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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 August 16, 2018

10 Huge Differences Between A Boss And A Leader

10 Huge Differences Between A Boss And A Leader

When you try to think of a leader at your place of work, you might think of your boss – you know, the supervisor in the tasteful office down the hall.

However, bosses are not the only leaders in the office, and not every boss has mastered the art of excellent leadership. Maybe the best leader you know is the co-worker sitting at the desk next to yours who is always willing to loan out her stapler and help you problem solve.

You see, a boss’ main priority is to efficiently cross items off of the corporate to-do list, while a true leader both completes tasks and works to empower and motivate the people he or she interacts with on a daily basis.

A leader is someone who works to improve things instead of focusing on the negatives. People acknowledge the authority of a boss, but people cherish a true leader.

Puzzled about what it takes to be a great leader? Let’s take a look at the difference between a boss and a leader, and why cultivating quality leadership skills is essential for people who really want to make a positive impact.

1. Leaders are compassionate human beings; bosses are cold.

It can be easy to equate professionalism with robot-like impersonal behavior. Many bosses stay holed up in their offices and barely ever interact with staff.

Even if your schedule is packed, you should always make time to reach out to the people around you. Remember that when you ask someone to share how they are feeling, you should be prepared to be vulnerable and open in your communication as well.

Does acting human at the office sound silly? It’s not.

A lack of compassion in the office leads to psychological turmoil, whereas positive connection leads to healthier staff.[1]

If people feel that you are being open, honest and compassionate with them, they will feel able to approach your office with what is on their minds, leading to a more productive and stress-free work environment.

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2. Leaders say “we”; bosses say “I”.

Practice developing a team-first mentality when thinking and speaking. In meetings, talk about trying to meet deadlines as a team instead of using accusatory “you” phrases. This makes it clear that you are a part of the team, too, and that you are willing to work hard and support your team members.

Let me explain:

A “we” mentality shifts the office dynamic from “trying to make the boss happy” to a spirit of teamwork, goal-setting, and accomplishment.

A “we” mentality allows for the accountability and community that is essential in the modern day workplace.

3. Leaders develop and invest in people; bosses use people.

Unfortunately, many office climates involve people using others to get what they want or to climb the corporate ladder. This is another example of the “me first” mentality that is so toxic in both office environments and personal relationships.

Instead of using others or focusing on your needs, think about how you can help other people grow.

Use your building blocks of compassion and team-mentality to stay attuned to the needs of others note the areas in which you can help them develop. A great leader wants to see his or her people flourish.

Make a list of ways you can invest in your team members to help them develop personally and professionally, and then take action!

4. Leaders respect people; bosses are fear-mongering.

Earning respect from everyone on your team will take time and commitment, but the rewards are worth every ounce of effort.

A boss who is a poor leader may try to control the office through fear and bully-like behavior. Employees who are petrified about their performance or who feel overwhelmed and stressed by unfair deadlines are probably working for a boss who uses a fear system instead of a respect system.

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What’s the bottom line?

Work to build respect among your team by treating everyone with fairness and kindness. Maintain a positive tone and stay reliable for those who approach you for help.

5. Leaders give credit where it’s due; bosses only take credits.

Looking for specific ways to gain respect from your colleagues and employees? There is no better place to start than with the simple act of giving credit where it is due.

Don’t be tempted to take credit for things you didn’t do, and always go above and beyond to generously acknowledge those who worked on a project and performed well.

You might be wondering how you can get started:

  • Begin by simply noticing which team member contributes what during your next project at work.
  • If possible, make mental notes. Remember that these notes should not be about ways in which team members are failing, but about ways in which they are excelling.
  • Depending on your leadership style, let people know how well they are doing either in private one-on-one meetings or in a group setting. Be honest and generous in your communication about a person’s performance.

6. Leaders see delegation as their best friend; bosses see it as an enemy.

If delegation is a leader’s best friend, then micromanagement is the enemy.

Delegation equates to trust and micromanagement equates to distrust. Nothing is more frustrating for an employee than feeling that his or her every movement is being critically observed.

Encourage trust in your office by delegating important tasks and acknowledging that your people are capable, smart individuals who can succeed!

Delegation is a great way to cash in on the positive benefits of a psychological phenomenon called a self-fulfilling prophecy. In a self-fulfilling prophecy, a person’s expectations of another person can cause the expectations to be fulfilled.[2]

In other words, if you truly believe that your team member can handle a project or task, he or she is more likely to deliver.

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Learn how to delegate in my other article:

How to Delegate Work (the Definitive Guide for Successful Leaders)

7. Leaders work hard; bosses let others do the work.

Delegation is not an excuse to get out of hard work. Instead of telling people to go accomplish the hardest work alone, make it clear that you are willing to pitch in and help with the hardest work of all when the need arises.

Here’s the deal:

Showing others that you work hard sets the tone for your whole team and will spur them on to greatness.

The next time you catch yourself telling someone to “go”, a.k.a accomplish a difficult task alone, change your phrasing to “let’s go”, showing that you are totally willing to help and support.

8. Leaders think long-term; bosses think short-term.

A leader who only utilizes short-term thinking is someone who cannot be prepared or organized for the future. Your colleagues or staff members need to know that they can trust you to have a handle on things not just this week, but next month or even next year.

Display your long-term thinking skills in group talks and meetings by sharing long-term hopes or concerns. Create plans for possible scenarios and be prepared for emergencies.

For example, if you know that you are losing someone on your team in a few months, be prepared to share a clear plan of how you and the remaining team members can best handle the change and workload until someone new is hired.

9. Leaders are like your colleagues; bosses are just bosses.

Another word for colleague is collaborator. Make sure your team knows that you are “one of them” and that you want to collaborate or work side by side.

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Not getting involved in the going ons of the office is a mistake because you will miss out on development and connection opportunities.

As our regular readers know, I love to remind people of the importance of building routines into each day. Create a routine that encourages you to leave your isolated office and collaborate with others. Spark healthy habits that benefit both you and your co-workers.

10. Leaders put people first; bosses put results first.

Bosses without crucial leadership training may focus on process and results instead of people. They may stick to a pre-set systems playbook even when employees voice new ideas or concerns.

Ignoring people’s opinions for the sake of company tradition like this is never truly beneficial to an organization.

Here’s what I mean by process over people:

Some organizations focus on proper structures or systems as their greatest assets instead of people. I believe that people lend real value to an organization, and that focusing on the development of people is a key ingredient for success in leadership.

Learning to be a leader is an ongoing adventure.

This list of differences makes it clear that, unlike an ordinary boss, a leader is able to be compassionate, inclusive, generous, and hard-working for the good of the team.

Instead of being a stereotypical scary or micromanaging-obsessed boss, a quality leader is able to establish an atmosphere of respect and collaboration.

Whether you are new to your work environment or a seasoned administrator, these leadership traits will help you get a jump start so that you can excel as a leader and positively impact the people around you.

For more inspiration and guidance, you can even start keeping tabs on some of the world’s top leadership experts. With an adventurous and positive attitude, anyone can learn good leadership.

Featured photo credit: Unsplash via unsplash.com

Reference

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