Leland+ for Leadership Coaching

A First-Time Manager's Guide to Success

A starter kit for new people leaders on what to do before your first day, and how to have an effective first week.

Promotion Readiness Scorecard

Score yourself across the five dimensions that actually drive promotion decisions -- Performance, Visibility, Leadership Presence, Sponsorship, and Business Impact. Identify your biggest gap and walk away with a prioritized 90-day action plan.

How to Give Feedback That Actually Changes Behavior

Most managers give feedback. Few give feedback that sticks. This guide breaks down the four reasons feedback fails, then gives you a repeatable four-part framework — Situation, Behavior, Impact, Next Step — with side-by-side examples showing ineffective vs. effective delivery. Includes a section on handling the most common reactions: defensiveness, denial, and empty agreement.

The Year-End Review Playbook

Most professionals approach the year-end review passively and leave the outcome to chance. This guide covers the full process high performers use: building a documented case throughout the year, writing a self-assessment for the calibration room (not just your manager’s inbox), preparing your manager to advocate for you in the room you’re not in, and using the review conversation to set the terms for next year. Includes before/after self-assessment examples and exact language for the conversations most people avoid.​​​​​​​​​​​​​​​​

New People Manager: First 90-Day Checklist

A phase-by-phase checklist for your first 90 days as a people manager: diagnose before you prescribe, provide clarity on direction, then raise the bar on performance, Includes the five most common new manager traps and a clear definition of what good looks like at 90 days.

Managing Up: A Field Guide

Managing up isn’t about flattering your boss — it’s about owning the relationship with the person who has the most influence over your career. This guide covers how to diagnose your manager’s style, what to ask them early in any new relationship, the most common managing up mistakes and how to fix them, and how to navigate specific situations when the relationship is strained.

Hidden Workload Audit & Reflection

This exercise will help you identify everything you're doing that is not on your “to-do” list, so you can see where your time is actually going and what’s pulling your attention away from meaningful work. Designed for anyone who feels busy but not making the progress they expect.

How To Have the Promotion Conversation

Most promotion conversations fail not because the person wasn't ready -- but because they handled it wrong. This guide covers when to have the conversation, what to say, how to handle pushback, and what to do after. Includes sample language and a follow up email template.

How to Have a Difficult Performance Conversation

Most managers know when a performance problem exists months before they address it. This guide gives you a structured approach to the conversation you’ve been avoiding: how to prepare, a five-part conversation framework, what to say at each stage, how to handle resistance, and what to do in the 24 hours after — including when to involve HR.​​​​​​​​​​​​​​​​

How to Build a High-Performing Team From Scratch

High-performing teams are built deliberately, not accidentally. This guide covers the five foundations every high-performing team requires — Clarity, Standards, Trust, Accountability, and Growth — plus how to set the right conditions in your first 60 days, how to manage different performers differently, and the warning signs that a strong team is starting to slip.

The Structured 1:1 Template for Managers

The 1:1 is the most underused tool in a manager’s kit. This template gives you a repeatable 30-minute structure that keeps 1:1s developmental rather than operational — including a five-section weekly framework, a monthly deep-dive question bank, and the five most common 1:1 mistakes and how to fix them. Designed to be shared with your direct report before each meeting.

Quick Leadership Reset

This exercise helps you identify where your leadership approach may be unintentionally slowing your team’s performance, especially during times of uncertainty.

How Korean Professionals Can Break Into Global Careers

Are you a Korean professional looking to break into global careers and make your mark on the international stage? Join me, Caolan, for an insightful session on navigating high-stakes career transitions and unlocking global opportunities. With a rich background in strategic communication and storytelling, I've helped ambitious professionals like you step into leadership roles and land positions at top companies. This session shows Korean professionals exactly how to transition into global roles with clarity and confidence. You’ll learn how to navigate English interviews, position your experience for international companies, and overcome the cultural barriers that often block career moves abroad. By the end, you’ll know the steps to take, how to present yourself to global employers, and what it really takes to secure your next role in the international market. With experience leading award-winning teams at On, AKQA, and Ogilvy, I bring a unique perspective on crafting compelling personal and professional narratives. During this event, we'll cover essential topics such as interview prep, skill-building, career planning, and more. Whether you're aiming to enhance your leadership skills or refine your strategic communication, this session will provide actionable guidance to turn your potential into results. Space is limited, so RSVP now to secure your spot and start your journey to global career success!

