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5 Common Habits of Effective Startup CEOs

5 Common Habits of Effective Startup CEOs

Being the CEO of a startup is a lot of hard work. You need to manage the inevitable chaos, wearing multiple hats as a leader,[1] a thinker,[4] and a doer.[2] It can easily be overwhelming when you need to balance everyday tasks alongside the “big picture” tasks that drive the vision and the future of your company.

Once a startup gets some traction, CEOs have to transition from “doer-in-chief” to leading the company and managing the big picture projects, products, cash flow, team culture, and generally becoming both the metaphorical anchor and captain of the ship. But when your company gets to this point, how do you remain an effective CEO?

Any CEO of a startup will tell you that there is no “typical” workday, but after doing some research I’ve found that many CEOs share quite a few habits that make them successful. Let’s take a look at these common habits and how you can use them too.

Organize A Schedule

One habit (some might call it a skill) of effective startup CEOs is to get organized. Really organized. They’ll make a daily schedule and follow it religiously.

Jason Zook, of Jason Does Stuff, is a vocal advocate of time-boxing.[3] He claims that “blocking off time on my calendar keeps me laser focused and highly motivated.”

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Kate Finley, CEO of Belle Communications, prefers to color-code her schedule,[5] assigning different colors to big-picture topics and scheduling blocks of time for social media, emails, project development, meetings, and even exercise and personal time.

An hourly schedule can prevent you from getting distracted from random tasks while giving you peace of mind that you’re spending dedicated time on your company’s needs. Find the best time to schedule out your day and make this skill a habit.

Compartmentalize Company Needs

One of the things that we’ve noticed effective startup CEOs do is that they successfully compartmentalize the different needs of their company. They focus on the specific areas of their business, setting aside time for product development, team building, and financials.

Fetchnotes CEO, Alex Schiff, has a daily meeting with his team. Schiff says this time is critical for his organization, in that it provides a “cross-functional view of what’s happening in the company.”

Finley takes time daily to work on media relations, team and project development, and general communications, while Ryan Carson of Treehouse compartmentalizes business needs by day. He meets with one manager to review product needs on Mondays, while saving sales and marketing for Thursdays.

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By blocking out time for managing your team and different departments you can be sure that you’ll cover all of your big picture needs while saving time for those other random tasks that inevitably arise.

Do Deep Work Early In The Day

More than one CEO, we found, prefers to concentrate on big-picture business strategy in the morning while leaving meetings for the afternoon.

Says Finley, “I find that [mornings are] best to get the majority of my work done before noon and save time for meetings later in the day.” Michael Karnjanaprakorn, head of Skillshare, goes so far as to schedule meetings only a few days a week, to maximize time for deep work and planning.[6] Once a month, he assesses his calendar and reviews what meetings are upcoming and cancels the inefficient ones. Karnjanaprakorn claims that this process “allows me to be proactive and control my time, instead of being reactive to my calendar.”

Make sure to carve out some space in your schedule in the mornings to do the most important strategic work, while your focus and willpower[7] are at their peak. Review your calendar regularly and cut out or reassess what’s ineffective.

Make Time For Family And Celebration

Startup CEOs know how important it is to take time for personal needs, family time, and celebration.

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Ryan Carson includes family time[8] as part of his daily schedule. Schiff makes time for fun with his team,[9] taking them out for laser tag after the successful completion of a major milestone.

Karnjanaprakorn uses a concept from Tim Ferris called “screen-free Saturdays,” where he refuses to work on his laptop or computer and only uses his smartphone for maps and communication with friends and family.

Separating yourself from your work can give you a much-needed mental break and allow you to approach the next work day – or the next week – with a fresh mind. Again, the easy task is to make more work for yourself; the hard task is taking some time to enjoy your success and spend time on yourself.

Give Your Schedule Space For Reflection

Startup CEOs know that it’s important to take care of themselves because it’s easy to feel like there’s always more work to be done.

“I like to have some time to myself free of office distractions to map out an agenda for what I want to accomplish each day. If I don’t, I find that I’m victim to the whims of whatever random task pops up,” says Chris Myers,[10] CEO of fintech BodeTree.

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There’s always something on your to-do list, and it can be difficult to turn off that part of your brain, even for a short amount of time.

Taking time out of your day to meditate,[11] reflect,[12] journal,[13] or just decompress,[14] is an important factor for success. You’re nurturing both physical and mental well-being, which will do nothing but benefit you and your startup in the long run.


