Leadership In Agile Environments

We just closed a $480K deal at Aligned - our biggest ever. But twice in the final weeks, it almost died. It was brutal. Two execs came out of nowhere with objections. We had no access. No time to fix it. But 22 (!!) stakeholders had already been engaged… And they saved it. That’s when it hit me: Multithreading isn’t a tactic. It’s deal insurance. Here’s the exact playbook we now run in every complex deal: 1. Early Exec-to-Exec Sponsorship Don’t wait until sh*t hits the fan. Initiate VP-VP or CXO-CXO alignment early. We send short, supportive emails without direct asks. Time after time, that builds genuine trust and establishes a safety net long before we need it. 2. Identify ‘Hidden Stakeholders’ Buyers often silently forward materials internally. By using Deal Rooms, we uncover up to 68% more stakeholders, often the real decision-makers influencing budget approvals or strategic buy-in. 3. Isolate Stakeholders 11 people on a call? You’re NOT multithreaded - it’s about quality, not volume. Our team opens separate 1:1 convos. They follow up with each buyer with next steps, suggestions or value that ties to something they said. 4. Proactive Signal-Based Engagement When stakeholders interact with key assets in the deal room, we use those signals to trigger follow ups - e.g. RevOps spends 20min on CRM integration; they might need more info, or could benefit from a dedicated session. 5. Multiple Champions Strategy Nothing beats having an army of internal champions instead of one. Whenever we see an opportunity to build champions, we do it. It derisks the deal in case someone leaves. Plus, budgets are shared, or are just easier to pass. 6. Real-time Alerts on New Stakeholders Our deal room sends instant alerts whenever there’s a new stakeholder (see #2). We then leverage this event as an opportunity for exec introductions or quick alignment note—”Hey, saw you joined the project”. 7. Support the Above-the-Line (ATL) Met an exec early? Keep them looped into POC updates, key milestones, or call takeaways. When we give regular status updates, it builds credibility and keeps momentum - as execs don't join every call, and appreciate the visibility. 8. Never Underestimate Below-the-Line (BTL) Decision-making today is flatter; end-users/junior stakeholders are increasingly influential. I’ve lost count on how many times AEs (our BTL buyers) were make or break in our deals. Give them genuine attention. Don’t underestimate any buyer. 9. Late-Stage Exec Reinforcement If a deal stalls, a concise, confident, personal email from me as CEO resets urgency. The message isn't pushy; it reinforces our shared vision, driving commitment. —— Multithreading isn’t a tactic. It’s insurance. A deal defense system. Built thread by thread, stakeholder by stakeholder. So when things break, and they will - You’re not the only one left to save it. P.S. The Deal Room we used to multithread is Aligned. It's free to try: https://lnkd.in/dYksGnfb

