Startup CEOs: A Guide to Successfully Scaling Yourself (While Scaling Your Business)

11 min read
Graphic illustrating the act of scaling yourself with the words "How to scale yourself." Features a professional and an upward arrow.

"How to scale yourself" graphic with a professional and an upward arrow.

Many founders and CEOs embrace the idea of scaling their startup, but you may be overlooking something equally important: Scaling yourself. The truth is, a company can’t out-scale its leadership (or, if it does, it’s often not long before that leader burns out).

As we’ll talk about below, what got you here won’t necessarily get you there. There will always be new challenges to overcome. The trick is developing a system to consistently meet and overcome these challenges while ensuring your time and resources are being invested in the most efficient way possible. 

It’s really this simple: As a company grows, so too must its leadership. So in this article, I’d like to share three ways of successfully scaling yourself alongside your startup.

#1: Scaling Yourself Means Embracing an Identity Crisis

In the early stages of their company, many CEOs embrace the “scrappy, do-it-yourself startup entrepreneur” identity: A leader of many hats (and just as many responsibilities) who works miracles with limited resources and an even more limited budget.

And while that approach is often necessary to establish initial success, it can become harmful. As a company becomes more successful and the pressures and responsibilities on the CEO mount, that well-intentioned “do-it-yourself” mentality can fast-track burnout.

As a leader, it’s important to be open to adopting new leadership “identities” to continue successfully scaling yourself as you meet the growing needs of your organization. A startup requires a different type of leader at different stages, and it’s important to ensure your leadership style is aligned with the needs of the company.

Upgrade and Ditch Your Old “Scrappy Entrepreneur” Identity

So don’t be afraid to let go of that “scrappy, do-it-yourself startup entrepreneur” identity for something more beneficial to your company. If you’re not certain what type of leader your company needs right now, here’s a short-but-powerful exercise:

  1. Compile a list of leaders you admire. This list can be compiled from leaders you personally know (such as your peers) or those you just know of (such as historical leaders or A-list entrepreneurs).Ideally, these leaders will be running a company that’s a stage or two ahead of where you are today.
  2. Under each name on the list, write down 1-3 specific traits you admire. Is it their ability to build a team? To delegate? To resolve conflict? To develop thought leadership?
  3. Next to each trait, rate yourself on a scale of 1-5, with one being “poor” and five being “great.” How good are you at that trait? Are these areas you could improve to continue scaling yourself?
  4. Compile a list of those traits you ranked yourself three or below on. This should give you a good idea of the type of “identity” or leader you need to become when scaling yourself.
  5. Ask yourself: What do I need to do to improve in these areas?


In many cases, it’s as simple as reaching out to the leaders you admire and asking for their help. If you don’t have a direct line to that leader, see if you can identify someone else who exemplifies that trait. If nothing else, start with a few high-quality books or blog posts.

It’s important to complete this exercise—or one like it—for every major milestone your startup passes. 

Chances are, the type of leadership needed to take your business to the next level will change … And you want to know that in advance, not after-the-fact, so you can continue successfully scaling yourself.

#2: Stop Wasting Your Most Valuable Asset When Scaling Yourself

When an early-stage founder wants something done, they generally have to do it themselves. And while that approach—or identity, as we mentioned above—may serve them well in the beginning, it can do more harm than good as the company scales.

As a leader, your time is your most valuable asset—yet many leaders consistently mis-invest that resource in what’s urgent rather than what’s truly important. This often leads to executives working increasingly-longer hours but feeling increasingly less productive.

It starts to feel like too much of their time is spent on tactical, low-impact aspects of being an executive—such as combating a constantly-overcapacity inbox, booking seemingly-endless meetings, or arranging nebulous travel details.

Unfortunately, this often comes at the expense of their direct reports’ needs, resulting in a CEO who feels like a bottleneck. As their backlog grows and increasingly-important responsibilities fall through the cracks, they begin to feel like they’re failing their team and undermining everything they’ve worked so hard to achieve.

Focus on What Matters Most (and Delegate Everything Else)

So what’s the solution? Learning to focus on what matters most and delegating everything else is key to successfully scaling yourself. If something doesn’t need to be done by you, it probably shouldn’t be. 

Remember, as a leader your time is as valuable as it is scarce, so it’s important to invest it only into the proactive tasks that matter most; because the truth is, you’re never going to “find” time to work on those important-but-not-urgent projects you’ve been putting off. You’ve got to make the time.

Here’s a quick exercise to help you figure out what daily tasks you could (and should) delegate so you can continue scaling yourself.

Step One:

Create an Excel sheet and log every task you’ve completed within the past week that took at least 5 minutes of your time. 

Be as thorough as possible: Try to include everything from writing follow-up emails to managing your calendar to taking meetings and everything in-between.

Step Two:

Review each task and categorize them into one of three categories:

  1. Tasks you know should be delegated.
  2. Tasks you could be convinced to delegate.
  3. Tasks you are completely unwilling to delegate.

Step Three:

Rate each task on a scale of 1-3—with 1 being low and 3 being high—based on the value they contribute to your startup’s success.

