Name: Ask a Chief of Staff: Strategic Planning: Build and Execute Annual and Quarterly Plans That Actually Work
Start: 2026-06-04T12:00:00.000-04:00
End: 2026-06-04T13:00:00.000-04:00
Location: Online Event

Personal

Ask a Chief of Staff

Having a strategy is one thing — building a planning process that actually runs is another. In this second session of our 4-part workshop series, we get into the mechanics: how to design an annual and quarterly planning process that works for your org's stage, how to structure goal-setting so teams are aligned and not just checking boxes, and — crucially — how to keep strategy from dying in a drawer the moment the year gets busy. You'll leave with a concrete framework you can bring back to your team.

This session is designed for mid-level managers who are being pulled into — or are already running — planning conversations at their organizations. Whether you're at an early-stage company where planning is still loose and flexible, or a more mature org where the process is complex and cross-functional, this session will meet you where you are and give you language and structure to run it better.

​​✨ How Should Participants Show Up?

Come with a sense of how your company currently does planning — or doesn't. The more honest you can be about what's broken or missing, the more useful the session will be. No prep needed, but if you have a planning cycle coming up, bring it — we'll use real examples throughout.

 is the Founder of Cadence Operators. She operates as an Executive Coach, Facilitation Partner, and Executive Search lead for Operating Leaders (e.g. Founders, Chiefs of Staff, Business Operations Leads, COOs, and Heads/VPs of Operations). She serves her clients as their second brain and thought partner, supporting them as they navigate the challenges of their roles and organizations. Her approach is “coachsulting”- a hybrid between coaching and consulting in which she asks powerful questions that guide the client in finding answers themselves while also providing concrete advice, training, and guidance from her own professional experiences.

Aarti was a Chief of Staff twice - more recently at Guild Education for the Co-founder and President of the Learning Marketplace team. Before that, she was Chief of Staff at 

 for the Product Development team. Aarti was also People Operations Director, leading a team of 10 operators, and a Program Director at EducationSuperHighway, where she developed consulting programs for the country’s 14,000 public K-12 school districts. Aarti began her career as a management consultant for PricewaterhouseCoopers, supporting several Fortune 100 companies.

Aarti is a Certified Professional Co-Active Coach (CPCC) and holds an ACC credential from the International Coaching Federation.

Ask a Chief of Staff is a premier executive search and career development platform dedicated to placing top-tier Chiefs of Staff and empowering professionals in strategic leadership roles. We serve ambitious professionals and high-growth companies by offering executive recruiting, mentorship programs, and career resources tailored to Chiefs of Staff. By addressing the lack of structured career paths for this role, we provide guidance, connections, and opportunities that accelerate leadership development and organizational success.

​​​​​​​​👋🏻 Disclaimer

By registering for and attending this workshop, you agree to be automatically subscribed to our newsletter mailing list. You can opt out at any time using the unsubscribe link provided in our emails.