I'm talking about those hairy meeting with many stakeholders and every calendar is booked solid for weeks. The project can't wait until the first shared "free" time.
EDIT: Full disclosure, I'm asking this as I'm gathering research for my startup, Heyea.
Those kinds of meetings can sometimes take up a large portion of my week. I have to do my homework to find times that have fewest major Must Attend conflicts for many participants, and often talk with senior stakeholders to pass the message that my meeting is of high priority and attendance is critical. Then I still need to reach out personally to the major stakeholders to ensure we will have a quorum and the critical participants are planning to attend. That must occur sufficiently before the meeting notice itself so that people can do their homework and we aren't just wasting more time.
If it's so important that it can't wait, then there there are very important actions which must occur, and that meeting not only lays out the expected outcomes but also sets the tone for how well the work will be organized and executed. Saving Changes...
Great question, Steven. I usually dedicate 15–20% of my week to resolving scheduling conflicts for critical meetings. When calendars are packed, I prioritize by aligning key decision-makers first, use asynchronous updates or pre-reads to save time, and only bring everyone together when collaboration is truly needed. It keeps momentum without overloading the team. Saving Changes...
I usually spend a significant portion of my week juggling calendars—often hours—just to align critical meetings. The trick is proactive planning: flag conflicts early, propose multiple time options, and use tools like scheduling polls or assistants to speed up alignment without delaying the project. Saving Changes...
Just updating as I made an edit, but I want to be 100% transparent. I'm gathering product-market fit research for my startup. I appreciate that I'm not crazy, because I had the same problem and pain point as a Project Manager. So, I set out to build this tool for that purpose.
Also, what tools do you use to help solve this problem today? I tried Calendly in the past, but getting people to vote on times was just as hard as sending emails. I often dealt with people who didn't respond, so I was back to reading everyone's calendars.
Does anyone use scheduling assistance tools today?
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1 reply by Keith Novak
Nov 14, 2025 11:35 AM
Keith Novak
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I sometimes have to raise a "help needed" to an executive sponsor who will have their assistant send out a meeting notice from their calendar instead of mine with their deputies CC'd for visibility. One of the problems with the digital collaboration tools I have tried is that my projects include representatives from multiple companies so firewalls make it difficult to exchange calendar information. If we can access each other's calendars at all, typically we just see times blocked out which could just mean one of their coworkers in on vacation. Trying shared calendars that require manual updates is very iffy on the reliability of inputs from many team members.
Saving Changes...
Luis BrancoCEO| Business Insight, Consultores de Gestão, LdªCarcavelos, Lisboa, Portugal
Great question. But the real issue usually isn’t scheduling.
When every stakeholder is “booked for weeks,” the problem is structural: unclear decision paths, too many people in too many meetings, and governance gaps that force coordination through calendars.
In my experience, PMs spend hours negotiating attendance for meetings that shouldn’t exist or could be async.
The real opportunity (including for your startup) is not finding time, it’s reducing the need for these meetings by improving decision clarity, async workflows, and meeting discipline.
Fix the system, not the calendar.
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1 reply by Thomas Walenta
Nov 14, 2025 12:28 PM
Thomas Walenta
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Fully agree with your point, Luis.
This is NOT a scheduling issue, but a governance issue. The project's internal governance (or decision framework) must be designed to promote efficiency, and that is 100% the responsibility of the project manager. Includes design of the org chart, reporting lines, external interfaces, regular meetings (including purpose and standard agendas), communications, escalation paths, etc.
Also, what tools do you use to help solve this problem today? I tried Calendly in the past, but getting people to vote on times was just as hard as sending emails. I often dealt with people who didn't respond, so I was back to reading everyone's calendars.
Does anyone use scheduling assistance tools today?
I sometimes have to raise a "help needed" to an executive sponsor who will have their assistant send out a meeting notice from their calendar instead of mine with their deputies CC'd for visibility. One of the problems with the digital collaboration tools I have tried is that my projects include representatives from multiple companies so firewalls make it difficult to exchange calendar information. If we can access each other's calendars at all, typically we just see times blocked out which could just mean one of their coworkers in on vacation. Trying shared calendars that require manual updates is very iffy on the reliability of inputs from many team members. Saving Changes...
Thomas WalentaGlobal Project Economy ExpertHackenheim, Germany
Nov 13, 2025 3:32 PM
Replying to Luis Branco
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Great question. But the real issue usually isn’t scheduling.
When every stakeholder is “booked for weeks,” the problem is structural: unclear decision paths, too many people in too many meetings, and governance gaps that force coordination through calendars.
In my experience, PMs spend hours negotiating attendance for meetings that shouldn’t exist or could be async.
The real opportunity (including for your startup) is not finding time, it’s reducing the need for these meetings by improving decision clarity, async workflows, and meeting discipline.
Fix the system, not the calendar.
Fully agree with your point, Luis.
This is NOT a scheduling issue, but a governance issue. The project's internal governance (or decision framework) must be designed to promote efficiency, and that is 100% the responsibility of the project manager. Includes design of the org chart, reporting lines, external interfaces, regular meetings (including purpose and standard agendas), communications, escalation paths, etc. Saving Changes...
Program Manager| HARPER SRLSanto Domingo / Distrito Nacional, Dominican Republic
Honestly, Steven, managing those “this-week-or-bust” meetings takes more time than we like to admit. When calendars are packed, the real work becomes negotiation, prioritization, and escalation, not just scheduling. In my case, I usually spend a good amount of time aligning with directors or sponsors to unblock time, because those meetings happen only when someone with authority helps re-prioritize what gets moved. The trick is keeping the why visible, when people understand what’s at stake, they make space. Without that, scheduling becomes a battlefield. Saving Changes...
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