What kinds of ongoing, cross-functional meetings do you think are important to have? Which teams are involved, and what agenda items do you recommend?

At the VP level, these are the meetings I try never to miss:

• Engineering, Design & Operations peers [Weekly] – Having this at my current has made the biggest difference. My peers are my "first team" and we have time set aside to proactively problem-solve together, instead of being brought together only in escalation situations. Anyone can add agenda topics, and we order them at the beginning of each meeting based on urgency.

• GTM Sync & Launch Readiness [Weekly] – This is a regular touchpoint with Marketing, Sales, and Customer Success leaders. The agenda is dually driven by Product/PMO which provide a status update on delivery and Marketing/Customer Success sharing targeting, comms, training, and assets. (Separately, I have biweekly 1:1s with CMO and CRO for strategic alignment.)

• HR [Weekly] – This meeting changes depending on growth stage and/or seasonality. It expands with hiring sprints, promotion cycles, and organizational transitions. It contracts at other times, to a 1:1 with my HR peer. Agenda includes tactical and urgent topics first, then reviewing a tracker to ensure progress on longer-term shared goals.

• Finance, Legal [Monthly] – These meetings are all about risk management. Legal keeps me up to date on AI concerns and changing regional regulations. Finance helps me understand our revenue and investment ranges, so I can understand where I need to mitigate Product downsides.

The structure and frequency of cross functional meetings vary by audience & project phases. 

With your core development team of engineering, design, data science and productOps, if there is one meeting I recommend - that would be a weekly touchpoint. Try to make every one participate in this touchpoint - mainly to avoid too many 1:1s & message passing that leads to chaos. This cross functional team meeting also helps bring forth unstructured discussions through which new ideas surfaces . You can also use this weekly touchpoint to give business context to the team, unblock each other and many times, just to build the team spirit needed to be effective as a team. 

When it comes to stakeholders, touch points vary depending on the phase of the project. For a project that is in active development, more frequent touch points help. For initiatives that have launched, lesser frequency is good enough. Frequency also depends on the level of stakeholder e.g., for someone at a VP level, once a month visibility or even async updates might be good enough. Make these engagements valuable - add elements that create discussion points. For someone senior, always include an executive summary. 

Don't forget to ask for feedback and fine tune the engagement model periodically.