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).
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In addition to Jon's slides immediately below, please see notes from the Sprint session further below:
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Jon’s career journey and evolution:
- Bridgewater
- Elemental CognitionÂ
- Garner HeathÂ
- VestwellÂ
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Prompt: How would you describe the word of leading a strategic planning process?
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Q: How do you define strategic planning?
Some answers: Big picture. Making plans. Resources. Communication.Â
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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 consideredÂ
These 4 questions lead to the strategic planning utilities belt
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Consensus-building and drawing out disagreements
- Utilizing goal setting frameworks & processes
- Setting KPIs (measure what matters)
- Conducting marker researchÂ
- 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 thinkingÂ
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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.

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