided a tool:

4) Requirements for a better solution
- Must-have capabilities:
- Non-negotiables (control, explainability, privacy):
- Preferred interaction model (rules, prompts, manual override):
- Tolerance for automation (low/med/high):
- Data access comfort (calendar only vs email/tasks too):

5) Concept reactions (if shown)
- Reaction to: calendar-as-source-of-truth + task-to-time-block conversion:
- Reaction to: transparent assumptions (estimates, buffers, constraints):
- Reaction to: user-controlled rules (e.g., protect deep work, no meetings after 4pm):
- Reaction to: lightweight follow-through (focus flow, end-of-day review):
- Biggest concern/anxiety:

6) Adoption + pricing
- Would they use it daily? Why/why not:
- Personal pay vs expensed vs team purchase:
- Price sensitivity ($6–10 Pro; $15–30 Enterprise):
- Buying path: who decides, security review, IT involvement:

7) Pilot interest
- Would they try a 2-week pilot connected to Google Calendar?
- What would success look like? (time saved, fewer missed priorities, less after-hours)
- Any blockers to connecting data?

Scorecard (0–3 each)
- Acute pain + current workaround:
- Calendar-first fit (Google stack + meeting load):
- Task volume + complexity match:
- Willingness to change behavior (daily engagement):
- Trust + privacy comfort:
- Differentiation pull vs existing tools:
- Ability to pay / buying path:
- Total ( /21 ):

Key quotes
- Quote 1:
- Quote 2:

Top insights
- Insight 1:
- Insight 2:

Next steps
- Follow-up needed:
- Candidate for pilot? (Y/N):
- Notes: