Leadership Development Program · A Guided Journey of Self-Discovery
THE 360° LEADER
Leaders cannot be built. They must be self-built.
The 360° Leader is not a course someone teaches you. It is a journey you author through rigorous assessment, real business cases, thoughtful conversation, and disciplined self-reflection, until you can name, in your own words, how you lead down, laterally, up, and inward.
8 Assessments
One Pair Every Session
4 Directions
Down · Lateral · Up · Inward
2-Hr & Half-Day
Keynote Breakouts to Full Program
1 Book
Digital Included, Free
The Premise
You cannot install leadership. You can only discover it.
Most leadership programs share one assumption: that leadership can be transferred from the front of the room to the seats. Teach the framework, hand out the slides, and leaders come out the other side.
They don’t. Because leadership is not information. It is identity: the way a particular person reads a situation, makes the call, and carries others through it. No two leaders do that the same way, so no lecture can hand it to them.
The facilitator’s job is not to build leaders. It is to curate the assessments, the cases, and the conversations, and to hold the discipline of reflection, so each leader can build themselves.
The 360° Leader replaces teaching with discovery. Rigorous assessment reveals who you are. Real business cases reveal how great leaders have handled the scenarios you will face. Conversation tests your read against your peers’. And journaling turns all of it into something no program can give you: your own leadership philosophy, in your own hand.
I
Natural is not enough
Some people carry natural characteristics that help them lead. None of them are sufficient. Raw temperament without deliberate work produces a capable manager, not a leader.
II
Self-knowledge comes first
You cannot develop what you have never measured. Learning who you are and where your leadership strengths actually sit is the first skill, not a preliminary.
III
Development is elective
No one can drive leadership into another person’s ethos from the outside. It has to be chosen, then worked at deliberately, session after session.
IV
Leaders pay first
Setting the bar for culture, work ethic, and what excellence looks like costs something. The sacrifice is the signal, and a team reads it long before they hear a word about values.
You cannot drift into leadership. It is an intentional journey.
Session VI · After the Case · Private Entry
To Myself
Today I saw my own habit in another leader’s story: winning on output, losing on trust. The assessment said the same thing in numbers. I will stop defending the habit and start replacing it. One relationship. Ninety days. Beginning Monday.
every entry, captured and curated into your book
The Inspiration · Marcus Aurelius
The greatest leadership book ever written was never meant to teach anyone.
Nearly two thousand years ago, the most powerful man in the world sat alone at night and wrote to himself. Marcus Aurelius never intended Meditations to be published. It was a private journal, an emperor examining his own conduct, naming his gaps, and holding himself to a standard no one else could impose on him.
That is the model for this program. Every participant writes their own Meditations. Every session ends in self-reflection and journaling on the day’s assessments, cases, and conversations. We collect every entry. And by the end of the program, that accumulated record, enriched by assessment results and refined across every session, becomes each leader’s personal Leadership Philosophy: printed as a hardcover book and delivered digitally, discovered and written by the only person who could have written it.
A philosophy handed to you is borrowed. A philosophy written by you is yours for life.
How the Journey Works
Five movements, repeated every session.
Every session runs the same arc, whichever directions it covers. The rhythm is the point: repeated across the program, it turns insight into identity and produces the raw material of each leader’s book.
I
Assess
One personality assessment and one leadership assessment per session reveal each leader’s natural style, strengths, and blind spots: the objective data behind self-discovery, accumulating toward all eight.
II
Expose
Published research and real business cases show how proven leaders handled down, lateral, up, and inward scenarios. A library of leadership witnessed, not lectured.
III
Converse
Facilitated, candid discussion, full room and small groups, where each leader tests their read of the case against their peers’ and their own assessment data.
IV
Reflect & Journal
Every session closes the same way, on the clock: silence, then writing. An automated form delivers questions written specifically for that day’s case and assessments, probing past the easy answer. Every response is captured.
V
Author
Across the program, every captured response and assessment result is curated into each leader’s Leadership Philosophy Book. A digital edition is included for every participant; a hardcover can be produced on request.
