Strategies for Effective Tech Startup Leadership

I kicked off a product advisory engagement last week w/ the technical co-founder of an early stage YC-backed startup. He's hungry to become a better product leader (he's an A+ engineer). Context: I'm coaching him around customer discovery + product validation, including internal communication loops to ensure learnings & insights from customers are incorporated into his team's product development process. He framed the initial problems and I tried a question-based approach. He stopped me. "I'd like you to tell me what to do specifically as if I was a junior PM at my own startup." Here are a few points I shared: 1) Intimately know your customer. His company has a few early customers so I told him he needs to become an expert on every user and decision maker. What are their goals in life, pain points in their daily workflow, etc. I should be able to quiz you about your customers and you know the answer every time. 2) Learn where deals die. Product leaders are first & foremost business leaders. Understand the GTM + revenue generating motion of the business, including how customers find you and convert from leads to paying customers. Blockers to closing deals are a P0. You should always understand the deal pipeline. 3) Fall in love w/ problems, not solutions. Engineers tend to feel a sense of pride in the elegance of the solution. However, early stage solutions are usually wrong and need iteration. The *problem* is what has longevity, not the solution. Falling in love with a problem will give you the energy and excitement to experiment w/ different solutions as you seek product market fit. 4) Be 10x better on a key dimension the customer cares about. You have a small team and need to focus on the biggest impact. I believe the right place to focus for a new product is in being 10x better along a key dimension your customer cares about. Bite off a part of their workflow that sucks and make it fun, seamless, or gone. Incrementality = death. 5) Delighting customers is the best way to grow. Your customers will know people just like them. The best way to get word-of-mouth (WoM) going is by blowing them away. WoM is free marketing that brings highly qualified prospects to your doorstep with their wallets out. Make your first customers your biggest champions. 6) Bring your team along for the ride. Don't wait to have a fully fleshed out solution in your head. Instead, regularly share your latest thinking about the business strategy, milestones, biggest bottlenecks for growth, and problems you think the business should be focused on. This ensures everyone on the team is living and breathing the same headspace as the founders. I've never seen a founder ask for this advice this directly but I absolutely loved it because it showed humility and a true growth mindset. Anything else you'd advise a founder through the lens of "what's the basic advice you'd give me as a junior PM at my own startup?" #startupadvice #productmanagement #ycombinator

Paul Graham: Counterintuitive Truths About Startups Startups operate in ways that defy conventional wisdom. Like learning to ski, your instincts will often lead you astray. Here are the most critical insights for aspiring founders: Foundations Matter + Trust your instincts about people: Choose co-founders and early employees you genuinely like, respect, and have known long enough to trust their character. + Domain expertise trumps startup expertise: Understanding your users deeply is far more valuable than knowing startup theory. Mark Zuckerberg succeeded because he understood his users, not because he was a startup expert. + Make something people want: Avoid "playing house" by going through startup motions without creating genuine value. Education trains us to game systems, but in startups, there's no boss to trick—only users who care if your product works. Growth Fundamentals + Real growth comes from user love: "Growth hacks" are often just shortcuts that fail. True growth happens when you make something users love and tell them about it. + Actual success is the best pitch: The most effective way to convince investors is to build a startup that's genuinely growing fast. Timing and Commitment + Startups are all-consuming: They will dominate your life for years in ways you cannot imagine. Even successful founders face constant worries—the problems just become more glamorous. + Don't start in college: College should be a time for exploration and following intellectual curiosity. Starting a startup will prevent you from being a real student. + Your 20s are for exploration: You'll likely be more successful if you wait until after exploring different interests. Finding Ideas and Co-Founders + Don't force startup ideas: The best ideas emerge unconsciously from: Learning about things that matter Working on problems that interest you Collaborating with people you like and respect + Side projects matter: Great startup ideas often begin as side projects because they're outliers your conscious mind might reject. + Follow the technology curve: Interesting problems often emerge at the leading edge of technology. Practical Considerations + Domain expertise matters most: Non-technical founders can contribute through domain expertise or sales skills. + Business school adds little value: Early-stage startups need doers, not managers. Learn by doing. + Early hires should be like founders: Self-motivated peers who need minimal management. + Do things that don't scale: For startups with some users but not explosive growth, focus on high-touch, personalized approaches. The ultimate advice for would-be founders is simple: learn. Follow your intellectual curiosity, develop deep domain expertise, and build relationships with people you genuinely like and respect. When the right idea emerges, you'll know it when it begins to take over an alarming percentage of your life.

