Strategic Planning Tactics for the first-time CoS

Strategic Planning Tactics for the first-time CoS

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).

In addition to Jon's slides immediately below, please see notes from the Sprint session further below:

Jon’s career journey and evolution:

  1. Bridgewater
  2. Elemental Cognition 
  3. Garner Heath 
  4. Vestwell 

Prompt: How would you describe the word of leading a strategic planning process?

Q: How do you define strategic planning?

Some answers: Big picture. Making plans. Resources. Communication. 

During a Strategic Planning process, ask yourself: (“the what”)

-what is the vision and mission of the company

-what outcomes would equate to success

-what activities could lead to the desired outcomes materializing

-what is the universe of constraints that must be considered 

These 4 questions lead to the strategic planning utilities belt

Consensus-building and drawing out disagreements

  • Utilizing goal setting frameworks & processes
  • Setting KPIs (measure what matters)
  • Conducting marker research 
  • Performing root cause analysis

On conducting market research, “measure what management cares about”

Model building: equal parts framework, tests assumptions, and is an opportunity to expose your thinking 

Q: Do you have have a recommended Strategic Planning Process and how does it connect to budgets?
A: Jon typically follows an OKR. People is usually a key part of the budgeting and planning process. Make sure those are align and in-sync with your interests.


If you are interested in learning more about Strategic Planning, please see more resources in the Knowledge Hub.