This quote got me thinking. Early in my career, I struggled with how people showed up. I was often called too intense, I was often perceived as overwhelming, but the truth of it is I SHOWED UP! I was engaged, I was committed, and I wanted to make an impact. Not knowing why there was such a difference between how I showed up and others, I learned … that ONLY 31% of employees are enthusiastic and energized by their work? Imagine that almost 70% of the people in your team are there because they just have to 🫣 I honestly can't imagine that, which is why I implemented some solutions in my teams, most of it worked, some of it I’m still testing & trying … Here are some things I did: 👉 Trust & Empower: I involve my team in decision-making processes and push decisions to them when possible. This fosters a sense of ownership and responsibility. 👉 Celebrate Feedback: I create an environment where feedback is frequent and constructive. It encourages continuous learning and growth. 👉 Connect 'Why' to Vision: I share a compelling vision to motivate team members and clearly explain why their contributions matter. 👉 Offer Development: I signal my commitment to personal growth with training and development opportunities. It sparks motivation and increases loyalty. 👉 Recognize & Praise: I acknowledge achievements and make saying ‘thank you’ my default. A little recognition goes a long way to boost morale and motivation. 👉 Promote Diversity: I embrace diverse perspectives and backgrounds to enrich the work environment, prompt healthy debate, and drive innovation. 👉 Encourage Collaboration: I encourage teamwork on projects. This builds a sense of community and belonging while also accelerating learning 👉 Challenge Comfort Zones: I push and encourage team members to expand their skills and what they think is possible. It promotes growth and enthusiasm. 👉 Cultivate Inclusivity: I ensure all voices are heard. For example, I make sure extroverts don't steal the show and create the space needed for quieter team members to speak. Be the leader that serves, empowers and inspires. And all will go just fine 🙌 #EmployeeEngagement #TeamMotivation #WorkCulture

Great decision-making is where efficiency meets inclusion. When I work with clients, I emphasize that true leadership goes beyond simply making decisions—it’s about making the right decisions in the right way. This requires a delicate balance between inclusion and efficiency, two forces that, when harmonized, create a powerful synergy. I’ve captured this in the matrix, which I use as a tool to help leaders reflect on their approach: 1️⃣ The Soloist This is a leader who operates in isolation, relying heavily on their own judgment. While this can sometimes lead to quick decisions, it often misses the mark because it lacks the richness of input that diverse perspectives provide. The Soloist may find themselves struggling with blind spots or overlooking critical factors that others might have caught. 2️⃣ The Commander Such leaders focus on efficiency, sometimes to the detriment of inclusion. This leader makes swift, decisive moves, which can be effective in certain situations but often leads to disengagement within the team. Without a sense of ownership or shared vision, the decisions of a Commander might falter in execution or lead to resistance. 