Navigating the Transition from Founder to CEO

Why So Many Founders Fail as CEO

Navigating the Transition

As an early-stage founder, you might love the lightning-fast speed, flexibility, and creativity that come from working in the start-up world. The adrenaline rush keeps you going through grinding days and “just one more hour” nights.

But as your company scales and changes, your role as founder also needs to change drastically if you want to achieve your most audacious goals. Suddenly, being an individual contributor to product development will become far less important, and managing relationships will become your highest priority. As CEO of a scaling company, your most pressing objectives will be to find, hire, and retain the best talent, woo investors, keep your team’s morale up, and ignite passion for your mission in those who follow you.

To help you artfully master this transition from Founder to CEO, we’re going to show you the 3 most common pitfalls founders run into — and how to avoid them!

Pitfall #1: The Reactive Black Hole

Does this sound like you? Your 2 pm meeting gets canceled and you suddenly have 30 free minutes. Jackpot! You can finally write that HR job description you’ve been putting off... right after you check your inbox, real quick. The top email is simple, you shoot out a response. But that email leads to another email, and another, and before you know it, your calendar is pinging you for your next meeting and your free half-hour is gone.

This infuriating time-suck of reactive work happens when urgency reigns supreme in your world. You feel frustrated with how quickly your work gets derailed by the constant ping of incoming questions and problems. And you never seem to have the time to do the deep thinking your company needs.

How to Avoid It: Combat Reactivity with the Superpower of INTENT

To cultivate a proactive mindset and give yourself the space for deep thinking, you need a pragmatic system of blocking off time, protecting it diligently, and using it for what really matters. We call this Whitespace Time.

Whitespace Time is a weekly recurring block on your calendar. The ideal is to schedule 4-hour blocks at the same time each week, but you can start with two-hour blocks and scale-up for greater impact. Use Whitespace Time only for projects that move the needle most. If you’re not sure where to start, focus on your key priorities as CEO: investing in relationships, setting vision, building, and strengthening your team. You might use the time to write the job description for your next hire or to think about how you can offer value to important people in your network who you want to re-engage.

By protecting your Whitespace Time, you can become a more proactive leader rather than a reactive figurehead. Get intentional with how you use your time to increase velocity and drive the projects that produce the biggest results.

Pitfall #2: The Mental Strain of Burnout

Too many founders feel like they’re teetering on the edge of burnout, and even mistake this as a sign they’re doing something right! Urgent-but-not-important tasks pile up on your desk and drain you of the mental space needed to do your best creative work. Every day feels grinding! You’re disconnected from your growing team, and since you’re stretched to the breaking point, you find it difficult to focus or do your best brain work.

How to Avoid It: Increase Output 10x while Cutting the Strain in Half with the Superpower of LEVERAGE

One of the most powerful ways to regain your mental space and bring massive leverage to the office of the CEO is by working with a rockstar executive assistant. I know what you’re thinking—isn’t an EA just someone who schedules my meetings? Not if you do it right! In fact, when you fundamentally change how you approach the role of an EA, they can become the most powerful resource for unlimited scale.

To start, you can utilize your EA to deliver experiences to your network and relationships at a far greater scale than you could alone through a process called LoopLeverage. LoopLeverage helps you close the loop whenever a commitment is made—either by you or to you.

Imagine this. You have a call with a previous colleague you’ve known for years. She offers to introduce you to an engineer who she thinks would be perfect for your growing team. You’re ecstatic since you’ve been looking to fill this role for months, so you thank her for the offer, end the meeting, and… promptly forget about the exchange! (No judgment, we’ve all been there). Four weeks later when you finally remember to follow up, she’s on vacation and you find yourself waiting another 2+ weeks before you finally get that introduction.

