Keeping Team Productivity High With Multiple Initiatives

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

I've managed 5 high-performing product marketing teams at startups and public companies, and there are 2 commonalities I've noticed at each: 1) it's easy for PMMs to get overwhelmed by the sheer volume of tasks on their plates, and 2) teams are rarely recognized for their true effort or impact by upper management. That's why I want to share my prioritization matrix 👇 It’s been a game-changer in how my teams approach projects and focus on what truly drives results. I’m curious—does this framework resonate with your approach to prioritizing tasks? Here's the concept: Rack up the wins by focusing on projects that offer high visibility and impact for lower effort and avoid those that drain your energy and don’t align with company goals. (Note: you could replace visibility with impact on this scale, but it's important that what you're working on is actually on the radar of those in upper management). Here’s how to prioritize: Quick Wins: These are the golden opportunities! High visibility, low difficulty — they bring great returns with minimal effort. Look for ways to get a few of these in your quarter. Strategic Initiatives: Aim for ONE strategic initiative per quarter. These are high-visibility, high-difficulty tasks that are aligned with your long-term goals. Go deep, plan ahead, and focus on the impact. You will be the most proud of these, but you need to be realistic about them. Routine Tasks: You’ve got to keep up with these, but don't let them consume too much of your time. Find a system to manage them efficiently. Avoid: Stay clear of high-difficulty, low-visibility tasks. These projects often don't yield the results you need, and they’re energy-draining. They don't align with your values or long-term success. 💡 Action Step: Review your current or upcoming projects. Classify them into high or low reward, and high or low effort. What projects are you spending too much time on that aren’t worth the effort? Time to realign and focus on what truly matters! #Productivity #TimeManagement #Prioritization #WorkSmart #StrategicFocus #CareerGrowth #Leadership How do you manage your / your team’s workload?

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.

As a CTO at Vital Interaction, I'm constantly navigating the delicate balance between being responsive to the dynamic needs of our business and ensuring our teams have the focus they need to deliver high-quality solutions consistently. While not the first time I have experienced this, here's what I've learned this time around: 1. Balancing Responsiveness and Focus - Set clear priorities and boundaries to allow teams to work deeply without constant interruptions. 2. Iterating on MVPs and Gathering Feedback - Allow ample time for customer feedback to refine our products and align with user needs. 3. Knowing When to Start the Next Project - Monitor project milestones and feedback to decide when to pivot to new initiatives. 4. Splitting/Aligning Teams for Optimal Focus - Dedicated teams focusing on specific projects to reduce context-switching and increase productivity. By fostering an environment that values focused work and strategic responsiveness, we can drive innovation and deliver exceptional value to our customers. How do you ensure focus and responsiveness within your teams? I'd love to hear your strategies and experiences! #Leadership #Focus #Innovation #Teamwork #HealthcareTech #CTO #VitalInteraction