3️⃣ The Consensus-Seeker It represents a leadership style that values inclusion, perhaps to the point of over-collaboration. While this approach ensures that all voices are heard, it can lead to decision paralysis, where the quest for consensus slows down the process and results in diluted outcomes. The challenge for the Consensus-Seeker is to find a way to be inclusive without sacrificing decisiveness. 4️⃣ The Collaborative Leader It is the gold standard—someone who excels at both including diverse perspectives and driving efficient, effective decisions. This leader knows that inclusion is not a box to be ticked, but a dynamic process that fuels creativity and innovation. By creating psychological safety and encouraging diverse viewpoints, the Collaborative Leader harnesses the full potential of their team, leading to decisions that are not only sound but also have strong buy-in and are well-executed. 🔎 Why does this matter? Because the success of a leader is not just measured by the decisions they make, but by HOW those decisions are made and implemented. A leader who can navigate the complex terrain of inclusion and efficiency will not only achieve better outcomes but will also cultivate a more engaged, innovative, and resilient team. 👉 👩💻 If you’re ready to explore how you can enhance your decision-making approach in your company and move towards a more inclusive and efficient leadership, let’s connect. Together, we can unlock the full potential of your leadership journey.

𝐒𝐭𝐚𝐤𝐞𝐡𝐨𝐥𝐝𝐞𝐫 𝐄𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭: 𝐌𝐞𝐞𝐭 𝐓𝐡𝐞𝐦 𝐖𝐡𝐞𝐫𝐞 𝐓𝐡𝐞𝐲 𝐀𝐫𝐞 Enterprise Architecture abhors a vacuum—it thrives on stakeholder engagement. Often, architects jump into collaboration without first assessing one critical factor: • 𝐖𝐡𝐚𝐭 𝐝𝐨 𝐬𝐭𝐚𝐤𝐞𝐡𝐨𝐥𝐝𝐞𝐫𝐬 𝐤𝐧𝐨𝐰, 𝐚𝐧𝐝 𝐛𝐞𝐥𝐢𝐞𝐯𝐞, 𝐚𝐛𝐨𝐮𝐭 𝐄𝐀? Before strategy, frameworks, or roadmaps, 𝐮𝐧𝐝𝐞��𝐬𝐭𝐚𝐧𝐝 𝐭𝐡𝐞𝐢𝐫 𝐚𝐰𝐚𝐫𝐞𝐧𝐞𝐬𝐬, 𝐩𝐞𝐫𝐜𝐞𝐩𝐭𝐢𝐨𝐧𝐬 and 𝐞𝐱𝐩𝐞𝐜𝐭𝐚𝐭𝐢𝐨𝐧𝐬. This will shape how you approach, gain buy-in, and drive outcomes. Here are 𝐭𝐡𝐫𝐞𝐞 𝐞𝐬𝐬𝐞𝐧𝐭𝐢𝐚𝐥 𝐦𝐨𝐯𝐞𝐬 for aligning EA with stakeholders: 𝟏 | 𝐆𝐚𝐮𝐠𝐞 𝐄𝐀 𝐀𝐰𝐚𝐫𝐞𝐧𝐞𝐬𝐬 𝐁𝐞𝐟𝐨𝐫𝐞 𝐄𝐧𝐠𝐚𝐠𝐢𝐧𝐠 EA means different things to people, how can you align? Approach: * 𝐀𝐬𝐬𝐞𝐬𝐬 𝐞𝐱𝐢𝐬𝐭𝐢𝐧𝐠 𝐤𝐧𝐨𝐰𝐥𝐞𝐝𝐠𝐞. What do leaders think EA does? What experiences shape their view? * 𝐏𝐨𝐬𝐢𝐭𝐢𝐨𝐧 𝐄𝐀 𝐢𝐧 𝐭𝐡𝐞𝐢𝐫 𝐥𝐚𝐧𝐠𝐮𝐚𝐠𝐞. If a product saw EA as 'overhead,’ shift the conversation to ‘rapid decision-making.’ * 𝐓𝐚𝐢𝐥𝐨𝐫 𝐞𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭 𝐛𝐲 𝐚𝐮𝐝𝐢𝐞𝐧𝐜𝐞. Finance, operations, and IT leaders have different concerns. Meet them on their terms. 👉 𝐎𝐮𝐭𝐜𝐨𝐦𝐞: When you shape EA’s role based on their reality, it becomes relevant, not theoretical. 𝟐 | 𝐀𝐥𝐢𝐠𝐧 𝐄𝐀 𝐭𝐨 𝐒𝐭𝐚𝐤𝐞𝐡𝐨𝐥𝐝𝐞𝐫 𝐏𝐫𝐢𝐨𝐫𝐢𝐭𝐢𝐞𝐬 EA isn’t all architecture, it’s solving business problems. Approach: * 𝐒𝐭𝐚𝐫𝐭 𝐰𝐢𝐭𝐡 𝐊𝐏𝐈𝐬. Growth? Efficiency? Risk? Align EA contributions to what leadership interests. * 𝐂𝐨𝐧𝐧𝐞𝐜𝐭 𝐭𝐞𝐜𝐡𝐧𝐨𝐥𝐨𝐠𝐲 𝐭𝐨 𝐢𝐦𝐩𝐚𝐜𝐭. Show architecture driving go-to-market, savings, or agility—over compliance. * 𝐀𝐧𝐭𝐢𝐜𝐢𝐩𝐚𝐭𝐞/𝐫𝐞𝐦𝐨𝐯𝐞 𝐫𝐨𝐚𝐝𝐛𝐥𝐨𝐜𝐤𝐬. If EA was a bottleneck, demonstrate accelerated decision-making instead. 👉 𝐎𝐮𝐭𝐜𝐨𝐦𝐞: EA is a strategic enabler, not afterthought. 