Agile Strategy Development

Agile is dead. I’ll wait while you process that. Here’s the deal: Agile didn’t die because the idea was bad—it died because we killed it. Let’s break it down. 1️⃣ The Checklist Mentality: Agile started as a revolution in thinking but got buried under its own rituals. Daily standups? Backlogs? Sprints? They’ve become corporate theater. It’s not about outcomes anymore, it’s about checking boxes. Agile was supposed to be adaptable. Now it’s just as rigid as the systems it was designed to disrupt. 2️⃣ Scaling Without Soul: Frameworks like SAFe slapped a “scale” sticker on Agile without addressing toxic work cultures. What’s left? More bureaucracy, less agility. Scaling a broken system doesn’t fix it, it amplifies the dysfunction. 3️⃣ Speed ≠ Value: Agile promised faster results, but we’ve confused speed with success. Delivering something fast is useless if it doesn’t make an impact or add value. Agile became a race to nowhere, a hamster wheel of meaningless output. 4️⃣ Leadership Didn’t Get It: Let’s be honest—most leaders never truly bought into Agile contrary to their cheerleading behind it. For old-school executives it’s impossible for them to let go of control, and Agile demands exactly that. Without leadership trust, Agile was destined to fail. 5️⃣ Consulting Snake Oil: As they are famous for doing, consultants turned Agile into a product and sold it like magic beans. They pitched it as the answer to everything, but it wasn’t designed to fix bad leadership or broken teams. Agile isn’t Change Management 2.0, and you failed miserably if you tried to implement it as such. 6️⃣ The Human Cost: Agile became synonymous with “do more, faster.” Guess what? That’s not sustainable. Teams burned out. Engagement dropped. People became Agile collateral damage. The Harsh Truth: Agile didn’t fail; we failed Agile. We ignored its heart, culture, collaboration, trust and turned it into a system for systems’ sake. Here’s a radical idea: forget Agile. Forget the buzzwords. Forget the frameworks. Start with your people. Ask the uncomfortable questions. And lead with empathy. Real transformation doesn’t come from processes or tools. It comes from people who feel heard, valued, and empowered. Agile is dead. Let’s stop pretending otherwise.

Over the years, I've discovered the truth: Game-changing products won't succeed unless they have a unified vision across sales, marketing, and product teams. When these key functions pull in different directions, it's a death knell for go-to-market execution. Without alignment on positioning and buyer messaging, we fail to communicate value and create disjointed experiences. So, how do I foster collaboration across these functions? 1) Set shared goals and incentivize unity towards that North Star metric, be it revenue, activations, or retention. 2) Encourage team members to work closely together, building empathy rather than skepticism of other groups' intentions and contributions. 3) Regularly conduct cross-functional roadmapping sessions to cascade priorities across departments and highlight dependencies. 4) Create an environment where teams can constructively debate assumptions and strategies without politics or blame. 5) Provide clarity for sales on target personas and value propositions to equip them for deal conversations. 6) Involve all functions early in establishing positioning and messaging frameworks. Co-create when possible. By rallying together around customers’ needs, we block and tackle as one team towards product-market fit. The magic truly happens when teams unite towards a shared mission to delight users!

Most organizations wait way too long to adopt portfolio-level agility practices. They’ve been told, “You can’t scale what’s broken,” so they wait until they nail agile at the team and product group level. What if fixing what’s broken REQUIRES focusing on the upstream that’s shaping the work and context of these teams?  Back in 2012 or so, I met an SVP responsible for a 1000-person delivery organization that was working in a traditional waterfall. Critical Chain optimized waterfall. But still. Component Teams. Heavy coordination and integration costs across multiple products. Build that takes 2 weeks to integrate. Riki and her team ran a very successful and profitable shop. However, they recognized that in order to satisfy their customers, they often had to accept change out of cycle, which created a constant fire drill. We discussed options. What Riki liked was starting with visualizing, understanding, and managing flow at the portfolio level, to break the waterfall. We got it going within weeks. (Did I mention Riki and the team were experienced, highly motivated operations-focused leaders? ). It didn’t take long for Flow times to start improving and for “Welcome Change” to be a more reasonable proposition. Over time, we’ve noticed how much “cross-product” work this portfolio delivered and started exploring ways to reorganize around value. We started introducing more and more agility principles and practices (eventually, they did reorganize to stream-aligned cross-product groups focused on the REAL product and leveraged team-level agile ways of working). Here’s the thing – Starting at the Portfolio level gives you, as a leader, tons of leverage to make an impact on the product-oriented agility of your organization – by tackling the systemic constraints to Product thinking, Flow, and Empiricism and allowing you to learn and model the behaviors you expect from your people. Yuval "Don't sleep on Portfolio Agility" Yeret

