A Tale of Two Startups: What I Learned About Planning

This newsletter is based on my Linkedin carousel series called "A Tale of Two Startups". You may access the carousel here.

Planning is the cornerstone of any successful business, but not all startups prioritize it. As the COO of two venture-backed SaaS companies—one that thrived and was acquired, and one that failed—I’ve seen how different approaches to planning can make or break a business. Whether it's quarterly goals or team bonding, planning plays a crucial role in aligning efforts and creating a cohesive culture.

Here’s what I learned from both experiences.

1. Planning Regularly vs. Skipping It

Acquired Startup:
At the successful startup, we held quarterly and annual planning sessions like clockwork. These meetings were essential for setting clear goals and ensuring that everyone was aligned. Planning became a key ritual that kept us on track, no matter how busy things got.

Failed Startup:
The failed startup was always “too busy to plan.” We skipped quarterly and annual planning, and as a result, there was no clear direction. This lack of foresight led to reactive decision-making and misaligned efforts across the company.

Lesson: Failing to plan is truly planning to fail. No matter how busy you are, planning should be a non-negotiable part of your company’s rhythm. Without it, you’re just running blind.

2. Setting Goals and Tracking Progress

Acquired Startup:
We set specific annual and quarterly goals, complete with targets and deadlines. Progress was checked weekly, and adjustments were made as needed. This helped keep the team focused on our long-term vision while also making necessary course corrections along the way.

Failed Startup:
The failed startup didn’t formalize goals or set specific targets. There were no dates attached to milestones, which made it easy to lose track of progress. Without clear goals, the team was constantly off track, and there was no framework for reviewing performance.

Lesson: It’s too easy to get off track without setting clear goals and regularly reviewing them. Formalizing your goals with specific targets and timelines is essential to ensuring steady progress and preventing misalignment.

3. Engaging the Team in Internal Projects

Acquired Startup:
One of the most valuable lessons I learned was that everyone in the company should be involved in quarterly projects that help remove friction and improve the business. This ensured that improvements were being made at every level, and everyone felt ownership of the company’s success.

Failed Startup:
In the failed startup, internal project work was rarely prioritized. The team was so focused on day-to-day tasks that no one took the time to step back and work on long-term improvements.

Lesson: Everyone should help carry the water. Engaging the entire team in quarterly improvement projects ensures that the company continues to evolve and grow. It also fosters a sense of ownership and commitment.

4. Communicating Initiatives Clearly

Acquired Startup:
We rallied the company around well-communicated quarterly initiatives. This created a sense of certainty and purpose, allowing the team to work together toward common goals. Everyone knew what the priorities were, and that alignment helped us succeed.

Failed Startup:
In contrast, the failed startup’s focus shifted constantly. Without a clear plan, the team was left confused and frustrated. The lack of communication led to uncertainty, which is one of the quickest ways to lose good talent.

Lesson: Certainty is a core human need. When your team doesn’t have a clear understanding of the company’s direction, it creates stress and confusion. Consistent communication of priorities helps keep everyone aligned and motivated.

5. Prioritizing Team Bonding

Acquired Startup:
We made team bonding a priority during our quarterly and annual planning sessions. This helped create a strong sense of camaraderie and connectedness, which ultimately improved our culture and strengthened the team’s commitment to the company’s success.

Failed Startup:
The failed startup rarely held events for team bonding outside of work. As a result, the team felt disconnected, and the culture suffered.

Lesson: Connectedness is a core human need. Being “too busy to plan” also means missing out on opportunities for team bonding, which is crucial for building a strong company culture.

What Can We Learn?

The difference between the success of one startup and the failure of another often comes down to one thing: planning. Whether it’s setting goals, engaging the team in improvement projects, or creating opportunities for bonding, planning is the foundation of a strong business. It not only provides clarity and direction but also fosters a sense of connectedness and purpose among the team.

If you want your business to thrive, make planning a priority. Hold regular planning sessions, set clear goals, engage your team, and communicate initiatives clearly. Most importantly, don’t be “too busy” to plan, because failing to plan is planning to fail.