𝟑 | 𝐁𝐮𝐢𝐥𝐝 𝐄𝐀 𝐢𝐧𝐭𝐨 𝐭𝐡𝐞 𝐁𝐮𝐬𝐢𝐧𝐞𝐬𝐬 𝐂𝐨𝐧𝐯𝐞𝐫𝐬𝐚𝐭𝐢𝐨𝐧 EA works best in collaboration, not isolation. Approach: * 𝐄𝐦𝐛𝐞𝐝 𝐚𝐫𝐜𝐡𝐢𝐭𝐞𝐜𝐭𝐬 𝐢𝐧𝐭𝐨 𝐛𝐮𝐬𝐢𝐧𝐞𝐬𝐬 𝐝𝐢𝐬𝐜𝐮𝐬𝐬𝐢𝐨𝐧𝐬. Decision-making improves when EA is a proactive presence. * 𝐒𝐡𝐢𝐟𝐭 𝐟𝐫𝐨𝐦 ‘𝐩𝐫𝐞𝐬𝐞𝐧𝐭𝐢𝐧𝐠 𝐄𝐀’ 𝐭𝐨 ‘𝐜𝐨-𝐜𝐫𝐞𝐚𝐭𝐢𝐧𝐠 𝐬𝐨𝐥𝐮𝐭𝐢𝐨𝐧𝐬.’ Stakeholders engage when architecture is a tool for their success. * 𝐂𝐨𝐧𝐭𝐢𝐧𝐮𝐨𝐮𝐬 𝐞𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭, 𝐧𝐨𝐭 𝐨𝐧𝐞-𝐨𝐟𝐟. EA isn’t a pitch—it’s a dialog evolving with business. 👉 𝐎𝐮𝐭𝐜𝐨𝐦𝐞: EA shaping decisions early rather than reacting later. 𝐓𝐚𝐤𝐞𝐚𝐰𝐚𝐲 𝐒𝐭𝐚𝐤𝐞𝐡𝐨𝐥𝐝𝐞𝐫 𝐞𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭 𝐬𝐭𝐚𝐫𝐭𝐬 𝐰𝐢𝐭𝐡 𝐮𝐧𝐝𝐞𝐫𝐬𝐭𝐚𝐧𝐝𝐢𝐧𝐠. Before pushing frameworks or models, assess 𝐰𝐡𝐚𝐭 𝐄𝐀 𝐦𝐞𝐚𝐧𝐬 𝐭𝐨𝐝𝐚𝐲—and how to reshape that narrative to unlock its full potential. How do align EA stakeholders? Let’s discuss.👇 --- ➕ 𝐅𝐨𝐥𝐥𝐨𝐰 Kevin Donovan 🔔    👍 Like | ♻️ Repost | 💬 Comment    🚀 𝐉𝐨𝐢𝐧 𝐀𝐫𝐜𝐡𝐢𝐭𝐞𝐜𝐭𝐬’ 𝐇𝐮𝐛 👉 https://lnkd.in/dgmQqfu2

Navigating Team Conflicts In team dynamics, some level of conflict is inevitable—even healthy. However, understanding the nature of the conflict can help leaders manage and resolve it more effectively. Here are four common conflict patterns and strategies for handling them: 1. The Solo Dissenter This conflict arises when one individual disagrees with the rest of the team. Whether due to personal differences or a challenge to the status quo, isolating or scapegoating this person is counterproductive. Instead, leaders should engage in one-on-one conversations to better understand their perspective and address any underlying concerns. Open communication can transform a dissenter into a valuable source of alternative viewpoints and broader system awareness. 2. The Boxing Match This frequent form of conflict involves a disagreement between two team members. If the issue stems from a personal relationship, external coaching may be helpful. However, if it’s task-related, the disagreement may benefit the team by introducing diverse ideas—provided the discussion remains civil. Leaders should avoid intervening prematurely, as genuine task-based disagreements often lead to more innovative solutions. 3. Warring Factions When two subgroups within the team oppose each other, an "us versus them" mentality can develop. This type of conflict is more complex, and solutions like voting or majority rule rarely resolve the issue. Leaders should introduce new options or third-way alternatives, encouraging both sides to broaden their thinking and find a compromise that addresses the core needs of both groups. 4. The Blame Game This challenging conflict involves the entire team, often triggered by poor performance. Assigning blame worsens the situation and creates more division. A more effective approach is to refocus the team on collective goals and explore strategies for improvement. Shifting the conversation from blame to team purpose and collective problem-solving can unite the group around a shared vision. By recognizing these conflict patterns and applying the right strategies, leaders can guide their teams through disagreements, fostering a more cohesive and productive environment.

