Are You Always Procrastinating? Let’s Overcome It!

Entrepreneurs are no strangers to procrastination — the silent killer of productivity lurking in the shadows, whispering, “You can do it later.” Later becomes tomorrow, tomorrow becomes next week, and suddenly, projects slip through the cracks.

Jeff Hardison, Head of Product Marketing at Calendly, thinks there’s a better way. With a user base of 20 million, the Calendly software has proved that with proper planning and preparation, procrastination can become a thing of the past.

If you’re looking for ways to stop putting off important tasks, you’ve come to the right place. Ramon Ray chatted with Hardison about top tips for squashing procrastination and tackling projects and meetings with new energy. Let’s get into it.

Listen to the entire episode on our YouTube channel or listen to it on our podcast.

The Procrastination Struggle Is Real

Procrastination, often considered the arch-nemesis of productivity, plagues individuals across all walks of life. Whether you’re an entrepreneur, a corporate professional, or a solopreneur, the temptation to delay tasks can be overwhelming.

Hardison advises changing your mindset to overcome procrastination. Instead of dreading meetings, you can start relying on them to improve productivity and even make more money — whether you’re a salesperson, a recruiter, a life coach, a yoga instructor, or anyone else who needs better time-management systems. With a simple Calendly link that you can send to prospects and clients, you can book up your calendar and reduce the typical back-and-forth involved with scheduling appointments.

“We’re trying to make meetings better,” Hardison says. “So we have a whole bunch of features that aren’t just about scheduling that meeting but preparing for it, participating in it, and then following up on that meeting.”

Here’s a closer look at the four stages of booking more meetings, from scheduling to follow-up.

Read: How to Stop Procrastination in Your Business

Tip 1: Schedule the Meeting

Hardison asserts that procrastination is the “biggest enemy” of productivity. And often, people procrastinate because they don’t want to get started on a task — or, say, reach out to schedule a meeting with an important individual.

Overcoming this productivity killer requires a willingness to stop overthinking things. Have a blog post you need to write? Don’t sit and stew about it; simply dive in and get started, even if only writing down a few thoughts.

“Just taking the act of starting to put something down — whether it’s writing, or it’s creating a slide deck, or it’s having that tough conversation with somebody, stop procrastinating and just do it,” says Hardison. “Get out of your head. One of the reasons we procrastinate is we think too much.”

With this approach, you’re living in the moment versus thinking about the past or worrying about the future. You can apply this philosophy to booking appointments, too. Send your Calendly link, book the meeting, and then move on to the next phase: preparation.

Tip 2: Prepare for Success

Preparation is crucial to overcome procrastination and ensure productive outcomes. With Calendly’s features, such as event types and workflow reminders, participants can enter meetings prepared and maximize everyone’s time.

Here are some ways to prepare effectively and set up everyone for success:

  • Write an agenda. Outline the topics and objectives you wish to cover during the meeting. A clear agenda sets appropriate expectations and keeps meetings on task.
  • Send materials for pre-reading. Before meetings, provide relevant files, reports, or slide decks to allow attendees to familiarize themselves with the content and come prepared.
  • Prepare talking points: Besides the agenda, jot down key points to guide the conversation and touch on all important topics.
  • Customize event types. Through Calendly’s customizable event types and advanced scheduling options, you can tailor meetings for various topics, from 15-minute “walk and talk” meetings to 30-minute Zoom sessions or even 45-minute phone calls.

Tip 3: Participate With Purpose

It might sound obvious, but actively participating in meetings is fundamental for fruitful outcomes. While preparing for meetings sets the stage for success, engaging dynamically is equally important so discussions can flow organically. Follow these tips for active participation:

  • Listen attentively to thoughts, needs, and concerns before jumping in with your solutions.
  • Be flexible to encourage spontaneous tangents and unexpected insights.
  • Invite a dialogue that encourages contributions from others and fosters an environment of collaboration and mutual respect.
  • Pivot in response to changing dynamics or new information. You may wish to build a buffer into meetings — 15 minutes before and after, for example — in case your meetings run long. Calendly offers advanced scheduling tools for this purpose.

Tip 4: Follow Up and Follow Through

The real work often begins after meetings conclude. Following up allows you to solidify commitments and move into the next phase of fulfilling deliverables and building client loyalty.

Leveraging Calendly’s integrations and workflow functionalities, you can automate follow-up tasks such as sending a thank-you note and inviting participants to book another call. Better still is to nail down follow-up meetings while wrapping up a call with a client or prospect.

Additional Takeaways for Entrepreneurs

Are you curious how Calendly can help you overcome procrastination in its tracks? Hardison offers a few final tips for users of any experience level.

For Beginners

  • Start with the basics: Get familiar with Calendly’s core features, such as scheduling meetings and sharing availability links. Focus on simplifying your scheduling process and reducing back-and-forth communication.
  • Explore event types: Experiment with options to customize your scheduling preferences according to the types of meetings you need.

For Intermediate Users

  • Enhance customization: Experiment with setting availability preferences, creating multiple event types, and implementing daily booking limits.
  • Add integrations: Integrate Calendly with other tools in your tech stack, such as email services and customer relationship management platforms. (By the way, Calendly does custom integrations, too!)

For Advanced Users

  • Automate workflows: Leverage Calendly’s advanced features, such as workflows and reminders, to automate repetitive tasks and streamline scheduling. Set up pre-meeting reminders, follow-up sequences, and confirmation workflows.
  • Explore routing functionality: Enable round-the-clock scheduling to enable customers to book meetings at their convenience, even outside traditional business hours.

Lastly, no matter your experience level with Calendly, you can overcome procrastination by prioritizing self-care. Proper sleep, nutrition, hydration, exercise, and mindfulness exercises can put you in the driver’s seat and give you the energy you need to handle any meeting that comes your way.

To learn more about Calendly’s free and paid options and how the platform can help you eliminate procrastination, go to

Read More: Can Procrastination Hurt You? And how to Overcome It?

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