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Becoming an Operator: 10 Traits and Habits of Silicon Valley’s Most Efficient, Productive, and Successful CEOs

After 10+ years coaching some of Silicon Valley's most brilliant leaders, these are the ten things the most successful have in common.

man draws rocket launching
man draws rocket launching

After 10+ years working with some of Silicon Valley’s most brilliant CEOs, executives, VCs, leaders, and influencers, I’ve found there are two schools of thought when it comes to success: Grinders and Operators.

Grinders are primarily driven by the belief that success comes to those who work hard and never give up; and to a degree, they’re right: Of course consistent hard work is necessary to succeed, and it is possible to grind your way to success.

But the question is … Is that the best way? In my experience—and that of many of my clients—no. And that’s where Operators come into play.

What is an Operator?

Operators believe in the importance of hard work, but they also believe that …

True success only comes when you pair hard work with extreme leverage and valuable relationships.

Operators are those who consistently push the limits of peak efficiency, drive innovation, and generate valuable opportunities for themselves and their network. Here in Silicon Valley, the title’s a badge of honor; one of the highest compliments you can receive. And it can be yours.

Because here’s the thing: Operators aren’t lucky, and they don’t just work harder than everyone else; they also work smarter. They get leverage, and invest their energy into the relationships and opportunities with the highest possible ROI.

The Ten Traits & Habits of an Operator

In working with numerous Operators over many years, I’ve discovered that while each Operator is unique, nearly all share 10 powerful traits. Adopt and master these and you, too, can become an Operator.

You’ll find each of the traits outlined below, as well as an accompanying habit to begin incorporating it into your day-to-day life.

#1: They Visualize Their Objectives (and Have Outside Accountability)

Operators have clearly-defined North Star Objectives and Goal Tests.

North Star Objectives are long-term aspirational goals designed to motivate, inspire, and uplift the goal setter. 

Think of them the way sailors view the North Star: A way to stay on course, no matter where you are. And if you don’t know where to go or what to do, all it takes is a quick glance to get back on track. For example: “I will become one of the top-ten venture capitalists in my industry in the next five years.

Goal Tests, on the other hand, are the tactical foundation for North Star Objectives. They’re specific, easy-to-understand and, most importantly, easy-to-measure. For that reason, they’re always written in a clear yes-or-no format. For example: “This week, I spent at least four hours in whitespace time, working on proactive activities that scale my business.”

Once they’ve defined their North Star Objective and Goal Tests, Operators also ensure they have some form of outside accountability: A coach, a friend, a team member; it doesn’t matter, as long as someone out there is holding you to your goals.

Habit #1: Define Your North Star Objective and Goal Tests

Take the time to work through the action items in Stop Setting Weak Goals: The Ultimate Guide to Creating Goals (That Actually Get Done) and define your North Star Objective and at least 3 goal tests. Then find someone in your network and ask them to hold you accountable.

#2: They Shun FOMO and Embrace Hyper-Focus

Operators understand the danger or FOMO (or the Fear of Missing Out). Inexperienced entrepreneurs chase any potential opportunity thinking it might be “the one.” Operators, on the other hand, know that opportunities are not created equally and …

Winning one right opportunity is often better than chasing 10 mediocre opportunities.

To become an Operator, you need a crystal-clear picture on what the “right” opportunities are for you and (as we’ll discuss in a moment) where they come from. Moreover, you need to develop the willpower to let interesting-but-unaligned opportunities pass you by.

Habit #2: Develop Your Relationship Objective

Use How to Generate Valuable, Relevant Opportunities with a Relationship Objective to clearly define the types of opportunities you want to generate from your network. We’ll talk about what to do with this objective in Trait #7.

#3: They Understand the 80/20 Rule and How it Relates to Their Network

Operators realize a simple-but-powerful truth: 

80% of the game-changing opportunities you need to take your business to the next level come from a single source: Your network.

But they also realize that, like opportunities, each connection in their network isn’t created equally. In most cases …

80% of your opportunities come from the same 20% of your network.

In light of this, Operators have learned to “rate” their network to identify, invest into, and fully leverage the most relevant, valuable members of their network.

Habit #3: Rate Your Network

Follow the action items in How to Rate Your Network to Get the Most From It to identify the most valuable members of your network. At the very least, I recommend identifying the 20 Legends (a term you’ll come to know well) who have historically sent you the most meaningful, relevant, valuable opportunities in the past.

#4: They Maximize Proactivity (and Minimize Reactivity)

Time management is one of the most universal challenges faced by people across the world; especially entrepreneurs. And it isn’t helped by the fact that our lives are becoming increasingly reaction-driven.

