Effective Tech Project Management Techniques

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

🤔 Useful Questions For Stakeholder Interviews. With good questions to ask when interviewing stakeholders — to understand their needs, key goals, gather requirements and keep them on your side ↓ --- 🔶 1. Design For Listening, Not A Conversation One of the most impactful strategies that worked for me over the years is to design the entire conversation around listening to stakeholders, not speaking about them or even with them. And typically it all starts with only one single question: “Please guide me through the product and explain its key features.” There is no small talk, no introductory questions, no dancing around the topic, no deep-dive into my workflow. I merely explain that in the next 45 mins I'm trying to find severe problems that are worth solving, understand the context about these problems and project goals — and ask for a permission to record the screen for studying it later. This opens the conversation immediately — and then I pay attention to features highlighted, features skipped, and ask plenty of follow-up questions to understand the motivations and the goals that a stakeholder has. --- 🔹 2. My Stakeholder Interview Template Dear Ms. Krajewski, As a UX lead on the project, my team and I are currently in the process of discovery. As we start our work, we’d like to better understand your pain points, expectations and success criteria. 1. What’s the purpose of this project for you? [Interest, engagement] 2. Where does this project fit in your daily work? [Their perspective] 3. What’s the most important thing to get right? [Priorities] 4. How would you describe the target audience? [Their view] 5. If you could understand one thing about users, what would it be? 6. What important insights did you learn about users recently? 7. What does success look like for you and your team? [Metrics] 8. What challenges are top priorities for your team? [Pain points] 9. What’s the success criteria for the project? [Ideal outcome] 10. What constraints or frequent issues should we know about? [Risks] 11. What is your ideal level of engagement for the project? [Max] 12. Anything else you think nobody said to me yet? [Hidden troubles] 13. Is there anybody else who you think I should speak to? [Leads] --- ♦️ 3. The Real Insights Aren’t In These Answers I absolutely love Anton Sten's point that the real insights usually won’t live in answers to all these questions. They live in the follow-up questions and answers — and often in a way of how a stakeholder responds, what they leave out, and what they overstate or repeat a number of times. As designers, too often we see our clients and stakeholders as adversaries. Yet we rarely know how our stakeholders work, so we shouldn’t expect them to understand what we need either. The crucial part is to be genuinely curious, positive and engaged to elicit useful insights. “The other person will only stay engaged as long as you do, and they can sense when you check out.” Useful resources ↓

Do you also feel your roadmap planning is a counterproductive waste of time? Change that to a productive exercise that will set your success 12 months ahead with the following 10 pieces of advice: 1) Start too early The earlier you start, the more time you have to align with stakeholders and refine priorities. October might feel early, but having a draft ready before the year ends allows for feedback and stressless adjustments. 2) Clarify goals and strategy A roadmap without a clear purpose is just a wish list. Tie it to business goals, customer needs, and your overarching strategy. This gives your roadmap direction and credibility. 3) Allow everyone to chip in Your roadmap will be stronger if it includes diverse perspectives. Devs will ask for essential technical investments, sales understand customer pain points, and support hears complaints daily. Use their input to ensure your roadmap addresses real needs. 4) Double-check with legal Don't overlook this! Legal compliance can make or break your plans, especially in industries like fintech, healthcare, or data-heavy products. A quick legal review now can save you from costly setbacks later. 5) Organize a brainstorming workshop Bring stakeholders together for a focused brainstorming session. Use sticky notes, whiteboards, or virtual tools to encourage creativity. Workshops help uncover ideas you might not have considered and build alignment early. 6) Put an effort estimate on the most promising items Prioritization isn't just about impact; effort matters too. Collaborate with your devs to estimate the time and resources needed for each initiative. This helps balance quick wins with high-impact projects and helps choose the actual roadmap items during prioritization. 7) Ask your designer to put some quick visuals for the selected initiatives A picture is worth a thousand words. Having simple visuals for key roadmap items can help stakeholders grasp the vision faster and ensure everyone is aligned on what success looks like. 8) Organize work by quarters, not months, and especially not sprints Quarterly planning gives enough flexibility to adapt while still maintaining structure. Monthly plans can feel too rigid, and sprint-level roadmaps are operational, not strategic. Keep your roadmap focused on the big picture. 9) Leave room to breathe Don't overload the roadmap. Unexpected challenges will arise, and new opportunities will pop up. Leaving 20-30% of capacity unplanned ensures you can adapt without derailing the entire roadmap. 10) Be careful with your comms Communicate clearly that the roadmap is a direction, not a commitment. You’re agile, not waterfall. Keep flexibility baked into your messaging to avoid frustration later. So, does your roadmap planning feel like it produces something meaningful? Let me know in the comments! #productmanagement #productmanager #roadmap P.S. If you liked this read, be sure to catch more with my free newsletter. Subscribe at: www. drbartpm. com :)