Scaling tech isn't just about the latest tools or platforms. The real game-changer is ignored by 90% of companies.👇 It's the human element. Tech adoption without people-first strategies often leads to failure. Here's what successful companies do differently: 1. They invest in upskilling their workforce 2. They foster a culture of continuous learning 3. They align tech initiatives with employee needs 4. They create cross-functional teams for better integration 5. They prioritize change management from day one Remember: Your tech is only as good as the people using it. The most advanced AI can't replace human creativity and problem-solving. Your team's ability to adapt and innovate with new tech is your true competitive edge. Don't just throw money at the latest gadgets. Invest in your people. Build a tech-savvy, adaptable workforce. That's how you truly scale technology and drive transformation. Empower your team to lead the tech revolution, not just follow it.

A dangerous myth in today’s technology space: Technical skills alone make you a leader. In my experience, highly technical people, while brilliant, are often not the most inspiring leaders. Make no mistake: Technical expertise is essential, especially in the tech industry. But it should serve as a foundation - not the whole structure - for leadership. True leadership requires a blend of emotional intelligence, vision, and the ability to inspire a diverse team to meet their KPIs and OKRs day by day - and year after year. Granted, brilliant technicians might know more about a given widget or whiteboard equation than anyone else in the room. But here’s the problem: They don’t understand the people part of the equation. For that, you’ll need a leader with the right blend of expertise and high EQ. That person should have a profound understanding of the tech they’re building, true. But they should have an even deeper understanding of the team they’re looking to create. True leaders in tech understand the importance of surrounding themselves not only with talented engineers, but also with brilliant product specialists, marketers, salespeople, and customer success teams: a range of different skill sets to engage in different types of problem-solving. And they know when to take charge of a project directly - and when to step back, delegate, and empower others to do the troubleshooting. To succeed in tech, find a brilliant technician who also comes with one of the oldest skill sets in business: high-EQ leadership. #LeadershipInTech #EmotionalIntelligence #DisruptOldThinking

𝗧𝗵𝗲 𝗙𝗶𝗿𝘀𝘁 𝟵𝟬 𝗗𝗮𝘆𝘀 𝗮𝘀 𝗧𝗲𝗰𝗵 𝗖𝗘𝗢: 𝗪𝗵𝗮𝘁 𝗥𝗲𝗮𝗹𝗹𝘆 𝗠𝗮𝘁𝘁𝗲𝗿𝘀 💡𝗧𝗵𝗲 𝗳𝗶𝗿𝘀𝘁 𝟵𝟬 𝗱𝗮𝘆𝘀 𝗮𝘀 𝗮 𝗳𝗶𝗿𝘀𝘁-𝘁𝗶𝗺𝗲 𝘁𝗲𝗰𝗵 𝗖𝗘𝗢 𝘀𝗲𝘁 𝘁𝗵𝗲 𝘁𝗼𝗻𝗲 𝗳𝗼𝗿 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴 𝘁𝗼 𝗰𝗼𝗺𝗲. But here’s the secret: It’s not about doing more—it’s about doing the right things. 🔥𝗙𝗼𝗰𝘂𝘀 𝗼𝗻 𝘁𝗵𝗲𝘀𝗲 𝗰𝗿𝗶𝘁𝗶𝗰𝗮𝗹 𝗮𝗿𝗲𝗮𝘀: 1️⃣ Build trust with your team and stakeholders. 2️⃣ Define clear priorities that drive growth. 3️⃣ Align your leadership style with the company’s biggest needs. 💡 𝗖𝗮𝘀𝗲 𝗦𝘁𝘂𝗱𝘆: A first-time CEO in AI technology struggled to make an impact during their first quarter, creating uncertainty among stakeholders. Together, we: ✅ Created a 90-day plan focusing on stakeholder alignment and team trust-building. ✅ Identified 3 strategic priorities to drive immediate growth. ✅ Refined their leadership style to balance technical expertise with visionary thinking. 🎯 𝗥𝗲𝘀𝘂𝗹𝘁: Stakeholder confidence soared, leading to a $5M investment, and the CEO’s team achieved their first major milestone within 60 days. 📌 𝗣𝗼𝘄𝗲𝗿𝗳𝘂𝗹 𝗖𝗼𝗮𝗰𝗵𝗶𝗻𝗴 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀: 1️⃣ What leadership habits must you leave behind to build trust and inspire confidence in your new role? 2️⃣ How will you ensure your priorities align with both short-term wins and long-term vision? 