Balancing Multiple Projects at Once

How I Track 10+ Projects at Once as a Program Manager at Amazon It’s a question I get a lot: How do you stay on top of everything without letting something slip? Different teams. Different timelines. Different deliverables. And a lot of noise. Here’s how I keep it all moving…and still make it home for dinner: 1/ I use one central tracking system for everything ↳ One doc, one view. ↳ If it’s not in the tracker, it doesn’t exist. ↳ I update it daily and keep it brutally simple. 2/ I start every week with a 15-minute self check-in ↳ What’s behind? What’s on track? What’s at risk? ↳ If I don’t do this Monday morning, the week runs me instead of the other way around. 3/ I color-code by priority and risk ↳ Green means I don’t need to touch it. ↳ Yellow means it needs a check-in. ↳ Red means I need to escalate or unblock. 4/ I follow up with context, not just reminders ↳ “Just checking in” turns into “We need this by Friday to keep X on track.” ↳ People respond to clarity, not pressure. 5/ I keep a running weekly update for leadership ↳ 3 bullets: what moved, what’s stuck, and what I need help with. ↳ It keeps everyone informed without another meeting. Managing 10+ projects isn’t about multitasking. It’s about systems, focus, and momentum. You don’t need to know everything. You just need to know where to look…and what to move next. How do you track your priorities without getting overwhelmed?

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 👇

I’ve had to protect my team in the past, particularly when their time or focus was at risk. I’ve seen this happen at companies like Microsoft, Google, and Amazon, where mandates and initiatives would stack during the same timeframe. While each initiative alone might have been reasonable, together they overburdened the teams. Those compiled costs may be invisible to the folks driving the individual mandates. You may have seen teams get overwhelmed by a major release, a review cycle, and bi-annual business planning all at once. This type of time management stress is usually manageable, but there are times when teams can be stretched too thin and compromise morale and quality. When you witness this, I believe it’s crucial to step in. You will hear from your team and you need to be close enough to the issues to decide how to respond. This can be tricky for a leader: on one hand, you want to ensure your team can succeed; on the other, you’re part of the broader leadership and need to support the decisions being made. Sometimes, you have very little room to maneuver. In those cases, I find it most effective to have a private conversation with key decision-makers. Meeting behind closed doors allows you to present the reality of your team’s capacity without putting anyone on the spot. Armed with clear data or project plans, you can often negotiate more realistic timelines or priorities. Another common pressure is when stakeholders create frequent direction changes. Repeated shifts in goals or features will thrash your team and waste energy. This often reflects deeper issues with strategy, alignment, and communication. However, you may not have time for a complete overhaul of your planning processes, and you still need a way to prevent thrash. A short-term fix is to set firm near-term milestones or “freeze” dates, after which any changes must go through a formal triage process. This ensures that if changes are necessary, they follow a transparent, deliberate sequence rather than blindsiding. After the freeze, broader project changes can be considered. Ultimately, I see my responsibility as a leader as fostering an environment where my team can perform at a high level, stay motivated, and avoid burnout. Part of a leader's role is to protect their team’s capability and long-term health. There will always be sprints and times when you need to push, but you also need to consider the long view and put on the brakes when required. People who feel supported are more productive, more creative, and likely to stay engaged.

