Technology-Driven Productivity Coaching

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

⏳ Your calendar isn’t just a schedule, it’s a strategy. One of the most overlooked leadership skills? 
👉 Time regulation. Not just managing tasks, but protecting your energy, prioritizing wisely, and using tools (like AI) to work smarter. Here’s what it looks like in action: 🧠 Value your energy, not just your hours.
 You don’t get bonus points for burnout. Productivity peaks when you build in time to recover.
 Emma, a senior marketing director I coached, began treating her time like an asset. She blocked 90-minute “deep work” windows twice a week, no meetings, no Slack. Her creative output soared. 🤖 Use AI as a force multiplier.
 Emma used AI to summarize decks, prep agendas, and analyze campaign data. These actions gave her back hours to lead and think strategically. I am improving my performance by using ai tools like Perplexity to accelerate my search, Speechify to listen to business and academic articles and books while I commute, and Grammarly to minimize rework! 🌱 Recharge with intention.
 She stopped skipping lunch. It sounds small, but it gave her afternoons back. Energy is a performance driver, not a luxury. 📅 Audit your calendar regularly.
 Emma color-coded hers into “strategic,” “operational,” and “noise.” After two weeks, she cut 30% of her recurring meetings and empowered her team to step up. 🎯 Measure what matters.
 She shifted her weekly check-ins to focus on what moved the needle and what still needs attention. 💬 Thought bubble:
 Time isn’t just what you spend—it’s how you lead.
If you don’t protect it, no one else will. As a leadership coach, advisor, and L&D professional, I empower business leaders and their teams to become more effective, cohesive, and adaptive to thrive in an AI-driven workplace. #Leadership #SelfRegulation #TimeManagement #Productivity #AI #FutureOfWork #LeadershipDevelopment #Coach #Advisor #JennyFernandez #Thinkers50 #MG100 #BestAdvice https://lnkd.in/eBcfga7Z

I’ve heard hundreds of time management tips over the years, but 90% of them aren’t practical for daily use. Why? Because they’re:   🚫 too theoretical 🚫 too abstract 🚫 too rigid These 5️⃣ are the ones I actually use every day—plus how to boost each one with AI (and the exact prompts I use). 👇 1️⃣ Prioritize ruthlessly Not every task deserves your time. Ask: If I only do one thing today, what will matter most? 🤖 AI prompt: “Here’s my to-do list: [paste list]. Please organize these using the Eisenhower Matrix—urgent vs. important—and suggest which I should do, delegate, defer, or delete.” 2️⃣ Use AI on the $10 task so you can focus on the $10K task If it’s low-impact or repetitive, delegate it to AI. Free yourself up for meaningful work. 🤖 AI prompt: “Here’s a list of my current tasks: [paste list]. For each one, tell me if it’s a $10 task or a $10,000 task. Recommend which I should delegate to AI and which I should prioritize myself.” 3️⃣ Eat the frog Tackle your hardest or highest-impact task first—before distractions set in. 🤖 AI prompt: “Here’s my calendar and to-do list for the week: [paste or describe]. Identify which tasks are most critical and when I’m best positioned (energy-wise or schedule-wise) to tackle them first thing in the day.” 4️⃣ Time-block more than meetings Protect chunks of time for deep, focused work—not just calls. 🤖 AI prompt: “Here’s my weekly calendar: [paste or describe]. Help me find 3 time blocks for deep work. Optimize my schedule to reduce context switching and maximize focus.” 5️⃣ Every ‘yes’ to something trivial is a ‘no’ to something meaningful Practice saying “no” with intention—your time is your most valuable asset. 🤖 AI prompt: “Act as my personal scheduler and productivity coach. I’ll list recent tasks, meetings, or requests. For each one, ask: Does this align with my priorities? What am I giving up by saying yes? Is this the best use of my time? Then recommend whether I should accept, delegate, delay, or decline—and how to respond.” ✨ Real game-changer: I don’t treat AI as a shortcut—I use it as a force multiplier. What’s your go-to time management tip? Drop it below 👇