3️⃣ What specific actions will you take to align your leadership style with your team’s needs and company goals? 💼𝗥𝗲𝗳𝗹𝗲𝗰𝘁𝗶𝗼𝗻: What’s one 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗯𝗲𝗵𝗮𝘃𝗶𝗼𝗿 𝗼𝗿 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗳𝗼𝗰𝘂𝘀 you’ll prioritize in your first 90 days to build momentum and establish credibility as a CEO? I’m Robert Moment, an 𝗜𝗖𝗙 𝗖𝗲𝗿𝘁𝗶𝗳𝗶𝗲𝗱 𝗘𝘅𝗲𝗰𝘂𝘁𝗶𝘃𝗲 𝗮𝗻𝗱 𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗖𝗼𝗮𝗰𝗵 and author of 𝙁𝙞𝙧𝙨𝙩-𝙏𝙞𝙢𝙚 𝘾𝙀𝙊𝙨 𝙁𝙖𝙨𝙩 𝙏𝙧𝙖𝙘𝙠: 𝙋𝙧𝙤𝙫𝙚𝙣 𝙇𝙚𝙖𝙙𝙚𝙧𝙨𝙝𝙞𝙥 𝙎𝙩𝙧𝙖𝙩𝙚𝙜𝙞𝙚𝙨 𝙩𝙤 𝙊𝙫𝙚𝙧𝙘𝙤𝙢𝙚 𝘾𝙝𝙖𝙡𝙡𝙚𝙣𝙜𝙚𝙨 𝙖𝙣𝙙 𝙈𝙖𝙨𝙩𝙚𝙧 𝙐𝙣𝙨𝙝𝙖𝙠𝙚𝙖𝙗𝙡𝙚 𝘾𝙤𝙣𝙛𝙞𝙙𝙚𝙣𝙘𝙚. I specialize in helping first-time tech CEOs master unshakeable confidence, transform their leadership, and 𝗮𝗰𝗵𝗶𝗲𝘃𝗲 𝘀𝘂𝗰𝗰𝗲𝘀𝘀 𝗶𝗻 𝘁𝗵𝗲 𝗳𝗶𝗿𝘀𝘁 𝟵𝟬 𝗱𝗮𝘆𝘀—𝗮𝗻𝗱 𝗯𝗲𝘆𝗼𝗻𝗱. 𝗥𝗲𝗮𝗱𝘆 𝘁𝗼 𝗰𝗿𝗲𝗮𝘁𝗲 𝗶𝗺𝗽𝗮𝗰𝘁? 𝗟𝗲𝘁’𝘀 𝘁𝗮𝗹𝗸. #First90Days #TechCEOs #LeadershipCoaching #StartupSuccess #ScalingStrategies #FirsttimeCEO #CEOCoaching #Startups

𝐄𝐟𝐟𝐞𝐜𝐭𝐢𝐯𝐞 𝐒𝐜𝐚𝐥𝐢𝐧𝐠 𝐏𝐚𝐫𝐭 𝟏: 𝐓𝐡𝐫𝐢𝐯𝐢𝐧𝐠 𝐀𝐦𝐢𝐝𝐬𝐭 𝐔𝐧𝐜𝐞𝐫𝐭𝐚𝐢𝐧𝐭𝐲 This four-part series will cover 𝘱𝘭𝘢𝘯𝘯𝘪𝘯𝘨, people, efficiency, and resources as crucial inflection points in startup growth. "𝙄𝙛 𝙩𝙝𝙚𝙧𝙚'𝙨 𝙤𝙣𝙚 𝙩𝙝𝙞𝙣𝙜 𝙩𝙝𝙖𝙩'𝙨 𝙘𝙚𝙧𝙩𝙖𝙞𝙣 𝙞𝙣 𝙗𝙪𝙨𝙞𝙣𝙚𝙨𝙨, 𝙞𝙩'𝙨 𝙪𝙣𝙘𝙚𝙧𝙩𝙖𝙞𝙣𝙩𝙮." – Stephen Covey Uncertainty is everywhere. In farming, you plant crops without knowing what the weather and markets will bring every season. In startups, the long-term volatility of customers, teams, investors, markets, and the overall economy can deter success. Uncertainty often causes fear. Instead of cowering in a corner, however, channel your energy based on your vision, values, and desired outcomes. 𝗢𝗽𝘁𝗶𝗺𝗶𝘇𝗲 𝗪𝗵𝗮𝘁 𝗬𝗼𝘂 𝗖𝗼𝗻𝘁𝗿𝗼𝗹 As a founder, YOU are the only certainty about the future. So, focus on optimizing what you control. Prepare scenarios and budgets for the expected, best, and worst cases. Determining responses will give you more options now and lower stress if anything bad happens later. Review data consistently for insights and revisit entire plans at least quarterly to make necessary adjustments. 𝗦𝗲𝗲𝗸 𝗔𝗱𝘃𝗶𝗰𝗲 𝗖𝗼𝗻𝘀𝘁𝗮𝗻𝘁𝗹𝘆 To keep developing as a leader and discover opportunities, regularly seek peers, investors, team, customers, etc. and ask them open-ended questions. Create a challenge network of people who will candidly say what you need to hear, not only what you want to hear. At least quarterly, approach them with specific obstacles and broad perspectives (e.g. where should we be in one year?) 𝗟𝗲𝗮𝗿𝗻 𝗗𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁𝗹𝘆 Constantly learn new concepts to stockpile ideas and adapt if needed. Seek multiple sources across different fields. Read articles and books outside your industry, review competing sources, and read fiction for new ideas. Create time to 𝘸𝘰𝘳𝘬 𝘰𝘯 𝘵𝘩𝘦 𝘣𝘶𝘴𝘪𝘯𝘦𝘴𝘴, not only in the business. For instance, I break away weekly to review and update my objectives. Regularly test new ideas by running experiments:  · Create a hypothesis  · Describe the expected outcomes  · Determine (limited) resources  · Measure results  · Decide the next steps 𝗗𝗲𝘃𝗲𝗹𝗼𝗽 𝗦𝗲𝗹𝗳-𝗔𝘄𝗮𝗿𝗲𝗻𝗲𝘀𝘀 As we become more self-aware, we will better handle pressure, form relationships, and make decisions. Some people increase awareness through internally focused activities such as writing, mindfulness, and breathing. Others look externally by engaging plenty of advisors, mentors, peers, and team members who can provide candid and constructive feedback. Finally, make room for activities that will reinforce you against day-to-day stress, such as exercise, a healthy diet, sleep, and time with family & friends. Give any new habit at least 6 weeks to feel the results. You cannot predict the elements, but by recognizing and optimizing what you control, you can maximize options. #leaders #founder #adapt #startups

