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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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Published on October 8, 2019

How to Advance Your Career (and the Big Mistakes You May be Making)

How to Advance Your Career (and the Big Mistakes You May be Making)

The late writer William S. Burroughs once said that “When you stop growing, you start dying.” It might have a morbid undertone, but it’s one hundred percent true in terms of one’s career.

The days of finding a job with one company that you can stick with for 30 years, and simply relax as you move up its company escalator are few and far between in today’s world. This isn’t necessarily bad news. On the contrary, it means that you’re the one in charge of shaping your career advancement.

By putting these principles and behaviors into practice, you’ll begin to see how to advance your career quickly. Ready? Let’s get started…

1. Define What Success Is for You

There’s no right or wrong definition of what success in your career looks like. The important thing is to figure out what success looks like for YOU. It might, and probably will, change along the way, but if you don’t have some sort of milestone on the horizon, then you won’t know which direction to go in.

Think about success in your career in terms of one year, five years, and 10 years. Once you have that, it’s time to lace up your boots and get to work.

2. Learn How to Develop and Follow a Plan

Nobody just stumbles upon success accidentally. Sure, they may stumble upon breakthroughs or new methods accidentally, but all success stories have one thing in common — a plan.

Establish a timeline for the things that you want to achieve in your career in the next year, five years, 10 years, and so on. Consider the skills that you’ll need to learn to make these things happen and work on acquiring them.

3. Surround Yourself With Those Better Than You

It’s a rule of thumb among musicians that if you want to get better, then you need to get out of the bedroom and play with people who are better than you.

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By surrounding yourself with people who are better than you and where you want to be, you’ll not only see how these people climbed to where they are in their respective fields, but you’ll learn from them and naturally want to push yourself to be better in your own job as well.

4. Seek Out a Mentor(s)

A mentor will not only be able to help you refine and reach your career goals, but will be invaluable in landing promotions and finding unadvertised job openings.

One unique approach is to work on fostering a relationship with a mentor both within and outside of your company. This will help in giving you different perspectives as you rise up through the ranks in your company and career overall.

5. Stop Wasting Your Mornings

You may not think you’re a morning person, but if you can learn to be one, you’ll thank yourself 10 years down the road.

Prepare a to-do list of tasks that you want to accomplish the day before and work on knocking them out for at least one hour before you respond to morning emails. The problem with responding to emails first, is you’re giving your attention to somebody else’s agenda, instead of plotting your own course for the day.

6. Arrange or Attend a Networking Party

If you’re attending networking events simply because you might get a few free drinks, you’re doing them wrong. These events are great for meeting new people and forming relationships. Your goal shouldn’t be to get hired by the end of the night, but to simply make a good impression by being friendly and authentic. So what’s next?

Reach out a few days later via email or on social media to follow up and connect!

7. Pick Up Some New Skills

Nobody wants to be the old dog that can’t learn any new tricks. To move up in your career, you’re going to likely need to pick up new skills along the way. Maybe your company offers on-the-job training or you have the option of taking online classes at night.

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By learning new skills, you’ll not only be able to expand upon what you can already do, but you’ll make yourself more valuable to your employer and future employers.

8. Exploit the Benefits Already at Your Disposal

Remember what we just said about the possibility of your company providing on-the-job training? Take advantage of these sorts of benefits!

If you’re working for a company that allows you to job shadow other employees or has company mixers, you should attend these. They not only allow you to develop your skills within the company, but show seasoned executives within your field that you’re interested in more than just clocking in for a paycheck.

9. Make Yourself Indispensable

Good help is hard to find and employers want to retain outstanding employees. If you can learn to make yourself indispensable to your company, you’ll not only communicate that you’re successful, but will have a lot more job security. What’s this entail though?

It’s actually not all that difficult. By being reliable, adapting to new challenges, and holding your own work and performance to a high standard, you’ll stand out among your peers and others will take notice. Easy enough, right?

10. Get Off the Fence

People who advance in their careers are those who don’t shy away from voicing their opinion and stand up with authority when the opportunity arises.

If a problem arises in your company and you think you might have a solution or are willing to work to find one, then let others know. Employers value and promote problem solvers. Start off with something small and work your way up towards tackling more difficult tasks and projects.

11. Don’t Wait for More Responsibility, Ask for It

If you want more responsibility in your job, then be open about it with your manager. Your manager may be so busy with their own work that they weren’t aware you were looking for more challenges.

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Just make sure you can handle it and that you already show strong performance in your current duties. And if your manager doesn’t seem supportive about offering you more responsibility, well, then it could be time to look for new employment.

12. Stop Wasting Time on What You Don’t Want

If your career goals start with “I should do this…” there could be a problem. This kind of language in referring to goals can doom them to failure because the want isn’t there.

Consider using the RUMBA method (Reasonable, Understandable, Measurable, Behavioral and Agreed) when setting your goals. That “agreed” part should really be “want.” By going after career goals that you actually want to accomplish, you’re much more likely to achieve them.

13. Seek Out Feedback and Apply It

Simply doing your job might not always push you up in your career advancement. Too often, employees just assume that their bosses will notice their performance strides and reach out when the time is right to advance.

Don’t be afraid to regularly seek out feedback and ask for constructive criticism. It not only shows that you value your manager’s opinion but demonstrates that you care about your job and want to become better in your chosen field.

14. Pick Your Bosses Wisely

Advancing in your career can move a lot quicker if you’re working for the right people. If your boss isn’t any good at their job or doesn’t value you, then moving up could become difficult.

A great boss though, will be able to help you capitalize on your strengths and be an advocate for your success. If there aren’t any strong developers of talent in your management chain already, then look around for some and seek them out as mentors.

15. Learn to Develop Your Sense of Timing

The odds of asking for a promotion or raise are in your favor with over 70 percent of respondents to a survey from PayScale reporting some success. One thing to keep in mind that can make all the difference is when you ask.

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Some corporate cultures may prefer that employees reach out about advancement during their annual review, but maybe you work for a more free-spirited startup. The best approach may be to take note of when others advance and ask about how the organization handles employee development.

16. Work Hard and Promote Yourself

Working hard and delivering a solid job performance are the keys to advancing in your career no matter what field you’re in. This doesn’t mean you need to be completely humble about your accomplishments either.

Keep a record of your positive impact within the organization and let others both within your company and your field know that you’re enthusiastic about your role and work.

17. Don’t Just Build Your Network… Cultivate It

It’s way too easy to add new people to your LinkedIn network and then forget about them for all eternity. Rather than just collecting business cards or social media contacts, you should be cultivating relationships with the ones you already have.

Follow up with people that you haven’t spoken to in a while, offer to connect them with somebody you know in their field, or ask about a new job title they may have taken on. Doing so could be the spark that leads to a potential job referral.

18. Join a Professional Organization

The National Association of (insert your industry here) and other professional organizations can still offer a great wealth of advantages from networking to industry insights, and skill development.

Even outside of professional organizations dedicated to particular job fields, civic organizations can also be fantastic for making new contacts. After all, so much about career advancement is who you know, and you never know who you’ll meet who knows somebody else who is looking for someone with your skills and experience.

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Featured photo credit: JESHOOTS.COM via unsplash.com

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