14 Ways CEOs Know When to Level Up

What is one way to know when it is the right time to level up your business?

To help you know when to level up in business, we asked business professionals and leaders this question for their insights. From growing in your personal life to having a growth mindset, there are several indicators that it’s time to level up in business.

Here are 14 ways to know when to level up in your business:

  • Never Get Too Comfortable
  • Listen to Client Needs
  • Have a Growth Mindset
  • Scale Using an Automation Platform
  • Grow in Your Personal Life
  • Pay Attention to Your KPIs
  • Increase Task Delegation
  • Reach More Markets
  • Consider Your Cash Flow
  • Streamline the Process
  • Start Mentoring New Hires
  • Have the Correct Systems in Place
  • Focus on Client Retention
  • Reinvest When Demand Exceeds Supply

Never Get Too Comfortable

One big way to know if it’s time for your business to level up is if you’re no longer scared of what the future may bring. If you’re comfortable with your profit margins and your customer service is solid, then you may be satisfied with where you’re at. 

However, savvy business owners know that such conditions are ripe for making growth-centered changes. Being in a comfort zone is great, but if you’re not breaking a sweat, you’re not breaking new ground.

Carey Wilbur, Charter Capital

Listen to Client Needs

Within the insurance industry, our clients’ needs may vary over time. It is essential to have important client conversations to better understand any life or family changes. In doing so, you may find opportunities to expand and level up your business.

For example, you might service a client for many years, but then they start a business and require other products and services. As part of your client life cycle, retention should be key, and a key part of retention is to constantly evaluate your clients needs as a way to level up in customer service and also in your product and service offerings.

Chris Abrams, Marcan Insurance


Have a Growth Mindset

Once you’ve pushed to the boundaries of what you thought was possible for your business, and you realize that you’re capable of even more — that’s the time to level up. Having a growth mindset is a key component of a successful entrepreneur, so it’s important to always be on the lookout for new opportunities. After all, when it feels like you’ve achieved all that you had set out to do thus far, there is no place else to go but up.

Allan Switalski, LendThrive


Scale Using an Automation Platform

The best time to level up is when your business is growing in size and scale. One of the best ways to level up is by investing in a low-code or no-code hyper-automation platform. 

At Comidor, we specialize in digital business transformations and offer state-of-the-art software development and automation solutions that would help to scale your business operations. This is no small feat, so before choosing a vendor, most companies should try before they buy. 

In our case, all clients can request a free trial. This way, they can get a better understanding of the capabilities and trust that our automation platform is right for their business growth and expansion needs.

Spiros Skolarikis, Comidor


Grow in Your Personal Life

I was recently on a Zoom where Ben Chestnut, CEO of Mailchimp, spoke about their recent $12B acquisition by Intuit. He spoke of a time many years ago when he was offered $1B for Mailchimp, and he turned it down. 

The prospective buyer told Ben to call him when his personal life was in a different place, and he would consider selling the company. The point is that people grow just like businesses do. 

At a certain point, people naturally look to  level up their personal lives with new challenges. When a CEO wants to level up in their personal life, it's a good time to level up their business as an outlet for growth.

Brett Farmiloe, Markitors


Pay Attention to Your KPIs

Scaling accordingly is one of the most challenging and critical aspects of “leveling” up that a business can make. Pay close attention to your KPI's. If a solid cost-benefit analysis shows solid retention and growth in new customers with fewer churns, then that would be a significant factor in letting you know to plan for bigger things. 

Your ROI should always be measured against what you spent in the past and what you can expect in the future. Therefore, understanding the conversions of your sales team in client or customer retention will be a key factor in the lifetime value of your product or service and the ability to increase your audience based on deeper investments down the line.

Nick Shackelford, Structured Agency


Increase Task Delegation

You will know that it is time to level up your business when you are increasing task delegation and outsourcing work instead of being a one-man operation. Transitioning to task delegation and outsourcing means that you are ready to step up another level into a supervisory role. 

This means letting other people do the nitty-gritty while you oversee the overall operation and lead your team towards your business goals.

Brogan Renshaw, Firewire Digital


Reach More Markets

When work becomes overwhelming for the current team to handle, it’s time to level up the business. The need to make headway in the business comes in different forms. It could mean diversifying your products to reach more markets, increasing manpower, or updating your device and equipment to the latest models. 

But whatever the need is, make sure to have enough financial capabilities and employ the right strategies to overcome bottlenecks or difficulties moving forward.

Michelle Ebbin, JettProof


Consider Your Cash Flow

Perhaps the strongest indicator that you need to level up your business is if you have a strong cash flow. Although strong sales numbers and consistently beating monthly and quarterly goals are great, such success means nothing if there is not a plan to profitability. 

As such, consider upping your business when you have reached a consistently positive cash flow for more than three months. This will allow you to take strategic risks, bring on more support, and scale the business to an even greater degree.

Inesa Ponomariovaite, Nesa's Hemp


Streamline the Process

You will know it is the right time to level up your business when you have streamlined your onboarding process. This means you have the training, guidelines, and an employee handbook in place. 

This is an indication that you are able to add employees to the company and have them be successful in their positions because you have provided them with the tools for success.

Peter Fishman, Mozart Data


Start Mentoring New Hires

One indicator that your business is ready for the next big step is when your team starts mentoring new hires with their knowledge and experience.

It means that the team you've mentored, had firsthand participation with your endeavors, and closely share the same vision as you can impart their experiences to junior employees. It shows that the workforce quality has a secure future ahead.

Workforce quality and innovation in your business may plateau if you miss out on this opportunity.

Lisa Richards, The Candida Diet


Have the Correct Systems in Place

If you have a trustworthy team, a concrete marketing strategy, a solid CRM system, and finances that are in order, then it may be time to level up. By having the correct systems in place to handle additional leads and revenue, you’ll be more likely to succeed when you take the next steps in your business. 

It’s important that your team is large enough to handle more clients. Your employees should be people that you can delegate tasks to easily. You're going to have a lot more on your plate, so you need to have people around you that you can count on. 

If your business feels solid on all fronts, then it's time to level up.

Isaiah Henry, Seabreeze Management


Focus on Client Retention

When the majority of your business isn’t coming from repeat clients or referrals, that’s a major sign that you need to level up. The best measure of a successful company is this: are your clients thrilled? 

And, of course, your employee's matter, but the truth is the clients will only be thrilled if you have a happy team so it’s still inherent in that question. At our company, we have a 92% client retention rate. That’s how I know we’ve greatly leveled up from where we started.

Shama Hyder, Zen Media


Reinvest When Demand Exceeds Supply

When the demand for your services exceeds what you can supply, you know it's time to build your team and partnerships by reinvesting in your business with talent and resources. But, the trickiest part here is also knowing when to do it so that window of opportunity doesn't pass you by. Timing is everything.

Yat-Cheong Au, AEC Alarms


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Mercy - CBNation

This is a post from a CBNation writer. CBNation is a Business to Business (B2B) Brand focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts ( and videos ( CBNation is proudly powered by Blue 16 Media.

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