Professional CV - two Masters and three Doctorates + work experience!

For anyone looking for a clean, simple, thorough CV template! Includes my background of multiple undergraduate degrees, two Master's degrees, and three Doctorate degrees, along with research bibliography and work experience. Translatable for those entering MBA, Masters, PhD, medical school, dental school, physician's assistant and more.

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.

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.

AI for Global Leaders: Mastering Cross-Cultural Communication

In today's globalized world, effective cross-cultural communication is no longer a soft skill, it's a critical leadership competency. But what if you could harness the power of Artificial Intelligence to navigate cultural nuances with precision and empathy? This forward-thinking webinar, led by global communication expert Caolan Hunter, will show you how. Drawing on his experience building his own AI communication tool and advising top global companies, Caolan will demystify how AI can be your secret weapon for analyzing communication styles, adapting to different cultural norms, and leading your international teams with confidence. This isn't just a talk on AI; it's a masterclass in modern global leadership. Event Outcomes & Learning Objectives: 1. Decode Cultural Communication Styles with AI. You will learn to use AI-powered tools to analyze and understand different cultural communication patterns, such as direct vs. indirect feedback, and formal vs. informal address. 2. Navigate Cross-Cultural Challenges Proactively. You will discover how to leverage AI simulations and practice scenarios to prepare for difficult cross-cultural conversations, anticipate potential misunderstandings, and build stronger relationships. 3. Develop a Personal AI Strategy for Global Leadership. You will walk away with a practical framework for integrating AI into your daily workflow to enhance your cultural intelligence and effectiveness as a global leader in 2026 and beyond.

The Hiring Room: Amazon TA Leader’s Interview Playbook

This is not a list of behavioural questions. It’s a comprehensive, end-to-end interview strategy guide from a former Amazon Talent Acquisition leader and Stanford graduate — designed to help you think, prepare, and perform like a top candidate. We begin before the interview even exists: clarifying who you are, what you want, and how to align your narrative with the roles you’re pursuing. From there, we move through resume positioning, strategic storytelling, behavioural frameworks, executive presence, and what interviewers are actually assessing behind the scenes.

Decoding Cultural Friction Before It Hits the Slack Channel

Are you ready to master the art of cross-cultural communication and prevent misunderstandings before they escalate? Join me, Caolan, for an insightful session on "Decoding Cultural Friction Before It Hits the Slack Channel." With extensive experience leading international teams and guiding executives to communicate with precision and authority, I will share practical techniques to enhance your conflict-resolution, negotiation, and active listening skills. I specialize in helping leaders thrive across cultures through strategic communication and storytelling. My background includes delivering talks at top universities and transforming brand narratives across continents. Whether you're working in a multicultural environment or communicating in a second language, this session will equip you with the tools to speak with presence and influence. Spaces are limited, so RSVP now to secure your spot and turn everyday interactions into opportunities for impact!

Mastering Communication for Koreans: Becoming a Global Communicator

Learn how Korean professionals can communicate with confidence in global environments. In this session, we’ll show you how to overcome language barriers, adapt to different cultural expectations, and present yourself clearly in international meetings, interviews, and cross-border teamwork. You’ll walk away with practical tools you can use immediately to improve clarity, influence, and communication impact in any global setting. Whether you're looking to enhance your presentation skills, understand nonverbal cues, or learn how to persuade and influence in diverse settings, this session is for you. I'm Caolan, your guide for this journey. With a rich background in leading international teams, I've helped countless professionals speak with precision, presence, and authority. I specialize in coaching leaders to thrive across cultures, blending practical techniques with a deep understanding of what makes people listen, remember, and act. Join us to transform your communication skills and turn everyday presentations into opportunities to influence.