When I was 30, I was a savage. 16-hour days, constant hustle, and no vacations and I don’t regret it one bit. But, now at 45, as a founder and parent of 3, I’ve traded grind for intentionality. Here’s how I balance work and life without sacrificing either: == 1) Skip alcohol and THC. I used alcohol to blow off steam after long days. I thought I deserved it. Now, avoiding those crutches has transformed how I sleep, wake up, and show up for my kids. 2) Sleep is a superpower. I’m in bed around 9:30pm and wake up around 530am. Better recovery leads to thinking clearer, leading better, and showing up fully. 3) Carve out personal space. I go for a 30-60 min run first thing. My biggest breakthrough thoughts come during my morning run. 4) Involve the kids. I used to compartmentalize “work” and “family.” Now, I bring my kids into what I’m doing whenever possible. Whether it’s having them sit on my lap during a podcast or showing them what Dad’s working on, it’s a way to connect and bring them into my world. 5) Outsource house chores. Mowing the lawn? Deep cleaning the house? This is like stepping over dollars to pick up dimes. I’m sure you enjoy it to a degree, but free yourself for what truly matters: family, health, and the work that moves the needle. 6) Use time blocks. I timebox everything—whether it’s deep work, family time, or even downtime. Setting alarms and blocking time on my calendar keeps me focused and prevents the day from running away from me. 7) Be ruthless about what matters. At 30, everything felt urgent. At 45, I know the difference between important and noise. For me, balance doesn’t mean doing everything—it means doing the right things. == The key is this: Seasons of life change. When you’re young, embrace the grind. Push your limits. Be unbalanced. But as life evolves, so should your approach. This is what works for me—what would you add to the list?

In the fast-paced world of management, where decisions are made in the blink of an eye and priorities shift constantly, asking for what you need can sometimes feel daunting. Recently, I found myself in a situation that many managers and aspiring leaders might find familiar. I had to follow up with a colleague about a project. This person is incredibly busy, juggling multiple responsibilities, and I hesitated to reach out. However, I needed to confirm details to plan my work for the upcoming months effectively. As managers, we often feel the pressure to have all the answers. There's an unspoken expectation that we should be able to figure things out on our own. This mindset can make asking for clarity seem like a sign of weakness. But let's flip the script: asking for clarity is not a weakness; it's a strength. It's a tool for efficiency and effectiveness. Why does it matter? - Efficiency Boost: When you ask for clarity, you streamline processes. You ensure that everyone is on the same page, reducing the chances of miscommunication and rework. - Time Management: By seeking clarity, you save time—not just for yourself but for your entire team. It prevents unnecessary back-and-forth and allows you to focus on what truly matters. - Enhanced Team Dynamics: Clarity fosters better interaction within teams. When everyone understands their roles and responsibilities, collaboration becomes seamless. It's important to acknowledge that some might view the act of asking for clarity as a weakness. However, the ability to seek clarity is a hallmark of effective leadership. It demonstrates a commitment to understanding and improving processes, which ultimately benefits the entire organization. - Be Specific: When asking for clarity, be specific about what you need. This helps the other person provide the information you require without unnecessary back-and-forth. - Provide Context: Explain why you need the information. This not only helps the other person understand your request but also highlights the importance of their input. - Encourage Open Dialogue: Foster an environment where team members feel comfortable asking questions. This creates a culture of transparency and continuous improvement. To become a more effective manager, embrace the power of clarity. Here are some steps you can take: - Model the Behavior: Demonstrate the importance of clarity by consistently seeking it yourself. Your team will follow your lead. - Encourage Questions: Create a safe space for your team to ask questions. This not only improves understanding but also fosters innovation. - Provide Feedback:When team members seek clarity, provide constructive feedback. This reinforces the value of their efforts and encourages continuous learning. In the world of management, clarity is a powerful ally. It enhances efficiency, improves team dynamics, and ultimately leads to better outcomes.

