4 Common Mistakes New Founders Make
When someone says “founder” or “business owner”, most people think of CEOs in fancy suits, riding expensive cars, and living in penthouse suites.
We don’t really think about the nitty-gritty parts of running a successful business — or the mistakes that new entrepreneurs make along the way.
The truth is, running a business involves a steep learning curve, especially if you’re transitioning from employee to employer like me. Things won’t be perfect all the time, but I try my best to turn these mistakes into learning experiences that can help me become a better leader and entrepreneur.
In this post, let me share the 4 common “mistakes” that I’ve encountered during my journey and the lessons that I’ve learned from them:
1. Not being able to manage time efficiently
I struggled to manage my time during the early days of Shepherd. I would fill my schedule with so many tasks, focusing on looking busy instead of accomplishing one big goal at a time. I thought that being busy equated to being productive. I couldn’t have been more wrong.
Busy ≠ Productive
Back then, I thought that having a long to-do list and a full calendar meant that I was doing my job. I would fill my days with meetings and time-consuming tasks like cleaning my inbox, putting out fires, and responding to every single message on Slack.
I equated multitasking with productivity, which actually isn't true. Studies show that multitasking is less efficient because switching from one task to another actually takes a toll on your brain. You end up doing a mediocre job or worse — you won’t accomplish anything at all.
How I learned to manage my time efficiently
“Being busy is a form of laziness. Doing less is the path of the productive.”
Focusing on one task at a time
Leaders need to wear many hats. Everyone will want a piece of your limited time, energy, and attention, so you need to be truly intentional about how you spend these resources.
For me, this meant accomplishing one thing at a time instead of dividing my attention into a lot of small but unimportant tasks. Reading The Four-Hour Workweek by Tim Ferriss really helped cement this into my daily habits, too.
Hiring an assistant
My assistant, Katrice, helps me prioritize my tasks using a Kanban board on our shared Notion account. She basically sets up my daily tasks there so that I don’t have to go to Slack or waste time checking my email. With everything in one place, I can focus on checking these tasks off without being distracted.
Managing my attention
Attention is a currency, so spend it on the right things. As for me, I’ve deleted social media apps from my phone so that I won’t be tempted to scroll idly during my work hours.
Most meetings are also distractions. Although I still schedule meetings from time to time, I often collaborate with people through chat or email. This allows me to do deep work without being distracted by my schedule.
Related: How I create productive habits for myself
2. Failing to categorize tasks
Sometimes, entrepreneurs get so busy running around doing things that they fail to prioritize their tasks. They end up doing everything themselves when they should only focus on the things that need their specific attention and expertise.
Using the Eisenhower Matrix to prioritize your tasks
The Eisenhower Matrix has helped me a lot in this journey. It helped me identify the tasks that I should be doing, delegating, and eliminating. It also gives me a glimpse of the tasks that I should carve out time for.
The Eisenhower Matrix is divided into 4 quadrants:
Q1: Important and Urgent Tasks - these are the tasks that you need to attend to immediately. For me, this meant doing client invoicing as it directly affects revenue.
Q2: Important but Non-Urgent Tasks - these are vital tasks that I have to schedule for later. For many entrepreneurs, this can mean creating an SOP knowledgebase or scheduling a strategic session with their team. Personally, Katrice plots these tasks for me on Notion so that I can check them off once I’m done with urgent items.
Q3: Not Important but Urgent Tasks - these are tasks that I can delegate to my assistant. A good example would be email management, accounting, and reviewing contract information.
Q4: Not Important and Non-Urgent - these are tasks that I have to eliminate completely. Since they’re neither important nor urgent, I shouldn’t be dealing with these at all. Some examples include checking Slack messages and idly scrolling on social media.
With the Eisenhower Matrix, I can now prioritize my tasks and get more things done.
3. Not delegating sooner
Another mistake is failing to delegate. This is something that I also see in a lot of our clients at Shepherd.