In brief, successful startup CEOs make the transition to a flexible, organized position and focus on the big picture, leading their teams to success. Depending on your personal habits and schedule, create a system that works best for your needs, while saving time to enjoy your hard work.

Featured photo credit: Brooke Cagle via unsplash.com

Reference

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Keith Shields

CEO, Designli

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Last Updated on October 18, 2018

10 Key Characteristics of a Highly Successful Entrepreneur

10 Key Characteristics of a Highly Successful Entrepreneur

When it comes to starting your own business and pursuing your dream of becoming an entrepreneur, it can be advantageous to go all in and embrace the flexibility of finally quitting your day job.

Keep in mind, though, that it takes a special kind of person to take the business world by storm: a person who has cultivated the key characteristics of entrepreneurial success.

People with these characteristics are likely to succeed, whereas people without them have difficulty moving forward with even the most brilliant business ideas.

These characteristics of an entrepreneur are so important that I’ve decided to cover all 10 of them in detail so that you can start your business with your best foot forward.

1. Successful Entrepreneurs Practice Discipline

Plenty of business experts claim that you can’t get anywhere as an entrepreneur without vision or creativity, but that’s simply not the truth. Instead, the one quality that no entrepreneur can be successful without is discipline.

To build an idea into a business, you have to have the discipline to spend time slogging through the least fun parts of running a business (like the bookkeeping), rather than taking that time to do something fun.

Andrew Carnegie, one of the most financially successful Americans of all time, grew up working dull and difficult jobs in factories. Despite going to bed hungry some nights, he continued doing his best work. He was eventually hired by a railroad company and continued to move up the ladder until starting his own successful businesses. Carnegie is a fine example of an entrepreneur dedicated to discipline and hard work. He truly earned his dreams of prosperity and success.

When you’re the boss, there’s no one to keep you at work except yourself — and there’s no short-term consequences for skipping out early.

Sure, if an entrepreneur plays hooky enough he knows that the business just won’t happen, but it’s very hard to convince someone that ‘just this once’ won’t hurt (and to keep ‘just this once’ from becoming a daily occurrence).

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2. Successful Entrepreneurs Keep Calm

Things go wrong when you run your own business.

Most entrepreneurs go through crises with their businesses — and more than a few wind up with outright failures on their hands. But when you’re responsible for a business, you have to be able to keep calm in any situation. Any other reaction — whether you lose your temper or get flustered — compounds the problem.

Instead, a good entrepreneur must have the ability to keep his cool in an emergency or crisis. It may not make the problem easier to solve, but it certainly won’t make it harder.

Honestly, losing your calm is a quick path to becoming the kind of person who gives up in the face of adversity. Instead giving in to frustration, remember classic entrepreneur Benjamin Franklin.

Franklin kept his calm as he experimented and tweaked his inventions again and again in pursuit of success. He didn’t give up during his many failures – he chose to innovate. You can choose innovation, too.

If an entrepreneur can handle failure without frustration or anger, s/he can move past it to find success.

3. Successful Entrepreneurs Pay Attention to Details

Restricting your attention to the big picture can be even more problematic than ‘sweating the small stuff.’

As an entrepreneur, unless venture capital has magically dropped out of the sky, a small expense can be a killer. It’s attention to detail that can make a small business successful when it has competition and it’s attention to detail that can keep costs down.

Attention to detail can be difficult to maintain — going over ledgers can be tedious even when you aren’t trying to pay close attention — but keeping your eye on a long-term vision is just asking for a problem to sneak in under a radar.

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After a business grows, an entrepreneur might be able to hire someone to worry about the details. In the beginning, though, only one person can take responsibility for the details.

Skeptical about the importance of details? Look no further than Howard Schultz, who grew a small coffee shop called Starbucks into one of the most globally successful coffee businesses in the world through his extreme attention to detail.

He is famous for taking all aspects of growing a business into account, paying attention not only to financially smart business decisions, but also focusing on socially responsible business decisions. Details can take you far.

4. Successful Entrepreneurs Embrace Risks

No entrepreneur has a sure thing, no matter how much money s/he stands to earn on a given product. Even if a product tests well, the market can change, the warehouse can burn down and a whole slew of other misfortune can befall a small business.

It’s absolutely risky to run a business of your own and while you can get some insurance, it’s not like most investment options. Even worse, if something does go wrong, it’s the entrepreneur’s responsibility — no matter the actual cause. In order to deal with all of that without developing an ulcer, you have to have a good tolerance for risk.