One of the hardest balances to master as a leader is staying informed about your team’s work without crossing the line into micromanaging them. You want to support them, remove roadblocks, and guide outcomes without making them feel like you’re hovering. Here’s a framework I’ve found effective for maintaining that balance: 1. Set the Tone Early Make it clear that your intent is to support, not control. For example: “We’ll need regular updates to discuss progress and so I can effectively champion this work in other forums. My goal is to ensure you have what you need, to help where it’s most valuable, and help others see the value you’re delivering.” 2. Create a Cadence of Check-Ins Establish structured moments for updates to avoid constant interruptions. Weekly or biweekly check-ins with a clear agenda help: • Progress: What’s done? • Challenges: What’s blocking progress? • Next Steps: What’s coming up? This predictability builds trust while keeping everyone aligned. 3. Ask High-Leverage Questions Stay focused on outcomes by asking strategic questions like: • “What’s the biggest risk right now?” • “What decisions need my input?” • “What’s working that we can replicate?” This approach keeps the conversation productive and empowering. 4. Define Metrics and Milestones Collaborate with your team to define success metrics and use shared dashboards to track progress. This allows you to stay updated without manual reporting or extra meetings. 5. Empower Ownership Show your trust by encouraging problem-solving: “If you run into an issue, let me know your proposed solutions, and we’ll work through it together.” When the team owns their work, they’ll take greater pride in the results. 6. Leverage Technology Use tools like Asana, Jira, or Trello to centralize updates. Shared project platforms give you visibility while letting your team focus on execution. 7. Solicit Feedback Ask your team: “Am I giving you enough space, or would you prefer more or less input from me?” This not only fosters trust but also helps you refine your approach as a leader. Final Thought: Growing up playing sports, none of my coaches ever suited up and got in the game with the players on the field. As a leader, you should follow the same discipline. How do you stay informed without micromanaging? What would you add? #leadership #peoplemanagement #projectmanagement #leadershipdevelopment

As a CTO who has successfully scaled AI and tech products, I’ve refined productivity strategies that can transform your leadership workflow and enhance your team’s output. If you’re leading in the tech industry, and grappling with overwhelming demands, the 3 targeted tactics I’m about to share are tailored for the unique challenges you face. My guiding principle each week is the 'Rule of Three': identifying three top priorities that serve as my North Star. These aren't just scribbled in a planner but physically placed on my office wall, a constant visual reminder of my core focus. This practice not only keeps me centered amidst the whirlwind of daily tasks but also ensures that every action is a step toward our most critical goals. Sharing these priorities with my direct reports does more than foster transparency — it aligns our efforts, synchronizes our strides, and forms the bedrock of our collective pursuit. It's a simple yet profoundly effective strategy that has continually steered us toward meaningful progress and impactful results. Next, time blocking has been a critical strategy. Carving out dedicated blocks for deep work, meetings, and even unexpected tasks allows me to create a rhythm amidst the chaos. This isn't just about sticking to a schedule; it's about allocating mental space and ensuring that high-priority projects get the uninterrupted attention they deserve. I always check each Friday that my time blocked schedule appropriately reflects the work I need to accomplish for my top three priorities. Lastly, I leverage automation and delegation. By automating routine tasks and delegating effectively, I maintain focus on what truly requires my expertise. It's not just about offloading work; it's about empowering my team by entrusting them with responsibilities that aid their growth while freeing me to lead more effectively. A framework I really like using is the Eisenhower matrix around categorizing work based on its urgency and importance. I try and focus as much of my work as I can on the important and urgent tasks. Implementing these strategies hasn’t just boosted my personal productivity; it sets a precedent for the whole team. When leaders manage their time effectively, it cascades down, fostering a culture of efficiency and clarity. Remember, in the world of tech and AI, where the ground shifts daily, these strategies aren't just nice-to-have—they're essential for survival and success. If you're leading in this space and looking to refine your approach to productivity, let's connect and share insights that propel us forward! #techleadership #productivitytools #teamleader

