Resources
Browse our collection of insightful and informative articles
Chase Damiano’s Conscious Conversation Framework: How to Get Buy-in From Your Team
Learn a framework designed to help you facilitate conversation with your team, elicit the best ideas, and make a decision to move forward collectively, with buy-in and trust at the center.
Chief Endurance Officer
Chase sits down with Gregory McDonough and shares how the endurance mindset impacted him by developing a sense of self-awareness. Chase also encourages aspiring entrepreneurs to embrace their business leaps. Tune in to this extraordinary episode and listen to the amazing advice Chase gives.
On uniting humankind
Humans beings zoom in on each others’ differences. We notice skin, hair and eye color. We judge heights and weights. We hear different languages, accents and dialects. We express various behaviors and attitudes. Two people may react differently to a similar circumstance. We identify with nations, ethnic groups and spiritual beliefs. Sexual preference and gender […]
What to do on sabbatical, and my three-month experience
A sabbatical is a rest or break from work – a voluntary decision to take a “time-out” from employment. Common reasons for taking sabbatical are to study, travel, volunteer, raise children, or start a side business. In my case, I was depleted, and my batteries needed a recharge. I made a hard decision to leave […]
Working IN the business vs. working ON the business
The difference may mean growing faster and more consciously. Less stress and less busywork. Big picture thinking and staying out of the weeds. And, placing a higher value on your time. Working in the business means actively existing a part of the system that delivers the product or service and achieves the vision. Working on […]
Manage your life as a Shareholder and Board, not just a CEO
We are all responsible for our own actions. We can live life reactively, responding to stimuli, or live life proactively, creating the life you want to live. We can live deterministically with fixed outcomes, opportunistically with unfolding outcomes, or anything in between. A popular framework is to “become the CEO of your life” – to […]
Leadership through relationships: a model for families and teams
Oxford defines the word “relationship” as “the way in which two or more people or things are connected, or the state of being connected.” We hold a relationship with every person we know, with every person we don’t know, and with ourselves. Relationships can be of any size: one’s relationship with oneself, two-person relationships, three-person […]
Who Does What for Whom and Why: The Importance of Defining Roles & Responsibilities Within Organizations
You’re watching a football game. You see the wide receiver catch the ball—you do not see them look to the quarterback for approval before doing so. Nor do you see the quarterback ask the wide receiver if they will catch the ball when thrown to them. In fact, all the players on the field do […]
Defining the Hat: How to Create Roles & Responsibilities
How many hats are your team members wearing? Too many? Ones that are ill-shapen? Or simply the wrong size? In other words, what jobs do you have your team members doing, and have you set up clearly defined responsibilities for the roles they fulfill? In my last post, I discussed why it’s so important to […]
OKRs: Providing Your Organization with Purpose
The more successful a company becomes, the more work there is to do. And as the work piles up, strategic planning sessions tend to be postponed or canceled in order to tend to more urgent operational concerns—putting out fires, attending last-minute client meetings, staff call-outs, and solving problems on the fly. Over time, the team […]
Internal Meetings: Scheduling and Scaling Touchpoints to Amplify Team Investment and Growth
Invest in team members’ growth, and business growth will follow When we talk about company leadership, we often talk about focusing “upward and outward.” Instead of driving output by yourself, you ought to be driving output across your team so that as the leader, you can take on new opportunities and continue to grow the […]
16 Leadership Commandments to Drive Investment, Humanity, and Trust
Almost every leader I know has certain values that drive their leadership philosophy. Some of those values are ubiquitous among leaders across industries; some are more specific to that leader’s sector, company, or personal experience. Over the years, I’ve read a lot about leadership, experienced the benefits and drawbacks of others’ leadership styles, and learned […]
Vision: The Endpoint to Guide Your Organization and Your Goals
A gymnast at the Olympics, just before their performance, visualizes themselves landing every move—they walk through the routine in their mind and see the moment they’ve won the gold medal and step up to the podium. An artist sees in their mind what their next work ultimately looks like as they’re creating it. It may […]
The Allegory of the Cave: Leadership Through Awareness
