Agile Ambition

An inflexible strategy? It’s a losing game, long before the board’s set. Because the world doesn’t care about your perfect plan. A fixed strategy is like playing chess without looking at the board. One unexpected move, and you’re forced into checkmate. The world’s moves aren’t predictable, and neither is success. Adaptability isn’t just an edge; it’s the difference between check and checkmate. In chess, you refine your strategy as the game unfolds. With rolling wave planning, you adjust like a master player—moving forward while the board shifts. Short-term clarity, long-term vision. Both evolve in real-time. Progress isn’t about forcing every piece into place. It’s about creating space to adapt and respond. An unyielding plan blinds you to new moves on the board. Victory isn’t the last move; it’s every pivot along the way. Strategy isn’t static. It’s dynamic, like the game itself. Ready to build a plan that thrives through change? Discover rolling wave planning: https://lnkd.in/gSTYUFzk ?? Comment with a time you watched a rigid plan fail spectacularly. ?? Repost to help others embrace adaptable planning.

Once upon a time, I was a die-hard fan of story points: - Our forecasts were hit or miss. We might as well have flipped a coin. - Backlog refinement became a quest for elusive story points instead of removing ambiguity and mitigating risk. - I thought story points were easier, forgetting developers had to translate hours into points from the start. - And heaven forbid anyone suggest a 4-point story! I was the self-appointed keeper of Fibonacci purity, always ready with a lecture. Sure, when you're just starting, it's easy to get caught up in the popularity of what other teams are doing. Sometimes, you grab what’s already out there rather than dream up your own from scratch. But here's the thing I never understood: What’s stopping teams from ditching story points for simpler, more effective methods? This Sunday, the newsletter asks: “Does Your Estimation Process Need a Trash Day?” We’ll explore simpler methods that actually work. Want to find actionable strategies to reduce estimation stress? Subscribe for free: https://lnkd.in/gssNxgJG

Your future plans are fantasies. Here’s the truth teams hate to admit… ...and it’s the reason your team is always behind schedule. A napkin sketch says, ‘Let’s explore,’ but a polished mockup says, ‘It’s final.’ Our brains see a difference—even if the plan is the same. Stakeholders see dates as promises. That’s where chaos begins. They don’t realize those plans are just snapshots of current assumptions. Preplanning too far? It’s like betting on quicksand—you’ll sink every time. It looks official on the roadmap, but in reality, things always change. Rolling wave planning embraces change as the only real constant. Near-term work gets the details; the future stays flexible. No more false promises, no more shock when the plan needs adjusting. Stakeholders see that the further out we go, the less certain we are. Build transparency, not false hope. You’ll deliver more often, with less stress. Your team deserves a realistic plan—not one built on fantasy. Discover the full approach to rolling wave planning: https://lnkd.in/g7wx4Gef ?? Comment with a tip help stakeholders embrace uncertainty. ?? Repost to challenge outdated planning habits. #betterwaysofworking #agileminset #uncertainty

Are you “busy” or actually making progress? Most teams can’t tell the difference—and it’s costing them. Let’s be real—when did you last say ‘no’ to a request? Saying “yes” to everything just dilutes what you’re truly capable of. Every “yes” chips away at your capacity—and your focus slips further. It’s tempting to keep adding, but at what cost to real impact? Great teams know this. They weigh every new request for impact. They deliver value by balancing intake with capacity. Are you leading the workload, or just scrambling to keep up? Progress doesn’t come from reacting; it comes from thoughtful choice. Your backlog isn’t a dumping ground for everyone’s requests. Guard it and make impact your filter—results depend on it. Ready to escape reactive planning? Here’s some experiments to start with: https://lnkd.in/gcsmrZeX ?? Comment with the biggest “yes” you wish you’d said “no” to! ?? Repost to help teams trade hustle for impact.

Is reactive planning throwing your team off course? When teams feel like they can’t control the work flow, they get stuck putting out fires instead of making real progress. Reactive planning doesn't just slow progress—it drains your team's energy and morale. But here’s the truth: while you might not manage every demand, you have the power to change how your team works with proactive planning. Here’s why it matters: Proactive planning keeps your team focused, ahead of the curve, and helps you avoid burnout. So, how can you take action? Most team struggles trace back to root causes. Addressing those with intention and experimentation is key. For example: Feeling overwhelmed by strategic planning? It’s probably piling up until it’s urgent. Sound like your team? Try steady stream refinement—block recurring time to keep work manageable and avoid last-minute scrambles. Ready to break the reactive cycle? The experiment map includes three practical experiments to help your team stay on track, or dive into the full newsletter here: https://lnkd.in/ginTW9Ce

Once upon a time, I was caught in a relentless loop of reactive work, drowning our long-term goals. - Stakeholders began to lose trust as missed deadlines piled up, priorities shifting like quicksand. - Just when we thought we were steady, another request hit, knocking us off balance. - The team spun its wheels, worn down by the lack of direction, burning out without progress. - Chaos ruled, and even urgent tasks fell through the cracks as we scrambled to keep up. Sure, in fast-paced environments, last-minute changes happen. Sometimes, we have to reprioritize. But here's what I could never quite grasp: Why does reactive planning—or worse, no planning—become the norm for teams? This Sunday’s newsletter, Avoiding the Rapids: Plan Proactively, dives into just that. Want to help your team stay focused and avoid the chaos? Subscribe for free: https://lnkd.in/gkGk2KDu

A single tactic can ease the burden of wasted efforts… Leverage the Sprint Review for strategic alignment. These experiments can help your team elevate your Sprint Review: - Feedback-Driven Agenda - Product Goals - Hypothesis-Driven Development - Reframe Blame This past Sunday’s newsletter, titled “Positioning the Ladder: Avoiding Fruitless Efforts,” focused on helping teams unlock the true value of Sprint Reviews. Don't miss out! Subscribe and catch up here: https://lnkd.in/gssNxgJG

Once upon a time. I worked on a team where Sprint Reviews were just glorified sign-offs: - Our demo-focused meetings limited stakeholder collaboration and valuable feedback: - Rigid adherence to plans happened because we lacked clear objectives, hindering our adaptability. - We operated like a feature factory, failing to connect our work to strategic goals. - Systemic impediments persisted because we didn't escalate issues effectively. Sure, sign-offs and approvals are necessary for companies that must meet compliance regulations. Sometimes, it's essential to track who approved changes for release into production. But here’s what I could never understand: Why do we keep sacrificing the value of the Sprint Review by turning it into a phase-gate? This Sunday’s newsletter edition will be titled “Positioning the Ladder: Avoiding Fruitless Efforts.” Want to help your team unlock the actual value of Sprint Reviews? Subscribe here: https://lnkd.in/gssNxgJG

A single process can alleviate the anxiety of emergency job searches: Proactive Career Management. Try these experiments: - Interview Prep Routine - Overachiever Archive - Cover Letter Automation - Purposeful Networking Check out my latest newsletter, “Checking the Tires: Avoiding Job Search Panic” where I describe these experiments to combat a career blowout. Missed it? Find it here: agileambition.substack.com

Imagine making the job search process less stressful (without creating a bunch of waste). It may seem improbable, but with proactive career management, this can become achievable. Sunday, I’ll share a newsletter called “Checking the Tires : Avoiding Job Search Panic.” I’ll be sharing four experiments to help you transition: - From interview cram sessions to consistent readiness - From forgotten achievements to captured wins - From nightmare cover letters to breezy introductions - From networking neglect to valuable relationships Ready to embrace a smooth job search? Subscribe to the newsletter: https://lnkd.in/gssNxgJG