Program Management

Org-wide planning

Summary

1. Set roles and responsibilities, making it clear who’s responsible for what and when.
2. Set a timeline and timebox the planning process. It should allow for proper discussions and work scoping and estimation, but not drag on for too long.
3. Important to set top-down goals that individuals and teams can align their goals to. These should be set by a leadership group that has truly debated and brought a diversity of opinions, ensuring all key stakeholders are represented. This is the “where we are going”, what our goals are and why.
4. Teams propose their individual plans, they should be able to clarify and challenge the top down goals.
5. Leadership then consolidates the plans and ensures there’s alignment, revising top-level goals as needed. It should be clear now not just what goals we plan to work on, but how. There may need to be iteration and lots of discussions to consolidate and ensure that resources are allocating the time to the right areas to make our goals achievable.
6. Individual teams then make tweaks to their individual plans and set up tracking to ensure that they can report on progress vs. goals.

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Details from FirstRound: The Secret to a Great Planning Process

The root cause of most bad planning processes: a basic lack of understanding of roles – who is responsible for what, when?

1. Who should have a say in the plan, and when?
2. What exactly does each stakeholder need to deliver, and to whom?
3. Who sets the timelines?
4. Who holds everyone accountable?
5. Who makes the final call?

The process

1. Identify the groups: Leadership (senior leaders), Teams (executing on work)
2. Leadership shares a high-level strategy with Teams. An inspiring high-level vision and strategy, concrete goal for the period.
   1. Leadership must remain open to feedback and pushback from the teams as they respond with proposed execution plans.
   2. Can share the strategy as a company strategy doc with Mission, Vision, Values, Goal, Strategy and 3-5 strategic pillars.
   3. Ensure that there’s enough context and why behind the plan, but call out assumptions or areas that need validation. It should be transparent and welcoming of feedback, no need to be overly polished or try to show that leadership has all the answers.
   4. For Key Initiatives, include a strategy, list of key projects, expected timeline and impact, resources needed, and risks and dependencies.
3. Teams respond with proposed execution plans that support the high-level strategy.
   1. Start to formulate a perspective and plan early. Begin with the problem and align on it first.
   2. Develop hypotheses on how to solve the problem, ideate, and create a strawman plan. Get feedback and iterate.
   3. Check resources, solidify the plan, and get buy-in from any dependencies.
4. Leadership integrates into a single plan, and shares with Teams, making the final decision on what is prioritized and resourced.
   1. Leadership needs to Prioritize, Allocate and Integrate.
   2. Consider if: you’re prioritizing the most critical work, the benefits are worth the investment, you’re confident the team will deliver, the team’s ambitious level is appropriate, there are benefits or risks the team missed, the overall portfolio of investments is appropriately balanced, you’re doing too much?
   3. Put the right amount of resources behind key initiatives. Usually it will feel like you have TOO many resources on too few bets. That’s a better way of succeeding than too few resources scattered across too many bets.
   4. Make sure you set the bar high, ambitious goals. Don’t do too many things. Be clear about tradeoffs and decisions – don’t be vague about disappointing news.
5. Teams make final tweaks, confirm buy-in, and get rolling. Commit to a goal with a given level of resources. Highlight gaps & risks with the final plan.
   1. Don’t shortchange this process. Teams have often spent dozens or hundreds of hours planning things that are ultimately changed or cut. You need clarity and alignment.
   2. Share the plan with Team leaders, make tweaks based on input, then share widely.
   3. To avoid too much drama:
      1. Bring leaders along by sharing conclusions and decisions as they happen, don’t wait until a big bang reveal.
      2. Share the reasoning of how tradeoffs are made.
      3. Listen to concerns and red flags.
      4. Get people excited. Help people see why you’re enthusiastic about the plan.

Assessing bets and risks

1. Pre-mortem: can surface risks and paths with likely negative results, use that to incorporate into your plan and prioritize efforts.

Reference: Thinking in Bets

Resources

1. Establishing and running a Working Group: https://about.gitlab.com/company/team/structure/working-groups/#process

Last Updated on January 21, 2023 by Omar Eduardo