The Curriculum
Four directions. A licensed Harvard case for each.
Real leadership runs in every direction: to the people who report to you, the peers you don’t control, the executives above you, and first, to yourself. The curriculum is built on the case method used at Harvard, Stanford, and Wharton. Not lectures on leadership theory, but real published decisions that leaders debated to a defensible conclusion, so each participant sees the scenario handled before discovering how they would handle it themselves. Every case below is licensed per participant.
Direction I · ↓ Down
Leading Down: From Expert to Architect
Core Concept
Most high performers are promoted for what they know, then struggle because they cannot let go of doing. The leader who insists on remaining the most capable doer becomes the single greatest constraint on the team’s growth. This direction works delegation, coaching, and multiplying your value through others.
The Case
HBS 409003
HBR R2505N
What The Room Debates
A manager of 43 people across four countries discovers his team is unraveling underneath a customer crisis he thought was a technical problem. The room works out where his real failure was, then tests the same question against their own teams.
📓 Session Close · Guided Journal Prompt
Where am I still the bottleneck, and what does my attachment to being the expert reveal about how I lead?
Direction II · ↔ Lateral
Leading Laterally: Influence Without Authority
Core Concept
Organizational speed lives or dies at the seams between departments. Leaders who generate speed build lateral trust before they need it and earn peer credibility before they spend it. This direction works influence, cross-functional collaboration, and conflict.
The Case
HBS 498054
HBR R0701J
What The Room Debates
A star producer generates enormous revenue and fails his 360 review on peer trust. Do you promote him? The room has to decide, and then decide what its own 360 would say.
📓 Session Close · Guided Journal Prompt
Whose cooperation do I need most, and when did I last invest in that relationship before I needed something?
Direction III · ↑ Up
Leading Up: From Reporter to Strategic Partner
Core Concept
Reporting is a function; strategic communication is a skill. Leaders who deliver status updates are easily replaced by a dashboard. Leaders who bring the real problem, framed with a recommendation attached, become irreplaceable. This direction works strategic thinking, accountability, and executive communication.
The Case
HBS 411031 to 411034
HBS 411036
What The Room Debates
The strongest pairing in the curriculum: a new general manager struggling to lead up without support, then the same events told from the chair of the executive who fired him. The room argues both seats.
📓 Session Close · Guided Journal Prompt
What truth am I softening in my reporting, and what is the cost of inaction in terms a senior leader cares about?
Direction IV · ◉ Inward
Leading Inward: The Foundation Beneath the Other Three
Core Concept
You cannot lead others from an empty tank. The leaders who endure build disciplined internal foundations across four anchors: Clarity, Discipline, Resilience, and Accountability, with emotional intelligence as the differentiator beneath all four. This is where the journey begins and where every session returns.
The Case
HBS 409048
HBR R0401H
What The Room Debates
A high-stakes call under real time pressure and incomplete information. Composure, judgment, and accountability are not theoretical here, and neither is the question of how each leader in the room behaves when the clock is running.
📓 Session Close · Guided Journal Prompt
Which anchor is lowest in me right now, and what recent situation exposed it?
The Curated Case Library
The cases, and where to find them.
These are the most widely taught leadership cases in executive education, drawn from Harvard Business School and Harvard Business Review and licensed per participant. Every title below links to its source. Case selection is finalized with each client and can be supplemented with additional Harvard, Stanford, and Wharton material to fit the cohort’s industry and context.
Leadership & Influence
A high performer who cannot lead laterally or earn peer trust. Anchors communication, influence, and executive presence.
HBS 498054
A new manager leading up, down, and laterally without clear authority. A four-part arc that carries across the transition-to-leadership sessions.
HBS 411031 to 411034
Goleman’s classic on emotional intelligence as the differentiator of effective leaders. Companion reading for Leading Inward.
HBR R0401H
Coaching, Teams & Accountability
Snook’s HBS note asking the question this program is built on: are leaders born or made, and what exactly is developing when a leader develops? Used as the opening frame.
HBS 408064
Building and aligning a high-performing cross-functional team under pressure. Anchors teams and collaboration.