I am a fan of Paul Graham. His much-discussed ”Founder Mode" essay does highlight some insights about founder-led companies, but it may oversimplify a complex, nuanced topic. Graham's essay argues for founders staying deeply involved in company operations as they scale, rather than delegating to professional managers. However, we should add some important nuances: ~ Founder’s Strengths Vary ~ Not all founders excel at every aspect of running a company. Many are particularly strong in specific areas: - Product development and vision; - Technical innovation; - Customer understanding; - Fundraising and investor relations. However, they may struggle with: - Organizational structure and processes; - Financial management; - Communication and human resources; - Scaling operations. Evolving Roles As companies grow, the demands on founders change. What worked in the early stages may not be effective at scale. Successful founders often need to: - Recognize their limitations; - Know where they want to focus to have the greatest impact; - Hire complementary talent; - Adapt their leadership style; - Learn new skills. Potential Pitfalls of Pure "Founder Mode" While founder involvement can be crucial, an overly rigid adherence to "founder mode" might lead to: - Burnout: Trying to stay deeply involved in every aspect as the company grows can be unsustainable; - Stunted Team Growth: Excessive micromanagement can hinder the development of strong leaders within the organization; - Missed Opportunities/Optionality: Founders may overlook valuable insights from experienced professionals in areas outside their expertise; - Scaling Challenges: What works for a small startup may not translate effectively to a large organization without adaptation. Balancing Involvement and Delegation The key is finding the right balance between staying involved and empowering others. As Jobs noted, "It doesn't make sense to hire smart people and then tell them what to do. We hire smart people so they can tell us what to do”. Rather than a one-size-fits-all "founder mode," effective leadership often involves: - Building Strong Teams: Hiring exceptional talent and giving them autonomy in their areas of expertise; - Selective Specialization: Founders focus intensely on critical areas while delegating others; - Prioritization: Adjusting involvement based on company needs, team strengths, and personal capabilities; - Reducing Information Barriers: Creating systems for direct communication across levels, like Bezos' approach at Amazon; - Adapting Management Style: Using different approaches for different team members and situations, similar to Grove's "task-relevant maturity" concept at Intel. While Graham highlights aspects of founder-led companies, the reality is often more complex/nuanced. Successful founders typically combine involvement in key areas with the ability to build strong teams, delegate effectively, and adapt their leadership approach as the company evolves.

Insider Secrets with Ankita Vashistha: Mastering Leadership and Team Building for Startup Success 🌟 Hey everyone, Ankita Vashistha here! Ready to unlock the secrets to building a stellar leadership team and driving your startup to new heights? Let’s dive into some insider tips that can transform your startup’s leadership dynamics: 1. Craft a Compelling Vision 🚀 Your startup’s vision is the beacon that guides your leadership team. Ensure it’s clear, inspiring, and aligned with your goals. A strong vision will unite your team and fuel their passion. 