Most professionals can't access quality career coaching. At $350-600 per session, traditional executive coaching remains out of reach for many who could benefit from personalized guidance. So one of our Supra members, Kavita Anand, taught 25 women at her company to build their own AI career coaches in a 90-minute workshop. In our recent Supra Insider episode, she walked us through the exact playbook she used: 1/ Craft Your System Prompt Start with this prompt to Claude: "Write a system prompt for an LLM-based co-pilot that specializes in career coaching. I want you to focus on scenarios that women in tech and product face. The coach should be inquisitive, use evidence-based research, and be supportive throughout sessions." Then customize based on your needs: ↳ Personality: Direct advice or Socratic questioning? ↳ Expertise areas: Technical leadership? People management? ↳ Communication preferences: One question at a time? ↳ Boundaries: When to use context vs. general advice 2/ Run Your "Kickoff Call" Share your situation: "I'd like you to have an initial coaching call with me. Ask me questions to understand my current situation, challenges, and goals. Here's my context: [Role], [Company type], [Years in role], [One current challenge]." Let it ask follow-up questions naturally. End with: "Summarize everything we discussed into a profile document." Copy that summary into your project knowledge - this becomes your coach's baseline understanding of you. 3/ Test Real Scenarios Pick actual challenges you're facing. Workshop participants used examples like: ↳ "I kept getting interrupted by an exec in my product review" ↳ "My manager asked me to prioritize three urgent projects" ↳ "I'm struggling to influence a stakeholder who outranks me" 4/ Refine Through Iteration Improve your system prompt based on responses: ↳ Add: "Ask follow-up questions about root causes" ↳ Add: "Challenge my assumptions when appropriate" ↳ Add: "Reference my past patterns when giving advice" Then use Claude's "retry" button to regenerate responses with your updated instructions. For advanced users: You can layer in company career documentation, past performance feedback, or notes from 1:1s. One workshop attendee said her AI coach started referencing her work patterns: "I notice you haven't looped in Design yet - that's been a blocker in your past projects." That's not generic AI advice. That's coaching based on your actual history. 🔗 Link to full episode: https://lnkd.in/dv7q5t4z --- Our full episode with Kavita covers: ↳ Why treating AI like a new team member beats quick prompts ↳ The psychology behind why 90-minute workshops drive adoption ↳ Claude vs ChatGPT: when to use each for different tasks ↳ How to avoid AI giving you confirmation bias instead of real coaching ↳ Why "tinkering" might be the most important skill in the AI era

This will be shocking to some people. My use of AI doesn't save me much time right now even though I know exactly how it could and have the skills to do it. It actually takes me longer most of the time, and here's why. I use our AI instruments to enhance my coaching and consulting with clients to raise our standards of delivery and personalize all parts of our content. Here's how: 1. Personalizing our Cortex content for every client to ensure that the exact problem they are having has a solution we have worked together on that makes it immediately relevant to them, their team, and their organization, which saves them hours of time and effort. 2. Creating specific prompts they can copy and paste into their favorite LLM to walk them through issues they are trying to solve to ensure relevancy that saves them hours of their valuable time. 3. Conducting deep research on topics that are immediately applicable to their upcoming leadership challenges so they can quickly determine the best decisions they can make, which saves them hours of time and energy. 4. Customizing training materials, used in coaching sessions, to match their specific development challenge and provide systems they can use to see the change they want to see faster, which reduces their risk of misinterpretation of how training may apply to them and their team. 5. Creating individualized, small group coaching, culture kits, and specialized small cohort training that will help them elevate themselves ahead of other leaders as they position themselves and their organizations for the future world of work. 6. Updating mainstays of our training/coaching content and releasing them to our clients for free - Time Mastery 2.0 and The New Playbook of Teamwork. 7. Working closely and tirelessly with Jenna Miilu, Allen Foster, Kim Levings, Jeanne Newby, SHRM-SCP, Certified Coach-CTA and TTI DISC, and Kimberly Eakin, and other curious members of our team to build new workflows and special assessments that produce personalized reports that clients can use to condense and synthesize information about themselves and their teams so they can take action to solve issues more quickly and precisely. 8. Testing new AI instruments and new methods leaders and their teams can use so our clients don’t have to. 9. Spending 30 minutes a day to upskill on AI. 10. Testing assumptions and strategies to gain wider perspective. Make no mistake, we are using systems thinking to develop some high speed automations. It has just been more important, over the last few years, to more deeply understand our clients and the challenges they are and will face, co-thinking with AI instruments, and then automate to remain focused on human-centered leadership. We are not trying to remove the human connection in what we do; we are working very hard to ensure that any human interaction provides a true, deep connection that helps our clients to be better leaders for those they serve. #noaiforthisone

AI is my new executive coach. Not a productivity hack. Not a tool. A coach. I didn't expect this. I started using AI the way most founders do — to write faster, code faster, ship faster. Somewhere along the way it became something else. The thing nobody tells you about being a founder is how lonely the decisions are. Your co-founders are in it with you, but they're also in it with you — they have the same blind spots, the same fatigue, the same emotional stake. Your investors want signal, not nuance. Your team needs you to be sure, even when you're not. Your spouse hears about it but didn't sign up to run the company. So most days, the hardest decisions get made alone, in your head, on a walk, at 2am. A good executive coach changes that. The problem is good ones cost $1,000+ an hour, take weeks to onboard, and meet with you twice a month if you're lucky. What I've found is that AI — used well — fills a meaningful part of that gap. Not all of it. But more than I expected. It asks me what I'm avoiding. It pushes back when my reasoning is thin. It remembers the last fifty conversations and notices when I'm contradicting myself. It's available at 6am when I'm trying to figure out what tomorrow should look like before the kids wake up. It won't replace a great human coach. But it's made me less alone in the work. And, more surprisingly, it's brought some joy back. The job is more fun when you have a thinking partner who actually has context. If you're a founder and you're using AI only to write emails and code, you're missing the bigger thing. Try talking to it about the decision you're avoiding.

