Pop Quiz: Your company has a new Chief Technology Officer (CTO). On her first day, she asks for a list of your company's most strategic technology initiatives many of which are being managed using both Agile and non-agile/waterfall frameworks in several different tools across multiple teams. Not only does she want the itemized list, but she wants to know what each initiative is about, which of her direct reports is accountable for them, how they are performing, when they are expected to deliver, and what are the latest accomplishments, next major deliverables, and biggest risks or issues for each (within the last 2 weeks). Based on the capabilities of your company today, would you be able to provide this to her? If yes, how quickly would it take to produce? Seconds? Minutes? Days? Weeks? Years!? Would the information you provide her be timely, relevant, and accurate? Could you produce this list again next week or next month with minimal effort on you and those who must provide this information? What format would you deliver it to her in? Is it a PowerPoint that has to be typed up, formatted, and reviewed, or is it an email, or a system generated report? If you found yourself sweating or queasy while answering these questions, not to worry, you're in good company! We've been there! And yes, it is possible to get to this level of reporting. This experience report steps you through these real-life challenges faced by Charter Communications, a 100-000 person broadband connectivity company and cable operator with multiple teams, tools, delivery frameworks, and priorities all under different, complex cross-functional organizations. Here, we share with you our most important lessons learned about how data warehousing, data hierarchy, governance, and some good old fashioned word of mouth communication can provide executives with the critical information they need while giving delivery teams the autonomy they desire to deliver in their framework of choice without swivel chairing data.