Using Data to Drive Strategy: To lead with confidence and achieve sustainable growth, businesses must lean into data-driven decision-making. When harnessed correctly, data illuminates what’s working, uncovers untapped opportunities, and de-risks strategic choices. But using data to drive strategy isn’t about collecting every data point — it’s about asking the right questions and translating insights into action. Here’s how to make informed decisions using data as your strategic compass. 1. Start with Strategic Questions, Not Just Data: Too many teams gather data without a clear purpose. Flip the script. Begin with your business goals: What are we trying to achieve? What’s blocking growth? What do we need to understand to move forward? Align your data efforts around key decisions, not the other way around. 2. Define the Right KPIs: Key Performance Indicators (KPIs) should reflect both your objectives and your customer's journey. Well-defined KPIs serve as the dashboard for strategic navigation, ensuring you're not just busy but moving in the right direction. 3. Bring Together the Right Data Sources Strategic insights often live at the intersection of multiple data sets: Website analytics reveal user behavior. CRM data shows pipeline health and customer trends. Social listening exposes brand sentiment. Financial data validates profitability and ROI. Connecting these sources creates a full-funnel view that supports smarter, cross-functional decision-making. 4. Use Data to Pressure-Test Assumptions Even seasoned leaders can fall into the trap of confirmation bias. Let data challenge your assumptions. Think a campaign is performing? Dive into attribution metrics. Believe one channel drives more qualified leads? A/B test it. Feel your product positioning is clear? Review bounce rates and session times. Letting data “speak truth to power” leads to more objective, resilient strategies. 5. Visualize and Socialize Insights Data only becomes powerful when it drives alignment. Use dashboards, heatmaps, and story-driven visuals to communicate insights clearly and inspire action. Make data accessible across departments so strategy becomes a shared mission, not a siloed exercise. 6. Balance Data with Human Judgment Data informs. Leaders decide. While metrics provide clarity, real-world experience, context, and intuition still matter. Use data to sharpen instincts, not replace them. The best strategic decisions blend insight with empathy, analytics with agility. 7. Build a Culture of Curiosity Making data-driven decisions isn’t a one-time event — it’s a mindset. Encourage teams to ask questions, test hypotheses, and treat failure as learning. When curiosity is rewarded and insight is valued, strategy becomes dynamic and future-forward. Informed decisions aren't just more accurate — they’re more powerful. By embedding data into the fabric of your strategy, you empower your organization to move faster, think smarter, and grow with greater confidence.

A leadership team I worked with had just wrapped a major strategy retreat. Values were refreshed. Vision was clear. Energy was high. But six weeks later? Alignment had faded. Mid-level managers were overextended. Stress was spiking. Not because the strategy was wrong, but because the team hadn’t committed to the rhythms that would sustain the change. You can’t lead on clarity and operate on chaos. Culture doesn’t stick without rhythm. When we stepped back in, we settled into the Design & Walk phase. The team didn’t need more content. They needed structure. We established new rhythms: -Biweekly leadership huddles focused on decision-making and alignment instead of updates (moving eyes forward). Reshaped 1:1s built around both results and relational feedback (focused on connection and alignment) -Quarterly reset sessions tying strategy to lived experience across teams What changed? (checking for alignment in strategy and culture) Impact? -Decision speed increased -Team energy stabilized -Managers felt more supported -Turnover dropped in key departments They didn’t just need vision. They needed clear support structures to live it out—together. Real results happen when strategic alignment and human connection move in rhythm. 📌 Where does your team need a rhythm that actually reflects what you say matters? #groundedandgrowing #leadershipdevelopment #organizationalhealth #culturebuilding #executivealignment #designandwalk #rhythms #teamstrategy #managerdevelopment

A VP told me the other day, “We’ve restructured the team, set new goals, added tools but still not seeing results.” So I asked, “Okay, but how are you supporting your managers?” They got quiet. No training, no feedback, no real investment in the people actually leading the work. That’s the part a lot of leaders miss: You can’t expect big results if you’re not pouring into the people driving them. That’s where I’d start the conversation, then, we’d get to work: ➡️Check in with your team’s sense of purpose. Ask if they feel connected to the mission. Where do they see themselves making an impact? Their answers will show you the gaps. ➡️Create consistent, open communication. Whether it’s 1:1s or team huddles, build space where people feel safe to share what’s really going on. ➡️Equip your managers to lead. Don’t just expect them to supervise, train them to coach, support, and inspire. ➡️ Bring your values into the day-to-day. Culture lives in decisions, feedback, recognition – not just your company handbook. This is not a one-time fix. This is laying the foundation for a culture that drives performance and results. Now, ask yourself: What part of your business could perform better with more focus on people and culture?