Project Managers, unlock 3X efficiency: Delegation is key for Project Managers (and all leaders). It's more than just assigning tasks. It's about empowering team members and focusing on priorities. Done correctly, it enhances efficiency, leadership & project success. 🔥Michael Hyatt's 5 Levels of Delegation A blueprint for effective assignment. 1. Do Exactly What I Say Team member tests a feature exactly as you instructed. 2. Research and Report Back Member investigates potential software solutions. You decide the best fit. 3. Give Options, I Decide Team suggests project timelines, you finalize one. 4. Make Decision, Inform Me Lead developer picks a tool and then notifies you. 5. Make Decision, No Need to Report Experienced team member resolves minor project issues. No need to brief you. 🔥 Value/Alignment Matrix A guide for what to delegate. ➨ Take Back Tasks crucial to the project and align with your expertise. Ex: Outlining the project roadmap—only you can set it. ➨ Delegate Key tasks but they don't need your unique touch. Ex: Scheduling meetings—you don't have to arrange them. ➨ Keep Doing (for now) Tasks in your wheelhouse but not critical to the project. Mentor someone for future assignment. Ex: Checking project metrics—could a data analyst manage? ➨ Stop Doing Tasks that neither play to your strengths nor benefit the project much. Ex: Old-fashioned documentation—it's not adding value. Master the skill of delegation. Elevate your project leadership. Increase your efficiency. P.S. What's your go-to delegation method?

Leaders waste more energy on divided focus than any other activity. I learned this the hard way in the SEAL Teams. During a training evolution, I was juggling radio communications, coordinating multiple teams, and making split-second calls. And I wasn’t doing any of it well. My commanding officer pulled me aside: "Mac, you're everywhere and nowhere. Focus or you'll miss the critical moment." He was right. I was spread so thin I couldn't see the patterns emerging right in front of me. This isn't just a military problem. I see it daily with my executive clients: → Scanning emails during strategy discussions → Mentally rehearsing a presentation while their team shares crucial updates → Attention bouncing between five urgent problems, solving none completely The cost isn't just productivity. Your leadership presence evaporates. Your team's trust erodes. In high-performance environments, attention isn't just a resource. It's your competitive advantage. When you focus fully: → You notice micro-expressions that signal team tension → You spot connections between seemingly unrelated data points → You make decisions from clarity rather than reaction Most leaders know this. Few practice it consistently. The difference isn't knowledge, it's discipline. The solution isn't complicated: 1. Practice intentional monotasking. Whatever deserves your attention deserves your FULL attention. 2. Create attention boundaries. Block time for deep work with zero notifications. 3. Build a daily mindfulness practice. Even 5 minutes trains your focus muscle. 4. Batch-process inputs. Schedule specific times for email and updates rather than letting them hijack your entire day. In my 17+ years as a SEAL, the leaders I trusted most weren't just the smartest or toughest. They were the ones who could maintain complete presence amidst chaos. They showed up fully. Their attention wasn't divided. Their focus created a gravity that pulled teams together. What deserves your full attention today? ——— Follow me (Jon Macaskill ) for leadership insights, wellness tools, and real stories about humans being good humans. And feel free to repost if someone in your life needs to hear this. 📩 Subscribe to my newsletter here → https://lnkd.in/g9ZFxDJG You'll get FREE access to my 21-Day Mindfulness & Meditation Course with real, actionable strategies.

If you're a marketer, or work in a creative role, time management is bullsh*t. I always wondered why it never worked for me. I tried all the tips (time blocking, focus hours, etc.). But it was never sustainable. Then, I gradually realized what the real solution was. Energy management. Just like we have a certain amount of time every day, we have a certain amount of energy every day. And as a marketer/content creator, your tasks can be deceptive. For example, your to-do lists may seem simple, for example: - write a video script - edit 3 video clips - work on new messaging But when you get into it, you're doing mentally draining work. So, you can block time for different things on your calendar all you want, and try to plan the most productive day/week, but if you're not considering the energy that goes into each task, it'll be difficult to follow through. And IF you're able to follow through, you won't be able to maintain it for a prolonged period of time, leading to burn out. So, to remain productive AND avoid burnout, you need to consider managing your energy, moreso than managing your time. Cruising at 85% every day will prevent you from burning out in a few weeks/months (and then having to operate at 20%). Sure, you can have those days where you go 100%, but trying to do that every day will lead to burnout much faster. So, if you find yourself having trouble figuring out how to juggle your tasks, get everything done, and not feel drained for the next few days, try analyzing your tasks for how much mental energy they consume, and restructure your days accordingly.