Now let’s reimagine this all-too-common situation with an EA. You get the intro offer, you end the meeting, you immediately send your EA a voice dictation with the details of the promised introduction. Your EA drafts a follow-up email for you to send, thanking your friend again for the introduction offer. Your EA also creates a reminder task in their task management system and titles it: “LoopLeverage | Did Celine give introduction to Jamal?” One week later when your EA sees the intro hasn’t been made, they proactively write up another draft:

Your friend feels terrible for keeping you waiting and makes the introduction that same day. In the startup world where velocity is your one unfair advantage, the difference between 6–8 weeks and 2 weeks can be everything.

Effectively leveraging your EA allows you to build the relationships you need to drive breakthrough opportunities, while also freeing up your time and giving you more mental breathing room.

Pitfall #3: The Failure to Evolve as Your Company Scales

Too many founders fail to realize that there comes a point when their whole job needs to change — the key focus shifting to relationships instead of product. Your scrappy-do-it-all founder mentality that helped you at the beginning of your journey will become a massive bottleneck as you steer your company’s growth as CEO. Founders often struggle to remove themselves as an individual contributor but this step is necessary if you want to effectively manage the relationships that determine your company’s success—whether that means finding, attracting, and retaining talent or generating opportunities from your network like game-changing fundraising.

The challenge is, relationships are always important but very rarely urgent. As a result, they most commonly wind up neglected—ultimately holding you back as you scale your company.

How to Avoid it: Build Irrationally Loyal Relationships with the Superpower of Fellowship

Mastering the superpower of Fellowship is all about understanding the importance of relationships, and properly investing into and deepening them with the right people. The simplest yet most powerful way to build Fellowship with your team and network is through a tactic we call Positive Alacrity. Positive Alacrity comes down to one little habit:

When you think something positive that you genuinely believe, voice it.

The power behind Positive Alacrity comes from delivering micro-moments of positivity that have a profoundly uplifting impact on those you interact with. By operating in micro-moments, you drastically reduce the effort it takes to provide great experiences to others, making it easy to create lasting feelings of happiness and fulfillment for both yourself and others.

To make Positive Alacrity a habit, start by recognizing when you have positive thoughts about people. These positive thoughts happen multiple times a day, but most of them go unnoticed. To build this skill, intentionally lookout for moments when you think something positive about individuals on your team, people in your network, and even strangers you meet throughout your day.

The next part is easy. When you notice a positive thought pop into your head, say it out loud!

Imagine you catch one of your team members taking the time during a busy week to support your intern. Rather than letting that thought slip by unnoticed, try practicing Positive Alacrity and voicing that thought. It might sound something like this:

“Hey Jada, I know things have been really stressful with quarter closing, but I noticed that you still took the time to help the intern learn pivot tables. I really appreciate how you put people first like you did there.”

You’ll notice our example is very specific. You could’ve just said “nice work helping the intern,” but specificity here is key! To get more specific, just think about what really impressed or inspired you about the encounter.

Ready to Unleash Your Superpowers?

Many entrepreneurs fail to prepare for the transition from early-stage founder to Superpowered CEO — it can be a rough change to go through, especially on your own! To artfully master this transition, you will need:

Intent: Ensure your time is invested in what moves the needle most
Leverage: Become a productivity powerhouse & use an EA to free up 8 hours/week
Fellowship: Build an insanely loyal following in your team and network

The tactics and skills outlined above are a great place to start. But if you want to go deeper and master the 3 superpowers, Mindmaven can help you learn:

• How to save 8+ hours/week by fundamentally changing how to hire and work with an executive assistant.
• How to become more proactive and highly focused on the things that move the needle most.
• How to build an irrationally loyal team you don’t have to worry will quit on you.
• How to utilize your one unlimited asset — your network — to generate those mind-blowing opportunities you usually only get through serendipity

LEARN MORE

Mindmaven is an executive coaching firm that’s spent the last decade working with 100’s of leaders, including unicorns like Roblox, Reddit, and Thumbtack, as well as heavy hitters such as Sequoia Capital, Andreessen Horowitz, Benchmark, and First Round Capital. Mindmaven’s coaches help CEOs and founders free up 8–10 hours each week by fundamentally changing how to work with an EA/Chief of Staff.