For many of us, Plato’s The Republic, written around 375 BC, was required reading in high school or college. Through Socratic dialogue, he contemplates questions of politics, governance, justice, and ethics. There are many lessons that, for centuries, leaders have taken from the book and used as guideposts for their leadership philosophy. My favorite lesson, […]
When the Problem Is You: My Process for Cultivating Self-Awareness
Founders are meant to problem-solve. That’s what we do. We see the symptoms and notice the impact. We work to uncover the root cause, then make changes to fix the issue. We either experience the benefits of those changes—or we try again. In typical founder ideology, if team performance is poor, we tend to determine […]
Purpose: Why You Are > What You Are
We often think of our “work self” and our “life self” as two separate personas. At the root, however, there is only one self: you. Who you are at work and who you are in life—it’s the same human. In fact, work is now a way of life. It’s a symbol of who we are […]
Optimizing Your Sleep as an Entrepreneur
Like myself, nearly all the founders and entrepreneurs I’ve met have struggled with their sleep. It’s classic: When you build your own business, you also build your own daily structure. But unlike a normal nine-to-five, there’s no set routine, so when there’s too much to do in a day and time is scarce, we tend […]
How I Manage My Time
In startup life, time is typically the biggest limiting factor on what we can accomplish both professionally and personally. Between all the meetings, strategy sessions, ideation, problem-solving, administrative tasks, and constant analysis of what is and is not working—not to mention things like taking care of your kids, getting dinner on the table, and spending […]
9 Keys to a Healthy Work-life Balance as an Entrepreneur
The endless to-do list involved with getting a company up and running can easily consume you, without you even realizing it. But startup/entrepreneur life shouldn’t be your only life. Here’s what happened to me… At my startup, I found myself working every weekday, every night, and every weekend too—waking up at 3 am with new […]
A Guide to Working with Me, Part I: Why Every Leader Should Write a Guide
“I think that founders should write a guide to working with them […] to clarify the founder’s role: ‘What do I want to be involved in? When do I want to hear from you? What are my preferred communication modes? What makes me impatient? Don’t surprise me with X.’ That’s super powerful. Because the problem […]
A Guide to Working with Me, Part II: My Guide
In Part I of this series, I laid out my case for why every leader should write a guide to working with them, and outlined the steps on how to write your own effective guide. For starters, writing and sharing your guide will help solidify and communicate your values. As a public document, it helps […]
The Opportunity: Why Entrepreneurs Should Put Purpose First
There’s a story I love to revisit that says when Sir Christopher Wren was commissioned to rebuild St. Paul’s Cathedral after the Great Fire of London in 1666, he asked three different bricklayers at work, “What are you doing?” The first bricklayer said, “I’m laying bricks.” The second said, “I’m building a wall.” And the […]
Rightsizing Your Email Habits: How to Become More Effective as an Entrepreneur
It can feel highly productive to mow through your inbox. But what if most of the time you spend on emails is just that: merely the feeling of getting things done? Is all that time spent really moving the needle on your work? As an entrepreneur, your most important work is to answer the big, […]
High-Yield Meetings: 8 Tips for Optimization + 6 Essential Meeting Structures
Meetings are where leadership happens. As I’ve written about previously, it’s the critical space where you, as a leader, can either amplify team investment and growth—or leave your team feeling more like their time was wasted with unproductive talk. Unfortunately, the status quo at most organizations is that meetings are boring and unproductive. There’s lots […]
Date Night: How to Build Your Relationships as You Build Your Business
When you’re an entrepreneur, most of your waking attention is spent on your work. And your work requires almost nonstop hyper-focus. Hence, it’s all too common for entrepreneurs’ relationships to fade into the background. But whether you find yourself outright sacrificing personal relationships, subjecting your partner to too much work talk, or letting calls interrupt […]
The Art of Letting Go: How Founders Must Come to Terms with the Reality of Separation
Letting go is one of the hardest lessons a founder has to learn. We put our heart and soul into our business. We live for our business. Early mornings and late nights, missed calls and cancelled plans. When we go home to our loved ones, we often struggle to turn off the business switch because […]
Measuring “Enough”: Exploring a Better Way to Think About Achievement
Growth rules the minds of most entrepreneurs and founders, but are we focused on growth just for the sake of it? Are we reaching for unattainable goals because of passion for our projects, or is it just because we can and don’t know what else to do? There are thousands of examples of entrepreneurs’ lives […]
The Necessity of Executive Feedback, Part 1
