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.

Crafting an MBA Essay That Actually Stands Out [5/12/2026] (Recording)

FREE LELAND + FOR 1 MONTH FOR ALL LIVE ATTENDEES. Strong MBA essays aren’t just well-written, they clearly communicate who you are and why you belong at a program. This session is for applicants who want to move beyond generic advice and craft essays that genuinely stand out. You’ll learn how to develop a focused personal narrative, avoid common mistakes that dilute your story, and align your essays with what admissions readers are actually looking for. Join live to hear from MBA admissions experts and ask questions about your own essay ideas. The panelists regularly work with applicants on essay development and will share the patterns they see across successful submissions. Expect practical feedback and insights similar to what’s covered in 1:1 coaching conversations.

Your MBA Application Roadmap

This is the companion deck for Leland's flagship MBA week, for the session I ran on mapping your MBA application roadmap. Given the high demand for these slides, I tried to make these available as soon as possible -- and completely free. Reach out if you're hoping to work on a roadmap for yourself, and are looking for 1:1 coaching. This is a gameplan, but working with a coach to execute on this is where we offer by far the most leverage. I hope this resource is a great kickstarter for you and gives you much better line of sight into what this process holds..

Inside Law Admissions: What Actually Gets You In [5/11/2026] (Recording)

1YR LELAND+ GIVEAWAY FOR LIVE ATTENDEES ($119 VALUE). Law school admissions can feel opaque, especially when strong applicants still struggle to understand what truly drives decisions. This session is for candidates who want a clearer picture of what actually gets you admitted. You’ll learn how admissions committees evaluate your academic record and experiences, what makes a personal statement stand out, and the patterns reviewers see across successful applicants. Join live to hear directly from a panel of law admissions professionals and ask your questions about your own application strategy. The panelists regularly evaluate candidates and advise applicants, and will share the perspectives typically discussed in admissions review conversations. It’s a chance to get grounded, practical insight before you submit.

The Playbook to Land Your First PM Role [5/11/2026] (Recording)

$50 COACHING CREDIT GIVEAWAY FOR LIVE ATTENDEES. Landing your first product management role is competitive, and many candidates struggle to translate their background into a compelling PM story. This session is for aspiring PMs who want a clearer, more strategic approach to breaking in. You’ll learn how to position your experience for PM roles, build credible product signals through projects or work, and navigate the interview process with more confidence. Join live to hear from PM professionals who have successfully made this transition and now help others do the same. The panelists regularly advise candidates and will share the patterns they see across those who land their first PM role and what stands out to hiring teams. Expect practical guidance and insights similar to what’s covered in 1:1 coaching conversations.

Build Your Personal Brand & Thought Leadership System with Claude + Notion [5/20/2026] (Recording)

Personal branding is your ticket to excelling in the AI age. Most professionals know they should be creating content yet almost none of us do it consistently. Not because we lack ideas, but because we have no system to enable consistency. In this session, we'll build one. Using the network analysis from last week, we'll use Claude to generate a content calendar built around your actual expertise, then turn each idea into multiple formats: a LinkedIn post, a story hook, a networking pitch, and more. Everything lives in a pre-built Notion template you duplicate at the start of the session, so you spend the full session generating content, not building infrastructure. Outcome for attendees: A content calendar tailored to their specific network audience and a reusable Claude + Notion workflow they can run every month independently Session pre-requisites: Claude account & Notion account — free is fine 🙂

Get Started on Your Deferred MBA Panel: Actionable Tips from Experts

Kick off your Deferred MBA journey with a panel of top Leland coaches who have helped countless applicants earn admits to programs like HBS 2+2, GSB Deferred, and Wharton Advance Access. They’ll break down what you should be doing right now—from crafting your narrative to securing impactful recommenders—to stay competitive ahead of this year’s deadlines. You’ll leave with clear, actionable next steps to start your application strong.

Sector Overview: Enterprise SaaS

Learn more about the Enterprise SaaS Industry, the market it operates in, sub-sectors, metrics, valuations, and what it means for VC.

VC Modeling Test ANSWER

Don't download this file until you have completed your timed practice assessment.

Top 5 Tips for Your Law School Application [5/12/2026] (Recording)

Join Indrani as she goes over her top 5 tips to help you put your best foot forward as you apply to law school! A great law school application requires research, authenticity and hard work, and Indrani will help you strategize. She will go over the importance of the LSAT, putting together a thoughtful school list, who should submit letters of recommendation, how to go about writing your essays and the optimal timeline for getting it all done! The session will end with ample time for questions and answers.

