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ENTERPRISE REFLECTION

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Enterprise Reflection WorkbookWhat’s working and not working in your organization right now? Find some quiet time to dive into this workbook by yourself. Or gather a group in a conference room to fill out the worksheets and discuss the results. Use the space below each question to jot down examples, quotes, insights, ideas, action items, or notes about where coworkers have differing opinions.

1. Let’s start with a big question. What does success look like? What do you want more of as a result of your work? Less of? Consider these five perspectives and write a few words or draw pictures in each section.

Personal Success

Team Success

Company Success

Customer Success

Societal Success


2. To be successful, do you need the insights of one type of specialist? Or a multidisciplinary approach?

Achieving our definition of success requires:

a. A deep understanding of multiple fields, related to technology, design, business, and policy.

b. Depth in one field, and some awareness of others.c. Expertise in one field.

3. How many people do you need to work with to execute your vision?

a. More than 150 peopleb. 10-150 peoplec. A small team of less than 10 peopled. Just me

4. If you’re working with other people, how are your typical team conversations going?

a. We have productive, thoughtful debates about how to accomplish shared goals. Everyone is willing to speak up, and the team has a common language for discussing the problems and solutions.

b. There’s a lot of agreement, but it seems like some important things aren’t being said in order to avoid conflict.

c. There’s a lot of debate, but it seems like everyone is pitching from their perspective and speaking different languages.

d. Meetings are tense and argumentative. e. We honestly don’t communicate enough, which is causing issues.


5. Zoom out to the big picture of your business. Now you can see the individual parts of your business model and how they interact. How well does everything fit together?

a. The components integrate well to create something better than the sum of its parts, and it’s clear how changing one piece will impact the rest.

b. Everything integrates smoothly, but it’s hard to make a change to one area without needing to reconsider everything else.

c. Everything technically integrates, but it’s disjointed, awkward, or inefficient as a whole.

d. The individual pieces are good, but we run into integration issues when we try to connect everything together.

6. What’s the risk of making a change to your products, tools, processes, or organization?

a. It could negatively impact safety or security.b. It could negatively impact customer service and our reputation.c. Not a big deal at all. Worst case, others might not notice or it will cause a minor

inconvenience.


7. Back to your definition of success from question #1. How much progress have you made toward it over the past few months?

a. We’re constantly moving the needle on our measures of success.b. We’re making progress toward the sub-goals but not the larger goals.c. We’re not making much progress at all, even toward the sub-goals we set.d. We’re not sure if we’re making progress or not.

8. Consider the resources you’re already investing in your goals (ex. time and money). Do you have a full picture of everything you’re already investing in or plan to invest in?

a. There’s a global picture of resources being spent, where everyone has access to the details they need to make decisions.

b. There are pockets of visibility but no shared picture of all resources being spent by everyone.

c. There’s no visibility at all into how time, money, or other resources are being spent.


9. Grab your to-do list/backlog, calendar, project plans, and vision and review them. How connected are they?

a. We have a vision and flexible project plans, and are constantly adding milestones and tasks to the calendar to achieve them.

b. We have a vision and project plans but haven’t added related tasks to the calendar. c. We’re getting things done but not moving closer to our vision because we haven’t

figured out what projects and tasks would be needed to achieve the vision.

10. Looking at your to-do list and considering your vision, which best describes your situation?

a. We’ve already researched possibilities, brainstormed, compared options, and have confidence that these items are good candidates to work on next in order to realize the vision or learn more.

b. There probably is a better or different way to approach the vision but we’re not sure what it is, how to identify it, or make sure it gets the attention it deserves.

c. These projects and tasks have been on the list for a while but they’re not linked to our current vision.


11. How does your organization decide what to work on and what the priority is?

a. Even with multiple stakeholders and goals to optimize, we have a common framework and process for deciding what to work on when.

b. It requires a mix of individual planning and negotiating or selling your ideas to others.

c. Many people are involved, but with so many dimensions to compare, prioritizing is overwhelming, time consuming, and no one seems happy with the final decisions.

d. One person or a small group tends to make the decisions.e. Everyone decides for him or herself.