HBS 409003
The same events as the Peterson arc, told from the executive vice president’s chair. Anchors accountability and the strategic read.
HBS 411036
Change, Decisions & Delegation
Kotter’s classic framework on leading organizational change. Anchors leading through change.
HBR R0701J
High-stakes decision making under uncertainty and time pressure. Anchors composure and judgment.
HBS 409048
Practical guidance on the delegation shift that removes manager bottlenecks. Paired with the Leading Down case.
HBR R2505N
Licensed, not summarized.
Each participant receives their own licensed copy of every case used in their program. They read the real thing, argue it in the room, and then write about what it exposed in them.
The Assessment Battery · Know Thyself First
Eight assessments. Zero cost to begin. A mirror you cannot argue with.
Self-discovery starts with data. The battery is drawn entirely from established, freely available instruments in the published literature: four personality assessments and four leadership assessments. Participants complete one personality assessment and one leadership assessment at each session, so the mirror sharpens gradually rather than arriving all at once. Organizations booking four or more sessions complete the full battery of eight, with key instruments retaken late in the program to document real growth. Each pair is matched to the direction that session explores, and every instrument name below links straight to where it can be taken.
Four Personality Assessments
Who you are: the raw material of your leadership.
Inward
Personality type and how it shapes the way you naturally lead, decide, and communicate.
Up
The open-science gold standard of personality research: your profile across the five factors that predict behavior at work.
Down
Your signature character strengths, and which to leverage intentionally when coaching and developing others.
Lateral
Your behavioral and communication style, and how it helps or hinders you across functions and through change.
Four Leadership Assessments
How you lead: measured, not guessed.
Inward
Built on Goleman’s four-domain model: self-awareness, self-management, social awareness, relationship management.
Lateral
Thomas-Kilmann-based: your default response to conflict, and where you avoid or escalate tension.
Down
The degree to which you lead by developing and empowering others, the multiplier behind Leading Down.
Up
Transparency, balanced processing, and internalized moral perspective, the foundation of bringing leadership the truth.
How the pairs work.
Each session pairs the instrument that reveals who you are with the one that measures how you lead, matched to the direction on the table that day: 16Personalities with Emotional Intelligence for Leading Inward, VIA Character Strengths with Servant Leadership for Leading Down, DISC with Conflict Management for Leading Laterally, and the Big Five with Authentic Leadership for Leading Up. Structured peer feedback is compared against self-perception, and key instruments are retaken late in the program, so each leader and their organization can see the movement in black and white. Premium proprietary instruments can be added at an organization’s request.
Session Formats
Two formats. Your company sets the cadence.
The journey is modular. The 2-hour session works two of the four directions in depth; the half-day intensive works all four. In both, the majority of the clock belongs to case discussion and reflection rather than presentation, and every session ends with journaling that is collected. Both formats are available two ways: as a single-day breakout session paired with one of Damon’s keynotes, or as the building blocks of the full Executive Leadership Development program. Each organization determines how many sessions to run and how to sequence them; the more sessions, the richer each leader’s book.
The 2-Hour Session
Two Directions In Depth · Keynote Breakout or Program Session
0:00 — Opening frame & reconnect: discoveries since the last session · 10 min
0:10 — Assessment pair debrief: one personality, one leadership instrument · 20 min
0:30 — First direction: research, business case & extended discussion · 35 min
1:05 — Second direction: research, business case & extended discussion · 35 min
1:40 — Guided reflection: automated prompts on the day’s cases, captured · 20 min
Two case studies, not four, so each one gets room to breathe: roughly 25 minutes of facilitated discussion and 10 of private writing per direction. Two sessions cover all four directions; the rotation is set with you.
The Half-Day Intensive
All Four Directions · Keynote Breakout or Program Session
0:00 — Opening: the self-built leader & the 360° frame · 20 min
0:20 — Assessment pair debrief: one personality, one leadership instrument · 20 min
0:40 — Leading Down: research, business case & extended discussion · 40 min
1:20 — Leading Laterally: research, business case & extended discussion · 40 min
2:00 — Break · 15 min
2:15 — Leading Up: research, business case & extended discussion · 40 min
2:55 — Leading Inward: research, business case & extended discussion · 40 min
3:35 — Guided reflection: extended prompts, dated commitments, captured · 25 min
All four directions and all four case studies in one room, with 40 minutes on each: roughly 28 minutes of facilitated discussion and 12 of private writing. The deepest entries in each leader’s book usually come from this session.
