Leland+ Content Library

Designing AI Systems That People Actually Trust and Use

​Most people using AI tools at work have the same quiet worry: what is actually happening to my data? It is a fair question, and most AI systems are not designed to answer it well. ​Join Andrew Quillen, former Head of AI at Spotify and Content Strategist at OpenAI, for a session on how to design AI systems that people actually trust. Andrew will walk through how to think about sensitive data, connectors, and access controls, how to prevent unintended exposure before it happens, and how to build systems where users always know what the AI can see and what it can't. He'll also cover the broader design principles, boundaries, visibility, and user control, that separate AI products people rely on from ones they quietly stop using. ​You'll leave with a practical framework for building AI that earns trust, not just attention.

Build Your Personal Budget with Claude

​Most personal budgets die by February. You build a beautiful spreadsheet in January, miss a week of updates, and never open it again. The numbers stop matching reality, and the plan stops working. ​In this exclusive AI Builder session, Ben Lazaroff will walk you step by step through building a personal budget powered by Claude. By the end of the hour you'll have a working AI that tracks where your money goes, flags when you're drifting, and tells you in plain English whether you can swing that flight home this summer. ​But the budget is just the on-ramp. The real takeaway is the playbook: how to hand any messy, recurring part of your life over to AI. First a budget. Next a meal planner, a job search tracker, a CFO for your side hustle. Same skill, different shape. ​Ben has spent his career thinking about how money moves: private equity at Bain, economic development policy at the Chicago Mayor's Office. Same rigor, much smaller balance sheet. ​You'll be building alongside him in real time. No demo, no notes for later. You'll leave with a finished budget and a clearer sense of what else you could build next.

Home for Ambition #2 — Weekly Live Show [3/25/2026] (Recording)

Home for Ambition is a weekly live show, by Leland, for people trying to stay ahead as work, learning, and opportunity keep changing. Each episode tackles a handful of timely, high-signal topics across AI, careers, education, and the future of work. We expect thoughtful debate, unique perspectives, and practical takeaways you can actually use. It is not a typical interview show or a generic news recap. It is a live roundtable built to help ambitious people make sense of what is changing, understand what matters, and leave with a sharper point of view on how to navigate what comes next.

Get Glowing Letters of Recommendation: Selecting and Preparing Your Recommenders [6/2/2026] (Recording)

GIVEAWAY DURING THE EVENT: Join for the chance to win a free coaching session! After this session, you'll know how to identify the right recommenders for your MBA applications and how to brief them so their letters reflect the qualities adcoms actually look for. We'll cover how to choose recommenders who can speak to leadership and growth, what context and talking points to give them, and how to handle situations where your best option is an imperfect one. Attending live means you can ask about your specific recommender situation and hear how the coach thinks through cases that don't fit the standard advice. The coach works with MBA applicants on this every cycle and brings a clear sense of what separates letters that land from letters that get skimmed.

Applying for an MBA in 2026? 6 Things You Could be Doing Now to Get Ahead

Planning to apply for an MBA in 2026? Join me, Meghna (HBS '28), for a high-impact session to help you get ahead in your MBA application journey. With acceptances and scholarship offers from multiple M7 and T15 programs, I’m excited to share the strategies, lessons learned, and insider insights that helped me navigate the process successfully, and that can help you do the same. In this session, we’ll cover practical, actionable strategies you can start implementing now - from refining your target school list and clarifying your “Why MBA,” to a structured framework for brainstorming essays and building a personalized application timeline. I’ll also share candid advice on where to invest (and where not to invest) your time and money when it comes to test prep, networking, and other application resources. Space is limited, so RSVP today to secure your spot and take the first step toward a standout application. Attendees will also receive an exclusive discount code for 1:1 coaching for the 2026 cycle.

Positioning for PE and the Buy Side in EMEA

Breaking into private equity and buy-side roles across Europe, the Middle East, and Africa requires a clear understanding of regional recruiting dynamics, fund structures, and candidate expectations. In this session, you’ll learn how EMEA recruiting timelines differ from the US, what firms prioritize in backgrounds and deal experience, and how to position yourself effectively whether you’re coming from banking, consulting, or another pathway. You’ll leave with a practical strategy for networking, technical preparation, and crafting a narrative that resonates with buy-side firms across the region.

How To Write Outstanding Law School Application Essays [4/16/2026] (Recording)

Your law school application essays are arguably the most important aspect of your law school applications. To have the best outcomes and plenty of options at the end of the process, you need to craft compelling essays with solid narratives that paint a picture beyond your numbers. We will talk about different essay prompts and how best to tackle them, why it makes sense to have two 'main' essays instead of just one, how to handle optional essays and the dreaded 'why x school' essays. We will also have time for some 'Ask Me Anything' at the end.

Analyzing Your Robinhood Investments with AI [6/2/2026] (Recording)

In this session, you will learn how to use AI tools to interpret your Robinhood portfolio data, identify patterns in your trading behavior, and surface insights that are difficult to spot through manual review. We will walk through how to prompt AI models to analyze your holdings, evaluate risk concentration, and translate raw transaction history into actionable observations about your investment habits. This coach works with data and investment analysis daily, and this session reflects how they actually approach using AI as a practical tool, not a theoretical one.

Prep for Success at PwC & Beyond: Build a Consulting-Ready Brand

Standing out in consulting recruiting takes more than strong grades—it requires a clear personal brand and professional presence. In this session, PwC Consultant and coach Annie W. will share how to position yourself for success at PwC and other top firms. You’ll learn how to communicate your strengths, refine your story, and showcase the skills consulting recruiters value most. Walk away with practical tools to build a consulting-ready brand that sets you apart.