Running Out of Time on the LSAT? Here's How to Fix It [6/2/2026] (Recording)

Running out of time on the LSAT can be frustrating, especially when you understand the material but struggle to finish sections under pressure. This session is designed for students who want a more structured approach to pacing and a better understanding of where time is actually being lost. You’ll learn how to diagnose timing breakdowns, build strategies for moving through questions more efficiently, and identify the habits that commonly slow test-takers down. The coach works with LSAT students regularly and will share the patterns they see across improving scorers, along with the diagnostic thinking they use when evaluating timing issues. If you want a more repeatable approach to managing LSAT timing, it’s worth joining live.

Build a Job Search Operating System (JSOS) [5/13/2026] (Recording)

Build Anything Series · Event 01 · Free · Live The job search is the most expensive workflow most people will ever run — and the one they're least equipped for. Spreadsheets, sticky notes, half-tracked outreach, lost interview notes. By the end of this hour, you'll learn how to create a complete Job Search Operating System to help you land your next offer. What we'll walk through live: - A real applicant tracker | every role, company, and contact in one view. Status, last action, next step, follow-up date. - Automated outreach + research | pull company context, drafts personalized outreach, surfaces the right people to message. - Synced notes, prep, offer comparison | interview notes that auto-link to the role, prep doc generation per company, structured offer comparison when it's time to choose. Who it's for: - People actively job searching or about to start - Career switchers, returning-to-work folks, recent grads - Anyone who's run a search before and remembers losing track of half of it Not a fit if: - You enjoy manual data entry and Excel-tab chaos - You'd rather pay $300 for a static prompt template that fails instead of learning the principles yourself - You want a one-click magic button I'll be honest about where AI helps and where it doesn't, and how to keep the system running without me. Bring your laptop and follow along, or lean in, watch, and replicate after.

New Ways to Use Claude Cowork to Land Your Dream Job [5/14/2026] (Recording)

BOOTCAMP SEAT GIVEAWAY FOR LIVE ATTENDEES ($999 VALUE). In this session, you'll learn how to use Claude's cowork features to actively strengthen your job search, from drafting tailored outreach messages to refining your positioning for specific roles. We'll cover how to prompt Claude effectively for marketing and sales applications, how to use it to pressure-test your personal narrative, and how to build a repeatable workflow that saves time without losing your voice. Attending live means you can describe your actual situation and get a response shaped around it, not a general answer. The coach works with job seekers on this daily and will share the patterns that consistently move candidates forward.

Inside the Mind of an MBA Admissions Committee [6/1/2026] (Recording)

What actually happens when your application is reviewed? This session offers a behind-the-scenes look at how admissions committees evaluate candidates, compare profiles, and make difficult decisions among highly qualified applicants. Attendees will gain insight into what drives admissions decisions beyond surface-level credentials and learn how to frame their candidacy in a way that resonates with the evaluators behind the process.

Consortium Example Essays

These essays helped an ally be admitted to Consortium and to UC Berkeley Haas and UCLA Anderson. They stand out due to the clarity in career goals, specific ways the applicant supported unrepresented groups, and multi-faceted plans for involvement and support in the future.

Claude Design: Build Campaign Ready Assets in 60 mins

​Most marketers leave a brief meeting with a direction and a timeline. You're going to leave this one with the assets. ​Join Albert C., a former marketer at Meta, for an exclusive AI Builder session where you'll produce three campaign-ready assets in real time. By the end of the hour, you'll have a landing page, a 5-slide social carousel, and a short product video, all built by you, on brief, from scratch. ​This isn't a walkthrough. You build alongside Albert C. the entire time, so you leave with finished work, not notes about finished work. ​The session covers prompt patterns for visual consistency, how to brief Claude on brand voice and color, and how to move efficiently across asset types without losing creative direction. You'll also walk away with a reusable prompt framework you can take back to any brief, for any product, so the work you do in this session isn't a one-time thing. ​Come with a product in mind. Everything else is provided.

Sector Overview: Deep Tech & Defense

Learn how VC approaches the Deep Tech and Defense industries. Learn about the market, key players, metrics, and valuations.

Sector Overview: Consumer Tech

Consumer Tech has a massive market. Learn about its key growth drivers, metrics, economics, and what excites VC's.

Sector Overview: Healthcare & Digital Health

Learn about the Healthcare & Digital Health industries, their key players, metrics, valuations, and what VC's look for.