2. Pinpoint Key Leadership Roles 🛠️ Identify the critical leadership positions needed for your startup’s growth. Define each role’s responsibilities and qualifications to build a well-rounded and effective leadership team. 3. Attract Elite Talent 🌟 Bringing on board top-tier leaders is crucial. Use your network and specialized recruitment channels to find individuals who not only bring expertise but also fit your startup’s culture and values. 4. Foster a Collaborative Culture 🤝 Create an environment where open communication and teamwork are the norms. A collaborative culture enhances decision-making and innovation, making your leadership team more dynamic and effective. 5. Embrace Diversity and Inclusivity 🌍 Diverse leadership teams are more innovative and successful. Ensure your team reflects a range of perspectives and experiences to drive creativity and inclusion. 6. Invest in Continuous Leadership Development 📚 Ongoing development is key to maintaining a strong leadership team. Provide training and growth opportunities to help your leaders adapt and excel in an evolving startup landscape. 7. Cultivate a Growth Mindset 📈 Encourage your leadership team to view challenges as learning opportunities. A growth mindset will help them navigate obstacles and drive continuous improvement. 8. Set and Track Performance Metrics 📊 Establish clear goals and performance metrics for your leadership team. Regularly review progress and provide constructive feedback to keep everyone aligned and on track. 9. Utilize Technology for Enhanced Collaboration 💻 Leverage technology to streamline communication and project management. Effective tools can improve efficiency and help your leadership team stay connected and productive. 10. Lead by Example 🌟 As a leader, your actions set the standard. Demonstrate the qualities you want to see in your team—integrity, resilience, and dedication—to inspire and guide them. Mastering leadership and team dynamics is crucial for startup success. By focusing on these insider tips, you’ll build a strong leadership team ready to tackle challenges and drive your startup forward. For more insider secrets and leadership strategies, feel free to reach out! #InsiderSecretsWithAnkita #LeadershipExcellence #StartupSuccess #TeamBuilding #LeadershipDevelopment #GrowthMindset #InclusiveLeadership #VentureCapital #BusinessGrowth #EntrepreneurLife

I recently wrote about being a non-technical founder, in which I noted you’ll need to hire folks to fill the gaps in your knowledge. ⛑️ I call it “building your bench.” 🛋️ It’s a constant process — because where the gaps are will change, right along with your company’s evolution. When a startup first launches, you might need a technical person and three engineers. 💻 Four years later, those needs will certainly look different. 🤔 I think about building a bench in approximately 18-month cycles. It’s not a perfect science, but every 18 months or so you're likely raising capital…developing a major new product….figuring out a big puzzle piece or new feature…seeing your customer base change. ✨ Very quickly your startup goes from a concept, to existing, to optimizing product-market fit, to (hopefully) hyper-growth. 📈 Is it possible that some people grow with you through all of that, evolving along with the company where it needs them? Sure. But it’s unlikely to be most people. That’s OK, and it’s very normal. The key is recognizing that these new phases are coming, and preparing for them. 🔮 How do you do that? 1. Hire for the gaps you have at this particular time. ⏩ Startups move so quickly through various stages, so it really helps to focus on your needs about 12-18 months out. In the earlier stages of your company, you’ll likely need people helping build, launch, and perfect your product, and a go-to-market team won’t be far behind. But you may not need, say, a robust commercial team until your company is more established. Staying focused on current and soon-to-be needs will help you fill your bench with who and what you truly need now. 2. Give titles, and people, room to grow. 