Leading Strategic Initiatives

This week at Fortune Brainstorm Tech, I sat down with leaders actually responsible for implementing AI at scale - Deloitte, Blackstone, Amex, Nike, Salesforce, and more. The headlines on AI adoption are usually surveys or arm-wavy anecdotes. The reality is far messier, far more technical, and - if you dig into details - full of patterns worth stealing. A few that stood out: (1) Problem > Platform AI adoption stalls when it’s framed as “we need more AI.” It works when scoped to a bounded business problem with measurable P&L impact. Deloitte's CTO admitted their first wave fizzled until they reframed around ROI-tied use cases. ➡️ Anchor every AI proposal in the metric you’ll move - not the model you’ll use. (2) Fix the Plumbing Every failed rollout traced back to weak foundations. American Express launched a knowledge assistant that collapsed under messy data - forcing a rebuild of their data layer. Painful, but it created cover to invest in infrastructure that lacked a flashy ROI. Today, thousands of travel counselors across 19 markets use AI daily - possible only because of that reset. ➡️ Treat data foundations as first-class citizens. If you’re still deferring middleware spend, AI will expose that gap brutally. (3) Centralize Governance, Decentralize Application Nike’s journey is a case study: Phase 1: centralized team → clean infra, no traction. Phase 2: federated into business-line teams → every project tied to outcomes → traction unlocked. The pattern is consistent: centralize standards, infra, and security; decentralize use-case development. If you only push from the top, you have a fast start but shallow impact. Only bottom-up ownership gives depth. ➡️ You can’t scale AI from a lab. It has to live where the business pain lives. (4) Humans are harder than the Tech Leaders agreed: the “AI story” is really a people story. Fear of job loss slows adoption. ➡️ Frame AI as augmentation, not replacement. Culture change is the real rollout plan. (5) Board Buy-In: Blessing and Burden Boards are terrified of being left behind. Upside: funding and prioritization. Downside: unrealistic timelines and a “go faster” drumbeat. Leaders who navigated best used board energy to unlock investment in cross-functional data/security initiatives. ➡️ Harness board FOMO as cover to fund the unsexy essentials. Don’t let it push you into AI theater. (6) Success ≠ Moonshot, Failure ≠ Fatal. - Blackstone's biggest win: micro-apps that save investors 1–2 hours/day. Not glamorous, but high ROI. - Nike's biggest miss: an immersive AI Olympic shoe designer - fun demo, no scale. Incremental productivity gains compound. Moonshots inspire headlines, but rarely deliver durable value. ➡️ Bank small wins. They build credibility and capacity for bigger bets. In enterprise AI, the model is the easy part. The hard part - and the difference between demo and value - is framing the right problem, building the data plumbing, designing the org, and bringing people along.

Uncertainty isn’t the enemy of leadership. Silence in uncertainty is. Markets shift. Geopolitics flare. Technology disrupts. No leader can predict exactly what comes next. The mistake isn’t saying “I don’t know.” The mistake is leaving it there. Silence creates space for fear. Scenarios create space for confidence. The leaders I know say this: “We don’t know the future…But here are three ways it could play out, and here’s how we’ll respond to each.” That shift replaces anxiety with structure. Here’s how scenarios guide decisions: 1. Best Case → Maximise Opportunity • If growth rebounds, be ready to scale • Line up resources and move first • Optimism matters only if you’re prepared 2. Base Case → Navigate Steady State • In uneven recovery discipline wins • Tier your investments • Forecast cash tightly • Normalise quarterly adjustments 3. Worst Case → Build Resilience • Protect non-negotiables • Pre-approve cost levers • Over-communicate with empathy, reinforce purpose • Trust is forged in downturns, not booms. The real power is in cascading this skill to teams: → Model vulnerability (“I don’t know yet”) → Teach them to sketch 3 scenarios in 15 minutes → Anchor every path to concrete actions → Repeat until it becomes part of culture At 6 months, fear gives way to clarity. At 2 years, resilience becomes second nature. Remember, great leaders don’t eliminate uncertainty. They equip their people to move confidently within it. That’s how you scale trust, resilience, and momentum, inside your company and across your partnerships. --------------------------- Avoid missing insights like this. Get cheatsheets like this each Wednesday. Subscribe to my free newsletter: https://philhsc.com ➕ Follow me, Phil Hayes-St Clair for more like this.