One of the main roles of a leader is to offer feedback. Working from a place of authority, leaders are often trusted to have the clearest perception of an organization’s vision and know the route to executing that vision. For feedback to work, it’s important for leaders to have the respect of their employees. Without […]
The Necessity of Executive Feedback, Part 2
In Part 1 of this series, I walked through my humble beginnings as COO of Commonwealth Joe Coffee Roasters in 2014. Two years later, after personally trying to will things into place and, in effect, creating a difficult work environment, both for myself and others, I received feedback from the employees of the company—feedback I […]
How Prioritizing Accountability Makes Teams More Effective
We often think of accountability through a negative lens—viewing it as a disciplinary function to hold bad actors accountable through blame and punishment. But accountability holds more positive power in the workplace than this reactive definition we tend to think of. The good news about accountability is, it can be developed. So, what is it […]
The Power of Syncing Up, with ignite CEO Jeff Rum
How do you strengthen team culture in a fully virtual workspace? It’s no secret that companies the world over have relied on quick and innovative thinking to overcome the obstacles set by the pandemic. Rising to meet these challenges in spite of uncertainty—and experiencing incredible growth as a result—is the cornerstone of ignite, the boutique […]
How Decision Frameworks and Self-Reflection Lead to Better Decisions
Every problem has a solution, if not many solutions. But many leaders often stick to one-size-fits-all decision-making systems without fully considering the factors at play, placing too much pressure on themselves to make something happen without utilizing the bountiful resources at their disposal. This self-imposed pressure can lead to emotional barriers that make decisions more […]
Handling a New Leadership Role: Shifting Focus from Processes to Outcomes
Our society often rewards great individual contributors with leadership positions. But shifting from individual contributor to leader isn’t the same as a promotion from entry-level contributor to senior-level contributor. It’s a totally different skillset. It requires an important mental shift, and that shift from being a talented and effective salesperson, engineer, writer, designer, accountant, strategist, […]
Building Mental Models to Unify Teams, with Wellfound Foods Founder & CEO Sarah Frimpong
How can you better scale team responsibilities to shepherd your company to the next level? This age-old question doesn’t exist within a silo. Leaders tend to hold the most in-depth knowledge of the vital processes that make their operations turn (or not). Often, though, that knowledge isn’t shared effectively between more than a select few […]
Disconnect to Reconnect
Jordyn, Zac, and I traveled to Maine last week. I’d never been to Maine before. We chose Acadia National Park and Portland primarily to spend some time in nature and welcome Zac back into our house for the summer.
Washington Post: Business Rx: These coffee makers think their craft should be a career, not a job.
Robert Peck says he was first exposed to the power of fresh-roasted coffee 12 years ago, while working with his mother at a coffee shop in his hometown of Culpeper, Va. Peck was a barista and his mother was a roaster and café manager. When Peck went off to college, she “dove deep into the craft of coffee,” he says.
Harvard Business School Publication: Commonwealth Joe Coffee Roasters
At the end of 2016, the leadership team of Commonwealth Joe Coffee Roasters—Robert Peck, Chase Damiano, and Jeremy Martin—had begun an ambitious retail expansion strategy in the Washington, D.C. metropolitan area for their specialty coffee business.
Just Get Started Podcast
Episode 101 Features Chase Damiano, a business advisor, consultant, and executive coach dedicated to helping founders, entrepreneurs, and CEOs get out of the weeds.
Rebelpreneur Radio
Chase Damiano is a business coach and consultant, helping founders get out of the weeds. His clients want to accelerate revenue and gross profit and build a well-oiled machine. He helps them achieve it without breaking the organization or breaking themselves. He is a former COO of a venture-backed start-up and ex-Accenture consultant.
One Away Podcast
Chase is an entrepreneurial management consultant and coach, helping early- and mid-stage entrepreneurs get out of the weeds. He works directly with founders, executives, and leadership team members to scale their companies and cultures through periods of high growth.
OKRs vs KPIs
All of this is about strategic planning and cultivating the mindset toward common languages within an organization. These are tools to create the outcome of alignment. These tools work for us, not the other way around.
Medium Term Podcast
In this episode Allan shares his failed partnerships and current collaborative mindset. Then Allan is joined by Chase Damiano (Forbes 30 Under 30, and founder of Chase Damiano LLC) to discuss his business and personal growth, and how they're linked.