12. How dependent are your projects on each other? Don’t forget to consider the dependencies from multiple perspectives (ex. technology, people, process, policy).

a. Everything is interconnected, but we have solid processes for understanding what exists, how to change it, and how to adapt to new information.

b. Everything is so interconnected that it’s difficult to figure out what’s connected, where to start and how to sequence the work.

c. There are a few dependencies to work out.d. Projects are completely independent. We could complete or drop one with no

impact to the others.


13. Which best describes your organization?

a. We always have way more ideas than resources to execute them.b. We tend to have just enough resources to complete goals on our list, with a small

backlog. c. We often find ourselves looking for new ideas or opportunities to invest surplus

resources.

14. Someone has a great idea but executing it could be expensive. What does your organization typically do?

a. Run a quick exploration sprint to discover alternative ways to provide the same value at a lower cost.

b. Find a smaller project within that large investment to test out beforehand for a fraction of the cost.

c. Defer the expensive project and focus on something faster and cheaper instead. d. Go all in with an expensive investment if it has a good business case and is within

budget.


15. Priorities have been set and you’re executing the work. Now what?

a. Any changes in priorities are clear, the reasoning makes sense, and shifting focus and resources happens smoothly.

b. New projects and tasks are added, without dropping current projects or adding more resources.

c. The plan never changes. Once something is added to the pipeline, we execute the entire project according to plan.

d. Priorities have already changed. There’s constant churn and shifting direction, causing a lot of confusion, rework, or frustration.

16. A new idea just came in and it would be perfect to execute. It fits your vision, your customer’s needs, and you have the means to execute it, although it might require shifting some resources. How long does it take before you can get started?

a. Why not today?b. A week or morec. A month or mored. A quarter or moree. A year or more


17. Plans can change, but as of right now, which best describes the projects you’re planning to work on next year?

a. A mix of small, short projects and large projects.b. A lot of big ambitious projects that will take a few months or longer to fully

complete.c. A lot of small projects that we can complete in a month or less.d. Not sure yet which projects we want to work on next year.

18. If you’ve been working on an initiative for a few months or years, which best describes your current situation?

a. Early investments are paying off. We’re creating exponential value and costs are decreasing.

b. We’re starting to see a little movement in a positive direction.c. We had a brief spike of created value or saved cost but now we’re seeing the

opposite, as if it’s time to pay off a debt. d. We’ve been making investments but as time goes by costs aren’t going down or

value isn’t increasing.e. We’re not sure how our costs or value created have been changing over time.


19. Imagine that someone could wander around your organization for a week with an invisibility cloak, listening in on meetings and casual conversations. Which phrase would they hear most often?

a. How will this investment help us realize our vision? b. How valuable is this change?c. How much will it cost? d. When will that project be done?

20. What was your biggest takeaway or insight after answering the questions in this workbook?


What’s Next?

Uncovering insights is just the first step. How will your findings from this workbook influence your plans for next year? Recharted Territory has a few resources that can help.

If your organization struggles with making progress on important complex problems or initiatives, you might be interested in the Enterprise Design Sprints Facilitator’s Guide. The guidebook covers a method for guiding a small team working in a complex enterprise through exploring a problem space, generating solutions, and gathering feedback in as short as a week. You can find the guidebook over at https://www.rechartedterritory.com/guidebook/

If your organization struggles with creating consistent habits to identify, prioritize, and quickly deliver value at scale, you might be interested in the Path to Portfolio program. Path to Portfolio is a coaching experience focused on blending autonomy and alignment in your organization with a lean-agile enterprise portfolio approach. It also includes a more in-depth diagnostic. Review the details and schedule a call to discuss your organization and the next steps over at https://www.rechartedterritory.com/services/

If you have just a few gaps to fill, you might be interested in exploring the RT Knowledge Base for more ideas and inspiration. If you can’t find the answers to your questions there, just send a message to [email protected] with your question and we’ll point you to the right resource or address your question in an upcoming post. The knowledge base can be found at https://www.rechartedterritory.com/articles/

If you’re a powerhouse on all levels and answered (a) for almost every question, congrats! We’d love to share your story with the community if you’re interested. Message [email protected] to start the discussion.

Action Steps

List two things you’re going to do within the next week to apply what you learned. This could be starting a conversation with a coworker, conducting research, messaging Recharted Territory, kicking off a new initiative... anything!

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enterprise reflection€¦ · enterprise reflection workbook what’s working and not working in...

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