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.

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.​​​​​​​​​​​​​​​​

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.

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.

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.

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.

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 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.

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.

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.

BossGPT: Using AI to Level Up Your Leadership - Prompts

AI prompts to go with webinar video

Are You Thriving or Surviving as a Leader?

Are You Thriving or Surviving as a Leader? A 3-Minute Leadership Check-In Why This Matters High-performing leaders are often the last to notice when they’ve shifted from thriving to simply surviving. This brief reflection is designed to help you pause, assess, and realign.

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.

Culture Code Cracked: Your Guide to Global Team Success

Unlock the secrets to thriving in global teams with our event, "Culture Code Cracked: Your Guide to Global Team Success." Join me, Caolan, an expert in cross-cultural communication and storytelling, as we delve into the art of effective communication across diverse cultures. With a rich background in leading international teams and delivering talks at top universities, I've guided executives and rising leaders to transform their communication skills. As work becomes ever more borderless, success depends not just on strategy, but on understanding. Discover how diagnostics and coaching can dissolve friction, deepen trust, and turn cultural differences into your team’s greatest advantage. From Seoul to Singapore, from global startups to local innovators, this session is designed for anyone building across borders. Be part of the conversation on how the next generation of global teams will work, learn, and thrive.

The Clarity Compass: 5 Coaching Questions

This is a short, reflective workbook for high achievers navigating transition, burnout, or ‘what’s next’ moments.

Global Mobility for Real People: Careers, Visas & Passports in 2026

Borders are tightening, digital‑nomad visas are mostly marketing, and “just get an MBA abroad” is no longer a complete mobility plan. In this session we look at global mobility as part of your life and career portfolio: how degrees, skills, employers, visas and, in some cases, second citizenships fit together over the next 10 to 20 years. Drawing on current data and real cases from Europe and Asia, we will cover what is realistically available to professionals who are not billionaires, how to read countries’ migration postures, and how to choose programmes, roles and locations that keep your options open. You will leave with: - A clear framework for thinking about mobility as risk management and opportunity, not fantasy - A map of the main routes that actually move the needle for early and mid‑career professionals - Concrete questions to ask when choosing schools, employers and countries if you want real global options, not just a nicer passport stamp

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.

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!

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!