When Delegation Goes Awry

When Delegation Goes Awry

Two days ago, I listened to "Brian Chesky’s new playbook", a recent episode of Lenny's Podcast, where they discussed Airbnb's radical transformation that revolves around the product manager role.

Aside from the focal point of his talk, I enjoyed much of the notions Brian shared in his talk. Including his just-do-it mentality, insights on the importance of educating users, the idea that product increments should contribute to a cohesive marketing narrative, and not to mention, his ambitious approach to goal setting.

Back in June, Brian announced a significant change during his conversation at Config 2023, where he stated, "...actually, we got rid of the classic Product Management function." Then, when I first read this quote from him, I doubted if our interpretations of the classic product manager role coincided. However, the very decision they made is not what I want to cover in this article.

What I want to shine a spotlight on, are two topics that stem from Brian's discussion in the podcast, when he explained why they rethought the product management role.

Perception of Interference

In some parts of his talk, Brian compares the extent he was involved in the details before and after the change. He states, "Before the crisis (=pandemic), a lot of people felt like I was too involved in different areas. Once the crisis happened, guess what happened? People were like, what do we do? We need you more involved. And so I got more involved." Then as the discussion continues until he admits "[After the transformation,] I basically got involved in every single detail".

The degree to which a CEO or product leader should be involved in the details depends on many factors. These factors include the company's size and culture, the level of expertise of ICs, how leaders expect teams to innovate, and the organizational structure, among others

No matter what the right amount is, product leaders shouldn't neglect how people perceive their participation. Even if people incorrectly feel leaders' involvement is unnecessary or unwanted, leaders should consider the factors that may contribute to such perceptions.

"Before the crisis, a lot of people felt like I was too involved in different areas."—Brian Chesky, Lenny's Podcast

When many people share a common interpretation of a leader's interaction with their colleagues, I consider it a plausible observation. Overlooking how people feel about their interaction with their leaders can influence their sense of agency. It can even impact how safe they psychologically feel when making decisions, restrain how big they think, and finally, it can create delegation hallucination, which I will explain shortly.

Delegation Hallucination

The worst scenario happens when a leader or CEO thinks they have delegated things away. However, other people do not feel the same. I call this situation delegation hallucination. Leaders who strongly believe in becoming aware of every detail, are more conducive to this hallucination.

The cycle usually starts by leaders' involvement into every details. After a while, a notable group of people start to feel the leader is overly involved. At this point, they may clarify their feelings by providing some feedbacks. As a result, the leader or founder takes a few steps back by delegating things away.

However, this delegation does not fundamentally change their sense of agency and their perspective on the scope of their responsibilities. Based on the similar cases where the leader has been involved, they still empirically restrain their thoughts and stay wary of every decision they make in order to avoid stepping on anybody's toes.

Here, not only does what the leader considers as delegation not work, but it also exacerbates the situation. The CEO or leader is no longer present everywhere to cover areas of business that do not formally belong to a particular division. Silos consolidate further and alignment diminishes.

The CEO starts to feel uneasy about not being involved in areas they are best at. The company's slow pace and its failure to repeat previous achievements, makes the idea of being "in the details" salient again.

While Airbnb's case might be partially different, some parts of the podcast reminds me of the hallucination:

  • Lenny: "... another very prominent CEO of a public company ... pointed out that there's this cycle that he sees a lot of founders go through where they initially run the show, they're in charge, they tell people what to build, and then over time they're encouraged to delegate and to empower and it leads to a bunch of optimization work and small thinking maybe ..."
  • Brian: "That's exactly how it went, and that's how it goes almost at every company I've heard of ..."

I have personally witnessed product managers who have stifled their big thoughts to ensure that they fit into the area they are allowed to step into. When the leader or CEO returns back into "the details", they often criticize product managers for overlooking a particular area of the product or small thinking. This surprises the product managers. They might think, "Historically, this has always been your territory. I didn't realize I had the authority to take action."


To sum up, I want to clarify that I don't want to advocate for or against CEOs or product leaders delegating. I just want to emphasize that when a leader decides to effectuate delegation, they should make it clear what they have truly delegated and make sure if people have the right perception of delegation.

This article has also been published in Persian.