Operators understand that, without intention, it’s easy to spend a whole day working only to get to the end and realize you didn’t actually accomplish anything. Rather than constantly reacting to the urgent, Operators consistently invest in the important; and instead of spinning their wheels in reactivity, they find massive traction in proactivity.

Arguably the easiest way to make proactivity a habit is to schedule it into your calendar, so Operators have become experts at prioritizing Whitespace Time: 4-hour blocks of purely creative, proactive time each week.

Habit #4: Schedule Whitespace Sessions into Your Calendar

Download our free eBook—Whitespace Time Management: The Proactive Entrepreneur’s Guide to Owning Your Time and Mastering Your Priorities—and schedule one Whitespace session a week for the next month.

#5: They Become Value Powerhouses (and Can Deliver Value at Scale)

In relationships, value is king; and …

The more value you put into your network, the more value you can expect to take out.

As a result, Operators have designed and implemented scalable systems that allow them to provide value across the whole of their network, with a focus on their Legends and Champions.

This value can come in a number of forms, including introductions, book recommendations, blog posts, or emails. The medium doesn’t matter, as long as the value can be provided quickly and easily.

Habit #5: The Power of One Email a Day

From today onward, adopt this simple practice: Every weekday, send at least one email to someone you wouldn’t otherwise reach out to. In other words, send one email a day you don’t have to send.

If you do this every weekday, you’ll wind up sending around 260 more emails each year. And while there’s no guarantees when it comes to relationships, I’d be willing to bet at least one of those emails will lead to some form of opportunity.

Not sure what to send? Download our quick-reference guide to the Five Freebies!

#6: They Use Meetings to Maximize Their Relationship ROI

Despite their high time- and resource-cost, meetings remain one of the single-most effective ways to build deeper, more meaningful relationships. Operators know this, and so use meetings—whether face-to-face or otherwise—to dramatically increase the quality of their relationships.

There are a number of ways they do this, from Congruent Communication to Icebreaker Sentences to Meeting Debriefs to Post-Meeting Follow-Up Emails, but regardless of which tactics they use there’s one constant: 

Every meeting is seen—and leveraged—as an opportunity to provide value and deepen connections.

Habit #6: Send a (Meaningful) Follow-Up Email After Every Meeting You Attend

If you’re going to invest 30-60 minutes in meeting with someone, you owe it to yourself and whoever you met with to send a follow-up email.

But there’s a catch: You don’t want to clog up the recipient’s inbox with a meaningless email. Great follow-up emails should always be perceived as meaningful, relevant, and valuable. We’ve written a three-step guide to writing follow-up emails your network actually wants to receive here: How to Write a Great Follow-Up Email After a Meeting.

Check it out, then commit to sending a follow-up email after every meeting for the next week.

#7: They Train Their Network on Exactly When to Think of Them

Above I mentioned the importance of knowing two things:

  • The types of opportunities you want to generate (with a Relationship Objective), and
  • Those in your network most likely to connect you with those opportunities (or your Legends).

Once an Operator has clarity on these two vital aspects of their business, they begin “conditioning” the Legends in their network about exactly what they’re looking for. They create what we call a Trigger Activation Statement, or a 3-5-sentence description of the types of opportunities they’re looking for.

Then they deploy this statement as often as possible; especially when meeting with new contacts. This ensures their network is always up-to-date on the specific types of opportunities they’re looking for. As a result, they receive more high-quality referrals and fewer misaligned opportunities.

Habit #7: Develop Your Trigger Activation Sentence (and Deploy it in Your Network)

Assuming you’ve identified the types of opportunities you’re looking for, the next step is to develop a punchy, succinct way of educating your network on those opportunities. Creating and refining this statement is one of the most valuable things you can do, and that’s why we walk our clients through it step-by-step.

But for the sake of this blog post, just focus on finding a way to state what you’re looking for in 3-5 sentences. Once you’ve developed a statement you feel comfortable with, identify at least one meeting in the coming week where you can practice using it and see what kind of response you get.

#8: They’ve Mastered the Art of Storytelling (and Have a Story Worth Telling)

Stories are one of the few things that transcend both time and culture across the world. One might even say that …

Our ability to craft and share stories is one of the most fundamental aspects of the human condition.

As humans, we love hearing and sharing great stories. That’s why Operators proactively create the stories they want others to tell about them, then share them. That way, when someone in the Operator’s network encounters the type of opportunity they want to hear about, they have an easy-to-share story that’ll make generating interest and facilitating an introduction as easy as possible.