The European Commission is laying down an important stepping stone in our path to climate neutrality by 2050. After careful thought and consideration, we are recommending that by 2040, the EU reduces its emissions by 90%, compared to 1990 levels. With our recommendation, we are staying the course of the green transition as agreed by EU leaders, as it will be increasingly important for our global competitiveness. And it comes at a crucial moment. The essence of the debate across many countries is how to decarbonise our economy to achieve climate neutrality, while keeping our businesses globally competitive and creating stable, future-proof, highly-paid jobs in Europe. The risk of deindustrialisation and social tension is very real. For us, Europe's industrial leadership and socially just, inclusive green transition are not only two sides of the same coin, but are imperatives. Therefore, our recommendation for a 90% target is both, in line with the scientific advice, and based on a thorough impact assessment. Importantly, it also reflects that we do not operate in a vacuum. Global competition around low emission technologies is – and will remain – intense, underpinned by assertive, sometimes unfair policies. This requires close collaboration with industry. So, we want what we call an “industry decarbonisation deal” to help create a large domestic market and a strong industrial basis for clean tech. Defining a 2040 climate target should provide certainty and predictability for investment decisions. Because we want to see Europe as a prime destination for investment and a prime source of jobs at all skill levels. We have identified enabling conditions to deliver just that. It starts with the full implementation of the 2030 climate and energy framework. But it also includes more efficient use of public financing to help create a business case for all emerging clean tech, the development of raw materials supply chains, ensuring affordable energy prices, and the development and deployment of the necessary infrastructure. At the same time, we must shore up public trust in the green transition. We do recognise the legitimate concerns of citizens and industry over the costs of the transition, and we will continue supporting them through our policy and regulatory measures as well as funding instruments. We are holding a series of clean transition dialogues with key industrial sectors, a strategic dialogue with farmers, and are seeking to expand and intensify outreach to citizens. Following the two dialogues with hydrogen and energy intensive industries, we will soon hold additional ones on critical raw materials, clean tech, mobility, infrastructure, and forestry. This outreach – and received input – will help the next Commission prepare legislative proposals for the policy framework beyond 2030 and deliver on the 2040 target, once agreed by the Member States and the new European Parliament in a fair and cost-efficient manner. #EUGreenDeal

If you are a lawyer, whether in a law firm or an in-house legal department, here are the questions you should be asking about legal tech and innovation: 1) Do you start with the client or business? • For firms: does your tech roadmap improve client experience and value? • For in-house: does it make your business stakeholders’ lives easier, faster, safer? • Can you clearly link each initiative to better service, speed, or risk management? 2) Are people and process ahead of the tech? • Have you fixed the workflow before adding a tool? • Are lawyers and staff trained, incentivized, and supported to change how they work? • Or are solutions gathering dust because the process gap was never addressed? 3) How strong is your adoption muscle? • Who actually uses the tools in daily work? • Do you have structured change management or only isolated pilots? • Have you learned from failed implementations and applied those lessons? 4) Do your leaders role model innovation? • Do they use and talk about technology in delivery or decision-making? • Are they preparing for second order effects like: - Training juniors differently as traditional tasks get automated - Rethinking time based billing or productivity measures - Developing new service lines or risk frameworks - Setting standards for ethical and responsible AI 5) Who are your internal champions? • Which lawyers or professionals are experimenting and sharing wins? • Do you showcase their success to inspire others? • Are you building a pipeline of digitally fluent next generation talent? 6) Can you demonstrate ROI and impact? • For firms: can you show hours saved, revenue protected, client satisfaction gained? • For in-house: can you show faster contract cycles, reduced risk, or business enablement? • Do your stakeholders, internal or external, feel the difference innovation makes? If you cannot answer these questions with confidence, your legal tech strategy may not be working for you. Picture Courtesy - The amazing Leila El Gharbi

One year after the Draghi Report, we took stock with President Ursula von der Leyen, Mario Draghi, and key stakeholders. My message is simple: Draghi’s priorities remain Europe’s priorities. And in today’s more competitive and uncertain world, they are more urgent than ever. We have started to deliver. But Europe must move faster, with greater ambition and impact. The Commission will play its role—and I will push forward on tech sovereignty, security, and defence. That means accelerating our leadership in AI, quantum technologies, semiconductors, and cybersecurity. But this cannot be done by Brussels alone. We need Member States, political forces, and business to act together. And we must break taboos: mobilise equity, invest boldly in European tech and strategic projects, and give Europe the tools to win.

