Startup CEOs: How to Scale Yourself (While Scaling Your Business)

Many founders and CEOs embrace the idea of scaling their startup, but overlook something equally important: Scaling themselves. The truth is, a company can’t out-scale it’s 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. As a company grows, so too must its leadership. And in this article, I’d like to share three ways CEOs can scale alongside their startup.

Quick favor before we get started: If you’re the CEO of a growing, venture-backed startup CEO, would you be willing to help my team and I with a project? We’re writing a book for startup executives, and want to make it as meaningful, relevant, and valuable as possible.

To that end, we’re interviewing startup leaders about their experience. As thanks to participants, we’re offering a free copy of our most popular book: Whitespace Time – A Proactive Entrepreneurs Guide to Time Management. Use it to ensure you’re always carving out time to focus on what matters most for your business.

Click here to participate in the survey and get your free book!

#1: Embrace 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” as the needs of your organization evolve. 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.

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 need 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 at you at that trait?
  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.
  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.

Remember: What got you “here” wont’ necessarily get you “there.” 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.

#2: Stop Wasting Your Most Valuable Asset

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.

So what’s the solution? Learning to focus on what matters most, and delegating everything else. I’ll introduce a powerful resource to accomplish that in just a moment but, first, here’s an exercise to help you identify what daily tasks you’re currently doing that could (and should) be delegated to someone else.

  1. Log every task you’ve completed in the last week that took at least 5 minutes of your time, and 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.
  2. Categorize each task into one of three categories: 1) Tasks you know should be delegated, 2) tasks you could be convinced to delegate, and 3) tasks you’re completely unwilling to delegate.
  3. 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.
  4. Isolate tasks categorized as “should be delegated” or “could be convinced to delegate” with a value ranking of “1” or “2.” Begin developing a game plan to delegate those tasks to someone you trust.

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. 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, who’s primary responsibility is empowering you to reach your fullest potential as a leader.

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.

If that sounds intriguing, you can read more about the role of an EM here. But either way, I recommend starting out by completing the Delegation Log exercise above.

#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 to work with someone who’s 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 mentorship you’ll find comes 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 for those who simply can’t “figure it out on their own.”

This couldn’t be further from the truth.

The people who are going to 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, their business, and their 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.

Your ability to change as grow as a CEO is vital to your continued to 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.

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:

  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 should be designed to help you uncover both how they think about the particular aspect of the business, as well as 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!

Can I Ask for a Favor?

There you have it: Three simple strategies and exercises to ensure you’re scaling yourself as you scale your company. If you take the time to complete each exercise, I think you’ll find yourself better equipped to lead your startup through its current challenges, and whatever awaits in the future.

But before I let you go, I have a favor to ask: If you’re the CEO of a growing, venture-backed startup CEO, would you be willing to help my team and I with a project? We’re writing a book for startup executives, and want to make it as meaningful, relevant, and valuable as possible.

To that end, we’re interviewing startup leaders about their experience. As thanks to participants, we’re offering a free copy of our most popular book: Whitespace Time – A Proactive Entrepreneurs Guide to Time Management. Use it to ensure you’re always carving out time to focus on what matters most.

Click here to participate in the survey and get your free book!

2019-08-23T19:21:39+00:00

About the Author:

Patrick Ewers is the founder and CEO of Mindmaven, an executive coaching firm and educational platform focused on helping startup CEOs, executives and their team members achieve their fullest potential and generate game-changing opportunities by better leveraging the most valuable relationships in their network.


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