Habit #8: Begin Crafting Your Story, then Share it with Others

Create a bullet-point list outlining what makes you unique and valuable, then use those notes to craft the first draft of your story. Try and limit it to 5-7 sentences, max, and remember: The easier and more enjoyable the story, the more likely your network is to share it.

Once you’ve finished your first draft, share it with 2-3 people in your network and ask for their feedback. Does it feel like an accurate representation of who you are? And could they see themselves sharing this story when talking about you?

One more quick tip: Before crafting your story, consider asking your network how they talk about you. Try, “If you were to introduce me to someone, what would you say about me?” The answers you get to this question can be incredibly valuable in developing your story.

#9: They’ve Push Productivity-Through-Leverage to the Limits

Operators know that the velocity of an organization is directly tied to the velocity of its leadership. They also understand that, as a leader, they can only do so much themselves or they risk burning out.

As a result, they’ve learned to maximize their productivity by increasing their leverage. They’ve built an exceptional team and have learned the art of “letting go and delegating.” Because …

Although a million things might need to be done, they don’t all need to be done by you.

Perhaps most importantly, they’ve hired an exceptional executive assistant and taken steps to turn that resource into what we call an Engagement Manager. We don’t have time for a deep-dive into this role here so, for the sake of simplicity, I’ll define it as a cross between a EA and a Chief of staff with two primary responsibilities:

  • Freeing up as much of your time as possible, and
  • Empowering you to invest that time into those things that truly move the needle most.

At the end of the day, Operators realize that the secret to productivity is leverage, and the secret to leverage is building an exceptional team.

Habit #9: Perform the Two-Lists Homework

Step one: Create a bullet point list of 5-10 items of those things that you feel are currently bogging you down, which causes you to spend your time on things that make you feel as though you are not your most productive self.

Step two: Create another bullet point list of 5-10 items of those things that you want to do more of and that you think will proactively move the needle forward the most. These are things that you know yield good results when you do them more often, but you feel that the reactive nature of your life only allows you do those things ad hoc and not as consistently as you would like.

The next step is normally something we’d do with our clients, but you can do it on your own by …

Step Three: Finally, take a look at the two lists. For the “Do Less Of” list, ask yourself: How could I get leverage on these tasks? How could I eliminate them or, at the very least, delegate them? For the “Do More Of” list, ask yourself: How could I free up time to invest into these tasks?

Take at least one of those revelations and act on it immediately. Repeat this exercise often and you’ll soon find yourself with more focus and more leverage than ever before.

#10: They Work with a Coach

One of the most fascinating things about us as humans is that we’re one of the only—if not the only—animals that can predict the future. And as such, we spend a lot of time doing so.

The problem, as Harvard psychologist Dan Gilbert points out, is that we’re really bad at it.  In fact, almost every method we use to predict the future has been proven inaccurate at best.

All except one: Mentorship.

It’s this simple: 

The secret to accurately predicting the future is to work with someone who’s already living the future you want to create.

Operators understand this at a core level, and that’s why almost every one I’ve met was working with at least one coach—often more than one; because they realized that the investment they put into their own growth would come back multiplied many times over.

Habit #10: Look into Coaching (or an Educational Product)

Regardless of where you are in your journey, there’s no doubt in my mind that you’d benefit from coaching. That said, I understand not everyone’s in a place where they can invest in a coach yet.

If that’s true for you, that’s okay: You can experience some of the same benefits simply by investing in your continued education and growth. For example: Purchase a book, invest in an online course, or attend a seminar.

Although I truly believe working 1:1 with a coach is a vital aspect of life as an Operator, any investment made in yourself will pay off—so I’d challenge you to identify and make one of those investments this week; whatever that looks like for you.

Speaking of which …

Take the Next Step in Becoming an Operator

This list was meant to be an introduction to the Operator. Although it covers the ten core traits, and I did my best to accompany each trait with something actionable, it certainly doesn’t paint a 100% complete picture of what it takes to become a True Operator.

But if this intrigued you and you’re serious about upping your game and earning the title of Operator, I’ve got good news: You can take one of two next steps:

  • If you’re a startup CEO or executive who’s either already working with an assistant, or who is open to investing in one, I’d like to invite you to schedule a free 1:1 consultation with one of our coaches. Over the course of this call, we’ll dive deeper in your specific challenges and explore some potential solutions to help you take things to the next level. Click here to learn more.
  • If you’re not ready to take the leap into coaching yet, I understand. That’s why my team and I built the Relationship Marketing Crash Course, a highly-actionable online program designed to give you the tools you need to start generating game-changing opportunities from your network. Click here to learn more.


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