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Private Event

Strategic Planning Sprint

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About Event


Strategic planning is a process for determining what a business should become and laying out the roadmap for how it can best achieve that goal. In many organizations, the focus tends to be on short-term strategic planning methods, such as OKRs. However, without a larger vision to tie OKRs to, the impact of quarterly planning falls flat.

As many organizations kick off the 2022 planning process, now is the perfect time to brush up on your strategic planning skills.

By the end of this Sprint, you will... 

  • Be able to guide your team to see what’s coming around the corner and the opportunity 3-5 years down the line 

  • Evaluate opportunities that support a healthy portfolio of business strategies 

  • Understand your CoS role in the strategic planning process and how to effectively manage the process

Sept 8 - Session 1: The Role of the Chief of Staff in Strategic Planning

  • Gathering feedback across the organization and managing the planning process

  • Leveraging strategic planning frameworks - developing your own plan (homework)

  • Hosting a strategic planning workshop

Speakers: Will Holtz (fmr CoS & Director of E-Commerce & Regulatory Strategy at Recess) and Stephanie Cheng (Director, Last Mile Delivery Product, Walmart)

Sept 13 - Session 2: Strategic Planning Tactics for the First Time Chief of Staff

  • Retro: How did we get to where we are now?

  • Vision: Where do we want to go? What is our vision of success?

  • Mission: What is going to get in our way? What do we need to be aware of?

  • Values: What do we need to do to get there?

Speaker: Jonathan Mark (SVP, Business Operations & Strategy at Vestwell)

Sept 16 - Session 3: Rolling Out and Executing Your Strategic Plan

  • Understanding the differences between a strategic plan and annual planning 

  • Communicating the plan to the organization

  • Aligning jobs/resources to strategy

  • Implementing and tracking KPI’s related to your plan

Speakers: Abby Parker (COO at Elate), Brian Webb (CoS at Clubhouse), Sydney Cummings (VP of Business Operations at Terminus), and Emad ElShawa (Chief of Staff at Fundbox).