We often equate leadership with the strategy forming role. Leaders are expected to chart a course, allocate resources and execute with precision. But, we live in an age where uncertainty is the norm. Geopolitical conflicts, supply chain disruptions, technological disruptions and macro-economic shifts are making the environment much more unpredictable. In this world, the traditional notion of leadership may not be enough. What distinguishes the most effective leaders today is their ability to combine strategy with empathy, communication and adaptability, qualities that are now critical for long-term success. Empathy is defined as “Understanding before acting”. When uncertainty prevails, people can experience fear, confusion or even paralysis. Strategy provides direction, but empathy builds trust. A leader who takes time to understand what teams are feeling is better positioned to inspire the extra energy people bring when they feel valued. Empathy doesn’t mean avoiding hard choices; it means delivering them with human-ness. That sustains loyalty in turbulent times. Communication is defined as “Clarity in the fog”. In uncertainty, silence is costly. People don’t expect leaders to have all answers, but they do expect clarity about what is known, what isn’t and how decisions will be made. Warren Bennis wrote, “Leadership is the capacity to translate vision into reality.” Amidst volatility, translation means simplifying so that teams understand the direction without being overwhelmed by noise. Adaptability is the “Courage to pivot”. Even the best strategies will be wrong at some point. The question is not whether leaders will face surprises, but how quickly they can adjust. Adaptability requires humility and courage to redirect resources even if it means abandoning sunk costs. This is where agility becomes a cultural, not just operational, advantage. Through crises, successful leaders do not just react with strategy. They craft a narrative that helps teams interpret events, stay connected to a higher purpose and turn uncertainty into shared meaning. They reframe adversity as purpose, build a unifying narrative for teams and embed human connection into their responses. At the heart of these qualities is a deeper role: leaders as meaning-makers. Strategy charts the course, but meaning explains why the course matters, especially when storms hit. This “meaning-making capacity” has been recognized in leadership literature (e.g. Podolny, Varney) even if the exact phrase has not always been front and centre. Viktor Frankl observed, "Those who have a 'why' to live, can bear almost any 'how.'" Leaders who provide that "why" enable their organisations to endure, adapt and grow. In today's world, the best leaders are not just strategists but translators of uncertainty to clarity, connectors of people to purpose and builders of cultures that adapt without losing direction. In an age of volatility, being a meaning-maker may be the most strategic act of all.

I used to make software to help machine manufacturers manage their machines remotely. Twelve plus years ago I had a client that would roll out software updates to their technology kiosks. Even though they only had single digit thousands of devices, they did not push them out all at once. They pushed updates to their zip code, then their town, then their state, then their timezone, and then the whole US. Why did they follow this procedure even though they thoroughly tested the updates? Because if there was a software failure they wanted to limit the potential damage that their update would cause. They would "roll a truck" to fix the problem. They knew that selecting machines closer to headquarters would mean that they would have a lot smaller headache. Additionally, even if they bricked all of the local machines, the number of machines with problems would be measured with two or three digits and not four digits spread across the country. That is why the most shocking thing to me about the recent Crowdstrike issue is that they deployed to millions of devices all at once! From Crowdstrike on how they intend to prevent this from happening again: Refined Deployment Strategy ● Adopt a staggered deployment strategy, starting with a canary deployment to a small subset of systems before a further staged rollout. ● Enhance monitoring of sensor and system performance during the staggered content deployment to identify and mitigate issues promptly. ● Provide customers with greater control over the delivery of Rapid Response Content updates by allowing granular selection of when and where these updates are deployed. ● Provide notifications of content updates and timing. I am glad that they are taking this issue seriously but it seems crazy to me that an event like this had to happen for these type of changes. Message to everyone solution provider that makes an agent or every customer that uses an agent. A staggered rollout strategy should be absolutely required. Even if your company does not use Crowdstrike/Windows, you should be looking at all of your vendors that have an agent. What do you think? Are you going to take a look at agents as part of your vendor reviews? #fciso #crowdstrike

Six strategic challenges the EU must overcome for a sovereign, credible and climate-resilient Europe: 1. Strategic industrial power Europe must take responsibility for building its clean future. Only a shared Clean Industrial Deal can secure the technologies and capacity we need to compete and decarbonize. ➡️ "What European Security Requires" - Project Syndicate: https://lnkd.in/dBAuRHXE 2. Autonomous climate diplomacy Europe must lessen its dependence on transatlantic alignment. We need a green diplomacy, rooted in climate justice and the green economy to protect our interests in a fragmented world. ➡️ "Europe Needs a Green Foreign Policy" - Project Syndicate: https://lnkd.in/dTsHDy_R 3. Resilient energy systems True energy security lies in renewables — not gas imports from belligerent neighbours or  hurricane-prone regions. We’re on the right path. Let’s not derail it. ➡️ My post: https://lnkd.in/dZCwMtqC 4. Credible global leadership Europe must lead — with or without the United States. As we approach COP30, backtracking would cost us a credibility we cannot afford to lose. ➡️ "COP29: Europe must step up" - Le Monde: https://lnkd.in/dy7rH6KK 5. Renewed multilateralism With Luiz Awazu Pereira da Silva, we wrote that today’s geopolitical fractures are a chance to rebuild multilateralism — starting with climate cooperation, not fossil geopolitics. ➡️"A new multilateralism?" - Le Monde : https://lnkd.in/dx_sXqNA 6. Political clarity on competitiveness With Jean Pisani-Ferry and Simone Tagliapietra, we made it clear: weakening the Green Deal undermines Europe’s long-term strength. ➡️ "EU must propel global climate momentum" (POLITICO Europe) : https://lnkd.in/d2rppniB These six points form a roadmap for a future where the EU embraces the transition with justice, realism and resolve. Let’s follow through. — Over the summer, I’m sharing a few pieces I’ve written in recent months — reflections on climate politics and how we keep moving forward, even in difficult times. Feel free to contribute and share. Thank you to all who stay engaged during the summer. Let’s reconnect in September.