We don't have to have all of the same opinions about agile to get along. I know lots of coaches and scrum masters with very different opinions who are excellent. You may believe in the Scrum Guide to the letter. I'm much more like "directionally correct and usefully wrong" about following agile frameworks. You might have a bunch of certifications. I choose instead to be a rabid reader and accumulate diverse, real stories to help me be a better coach. We don't even have to define the Agile Mindset exactly the same way. HOWEVER... if you don't think these 7 cultures and mindsets are a crucial part of "being agile", then we are miles apart! * An Iterative Mindset -- Deliver value in small, iterative steps allowing for early and frequent feedback on each piece of work, which helps eliminate waste and build better products faster. * A Product Culture -- Form long-lasting, durable, product teams that reflect the company’s focus, vision, and purpose. Share a product vision that influences the teams’ backlogs and day-to-day work. * A Customer-Centric Mindset -- In customer terms, give the teams an appreciation for WHY it matters to the users before doing anything. Don’t guess what customers want, be customer-driven and empirical. * A Culture of Learning -- Team members share knowledge, make learning a priority, and invest in communities that grow people and skills that benefit the company. All failures are opportunities to learn something. * A Culture of Experimentation -- A Design Thinking mindset should be utilized from idea formation through delivery. Instead of requirements, think hypotheses. What’s the smallest thing we can do to learn something? * A Culture of Continuous Improvement -- Teams are empowered to change and improve their own process. Self-reflection, transparency, courage, and respect lead to sustainable value delivery and better results. * A Culture of Psychological Safety -- People will not be punished or humiliated for speaking up with any ideas, questions, concerns or mistakes. This breeds greater innovation, inclusive collaboration and a greater flow of ideas that can impact our products, people, and company. THIS is how I define the Agile Mindset. And that feeling you get when the team "gets it"... that mysterious sort of time when it "clicks" is because these 7 things have started to grow and become habits, beliefs, and BEHAVIORS of the team.

Clearing the Systemic Barriers to Authentic Agility Most so-called Agile “transformations” (oh, if ever there were a misnomer) don’t fail because of the framework, tooling, or training - they fail because of deeply embedded impediments that fall into four systemic categories: Culture, Structure, Process, and Technology. These factors form a complex ecosystem, and if you treat them like separate problems, you’ll get performative agility without real adaptability. Agility isn’t a checklist or a destination. It’s a continuous journey of adaptation. Ignore the interplay between these domains at your peril. Barrier #1: Culture - The Invisible Operating System That Resists Change Problem: Traditional organizational cultures prioritize control over creativity, rewarding compliance while punishing exploration. The result is risk-averse bureaucracy. Questions: Do people feel safe admitting mistakes? Are failures learning opportunities or liabilities? Can the status quo be challenged without retaliation? Strategies: Foster psychological safety with blameless retrospectives and candor-friendly spaces. Celebrate smart failures. Promote learning with cross-functional exposure, rotation programs, and curiosity-based metrics. Barrier #2: Structure - Your Org Chart Is Showing Problem: Hierarchical, siloed structures slow decisions and disconnect teams from value delivery. Questions: Are teams aligned to customer outcomes or department KPIs? Where do decisions get made? How often do handoffs or approvals delay progress? Strategies: Align teams to value streams. Push decision-making closer to the work. Use lightweight governance and clearly delegated authority to reduce drag. Barrier #3: Process - When Following Rules Becomes Valuable Problem: Agile rituals become performative when teams confuse ceremony with value. Questions: Are Agile events energizing or exhausting? Do metrics reflect outcomes or activity? Are teams allowed to evolve their way of working? Strategies: Design outcome-oriented processes. Audit meetings regularly. Enable process experimentation within safe bounds. Focus on feedback loops, not rituals. Barrier #4: Technology - Tools as Thrust or Drag Problem: Legacy systems and fragmented tools create cognitive friction, slow feedback, and kill momentum. Questions: Do your tools promote collaboration or reporting? Can teams release frequently without manual overhead? Does tech accelerate flow or block it? Strategies: Invest in CI/CD, test automation, and self-service platforms. Retire tools that reinforce control or don't add value. Prioritize fast feedback, simplicity, and team autonomy in tool selection. Agility Isn’t Implemented - It’s Cultivated True agility requires systemic change across all four domains. It’s messy, non-linear, and context-dependent. Focus on domain interactions. Create safe-to-learn environments. Measure progress by adaptability, not just delivery. Don't chase transformation; enable evolution.