You don’t need to channel your inner frat boy and take on absolutely stupid risks, but you need to know just how much you can afford to risk — and get a good idea of how likely you are to lose it. If the numbers make you uncomfortable, the risk is too great.

Embracing risks is essential for growth and additional success, as well. Walt Disney, for example, could have stayed comfortable with his advances in the film and animation industries, but decided to expand his brand with a new dream: a theme park that soared above the competition. Without taking this risk, the incredibly successful Disney theme park empire would never have come about.

An entrepreneur has to be willing to accept pretty big risks, with some level of comfort.

5. Successful Entrepreneurs are Balanced

You can take any characteristic too far. There’s a point at which attention to detail can become obsession or calm can become unemotional response.

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As an entrepreneur, you have to be able to balance your characteristics, getting the most of them without going over the edge. But balance for an entrepreneur goes far beyond keeping your characteristics in check, though.

Just as an entrepreneur doesn’t have a boss to keep them at work when necessary, they don’t have one to send them home when they’re done. If you are working for yourself, you have to decide how to balance your work and home life — and if you have a day job to add into the equation, balance just gets more complicated.

Oprah Winfrey, one of the most successful and influential entrepreneurs out there, understands the importance of balance. Winfrey has a lot going on; she runs her own media kingdom, acts, produces films, publishes print, and more. In an interview with Fast Company,[1] she talks about her efforts to balance priorities and self care, saying that she must ask herself what is truly important in each limited day.

You may or may not have as much on your plate as Oprah, but learning how to balance whatever you have going on in life will certainly help you farther along down the road as you learn to be a great entrepreneur.

6. Successful Entrepreneurs are Passionate and Motivated

In order to develop any of the above characteristics, you must have a foundation of passion. Staying disciplined day after day during the building of your business takes unrivaled motivation.

Before you start any business, ask yourself if you can sustain true excitement about your idea during even the darkest days ahead of you. If the answer is yes, then good for you! Nurture your natural motivation by taking these action steps throughout your business journey:

  • Commit to making short and long-term goals. Check in with them often to stay on task.
  • Have a plan in place for the inevitable days when you feel discouraged. Make a list of things that will help keep you motivated and focused.
  • Share your ideas with trusted individuals who are just as excited as you are. They will help keep your enthusiasm rolling even when you are feeling down.

By being prepared for apathetic days and holding fast to your authentic passion, you can actually enjoy your journey to success.

7. Successful Entrepreneurs Adapt

Remember this one word: flexibility. Seasoned entrepreneurs know that change is not only a part of life, but also a part of the business world. Expect change and choose to adapt.

As a new entrepreneur, it will be tempting to cling to your original business plan with no exceptions, even if you notice it isn’t working. Good entrepreneurs know that it’s okay to make smart, informed changes in order to ensure efficiency.

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8. Successful Entrepreneurs are Marketing and Sales Experts

No matter what kind of business you are starting, a knowledge of marketing and sales will save you many headaches. A passion for creating a beautiful handmade lifestyle product is not enough to run a successful lifestyle brand; it is critical that you understand key business principles in addition to your natural skills or great product line.

Not sure how to start? Taking business courses is a great idea, but you can also easily brush up on sales and marketing through free online resources. Check out these 10 Sales Skills Everyone Should Master To Be Successful to begin now.

9. Successful Entrepreneurs Have Strong Money Management

Along with sales and marketing skills, money management is a very useful tool in the box of the entrepreneur. Understanding how to best manage your money can be the difference between early success and early failure in the business world.

If money management isn’t your strongest skill, prepare to hire a financial expert to help you with any tricky business that comes up. Financial guidance and knowledge is never a bad idea.

10. Successful Entrepreneurs Ask Questions and Continually Improve

Pride is a natural human quality, but it’s important to humbly conduct some constructive criticism every now and again on both yourself as a leader and your new business as a whole.

Assess how things are going and be willing to make positive changes if necessary. Here’re 15 ways to cultivate lifelong learning.

If you are always improving, then how can you ultimately fail?

The Bottom Line

Let me remind you of one important fact: the qualities of an entrepreneur listed here are not exclusively available to some people and elusive to others.

Although some people may have natural strengths and weaknesses, these qualities can be learned by anyone interested in taking up the entrepreneurial challenge. It might not be easy to change old habits, but it is absolutely possible to cultivate these characteristics in yourself.

Whether you’re a business owner or an aspiring entrepreneur, with hard work, you can train yourself to develop the qualities that truly determine the entrepreneurial spirit and future success.

Featured photo credit: Unsplash via unsplash.com

Reference

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