Forget top-down mandates. Real business agility comes from unleashing the innovators within your organization. Over the years at Make, we have spent a lot of time with our customers. Many of them disrupting their industry with new digital first business models. In these conversations, we consistently come across a certain mindset in people using our technology. They are re-thinking how to operate, re-imagining their business. These innovators are the ones driving real change, enabling businesses to stay nimble and agile. Those people are the ones making the difference, empowering them is the key to achieving business agility. So today, let me share with you a recipe that includes what we believe are the key ingredients to unlock this potential in your organization. First, there is the WILL. It’s the drive to innovate. This one is about the mindset. It’s the belief that they can solve and overcome any challenge. Fundamentally it’s their urge to discover, to persevere and to make breakthroughs. And you can impact this by inspiring them. By celebrating those who drive change. By showcasing where transformative solutions like visual automation, AI agents or no-code tools can be used to overcome day-to-day business challenges. It’s about inspiring people through use cases and success stories - to motivate people to achieve more of their own potential. Second, there is the SKILL. People’s ability to drive innovation. Whether people have a highly technical background or are self-taught doesn’t matter. It’s about fostering a culture of continuous learning and adoption of new technology. It’s about allowing your people to spend time on acquiring new skills to drive change, and to reinforce it with supporting these learning opportunities. And third, it’s about your business ENVIRONMENT. The organization around the individual, strengthening the innovators. The right environment is about promoting a culture of innovation, experimentation. Empower individuals. Let them fail fast and iterate. Allow them to challenge the status quo and embrace change. If you bring those ingredients together, you are creating a sweet spot. You are setting yourself up for making business agility a reality.  So, don’t wait for innovation to find you. Start to transform your business by impacting those three aspects for the innovators in your team. What steps are you taking to foster innovation in your company? #businessagility #nocode #automation 

🔥 Scrum Masters: The Leadership Gap That No One Talks About Scrum Masters feel stuck. But is it really leadership holding you back—or your missing skills no one told you about? 🚨 We talk about leadership debt in organizations, but what about the leadership debt within Scrum Masters? Scrum Masters struggle to: ❌ Identify and influence the right stakeholders. ❌ Align Agile expectations with leadership realities. ❌ Coach beyond the team and impact the system. Yet, the most common complaint? "I don’t have leadership support." But here’s the hard truth: Have you earned their trust? Leadership Debt: Not Just a Management Problem 📌 Leaders want agility but reinforce control. 📌 They demand outcomes but incentivize outputs. 📌 They push transformation but resist changing themselves. 💬 And Scrum Masters? Too often, they focus on protecting the team instead of transforming the system. Agility doesn’t fail because leadership doesn’t “buy-in.” It fails because leadership isn’t aligned. Scrum Masters: Are You Managing Stakeholders or Avoiding Them? ✅ Are you speaking the language of business? ✅ Are you educating leadership on agility—or just blaming them? ✅ Are you managing up—or just coaching down? 👉 Scrum Masters who avoid stakeholder management aren’t enabling agility. They’re just creating high-performing teams trapped in low-performing organizations. Fix the Debt. Close the Gap. Drive Real Change- You weren’t hired to protect the team from leadership. You were hired to reshape the system that holds them back. ✅ Measure What Matters → EBM, not vanity Agile metrics. ✅ Educate Upwards → Leadership agility is as critical as team agility. ✅ Call Out the Disconnects → The system needs fixing, not just the team. ✅ Make Leadership Part of the Change → Transformation isn’t just for teams. 🚨 If you don’t step up as a leader, someone else will define agility for you. 💬 Scrum Masters—what’s been your biggest challenge in working with leadership? #ScrumMaster #ManagementandLeadership #scrum #ReTHINKscrum #agile #ReTHINKagile