Last week, I posted about data strategies’ tendency to focus on the data itself, overlooking the (data-driven) decisioning process itself. All it not lost. First, it is appropriate that the majority of the focus remains on the supply of high-quality #data relative to the perceived demand for it through the lenses of specific use cases. But there is an opportunity to complement this by addressing the decisioning process itself. 7 initiatives you can consider: 1) Create a structured decision-making framework that integrates data into the strategic decision-making process. This is a reusable framework that can be used to explain in a variety of scenarios how decisions can be made. Intuition is not immediately a bad thing, but the framework raises awareness about its limitations, and the role of data to overcome them. 2) Equip leaders with the skills to interpret and use data effectively in strategic contexts. This can include offering training programs focusing on data literacy, decision-making biases, hypothesis development, and data #analytics techniques tailored for strategic planning. A light version could be an on-demand training. 3) Improve your #MI systems and dashboards to provide real-time, relevant, and easily interpretable data for strategic decision-makers. If data is to play a supporting role to intuition in a number of important scenarios, then at least that data should be available and reliable. 4) Encourage a #dataculture, including in the top executive tier. This is the most important and all-encompassing recommendation, but at the same time the least tactical and tangible. Promote the use of data in strategic discussions, celebrate data-driven successes, and create forums for sharing best practices. 5) Integrate #datascientists within strategic planning teams. Explore options to assign them to work directly with executives on strategic initiatives, providing data analysis, modeling, and interpretation services as part of the decision-making process. 6) Make decisioning a formal pillar of your #datastrategy alongside common existing ones like data architecture, data quality, and metadata management. Develop initiatives and goals focused on improving decision-making processes, including training, tools, and metrics. 7) Conduct strategic data reviews to evaluate how effectively data was used. Avoid being overly critical of the decision-makers; the goal is to refine the process, not question the decisions themselves. Consider what data could have been sought at the time to validate or challenge the decision. Both data and intuition have roles to play in strategic decision-making. No leap in data or #AI will change that. The goal is to balance the two, which requires investment in the decision-making process to complement the existing focus on the data itself. Full POV ➡️ https://lnkd.in/e3F-R6V7

As organizations feverishly plan the next year, it presents a vital opportunity for data teams to shape and drive this process analytically. It is one of their key jobs-to-be-done. But, what does this look like? Let's consider a base financial model that outlines the desired direction for the business. The metrics of interest at this level are usually the highest-level outputs such as revenue and costs. 1) Breakdown Outputs: The first area where a data team can help is in breaking down these outputs into more granular and operational input pieces. How should we assess the contributions from various cohorts of users or accounts? From existing or new product lines? From new features? From different markets? By increasing supply? By driving engagement? By improving application performance? Or upgrading the operations? Data teams as one of very few teams with a holistic view of the business, can translate these top-line KPIs into targets for specific teams. 2) Resolve Conflicts: A second role for data teams is identifying and resolving conflicts. It is tempting to want all metrics to move up and to the right - but in reality, metrics are often in conflict. For instance, if you focus on driving traffic, you may see a drop in conversion rates. If you want to drive higher revenue per account, expect higher churn. If you want to improve margins, new acquisition efforts may slow down. Balancing these metric equations is vital for establishing metric goals, as failing to do so can demotivate even high performing teams who will struggle to connect their work to overall progress. 3) Inform Trade-offs: Data teams can help in making informed trade-offs. Drawing upon their experience of what’s worked, they can shape strategy discussions. A consequence of this is focus - deciding what to worry about, and what to de-prioritize can be liberating for operational teams. All these pieces of work are ultimately accomplished with a significant amount of data and code. Apart from spreadsheets or notebooks, which are both do-whatever-you-please tools, there aren’t many options for analytics or business teams. The flip side of having open-ended flexibility is that these operations are expensive - requiring experts to hand-craft queries, retrieve data, build models, and execute calculations. In practice, due to these productivity constraints, the planning process usually does not end up as analytically rigorous as desired. Worse yet, it can be half-baked where executives believe they are thorough, but the numbers are backed by false precision. All said, it is worth noting we are just getting started. Data teams are playing a greater role in shaping how organizations debate strategy, allocate capital, make bets, create plans, establish tactics, and set and monitor metric goals. I’m excited to see this elevate the visibility and ROI of data teams.