Month at a Glance

VP of Sales at a SaaS company who consistently overcommits and shows up late or unprepared to important meetings. She uses Outlook for appointments and Asana for project deadlines, but keeps accepting meeting requests without seeing the cumulative load. Her team is starting to notice the pattern.

Frame this as a capacity audit, not time management. 'Before we talk about saying no to requests, let's see what yes actually looks like across a month.' Most sales leaders resist acknowledging overcommitment because it feels like admitting they can't handle the role. Position this as strategic visibility: 'You wouldn't forecast revenue without seeing the full pipeline. Same principle here.'

Notice if she fills in meetings but skips travel time, prep time, or recovery time between calls. ADHD executives often calendar the event but not the cognitive load around it. Watch whether she writes 'board prep' as one item or breaks it into the actual tasks. Single-word entries usually mean she's not seeing the real time cost.

Start with the densest week on the grid. 'Walk me through Tuesday the 15th - what does that day actually require from you?' Then ask: 'What would need to be true about Monday the 14th for Tuesday to go well?' This connects the dots between adjacent days that look manageable in isolation but create impossible sequences.

Marketing Director at a mid-size company who excels at tactical execution but struggles with strategic focus. She came to coaching because her CEO said she needs to 'think more strategically.' She can list fifty things she's working on but can't articulate what success looks like this quarter.

Present the priorities section as the main event, not an afterthought. 'The calendar part is easy - you already track that stuff. The five lines at the bottom are where the real work happens. Those five things are your filter for everything else.' Expect resistance to limiting it to five. She'll want to list twelve priorities, which defeats the purpose.

She'll fill the calendar grid quickly and completely, then stare at the priorities section. If she writes vague goals like 'improve brand awareness' or 'support sales team,' she's avoiding the specificity that makes priorities useful. Look for whether she can connect calendar items to priority lines - or if they seem to exist in separate universes.

Start with the disconnect. 'You have 23 meetings this month and 5 priorities. Draw lines between them - which meetings serve which priorities?' If most meetings don't connect to any priority, that's the conversation. Ask: 'What would you decline if these five priorities were actually your job?' This usually surfaces the real strategic challenge.

Operations Manager who took over a dysfunctional team six months ago. Half her calendar is filled with meetings that should be handled by her direct reports, but she keeps stepping in because 'it's faster to do it myself.' She says she needs better time management but the real issue is delegation avoidance.

Frame this as a delegation audit disguised as a calendar exercise. 'Let's map out your month, then we'll look at which of these meetings you should actually be in.' Don't lead with delegation - she already knows she should delegate more. Lead with the visual evidence of what non-delegation actually costs across thirty days.

Look for meetings with titles like 'vendor check-in' or 'project status' that should belong to someone else. If she writes her name as the owner for tasks that have clear direct report owners, she's using the tool to organize her avoidance rather than address it. Notice if she schedules back-to-back meetings without buffer time for the handoffs delegation requires.

Start with pattern recognition, not judgment. 'Circle the meetings that only you can do. Now circle the ones that someone else should own.' The visual usually makes the problem obvious. Then ask: 'What would need to be different about your team for you to trust them with the uncircled meetings?' This opens the delegation conversation from a systems perspective rather than a personal failing perspective.

Senior Project Manager with ADHD who excels in crisis mode but struggles when things are running smoothly. She gets pulled into whatever feels most urgent each day and realizes at month-end that important but non-urgent work never happened. Her performance reviews mention 'lack of strategic thinking' but she feels like she's always busy.

Position this as a pattern interrupt, not a planning tool. 'Your brain is wired to respond to what's urgent right now. This tool puts the whole month in your peripheral vision so urgent doesn't crowd out important.' Acknowledge that monthly thinking doesn't come naturally: 'We're not trying to change how your brain works - we're giving it a visual anchor.'

She'll fill in deadlines and meetings easily but struggle with the priorities section because ADHD brains often work in immediate-term and someday-term, not month-term. If she writes priorities that are all urgent or all vague, she's missing the middle distance. Watch whether she can estimate how long priority work will take - ADHD time blindness often shows up here.

Start with time allocation, not task completion. 'You have five priorities and twenty working days. How many days does each priority need?' If the math doesn't work, that's useful data. Then ask: 'Looking at your calendar, when will priority work actually happen?' This often reveals that her calendar is full of other people's urgencies with no protected time for her own important work.