The European Commission has set the right direction by putting competitiveness at the heart of its agenda — affordable energy is a key element of it. With the unveiling of the Clean Industrial Deal (CID) yesterday, we are beginning to see promises being transformed into actionable steps. Now, we need to see more bold steps. Central to the CID is the ‘Affordable Energy Action Plan’, which aims to reduce energy prices by accelerating investments in renewable energy, expanding grid infrastructure in a cost-effective manner, and enhancing both supply and demand-side flexibility. It rightly addresses the systemic challenges in the energy system and seeks to strengthen the EU internal energy market. However, the Commission could have taken more substantial steps to strengthen a truly integrated EU internal energy market to foster long-term security and affordability. But positively, the Action Plan does not rush to abandon the proven and working elements of the system, such as the electricity market's price formation and financial market regulations for derivatives. Hasty interventions would not have neither addressed the root causes of the energy crisis nor the underlying drivers of energy costs. Now is the time for the Commission, the European Parliament, and the Council of the EU to act decisively on these announcements, ensuring that regulations bolster Europe's competitiveness rather than diminish it. The EU Emissions Trading System (EU ETS) should serve as a benchmark for all initiatives: it is targeted, cost-efficient, and market oriented. Where the EU ETS is applicable, there is no need for intricate regulations such as the overly prescriptive criteria defining green hydrogen or the upcoming definition of green batteries, which unnecessarily increase costs without reducing any additional tonnes of CO2. The Commission should also assertively speed up its decisions concerning capacity renumeration mechanisms and decarbonisation measures, ensuring that Member States' proposals receive approval within six months after the start of the discussion. This is essential for the success of the energy transition. And finally, we must make progress reducing overregulation and bureaucracy. The reduction of Corporate Sustainability Reporting Directive and Supply Chain Act obligations is a positive first step. But the reductions must go further and apply to all companies, not just the small ones. The prosperity of the EU, along with its competitiveness and attractiveness compared to other global markets, will depend on prioritising cost efficiency and pragmatism. I am optimistic that we can turn things around if bold action follows.

Common launch mistake: Rolling out new features to ALL customers. Pushing out a new feature to a sizable customer base comes with risks: - Higher support volume if things go south, affecting many. - Lost opportunity to refine the product with a focus group. - Difficulty in rolling back changes in certain cases. That's why products, especially those with huge customer counts, adopt a gradual rollout strategy to mitigate risk. There are multiple options here like: ✔️ Targeted roll-out Selective release to specific users or accounts. ✔️ Future-cohort facing Only new sign-ups get the feature, existing users keep legacy version ✔️ Canary release Test with a small group first, then expand after confirming it's safe. ✔️ Opt-in beta Users voluntarily choose to try new features before official release. ✔️A/B rollout Two different versions released to different groups to compare performance. ✔️Switcher Everyone gets new version by default but can temporarily switch back to old version. ✔️Geo-fenced Features released to specific geographic regions one at a time. Some factors to consider: ✅ User base capabilties How savvy is your user base? How adaptive would they be the change you're rolling out? If you need to ease them over time, think about a switcher or an opt-in beta. ✅ Complexity How complex is the product update and is it in the way of a critical path? If it's a minor update, a universal deployment will suffice. However, you might opt for an opt-in or canary release for more complex changes. ✅ Risk Assessment What's the risk profile of the update? Ex: If it's performance-intensive and could affect server load, consider using a phased release to observe patterns as you open the update upto more users. ✅ Objective Is this a revamped version of an existing product use case? Do you want to experiment which works better? Strategies like canary releases or A/B testing are valuable in this scenario. ✅ Target users Do you have different user behaviors or preferences across markets or geographies of operation? Do certain cohorts make more sense than others? Think about geo-fenced roll-outs (we used to use this a lot at Bayt when launching job seeker features). --- What rollout strategies do you use for your product?