Agile Planning for Deadlines

Teams in large organizations often have tunnel vision for their current priority. Cross-functional deadlines get missed and important programs are jeopardized. Here are 5 steps to avoid this. Ideally, everyone in your organization would understand the importance of supporting the work for cross-functional efforts. Unfortunately, that is almost never how it works for a complex business. For example, while I was working on streaming the Olympics, I knew the deliverables more than eighteen months in advance. However, most of my partner teams were supporting other urgent programs during this time and other priorities took precedence. To ensure that these other priorities didn’t stop us from missing our deadline, I needed to continue driving visibility and get stakeholders to complete the work in parallel to other priorities. My method for getting support and driving alignment was to ensure everyone understood WHY they needed to complete the work and when it was really urgent. If you are fortunate, as I have been, you will have a program manager who develops the schedule and helps you over-communicate it to senior leadership. If you don’t have someone, you will need to grow one and train them to: 1) Backwards Plan You must backwards plan the entire schedule, especially for hard-deadline programs. 2) Identify Deliverables One of the key outcomes of the backwards planning is to establish critical deliverables, who owns them, and the deadline or milestone for their completion. 3) Quantify Impact If you can’t explain the impact of missing a deliverable, nobody will care. You must be crystal clear on what happens to the program when something is missed. 4) Communicate Communicate the entire plan at the start. Then, communicate progress on a regular basis. Communicate clearly and often. If you think you are over-communicating, you may be starting to communicate enough. 5) Escalate People are often afraid of this, but it is an important tool. You should absolutely try to resolve any issues with your partners before escalating, but don’t be afraid to escalate when necessary. Always do it with your partner’s knowledge, even if you don’t have their consent. This is a high judgement call - the type of call that executives need to be capable of. I’ve had partner teams who clearly had no plan to deliver what I needed by the date they had been provided. I would always approach that team’s leadership to see how a plan could be developed. In some cases, they were simply overloaded with work on other programs. Escalating the issue actually ended up being helpful to them. What do you do to drive long, cross-functional programs with hard deadlines? For a live discussion on topics like this, please join Ethan Evans and me on February 15 & 16 for our class: “Lead Large-Scale Tech & Excel as a Technology Executive:" https://lnkd.in/eQQUhMvf Use the code FAST25 through December 3 for a 25% discount.

Planning a Release? Don’t just ship strategize. Too many teams jump into sprints without a solid release plan. The result? Missed deadlines, scattered priorities, and stakeholder confusion. Here’s how to get your Release Planning right: 1️⃣ Define Clear Objectives Know your "why." Every release should serve a purpose aligned with your product vision. What are we actually trying to achieve? 2️⃣ Prioritize Features Not all features are created equal. Focus on delivering value first, not just volume. 3️⃣ Estimate Effort Unrealistic deadlines kill morale. Effort estimation ensures your team isn’t sprinting toward burnout. 4️⃣ Create a Timeline Map it out. A clear timeline, clear expectations for the team and stakeholders. 5️⃣ Align Stakeholders If everyone’s not on the same page, expect chaos. Bring the dev team, PO, and stakeholders together early and often. A good release plan isn’t about perfection it’s about clarity, focus, and alignment. How does your team approach release planning? What’s worked (or failed) for you? Let’s elevate the way we plan, build, and ship. DM me if you need help to land a scrum job.

Flexible plans don’t miss deadlines. They meet reality. Most delays don’t come from poor planning, they come from plans that can’t adapt. Here’s how I build timelines that flex without losing control: • Spot the vulnerable zones → Dependencies, approvals, or external inputs? Flag them early. • Add purposeful buffer points → Strategic slack buys time where it matters most. • Reprioritize often, not later → Short cycles help you pivot fast and stay focused. I’ve delivered projects on time not because nothing changed, but because the plan was built to handle change. Control isn’t about rigidity. It’s about designing for movement. How do you build flexibility into your timelines? Drop it below, I’d love to hear how you handle it.