People often ask how we manage complex projects as a team of 100 people in 35 countries, and since I'm currently revamping our documentation on this subject, that info is top of mind. Here's 29 pages of content condensed into 1 LI post for a sneak peek into our DO (Doist Objectives) System 👀 It starts with our annual roadmap, which the leadership team builds in Q4 of the prior year. To execute that plan, we organize our work into four areas of priority (Strategic Priorities, aka SPs), each running multiple initiatives simultaneously in quarterly "cycles", and overseen by a Directly Responsible Doister (DRD): • Brand (DRD: CMO): Marketing campaigns, brand evolution, growth initiatives • Product (DRD: Head of Product): New features, user experience improvements, product strategy • Engineering (DRD: CTO): Platform stability, performance optimization, technical infrastructure • Doist (DRD: 🙋🏻♂️): Internal tools, company operations, team effectiveness Planning kicks off four weeks before each quarter when the CXOs provide the DRDs with general guidance and goals. We respond by proposing general plans for DOs (Doist Objectives; projects/initiatives) in line with our annual roadmap. Two weeks before the new quarter begins, the DOs are agreed upon and the team Heads assign team members to cross-functional "Squads" as "Squad Leaders" and "Squad Members". **See photos below to illustrate the squad infrastructure. Each SP typically runs 2-5 major DOs per quarter, meaning we're executing 12-16 significant projects at any time. The quarter begins with a two-week "Foundation Phase", where squads: • Deep dive into the challenges and opportunities their squad faces • Conduct user research • Create comprehensive specs detailing their proposed solutions • Align on execution approach • This phase ensures we have the space to avoid diving too deep into the upcoming cycle while working on the current cycle From there, squads maintain momentum for the following 10 weeks in the "Execution Phase" through established rituals: • Weekly "snippets" in Twist for progress updates and transparency (our version of an async standup meeting) • Bi-weekly recorded demos to showcase work in-depth • Monthly retrospectives on squad health for continuous improvement • Monthly companywide updates on each strategic priority's DOs • Monthly strategic reviews/adjustments by the leadership team • Expectation = each squad should "ship" something weekly Of course, we manage most of this using Twist for communication and Todoist for project management, but more so than the tools, this system works for us because we emphasize clear ownership/autonomy, transparent communication, and just enough processes to stay coordinated without slowing the team down. That was a lot to digest, but I hope it's helpful. Let me know if I can expand on anything or answer any other questions 👇

How to Extract Information from Stakeholders 🎯 Getting accurate information from stakeholders can make or break your financial planning process. Each stakeholder speaks a completely different language and focuses on totally different metrics. The secret? Knowing exactly what to ask and how to ask it. ➡️ CEO CONVERSATIONS CEOs think big picture, so focus on strategic direction and vision. You want company strategies for next quarter, budget allocation expectations, risk tolerance levels, and market positioning goals. The money question: "What are the top 3 strategic priorities that should drive our Q4 planning?" ➡️ HEAD OF SALES Sales leaders live and breathe pipeline projections and customer acquisition costs. Get those sales pipeline projections, customer acquisition costs, territory performance data, and resource requirements for targets. My go-to approach: "What's the realistic revenue projection for Q4, and what support do you need?" ➡️ MARKETING DIRECTOR Marketing lives for lead generation and brand metrics. You need campaign performance metrics, lead generation forecasts, brand awareness initiatives, and marketing budget requirements. Hit them with: "How many qualified leads can marketing deliver to support the sales targets?" ➡️ HR MANAGER HR thinks talent and workforce planning 24/7. Grab headcount projections, recruitment timelines, employee retention rates, and training and development needs. Start here: "What's our hiring timeline to support the growth plan, and any retention concerns?" ➡️ ENGINEERING LEAD Engineering leaders obsess over product development roadmaps. Collect that product development roadmap, technical debt priorities, infrastructure requirements, and team capacity information. The must-ask question: "What features can be delivered by Q4, and what technical investments are critical?" ➡️ ACCOUNTING MANAGER Accounting thinks financial health and compliance every single day. Get cash flow projections, budget variance analysis, financial compliance requirements, and cost optimization opportunities. The essential question: "What's our cash flow outlook, and are there any financial constraints for our growth plans?" ➡️ UNIVERSAL BEST PRACTICES These six practices work with EVERY stakeholder: Be Specific: Ask for concrete numbers, dates, and measurable outcomes rather than vague commitments. Respect Their Time: Come prepared with focused questions and provide context upfront. Speak Their Language: Use terminology and metrics relevant to their department and priorities. Validate Understanding: Repeat back key points to ensure alignment and avoid miscommunication. Follow Up: Send summaries of key decisions and next steps within 24 hours. Close the Loop: Show how their input directly influences decisions and outcomes. === What's your approach to stakeholder communication? Share your best practices in the comments below 👇

