The Cost of Pretending.
Jared Flatow · Draft
Building a great engineering team takes more than hiring great engineers. The best engineering cultures I've experienced are built around trust, intellectual honesty, and a shared commitment to solving problems. But those principles cannot stop at engineering. They must extend throughout an organization for even the most capable teams to succeed.
You can have exceptional talent, valuable technology, plenty of capital, and a real market with substantial demand, and still fail. Not because the people building the company don't know what to do, but because they aren't allowed to do it.
One of the most destructive ways this happens is when a startup founder's authority outpaces their judgment.
Founders can acquire extraordinary authority long before developing the experience or maturity to exercise it. Entrusted with millions of dollars and surrounded by people reinforcing their importance, they begin to identify as visionaries. Eventually, that story becomes their identity.
The pretending begins when maintaining that identity becomes more important than confronting reality. Admitting ignorance becomes weakness. Disagreement becomes disloyalty. Rather than engaging with people who challenge their judgment, they assert authority. The company must appear to be succeeding under their leadership, whether or not it actually is.
The founder's psychology becomes the company's bottleneck.
The consequences are painfully familiar. A team spends weeks evaluating an approach, only to have its decision overturned by someone who hasn't engaged with the tradeoffs. Problems are raised but never meaningfully addressed. People are expected to take responsibility for decisions imposed on them, even when their objections remain unresolved.
Knowledge is distributed throughout an organization. Engineers encounter the constraints of building. Salespeople encounter the constraints of selling. Each sees things others cannot, and each has blind spots of their own.
Bringing these perspectives together is one of the most rewarding parts of building a company. When people reason openly and challenge each other's assumptions, they discover solutions none could have found alone. But invoking authority doesn't resolve a disagreement. It merely ends the conversation.
When authority substitutes for reasoning, uncomfortable truths become increasingly difficult to express. Worse, pretending becomes acceptable throughout the organization. Targets are chosen to guarantee victories rather than measure progress. Problems are concealed, failures rationalized, and appearances managed. Eventually, the organization loses the ability to distinguish genuine progress from its own propaganda.
Meanwhile, the people doing the work may still believe in what they're building. They want to succeed, but are prevented from doing what they know needs to be done.
New executives arrive with genuine mandates to improve things, often welcomed precisely because they bring independent judgment. But eventually that independence collides with a need to preserve authority and self-image. Those willing to accommodate gain influence; those who continue challenging the narrative are marginalized or leave. New people arrive, and the cycle repeats. The underlying conflict survives every reorganization.
The founder may never understand what happened. Every setback can be rationalized, every departure explained away, every failure blamed on circumstances or the market.
The cost is the talent, capital, time, trust, and opportunity squandered along the way. People who believed in the company and worked to build it pay for a fiction maintained to protect someone else's identity.
Authority cannot compensate for a lack of leadership.
As a leader, much of my work is keeping everyone oriented around reality. What do we know? What don't we know? What's changed? What are we trying to accomplish, and what's preventing us?
When we disagree, we examine assumptions, uncover constraints, explore alternatives, and map out the design space. Often there's a moment when things click. What seemed like competing opinions resolves into a shared understanding of the problem, and we can see which direction makes sense and why. There is no argument to win.
I make my own reasoning and uncertainty visible so everyone can contribute, challenge assumptions, and learn from one another. The result isn't just a better decision. People develop the judgment and confidence to solve problems independently.
When people are respected, informed, and given real ownership of their work, they don't need to be constantly managed or motivated. They want to build things they're proud of, and they can accomplish extraordinary things together.
The job of leadership is to make that possible, not stand in the way.