Leading in the digital age is not just about mastering technology; it’s about mastering change. As someone guiding an organization through rapid shifts, I’ve learned that digital transformation is, at its core, about people. I used to think building digital capabilities meant investing in the latest systems, but I quickly realized that the most critical investment is in developing a culture of adaptability. Digital IQ starts at the top. If I don’t immerse myself in emerging tech, competition and customer trends, how can I expect my team to embrace them? Instead of attempting to overhaul the entire company, I started with digital-ready teams, those eager to experiment, collaborate, and drive results. Their success became proof of concept, showing the rest of the organization what’s possible. Change requires persuasion, not mandates. A digital leader must inspire transformation at every level, ensuring that innovation, agility and collaboration become part of the mindset. Transformation is sustained when people evolve alongside technology. #digitaltransformation #organizationalchange

When traditional leadership approaches hit the wall of 21st century change, many organizations stagnate, with innovation grinding to a halt and talent heading for the exits. Fast forward to transformative leaders — their organizations thrive amid disruption, turning unprecedented change into competitive advantage while competitors struggle to keep pace. The difference? These leaders abandoned the outdated "know-it-all" paradigm for a "learn-it-all" mindset — treating adaptation not as an occasional necessity but as their core leadership function. The Lesson? Leadership is no longer about maintaining the status quo—it's about continuous transformation and navigating complexity with agility. Common Leadership Adaptation Pitfalls: 📍 Cognitive Rigidity — Clinging to past success strategies instead of embracing new paradigms. 📍 Fear-Based Decision Making — Creating defensive cultures that suppress innovation. 📍 Resistance to Technology — Dismissing disruptive technologies instead of leveraging them. 📍 Hierarchical Thinking — Maintaining control rather than empowering collaborative innovation. 📍 Status Quo Comfort — Avoiding necessary changes until crisis forces action. ✅ How to Develop Adaptive Leadership Capacity: 📍 Intellectual Humility — Acknowledge knowledge gaps and actively seek diverse perspectives. 📍 Technological Fluency — Develop deep understanding of AI, automation, and digital transformation. 📍 Intrapreneurial Mindsets — Create safe spaces for calculated risk-taking and bottom-up innovation. 📍 Emotional Intelligence — Navigate complex human dynamics with empathy and self-awareness. 📍 Continuous Learning — Invest in personal and organizational growth as a strategic priority. Adaptation isn't a leadership challenge — it's the essence of modern leadership itself. 📩 Get practical leadership strategies every Sunday in my free newsletter: CATAPULT. 🧑💻 Want to become the best LEADERSHIP version of yourself in the next 30 days? Book a 1:1 Growth Strategy Call: https://lnkd.in/gVjPzbcU #Leadership #AdaptiveLeadership #FutureOfWork #ExecutiveCoaching #OrganizationalChange

Interview Conversation Role: RTE in #SAFe framework Topic: Conflict Management 👴 Interviewer: "Imagine the Product Manager and System Architect disagree over feature priorities, with the PM focusing on customer needs and the Architect concerned about tech debt. As the RTE, how would you handle this?" 🧑 Candidate: "I’d remind them to focus on the PI objectives and find a middle ground." 👴 Interviewer: "Say this disagreement is slowing decision-making, impacting team alignment, and morale is dipping. What specific actions would you take to mediate?" 🧑 Candidate: "I’d encourage both of them to think about the project’s overall goals." What a skilled Release Train Engineer should say: ------------------------------------------------------ In cases like this, it’s crucial to foster open, constructive discussions without losing sight of both customer value and technical stability. 🌟 I’d start by facilitating a conversation with the PM and Architect to unpack their priorities and establish a shared understanding. 📅 In a similar situation, I scheduled a conflict-resolution workshop with both roles, focusing on ‘value vs. sustainability’ using the Economic Framework. 🏹 We assessed the impact of each priority on the PI objectives, assigning weights based on business and architectural needs. The workshop helped clarify the ROI of tech improvements and immediate features, allowing them to make informed trade-offs. 🛠 To make it concrete, we identified one high-priority feature to advance and a critical refactor for the next PI. By reaching a balanced decision, we addressed urgent customer needs while setting a feasible path for addressing tech debt. 🚩 Impact: This approach helped restore team alignment, fostered trust between the PM and Architect, and improved the ART’s overall efficiency. ✍ As an RTE, my role is to mediate these discussions by grounding decisions in shared values and structured prioritization, ensuring both immediate and long-term value are achieved.