Want to become a strong Technical Project Manager in RPA and AI? Let me share 3 things based on my experience. 1-Get your hands dirty with real bots Managing automation projects is not just about timelines and stakeholders ,it’s about understanding the process logic. If you’ve never designed or configured a bot yourself (even a small one), you’re missing a big piece of the picture. Once you build and break a few workflows in UiPath or Automation Anywhere, you start thinking differently , like an automation architect and not just a project lead. 2-Use proven delivery frameworks and templates Every RPA project follows similar stages ,discovery, design, development, UAT, deployment, and support. Yet, many teams still start from scratch every time. Having standard templates (PDD, SDD, test cases, hypercare checklist) and a delivery playbook can cut your project cycle time by 30–40%. 3-Leverage AI and analytics to manage smarter AI can now help you manage automation projects more efficiently , not just technically, but operationally. Use AI to write better documentation. Tools like ChatGPT or Copilot can help you draft PDDs, summarize process maps, or create test case outlines from your discovery notes. Analyze logs automatically. Instead of manually reviewing Orchestrator logs, use AI-powered log analyzers (like UiPath Insights, Power BI with AI visuals, or ElasticSearch dashboards) to detect recurring exceptions, long-running jobs, or unattended downtime. Automate your project tracking. Use AI to summarize daily stand-ups, extract action items, or even update Jira or Azure DevOps tasks automatically. Measure business impact continuously. Combine RPA data (execution time, volume, error rate) with business metrics (cost saved, hours returned) to build ROI dashboards that update weekly. What else you can add? Sarah Ghanem

Interview Conversation Role: RTE Topic: Leveraging Jira Align 👨💼 Interviewer: "As an RTE, how do you use Jira Align to manage dependencies across teams in an Agile Release Train?" 🧑 Candidate: "Jira Align helps track tasks and dependencies between teams." 👨💼 Interviewer: "Imagine Team A is blocked because Team B’s feature isn’t ready, and this delay could impact the PI objectives. How would you use Jira Align to resolve and track such dependencies?" 🧑 Candidate: "I’d ask the teams to resolve it in their sync-up meetings." What a skilled RTE should have answered: ---------------------------------------------- 💡 Jira Align is a powerful tool for visualizing and proactively managing dependencies across teams and ARTs. Here’s how I’d approach the situation: ✍ 1. Proactive Identification: During PI Planning, I’d ensure teams clearly log dependencies in Jira Align’s Dependency Map. This allows us to identify blockers early and assess their impact on delivery timelines. ✍ 2. Continuous Tracking: I’d regularly review the Program Board in Jira Align to monitor the progress of dependencies. For example, if Team A relies on Team B’s feature, Jira Align enables both teams to align their schedules and track progress through automated updates. ✍ 3. Issue Resolution: In case of a delay, I’d leverage Jira Align to trigger an escalation. The tool’s centralized data makes it easy to identify priority dependencies, communicate risks to stakeholders, and propose adjustments to mitigate the impact on PI objectives. ✍ Example in Action: In a previous ART, a critical dependency delay between two teams risked derailing a feature release. By using Jira Align’s Portfolio Room, we aligned stakeholders, reprioritized deliverables, and reallocated capacity to keep the train on track. ✍ Impact: Jira Align ensures transparency, alignment, and faster conflict resolution, ultimately enabling ARTs to deliver value predictably. ✨ Key Takeaway: Managing dependencies is about more than meetings—it's about leveraging tools like Jira Align to proactively track, manage, and resolve risks. Transparency is the backbone of seamless execution. Join community for deeper insights: Link in the comment below #SAFe #ReleaseTrainEngineer #JiraAlign #AgileTransformation #DependencyManagement

