Key Takeaways
- Leaders who are right most of the time but right alone end up with no one willing to be honest with them.
- Decisiveness is a virtue. Decisiveness without listening is a liability.
- The best leadership training is making real decisions with real consequences in a real organization.
Saim Abbasi's first experience managing a team was at SA Capital, and the honest version of how that went is not the version that makes it onto highlight reels. He made the kinds of mistakes that most first-time leaders make, and a few that were specific to the particular combination of confidence and inexperience that defines most early founders.
The Certainty Problem
The first major mistake was confusing confidence with certainty. Confidence is the ability to make a decision and commit to it fully. Certainty is the belief that you do not need more information than you already have. These look the same from the outside but they produce very different team environments.
When Saim closed down questions and discussion too quickly, the team learned that raising doubts was not welcome. So they stopped raising doubts. And the leader who was no longer getting honest feedback from his team started making decisions based on incomplete information and wondering why execution kept getting harder.
Feedback Flow as a Leadership Metric
The diagnostic Saim uses now for his own leadership health and for the founders he coaches is simple: when was the last time a team member told you something you did not want to hear? If the answer is more than two weeks, the feedback flow has been cut off somehow, and the leader is flying without instruments.
Creating the conditions for honest feedback requires explicitly inviting it, demonstrating that delivering bad news is safe, and visibly using the feedback to change decisions. All three components are necessary. One or two out of three tend to produce feedback that is filtered and shaped rather than honest.
What Saim Does Differently Now
The specific practice that changed the most for Saim Abbasi between his first company and his current work at Iron Key Capital is the use of pre-mortems before major decisions. Before committing to a direction, he asks the team: assume this fails. What were the three most likely reasons? That question surfaces objections that people might have held back from raising directly, and it frames the skepticism as useful analysis rather than criticism.
It sounds simple. It is. And it produces better decisions than the alternative.
"The first time you lead a team, you are learning by doing on people who trusted you enough to follow you. Take that seriously."