Step Four: 

Highlight any tasks categorized as “should be delegated” or “could be convinced to delegate” with a value ranking of “1” or “2.” Begin outsourcing those tasks to someone you trust, such as your Engagement Manager or Chief of Staff.

Ready to start scaling yourself but not sure who to delegate to? If that’s the case, I’d like to introduce you to a unique resource I call the Engagement Manager.

What Does an Engagement Manager Do?

An Engagement Manager, or EM, is one of the most valuable hires an executive can make. They’re a hybrid between a skilled EA and a chief of staff, whose primary responsibility is empowering you to reach your fullest potential as a leader.

An EM helps you accomplish this by focusing on two primary objectives: Freeing up your time and increasing the quality (and consistency) of your interactions.

We’ve written extensively about the unique-and-powerful role of an Engagement Manager (and how to turn your current EA into an EM) here, and I highly recommend checking it out.

For now, here’s just a small sample of how an Engagement Manager could help you focus on what matters most.

  • Inbox Shadowing: With the right skills, permissions, and calibration, an engagement manager can reduce the time you spend on email by 40-60% by prioritizing your inbox into three key categories before you even see it (and even drafting emails on your behalf).
  • Clearing the Bottleneck: An EM can improve your velocity and throughput by tracking your commitments, structuring your day around your most important priorities, and ensuring you follow through on near-100% of your responsibilities faster than ever.
  • Legendary Leadership: An EM can help you build stronger relationships with your team—often boosting morale and lowering attrition as a result—by enabling you to deliver higher-quality interactions across the company at deeper, more personal levels.

Don’t be afraid to invest money into tools and resources that free up your time and make your job a little more efficient. Remember: You aren’t that scrappy founder anymore and there’s nothing noble about working 12 hours when you could get the same work done in eight; it just isn’t sustainable for you or your business.

For one of the most valuable investments you can make in your career, check out The #1 Shortcut to Reaching Your Fullest Potential as a Startup CEO and Leader.

#3: Leverage the Only Proven Method to (Accurately) Predict the Future

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 working with someone already living the future you want to create.

As many high-performers will tell you, professional mentorship is vital to reach your full potential as quickly and efficiently as possible, and some of the best professional mentorships you’ll find come from working with a coach.

But here’s the thing: Most people are incredibly disillusioned when it comes to coaching, and one of the most common misconceptions is that coaches are for underachievers or those who simply can’t “figure it out on their own.”

This couldn’t be further from the truth.

The people who will get the most out of a coaching relationship are those who are already good at what they want to do but want to be great. Those who want to go from ordinary to extraordinary, who want to exercise mastery over their life, business, and relationships.

Because here’s the often-unspoken counter-intuitiveness of entrepreneurship: What got you to “good” often won’t get you to “great.” Or, at the very least, it won’t be the most efficient path to greatness.

Successfully Scaling Yourself Through Mentorship

Scaling yourself through your ability to change and grow as a CEO is vital to your continued success. The problem is most CEOs learn by doing, and “doing” is the most inefficient (and often painful) way to learn anything.

And before you think this is a pitch for our coaching program, let me specify: You don’t have to work with us (though we’d be honored by the opportunity). You don’t have to work with a “paid” coach at all to continue successfully scaling yourself in this way.

You can find unofficial coaches and mentors just by looking at your startup ecosphere, but you’ll want to go about it the right way. 

Here’s a short exercise you can complete to get the ball rolling toward scaling yourself:

  1. Identify 3-5 aspects of your business or your leadership that you want to improve. For example: Product dev, marketing, delegation, or team building.
  2. For each aspect, identify one person in your network (or slightly outside your network) who you feel is operating at the levels you want to reach.
  3. Come up with 5-7 questions you can ask each person. These questions are to be designed to help you uncover both how they think about the particular aspect of the business, and the specific actions they take.
  4. Reach out (or ask for introductions) to each of these people. Ask if they’d be willing to spend 30 minutes helping you with a research project you’re working on.
  5. After implementing the strategies you learn from the meeting, reach back out to them in 2-3 weeks, thanking them for their insights and sharing some of the positive results you’ve created.

Continue building a natural, value-focused relationship with them over the coming weeks and months. Although not an official mentor or coaching relationship, I think you’ll find these informal arrangements can be incredibly valuable and rewarding.

Not sure how to build these relationships? Check out our Relationship Management Crash Course!

Keep In Mind: None of This Matters Unless…

None of this matters if you fill up the time created by these three simple strategies with more Slack messages, emails, and ad-hoc meetings. 

To ensure you’re successfully scaling yourself as you scale your company, you need to invest your newfound time in high-impact tasks that move the needle. 

That’s why we developed a time management approach called Whitespace Time. Put simply, Whitespace is all about focusing on what’s proactive and important rather than what’s reactive and urgent.

Get your free copy of our Whitespace Time – A Guide to Proactive Time Management eBook here, to ensure you’re successfully scaling yourself by carving out time to focus on what matters most!

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