🌱 It may be tempting to hand out executive-level titles, but this can create problems later as the company grows, new team members join, and plans evolve. If you give your engineering lead a Chief Technology Officer title at the beginning when all you really needed was someone to lead engineering, it’s going to be awkward and confusing a few years later when you need to hire a true CTO. 3. Know you’ll need to revisit your bench at every stage in the company lifecycle. 🧬 The people who do really well in the zero-to-one stage — zero customers, zero revenue, attempts that may not have panned out — are a particular breed. Some of them love zero-to-one and repeat that in each job as they move from startup to startup. It’s an incredible, important skill. But they may or may not be the people who lead in the one-to-two stage: scaling the business to hockey-stick growth 🏑 or transitioning from a product focus to commercialization. Final takeaway: Don’t be caught flat-footed. Build your bench! 🛋️

As an introverted leader, I often dealt with people talking over me. For a while, I tried to be louder. But that wasn’t my style. Eventually, I realized there was a better way to handle these people: Let them talk. Quiet leadership isn’t about shouting down the loudest voice in the room. That is a losing game that isn’t genuine to who we are as quiet leaders. Our way to “win” is to bring clarity, substance, and calm confidence to the conversation. As introverts, our strengths are preparation, active listening, and data-driven insights. So, to handle louder colleagues who are misbehaving or dragging conversations off track, we should lean into those traits. Then, we let them talk. Let them share their ideas and try to sell their ideas. When they are done, we use the data we have prepared ahead of time to share what we know is correct. Ask how their ideas tie back to the data or the goals outlined in your company’s strategy. We can also use our quiet skills to get ahead of them by laying out our points in meeting agendas, sending pre-reads, and by starting the conversation off on the right track. The final way we as introverts can tackle loud counterparts who are bringing less effective ideas into the organization is with coalition-building. Share your results and findings regularly with your boss, colleagues, and skip-level manager. This way, you build trust in your work and they learn to listen to you even if your voice is a little softer than everyone else’s. To read some more advice on Tech Leadership, especially as an introvert, check out this week’s Level Up Newsletter. In it, I answer four questions, one of which directly influenced this post. The four questions are: 1) “How do you navigate teams that are overconfident & miss dates or teams that purposely sandbag estimates to give them more time?” 2) “How do you motivate platform teams who are critical to your product but have little skin in the game or enthusiasm for your product?” 3) “If there is a critical failure (e.g., scoreboard outage during a live event), how do you organize an incident response team to mitigate the issue within minutes? What proactive measures should be in place to ensure rapid recovery?” 4) “How can an introverted leader, who is successfully driving growth and financial success, effectively handle extroverted counterparts who loudly downplay their achievements and push less effective ideas onto the company's main agenda?” Read the newsletter here: https://lnkd.in/eiqm8edD And let me know if you have other questions you would like me to answer. Introverted leaders- How do you lead as one of the quieter people in the room?