Driving Force Podcast
Chase helps get entrepreneurs out of the weeds. He works as a business advisor, consultant, and coach to founders and CEOs and more specifically, helps them clarify their vision, building scalable operational strategies,
Outwork Outcare Podcast
Lessons learned at CWJ
How’d you know it was time to leave
Dive into RASA
Different areas where entrepreneurs have the biggest struggle
Why they get caught up in the weeds. Where do they focus that isn’t right?
Biggest lessons that you share with your clients.
Inevitable: The Future of Work
Management consultant turned start-up entrepreneur, Chase Damiano, is now channeling his passion around and hard-won knowledge of how to achieve and sustain business success into helping others do just that. Learning to point the finger at yourself may be your first step in better directing everyone around you forward. This and other very vulnerable insights are accessible to you…and likely will better equip you to reach out to your team in more personally meaningful ways at the very moment we need to help each other achieve what some are calling “post traumatic growth.”
TechTalk Healthcare
Chase is an entrepreneur, strategist, coach, mentor, and motivational speaker and consultant and excited to help you achieve your wildest dreams. Others say he is a coach, mentor, and motivational speaker. Chase wants to be a partner in your success.
Leap To Purpose
Leap To Purpose is an interview-based podcast that explores the stories of those that took an entrepreneurial leap to follow their purpose. Learning from the experiences of those that have successfully made the transition, Leap to Purpose seeks to educate and inspire others to do the same. If you’re feeling like you were meant for […]
Finding Your Leadership Style Through Self-Assessment
When leaders are aware that they need to improve in their roles but aren’t receiving the candid feedback they truly desire, they often resort to personality assessments. Frankly, everyone in this day and age does, regardless of the context. We’ve lived through the peak Buzzfeed era, filling out endless quizzes, like “Which Hogwarts House Are […]
Managing Up: Creating Purposeful Conversations With Your Boss
You need feedback on your performance or a project, and the only person who can help you is your boss. How do you make this happen without wasting their time and energy? Navigating the relationship with your boss can be one of the most challenging aspects of work—especially if you directly report to the founder […]
How to Run an Executive Retreat
Today’s zeitgeist tends to portray executive retreats as campy team-building weekends filled with trust falls, Two Truths and a Lie, and egg-and-spoon races. So, understandably, many executives don’t give them much thought. But when you enter a retreat ready to make a difference with thorough plans for the outcomes you want to achieve, they can […]
How to Take a Vacation as a Founder
As founders, we don’t always give ourselves permission to take vacations. We feel like we have to grind it out to reach our goals. We feel like we’re running on a treadmill, and if we stop… CRASH. We fear that we’ll ruin our streak of productivity, the delicate flow that we’ve created through day-in-day-out nose-to-the-pavement […]
The Leadership Traits that Inhibit Team Performance
Entrepreneurial companies are expected to think fast, move quickly, try new things, and iterate rapidly. These behaviors help companies learn as they go—both product and services companies alike. Great leadership navigates us through these winds of change. Teams must pay attention, gather data, and listen to customers. With luck and persistence, we create the business […]
What it Means to Empower Employees
Members of healthy relationships have equal power. Our most egalitarian relationships may be found with our spouses, close friends and peers, and business partners. Relationships with unequal power tend to be found in parent-child relationships—and often with our direct reports. Hierarchical teams are built for one “leader” to have more power than their team members. […]
Treat Your Time as an Investment
The only truly scarce resource is human time. I made tons of mistakes when I started my first company, especially about managing my time. My pervading belief: “Ah, I’m free from the clutches of corporate life! I can live on my own terms and use my time however I want!” (Well yes, but that was […]
What Success Looks Like
“What does success look like?” Jim Collins calls it a Big Hairy Audacious Goal. Stephen Covey calls it Begin With the End in Mind. A common pattern I see among new leaders is a lack of clarity in what creates a successful outcome. Many of us lack a connection to our final destination. Here’s the […]
The Role of the Chief Alignment Officer
Growth creates more complexity. More funding → more headcount → more functions/departments → more revenue → more experiments. The number of opinions, decisions, relationships, and friction points grows exponentially. Left unaddressed, this creates pressure on a leadership team. Work expectations begin fragmenting across business units. New hires don’t integrate with the existing teams. Teams stay […]