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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

More by this author

Keith Shields

CEO, Designli

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Last Updated on February 11, 2021

10 Secrets of Making Every Presentation Fun, Engaging, and Enjoyable

10 Secrets of Making Every Presentation Fun, Engaging, and Enjoyable

Not a lot of people are good at public speaking. You could even say that virtually everyone needs to get some practice, and preferably good guidance, before they can learn to stay calm when facing a room full of people. Having all eyes on you is an uncomfortable experience and it takes time to get used to. However, even if you can manage to control your stage fright and stay focused, it doesn’t necessarily mean that your presentation won’t put people to sleep. This is usually the case with long presentations on a very dull subject, with the presenter speaking in a monotone voice and dimming the lights to play a PowerPoint presentation.

You have to work hard to develop the right skills

If you want to be remembered and actually get people engaged, you need to make your presentation fun and enjoyable, without coming off as corny or desperate to please. I know, it doesn’t sound that easy at all! A good presentation during a promotional event or given to an important client can be a game changer for your business, so it is easy to get stressed out and fail to perform all that well. Luckily, giving an interesting lecture is something that can be practiced and perfected. There is plenty of advice out there on the topic, but let’s look at the most important aspects of giving a memorable and fun presentation.

1. Make your presentation short and sweet

With very long, meandering speeches you tend to lose the audience pretty early on, and from then on out it’s just a test of endurance for the few bravest listeners. Not only will people’s attention start to drop rapidly after sitting and listening to you talk for 30 minutes, but you also risk watering down your core ideas and leaving your audience with little in the way of key phrases and important bits of information to take away from the whole ordeal. Famous speakers throughout history have known the importance of condensing the information by using well thought out sentences and short phrases loaded with meaning.

JFK’s famous: ”It’s not what your country can do for you, but what you can do for your country,” expresses so much in very few words and gets the audience thinking. Ancient Spartans, for example were famous for their quick, dry wit, often demolishing their opponent’s argument with a single word or phrase. You’ll want to channel that ancient spirit and be as concise as possible when preparing your presentation.

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2. Open up with a good ice breaker

At the beginning, you are new to the audience. There is no rapport, no trust and the atmosphere is fairly neutral. Even if some of the people there know you personally, the concept of you as an authority on a particular matter giving a speech will be foreign to them. The best way to encourage a warm and friendly atmosphere is to get some kind of emotional response out of the audience right at the beginning. It doesn’t matter what emotion it is, you just need to connect with them on a more personal level. It can be shock, curiosity, laughter, knowing smirks, nervousness – whatever gets them out of that initial feeling of indifference. There are different kinds of effective ice-breakers, but generally speaking, the most successful ones utilize one of these tactics:

  • Joking
  • Tugging on their heart strings
  • Dropping a bombastic statement
  • Telling an interesting and relevant anecdote
  • Using a metaphor or drawing comparisons

You can make a small, self-deprecating comment, stir the presentation one way and then suddenly surprise the audience, use sarcasm, open up with a short childhood story that taught you a lesson, quote a famous person and elaborate on it from personal experience, use an inspirational anecdote or hit them with a bit of nostalgia. Just remember to keep it short and move on once you’ve gotten a reaction.

3. Keep things simple and to the point

Once you’re done warming up the crowd you can ease them into the core concepts and important ideas that you will be presenting. Keep the same presentation style thoughout. If you’ve started off a bit ironic, using dry wit, you can’t just jump into a boring monologue. If you’ve started off with a bang, telling a couple of great little jokes and getting the crowd riled up, you have to keep them happy by throwing in little jokes here and there and being generally positive and energetic during the presentation. You need a certain structure that you won’t deviate too far from at any point. A good game plan consists of several important points that need to be addressed efficiently. This means moving on from one point to another in a logical manner, coming to a sound conclusion and making sure to accentuate the key information.

4. Use a healthy dose of humor

Some of the best speeches and presentations in the world, which have been heard and viewed by millions, all feature plenty of humor. No matter the subject, a great speaker will use natural charisma, humor and beautiful language to convey their points and get the crowd excited about what they are saying. A great example of building rapport with the audience through the use of humor is Barrack Obama talking about the government building Iron Man.

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It is silly and fun, and absolutely not something that you would expect from a man in a position of power speaking in such a serious setting – and it’s exactly why it works. The more serious the situation and the bigger the accent on proper social behavior, the harder your jokes will hit.

5. Try to tell a story instead of ranting

Some people can do all of the above things right and still manage to turn their short and fun little presentation into a chaotic mess of information. You don’t want your speech to look like you just threw a bunch of information in a blender in no particular order. To avoid rambling, create a strong structure. Start with the ice breaker, introduce the core concepts and your goals briefly, elaborate on the various points in a bit more detail, draw logical conclusions and leave your audience with a clear takeaway message. You want to flow naturally from one part to the next like you are telling a big story chapter by chapter.

6. Practice your delivery

Standing in front of the mirror and practicing a speech or presentation is a technique as old as mirrors – well, come to think of it, as old as human speech, since you can see yourself reflected in any clear and calm body of water – and that means that it is tried and true. The theory is incredibly simple, yet the real problem is actually putting in the effort day in and day out. Work on your posture, your tone of voice, accent, pauses between sentences and facial expressions. The most important thing is to talk slowly and loudly enough to be heard and understood clearly. Many famous speakers, such as Demosthenes and King George VI, overcame speech impediments through hard work.

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7. Move around and use your hands

Although you won’t instill confidence in your project if you are very jittery, moving around erratically, not knowing what to do with your hands and making fast movements, standing dead still can be just as bad. You shouldn’t be afraid to use your arms and hands when talking as it makes you seem more passionate and confident. The same goes for moving around and taking up some space. However, try to make slower, calculated and deliberate movements. You want your movements to seem powerful, yet effortless. You can achieve this through practice.

8. Engage the audience by making them relate

Sometimes you will lose the audience somewhat in techno-babble, numbers, graphs and abstract ideas. At that point it is important to reel them back in using some good, old-fashioned storytelling. Make comparisons to events from everyday life that most people are more than familiar with. By making things look simple, not only will you help your audience get a better understanding of the subject by enabling them to visualize the information more clearly, you will also draw a connection between you. After all, you are all just regular people with similar experience, you just happen to be performing different roles at the moment.

9. Use funny images in your slides

Although slides are not really necessary at all times, if you do need them to make your point and present your information more effectively, it’s best to liven them up. They say that facts aren’t always black and white, and your presentation should reflect this. Add a bit of color, make the information stand out and use an interesting animation to switch from slide to slide. You can use the slides to add some more humor, both in terms of the text and the images. An image that is used to elicit a positive response needs to be funny within the context of what you are discussing. For example, if you are discussing the topic of authority, an image of Eric Cartman from South Park in a police uniform, demanding that you respect his “authoritah,” is a nice way to have a bit of fun and lighten things up.

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10. End on a more serious note

When all is said and done you will want the audience to remember the core concepts and keep thinking about what you have said after the presentation is over. This is why you should let things naturally calm down and end with an important idea, quote or even a question. Plant a seed in their mind and make them think. Let us turn to Patrick Henry for a great way to end a speech: “Is life so dear or peace so sweet as to be purchased at the price of chains and slavery? Forbid it, Almighty God! I know not what course others may take; but as for me, give me liberty or give me death.”

As you can see, there is quite a bit to learn when it comes to giving a good presentation, one that is both memorable and fun. Be sure to work on your skills tirelessly and follow in the footsteps of great orators.

Featured photo credit: Austin Distel via unsplash.com

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