Something truly amazing is happening to the world’s leading senior leaders and executives, and it’s separating them from the rest. It’s never mattered more to Unlearn your Old Playbook. The leadership habits that got you here—endless meetings, manual follow-ups, relying on memory—won’t get you there. In fact, they’ll hold you back. Here are 10 lessons I’ve learned firsthand from coaching senior leaders on how to leverage AI in their daily work: 1️⃣ From Productivity to Presence Productivity is table stakes. Presence is the prize. You don’t need more output. You need more presence. AI Coaching teaches you how to tame the noise and show up more—for work and life. 2️⃣ Time is the Real ROI Forget “performance hacks.” The real win is making it to your kid’s game, yoga class, or dinner without Slack and the 5 emails you still need to write buzzing in the back of your mind. 3️⃣ Your Leadership Edge: Headspace You don’t need more apps. You need mental freedom to tackle meaningful, complex problems and still have a life. AI Coaching makes that possible. 4️⃣ It’s Traits → Tasks → Tools, Silly Starting with tools is the fastest path to failure. Tools don’t change leaders. Behaviors do. Stop asking “What tool should I use?” Start asking “What trait should I amplify?” 5️⃣ Scaling Your Leadership Behaviors Technology follows behavior. Not the other way around. Know yourself. Understand how you work, process, and decide at your best. AI Coaching builds systems around your habits, so your best traits scale across tasks and tools, for both you and your team. 6️⃣ From Meeting Chaos to Clarity Senior leaders don’t need more meetings. They need every meeting to pay off. AI Coaching turns every discussion into assets—captured, synthesized, and ready for action. 7️⃣ Nobody Dreams of Dashboards You don’t want another tool. You want to finish the day, shut the laptop, and be done. AI Coaching gives you that moment back. 8️⃣ From Information Exhaustion to Insight Advantage You don’t need more data. You need clarity. AI Coaching helps leaders turn overload into sharp, confident calls—gut instincts plus solid data insights for decisive action. 9️⃣ A Thinking Partner That Never Tires Need to test a strategy, prep a board deck, or spar with ideas? AI Coaching shows you how to train AI as your intellectual challenger—the colleague you’ve always wanted on call. 🔟 Gone in 90 Seconds 50+ senior leaders I’ve worked with have cut meeting follow-ups from 30 minutes to 90 seconds. AI Coaching isn’t theory, it’s practical systems that win back time, expand creative problem-solving capacity, and protect momentum. ⭐ Bonus 11. Because Life Isn’t Only About Work AI Coaching isn’t about faster emails. It’s about creating space for creativity at work and presence at home. It’s about doing the best work of your life—and living the best version of your life too, with plenty of time for what actually matters. 👉 If you want to create that life, get in touch.

Training events don’t fail due to a lack of quality; they fail because they lack reinforcement. In today’s fast-paced environment, skills learned in workshops can quickly fade without structure, reflection, and accountability. The real differentiator is not the training itself, but what occurs in the 12 weeks following the event. This article presents a straightforward model for utilizing AI alongside coaching to reinforce learning in real time. It emphasizes one clear principle: small, consistent prompts combined with real-world application and structured reflection lead to lasting behavior change. AI does not replace leaders; it enhances their rhythm. Coaching does not complicate training; it sustains it. For those committed to transitioning from event-based learning to embedded leadership habits, this framework offers a practical starting point. Association for Talent Development (ATD) SEWI-ATD - Southeastern Wisconsin Chapter of the Association for Talent Development CNY ATD Arianna Stucker Brian Hume Bradley Wilson Crystal Stanfield Dropbox Erica Chappelear Froedtert Health Greylock Partners Mindy Honcoop, Empowering HR Leaders Dr. Iris Ware, PhD, MAIR, LPA, HCS, CPT, LOS JR Rauth #LeadershipDevelopment #CoachingCulture #AIinLeadership #TrainingReinforcement #ManagementExcellence #WorkplaceLearning #OrganizationalDevelopment #ContinuousImprovement