My most recommended resources for Operators
A Year in the Life of a COO: How I Set Myself Up for Success
Advice for new executives is often vague, aspirational, or overly conceptual, and those transitioning into a C-Suite position for the first time—or growing into the role from an adjacent one like Chief of Staff—have much gain from actionable guidance that can help them find their feet. That’s what I aim to do here.
Your operations roadmap is your current set of explicit, fully articulated goals for improving the company’s “how”—its processes, systems, tools, reporting, communication, and more. The roadmap should cover both near-term and long-term initiatives, and while it serves an important organizing function, it also has two other vital benefits.
My approach to self-care is grounded in the concept of the stress cycle, and focuses on the rhythms that we need to build into our days and weeks if we want to perform at a high level for multiple years.
An effective COO is responsive to the unique needs of both the company and its CEO, so the role always varies between occupants and firms—sometimes to such an extent that two COOs might have almost completely dissimilar duties. Because the scope of a company’s operations is so broad, there is an extent to which the COO is a gap-filler position, an organization-focused executive brought in to compensate for vulnerabilities or to create strategically vital bandwidth for the leadership team.
You will succeed or fail by your calendar. It requires constant, proactive management as well as tight coordination with your administrative assistant. It also requires a shift in both mindset and priorities.
Using the Second Brain framework by Tiago Forte has transformed how I channel my reading into actionable insights in my role as a startup COO in a corporate setting. This technique lets me operate efficiently and authentically by effortlessly commencing projects with resonating ideas.
In an ever-increasingly complex business world, leaders cannot disappear for weeks at a time to pursue a flow state at an ashram. While a thorough rest and recharge are always helpful, it’s more realistic to look for ways to trigger a flow state that simultaneously drive results in your business.
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Operator Reading List & Resources for COOs and Heads of Operations
Learn the role
📖How to be a Chief Operating Officer by Jennifer Geary
a comprehensive fundamental overview of everything that may fall with your purview as Head of Operations / Chief Operating Officer.
📖The Second in Command: Unless the Power of Your COO by Cameron Herold
This is written for CEOs looking to scale, and the book can read as a marketing tool for the COO Alliance, but it includes a good overview of the role and provides insights into the reality of stepping in as the first-ever COO.
📖Riding Shotgun: The Role of the COO
An excellent, candid overview of the “toughest job in a company”.
Find your Tribe
Operators Guild: Home to the world’s top operators
Venwise: Where the C-Suite connects for advice
Invest in becoming your Best Self
📖The Slight Edge: Turning Simple Disciplines into Massive Success and Happiness by Jeff Olson
📖Leading Lightly: Lower Your Stress, Think with Clarity, and Lead with Ease by Jody Michael
Stay Inspired
Resources for Building a Performance Culture
My most-recommended books, tools, and resources for anyone working on creating a performance culture:
Read The 4 Disciplines of Execution, which uses research to explain the foundational elements of what drives execution. This book will help you diagnose and articulate which disciplines are missing.
Then, implement Mastering the Rockefeller Habits immediately. If your team isn’t effectively executing, you need to implement a proven framework ASAP so you can begin to build a performance culture. This isn’t the time to start from scratch and design your own system.
OKRs and Goal Setting
My most-recommended books, tools, and resources for anyone tasked with implementing a new goal-setting system in an organization.
Read Measure What Matters by John Doerr. Even if you’re not setting goals, read this book so you can understand the lingo. Venture capitalists love this book, so I recommend reading it if you’re fundraising or working with investors.
Short on time? Read a few of these articles listed in The Best OKR Reading List in the World.
Subscribe to the Measure What Matters blog.
So now that you understand OKRs, dive into specialized resources such as Stride Consulting’s OKR Best Practice’s for Technology Teams.
OKR management Tools
WorkBoard. WorkBoard’s CEO and Co-Founder, Deidre Paknad, is incredible. I saw her speak at the 2019 Chief of Staff Summit in DC. It’s also an amazing product that I recommend.
Lattice. Lattice transforms your people strategy by connecting performance management, employee engagement, and career development in one unified solution. If you’re already using Lattice, start with this as it’s one less platform to implement and manage. If you’re not using Lattice, check it out with your People leaders! (Update July 2024: Lattice made a highly questionable announcement related to AI and immediately walked it back. While I question their judgment, I still strongly recommend their product.)
What else would be helpful? Reach out and let me know!
Articles for Operators
The retreat is both a laboratory and ultimate safe space, one designed to let you “try on for size” unfamiliar, nerve-wracking leadership styles and get real-time feedback on the efficacy of each approach. It’s both familiar and intensely challenging. It’s summer camp, or a new school, or the first day at a new job, except that this time there’s nothing you could do that would screw it up.
When we take the time to reflect, we open the door to uncovering hidden insights that can help us to make better decisions in the future.
In practical terms, I use the mantra as a sort of verbal touchstone during meetings, planning sessions, and even heads-down work. Its wry inversion of negativity reliably makes people chuckle when I invoke it during challenging conversations, and I’ve learned that saying it aloud can diffuse tense moments and break through impasses.
Unsurprisingly, I’ve learned the most (and the fastest) when I’ve been uncomfortable. But that’s the fun of it all, isn’t it?
A reader asked me how I keep track of connections, especially with fellow Chiefs of Staff and other new people I encounter on a regular basis. I just so happened to have recently implemented a whole new system!
Let’s talk about why Bed Bath & Beyond needs to figure out what they’re going to be great at, choose what they’re going to be bad at, and own that decision unapologetically.
Meetings that used to be impromptu now require planning, and a room, and remembering all the proper attendees, and omg why can’t I find a time that works for everyone?!
So where can we start? Consistent vocabulary.
Take a page from Chik-fil-a and hire the nicest people possible, then train them on your well-worn playbook. Prioritize smiles and patience over technical expertise for your frontline team.
Here’s a little know secret: the muck rises to the top.
It’s really hard to walk up to someone and say “hey, I think you’re out of line with our values”
As with all attempts to change behavior, consistency is key.
I adopted a system I called “scrum-lite” that revolved around a daily-standup, a whiteboard, and many many post-its. I was like a fish out of water managing my ballooning team, including a second layer below me, and I needed a system that would give me confidence in both our progress and direction.
Radical candor is really, really uncomfortable.
I posit that a reluctant boss is likely in the role for all the right reasons. They’ve been encouraged (pushed) to take the job based on their performance, rather than their personal relationships or personality.
The article is an inspiration for anyone who’s been responsible for business operations large or small.
The system isn’t ideal, and I still need swaths of time to do thinking-intensive work, but I’ve learned to appreciate capitalizing on these micro pockets of time so that when a free hour comes along, I can jump right into the task that needs an hour, rather than catching up on tiny tasks.
When was the last time you worked with your team to train them (or retrain them) to listen.
On another occasion, it was my responsibility to terminate an employee who called in before his shift to share offensive, drunken feedback with me.
Can the Targets of the world still surprise and delight their customers? Absolutely.
Corporate America spends some absurdly large sum of money every single year trying to engage knowledge workers and remind them about the importance of the customer. Lisa and team provide three simple lessons.
Have you been fortunate to work for someone who taught you how to step up when times get tough?
I firmly believe that you must have a system. Not an app, not a tendency, but a system.
I’ve sat through exec team meetings every week for the last 4 years. Some good, most okay, some downright bad. The better meetings all happened to include a meeting leader focused on making the most out of the time. The worst? They relied on the group to figure it out on the fly.