My Venture Diary — A Hard Lesson in Team Alignment

[EP13] I made a major mistake.

After a week of feeling down, my funk has finally lifted. However, I didn’t accomplish much this week for my venture. The main reason? I asked some critical questions that I should have discussed with my two teammates before officially starting the project, and I’ve been waiting for their responses.

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My First Major Mistake

I’ve led teams in school and at a company, and I’ve read countless books on leadership. But that doesn’t mean you’re automatically prepared. As a first-time entrepreneur, I made a significant, and perhaps the most important, mistake: I didn’t confirm my teammates’ actual commitment levels. Instead, I relied on my intuition, judgment, and their partial commitment to move forward.

While I secured bootstrapping funds and developed a clear, logical plan, I didn’t approach the most crucial aspect — choosing the right people — with sufficient caution. This oversight forced me to take a short pause.

In EP4 of My Venture Diary — What Makes A Good Team? I discussed what I was looking for in teammates. My criteria weren’t wrong, nor have I changed my mind. The problem was that I assumed they met my expectations —…