Most founders, old and new, struggle to:
let go of tasks
delegate important aspects of their business to someone else
identify what to delegate
find a trustworthy assistant to help them out
I get it. I’ve been there, too. Like time management, there is also a learning curve to delegation. But in the end, the cost of not being able to delegate will always take its toll on you and your team.
Leaders who don’t delegate often end up being a bottleneck, causing delays in projects. Their schedule is filled with tasks, so they often have to work long hours. This defeats the goal of having time freedom. Most of all, not delegating prevents them from doing their main job, which is to scale their companies.
Delegate early
A huge part of what makes Shepherd successful is that we walk our talk. We don’t just promote delegation to other business owners; we also practice delegation ourselves.
We delegated fast and early. Once we knew that we were ready to scale, we offloaded big tasks like client services, project management, marketing, and team engagement to other members of the team. This way, my co-founder Marshall and I can focus on growing the business. The added bonus is that we were able to empower team members and turn them into leaders themselves. It’s a win-win for everyone.
How to be better at delegation
Learn from the experts
Marshall actually has a free course that teaches people how to delegate to a remote assistant. Check it out here!
Communicate clearly
To see specific results, you need to give specific instructions to your assistant. Instead of assigning them tasks right off the bat, onboard them properly. This is where you communicate your expectations, work preferences, and other instructions to your assistant. If you can share some documentation like SOPs, that would be even better.
Hire the right assistant
Aside from skill, hiring someone who matches your energy, values, and goals is also important! Create a thorough job description and ask the right questions during the interview. Of course, you can also use a headhunter agency like Shepherd to do this for you. 😉
Related: How to onboard your assistant
4. Not believing in your team’s potential
As a business owner, you’re not just a boss. You’re a leader, too.
Aside from motivating your team to achieve business goals, you need to guide them toward their career goals as well. There’s no better feeling than seeing a mentee grow into their role and achieve greater heights!
One of the biggest mistakes a new leader can make is failing to see and uncover their team members’ potential. Many leaders take people at face value and fail to see diamonds in the rough. To be fair, this skill is easier said than done. It takes a mix of experience, intuition, and trust to see potential in others.
I’ve made my share of mistakes in this area, too. But over time, I’ve learned to develop a 4-step process to help me uncover a team member’s potential, especially when delegating a new task.
Here’s how it goes:
Step 1: Show your mentee how to do a task.
You do a task and your mentee observes. During this stage, let them know why the task is important. Sharing your goal and thought process helps your mentee develop initiative and solve problems on their own.
Step 2: Do the task together.
This helps you uncover potential issues while in a safe environment and provide real-time feedback.
Step 3: Let your mentee do the task while you observe.
Help your mentee gain muscle memory by letting them do the task by themselves. By flipping the tables, you can evaluate if your mentee absorbed the lesson well. You can provide additional feedback after they finish the task.
Step 4: Allowing your mentee to become a mentor to others.
This is by far my favorite part of the process. This is where you watch your mentee grow into a leader and teach someone else. If you did a great job as a leader, they’ll be able to clear this stage with ease.
By building their confidence, giving them agency, and challenging them to do new things, you can help develop your direct reports’ full potential. As a leader, there’s no better feeling than seeing someone succeed and fulfill their dreams!
What makes these “mistakes” worth it
The shows here in the Philippines always portray business owners as rich, powerful, and extravagant. They don’t show the real side of running a business: stumbling through mishaps, climbing steep learning curves, and learning from mistakes along the way.
Entrepreneurship is hard, but I wouldn't have it any other way. Yes, it’s challenging, but it’s also been a journey of self-discovery for me. Thanks to entrepreneurship, I get to learn new things everyday. I get to be in charge of how I improve myself and the others around me. Most of all, it allows me to create wonderful memories with the people that matter most. And I think that’s something worth learning these “mistakes” for. 🙂
How about you? What lessons have you learned in your entrepreneurship journey?