How to Work With Me - Personal Read Me Guide Example

This 'How to' guide is my favorite tool to set and communicating boundaries at work while acting as a great collaborator. I wrote this note when I was Group PM at LinkedIn in their Sunnyvale (CA) HQ. I shared it with new collaborators every time I changed scope or team and started working with new partners (which happened a lot!). Many colleagues told me they really appreciated my transparent approach to collaboration and the example I set in communicating my boundaries. Some even created their own version and thanked me for it. Feel free to copy it and create your own version. Make sure to adapt it to your personal style and needs, as well as your organisation’s work culture.

How to Land Your First Job in Product (March 2026)

Breaking into product management without prior PM experience can feel daunting, but with the right positioning and preparation, it is absolutely achievable. In this session, you’ll learn how to translate internships, side projects, consulting, engineering, or business experience into a compelling product narrative, build a resume that signals product thinking, and prepare for common PM interview formats. Whether you’re a student or early-career professional, you’ll leave with a clear roadmap to land your first product role.

Home for Ambition #3 — Weekly Live Show [4/1/2026] (Recording)

Home for Ambition is a weekly live show, by Leland, for people trying to stay ahead as work, learning, and opportunity keep changing. Each episode tackles a handful of timely, high-signal topics across AI, careers, education, and the future of work. We expect thoughtful debate, unique perspectives, and practical takeaways you can actually use. It is not a typical interview show or a generic news recap. It is a live roundtable built to help ambitious people make sense of what is changing, understand what matters, and leave with a sharper point of view on how to navigate what comes next.

Next Cycle, New Reality: Preparing for Law School Admissions in 2026-2027

Law school admissions continue to evolve, with shifting applicant volumes, changing evaluation priorities, and increasing competition at top programs. In this session, we’ll break down what to expect in the 2026–2027 cycle, how to interpret trends in LSAT scores and medians, and what admissions committees are prioritizing beyond the numbers. You’ll learn how to build a smart timeline, strengthen your narrative, and position yourself strategically in a competitive landscape.

Why Getting Started Now Matters for College Applications

The strongest college applications are built over time, not rushed together senior year. In this panel, admissions experts will break down why starting early gives you a meaningful edge and what students should actually be doing now to stay ahead. You’ll learn how to think strategically about academics, extracurriculars, leadership, and narrative development long before applications open. Whether you’re a freshman, sophomore, or junior, this session will help you understand how small decisions today can shape stronger outcomes later.

Outreach Email Frameworks Skill

"/copy-frameworks" writes outreach emails using campaign-tested frameworks (SPARK, PAS, AIDA, Nudge) with two variants per request. To install, run this in your terminal after downloading the file: unzip ~/Downloads/copy-frameworks-skill.zip -d ~/.claude/skills/

Supercharge Your Job Search with AI

AI can be your secret advantage in the job search, helping you craft stronger resumes, uncover company insights in minutes, and walk into interviews fully prepared. In this workshop, you’ll learn how to turn AI into your personal career assistant—one that helps you rewrite your resume with impact, uncover insights about companies in minutes, and prepare stories that shine in interviews. You’ll see how to use AI to highlight your transferable skills, reframe experience for a career pivot, tailor your resume for each role, and even turn your best achievements into polished STAR stories. We’ll also explore how to use AI to research company strategy, culture, and recent initiatives, so you walk into interviews informed and confident. Outcomes: You’ll leave with an AI-powered job search workflow: one that helps you write stronger resumes, research faster, and interview smarter. Learning Objectives: *Understand how AI can accelerate and improve the job search process. *Use AI to reframe and tailor resume content for specific roles or industries. *Apply prompt frameworks to research companies and identify key insights. *Collaborate with AI to develop authentic STAR-format interview stories.

How to Lead the Room with Executive Presence

Executive presence is one of those phrases that gets thrown around a lot in leadership conversations. You've probably heard it. You may have even been told you need more of it. But here's the problem: most people can't tell you what it actually means. It's not charisma. It's not being the loudest person in the room. It's not even being the most polished. Executive presence is the ability to make people feel — in your presence — that things are under control, that someone capable is leading, and that their time and attention is being respected. It's a signal. And like any signal, it can be developed, sharpened, and directed. This guide is built around three pillars that I've seen transform how executives show up: Clarity, Credibility, and Confidence. They're related — and yes, they overlap. But they each do distinct work, and understanding the difference matters.

How to Ace Product Management Technical Interviews

Product management interviews often include technical questions that catch candidates off guard—from system design to product architecture and data thinking. Many strong applicants struggle not because they lack the knowledge, but because they don’t know how interviewers expect them to think through these problems. In How to Ace Product Management Technical Interviews, you’ll hear from experienced PM coaches who regularly work 1:1 with candidates preparing for competitive product roles. This panel gives you access to the frameworks, evaluation criteria, and preparation strategies they use when helping clients get ready for technical PM interviews.

AI Tools You Need to Know for Product Management

This session takes a practical, hands-on approach to AI tools for Product Managers. Rather than a generic tool roundup, attendees will see how AI fits into the actual PM workflow: from discovery and research to documentation, stakeholder communication, and process automation. Every example comes from real client projects and production workflows.

AFOQT Math Formulas Sheet

You don’t need to memorize hundreds of formulas — you need to understand when and why to use each one.