Build the journey that fits your organization.
The program scales from a single keynote breakout to a multi-year leadership operating system. Four or more sessions means every leader completes all eight assessments. Whatever the cadence, every session feeds each leader’s journal, and the spaced rhythm is what turns insight into installed identity.
The close is engineered, not improvised.
Every session ends with the same protected block of reflection time and an automated form built for that day. The questions are written against the specific cases and assessments the cohort just worked, and they are designed to probe: not what did you think of the case, but where did the case find you.
The Signature Deliverable
Your Meditations: a Leadership Philosophy Book written by you, published for you.
This is what the entire journey builds toward. Every captured response, every assessment result, every conviction logged at the close of every session is collected and curated across the program. At the conclusion, each participant’s record is edited into their own Leadership Philosophy Book, the beginning of their defined 360° Leadership style. Because the automated prompts differ from session to session and every answer is personal, no two books in a cohort read alike.
Every participant receives a digital edition at no additional cost.
A custom-bound hardcover can be produced on request, for individuals or for the full cohort.
No off-the-shelf program can produce it, because no one else could have written it. Like the emperor’s journal it is modeled on, it was never written to impress an audience. It was written to govern a life.
The 360° Leader Series
Meditations
on My Leadership: a philosophy discovered, written & owned by its author
Digital Included · Hardcover On Request
Who It’s For
Built for emerging leaders, and the organizations betting on them.
Emerging & high-potential leaders
Individual contributors and new managers transitioning from doing the work to leading it.
Technical & specialist leaders
Engineering, product, operations, finance: experts whose next level depends on influence, not expertise.
Mid-to-senior managers
Directors and department heads who translate strategy into execution and hold the culture together.
Succession benches
Cohorts an organization is deliberately developing toward enterprise leadership.
Intact teams
Leadership teams building a shared language for how they lead in every direction.
Organizations of any size
Cohorts of roughly 15 to 30 leaders per program, in-person or virtual, with cadence set by you.
Your Guide on the Journey
Damon Dunn
Three-Time CEO · Stanford Football Team Captain, All-Pac-10 · NFL Alumnus
Harvard Business School Executive Education · Hoover Institution Fellow
TIME 40 Under 40 · Author · LOCKED IN Keynote Speaker
Damon doesn’t position himself as the leader at the front of your room. He positions himself as the curator of your leaders’ journey, because he believes what this program is built on: leaders cannot be built by someone else. They must be self-built.
What he brings is three decades of building organizations and the leaders inside them. He is currently CEO of Sign Talent Solutions, providing global talent solutions to United States companies. Before that he was founder and CEO of a 38-unit Dunkin’ portfolio across six states, grown from an initial five-store platform to more than 700 employees, where he built the leadership pipeline himself and developed front-line hires into general managers, area directors, and regional directors. Earlier he served as President of Tricor Southwest Corporation, allocating over $200 million of capital across retail development and returning 5x cash-on-cash to investors.
The rest of the range matters just as much. As a Stanford team captain and an NFL player with the Jaguars, Browns, Jets, and Cowboys, he lived inside cultures where the standard was set daily and publicly. As a fellow at the Hoover Institution and the Pacific Research Institute, he studied why people standing in the same circumstances create different futures. At Harvard Business School Executive Education, he experienced the case method this program adapts.
That range is the point. Franchise operations, real estate capital, global talent, elite athletics, and policy research are five very different pressure systems with five very different leadership models, and he has watched leaders develop inside all of them. The pattern held everywhere: the ones who grew did the work on themselves. Nobody installed it in them.
So he selects the assessments, chooses the cases, drives the conversation, and protects the silence at the end of every session, so each leader can do the one thing no facilitator can do for them: discover how they lead.