🎄 Day 14 of the #AdventOfOR 2025! The single biggest mistake in optimization projects? Engaging stakeholders once. Most teams nail the "Early" part (kickoff, problem framing, initial requirements). But then they disappear into complex code. Weeks later, they return with the perfect solution... but trust has eroded. Engagement isn't a single event. It's a continuous cadence: Early AND Often. Why is this continuous interaction essential? 🤝 Maintains trust: Consistent updates prevent the project from becoming a black box. 🎯 Ensures relevance: Requirements shift; regular check-ins keep your model aligned with business reality (just like we got new requirements on Day 12!). 🪡 Drives adoption: Stakeholders own the solution when they help build it. The secret to making it work is lowering the cost of understanding the model's progress. But you don't need to do heavy presentations; do easy, frequent demos with tools that help: 🔹 GAMS MIRO for interactive apps stakeholders can explore 🔹 Streamlit or Taipy for quick Python dashboards 🔹 Nextmv for comparing runs and sharing scenarios When showing progress becomes easy, you'll do it more often. When you do it more often, trust compounds. 🫵 Your turn: What's the single biggest piece of friction that currently stops you from sharing model progress (work-in-progress, not final results) with your stakeholders more often? (e.g., "It takes too long to clean the output," "We lack visualization tools," "I only share final numbers.")

$135 million lost for every $1 billion spent. Lack of clarity kills projects. 37% of projects fail due to poor communication and unclear requirements. Here's how to make clarity your secret weapon: ☑ 𝗗𝗲𝗳𝗶𝗻𝗲 𝗣𝗿𝗼𝗷𝗲𝗰𝘁 𝗢𝗯𝗷𝗲𝗰𝘁𝗶𝘃𝗲𝘀: Clearly state the overall goals and align them with organizational strategy. Don't leave desired outcomes and impacts unspecified. → Projects with clear goals are 2.8x more likely to succeed. ☑ 𝗜𝗱𝗲𝗻𝘁𝗶𝗳𝘆 𝗞𝗲𝘆 𝗦𝘁𝗮𝗸𝗲𝗵𝗼𝗹𝗱𝗲𝗿𝘀: List everyone involved or affected, and define roles, responsibilities, and interests. Don't overlook establishing a communication plan. → 57% report stakeholder misalignment. ☑ 𝗢𝘂𝘁𝗹𝗶𝗻𝗲 𝗣𝗿𝗼𝗷𝗲𝗰𝘁 𝗦𝗰𝗼𝗽𝗲: Define what's in-scope and out-of-scope, and identify key deliverables and milestones. Don't ignore alignment with stakeholder expectations. → 71% struggle with unclear scope. ☑ 𝗘𝘀𝘁𝗮𝗯𝗹𝗶𝘀𝗵 𝗣𝗿𝗼𝗷𝗲𝗰𝘁 𝗚𝗼𝘃𝗲𝗿𝗻𝗮𝗻𝗰𝗲: Set up a governance structure, specify decision-making processes, and identify key roles and responsibilities. Don't skip regular clarity check-ins. → 51% have regular clarity check-ins. ☑ 𝗗𝗲𝘃𝗲𝗹𝗼𝗽 𝗮 𝗥𝗶𝘀𝗸 𝗠𝗮𝗻𝗮𝗴𝗲𝗺𝗲𝗻𝘁 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝘆: Identify potential risks and challenges, assess likelihood and impact, and outline mitigation strategies. Don't neglect to maintain detailed documentation. → 89% of successful projects maintain detailed docs. ☑ 𝗖𝗿𝗲𝗮𝘁𝗲 𝗮 𝗛𝗶𝗴𝗵-𝗟𝗲𝘃𝗲𝗹 𝗧𝗶𝗺𝗲𝗹𝗶𝗻𝗲: Develop a timeline with key phases and milestones, and ensure it's realistic and achievable. Don't forget to align it with resource availability. → 86% implement milestone tracking. ☑ 𝗗𝗲𝗳𝗶𝗻𝗲 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲 𝗥𝗲𝗾𝘂𝗶𝗿𝗲𝗺𝗲𝗻𝘁𝘀: Identify necessary resources (people, tech, budget) and assess availability. Don't waste time reworking unclear tasks. → Teams waste 21.8% of their time reworking unclear tasks. Because at the end of the day: → Clarity isn’t just a nice-to-have. → It’s a must-have for project success. Why not make it your superpower? Choose clarity. Ensure success. Be the leader.