Thoughts About ‘Learn to Let Go’ and Why It’s Bad Advice

When I write blog posts, I always try to shake off any thoughts about the future talkbacks I’m going to receive. Trying to dodge hostile comments when you write is a surefire recipe for mediocre posts. Even now, as I’m writing the headline of this post, I can already envision the reactions. The organizational culture of all startups operates under pretty straightforward rules, and ‘Thou Shalt Learn to Let Go’ is one of the commandments being preached.

To let go = Good

To give 100% independence to employees = Good

A CEO that is involved in the minor details = Bad

Micromanagement = Bad

But is that really in the best interest of the organization and its employees? Not necessarily.

Failing to let go does not have anything to do with one’s ego but rather with the company’s vision.

From the get-go, I’ve always been involved in every aspect of the business - from the smallest product detail to the development process. However, I’ve simultaneously tried to ‘let go.’

As mentioned above, the inability to ‘let go’’ is usually perceived as a symptom of an overinflated ego, distrust in the capability of others, and the habit of petty nitpicking. I was constantly caught in the tension between ensuring that everything complies with the company’s vision and trying to let go. In the past couple of months, I ended the struggle and went back to my hands-on self. I’m now closer to the product, marketing, and development. But, most importantly, I allow myself to be much more ‘petty’ and argue the details that do not feel suitable for the company.

We are all fighting time constraints. Every startup CEO out there is buried under a pile of action items at any given moment. Usually, the pile contains an endless list of genuinely crucial tasks. Come to think about it, this is also true for all of the managers and team members working in startup companies. When I detect that a particular area of the business is operating perfectly without my interference, it clears a lot of time for me to focus on other important areas and makes me appreciative. So, why not let go of a big part of the areas and focus only on the critical ones?

I believe the basic assumption regarding ‘let go’ is wrong: You don’t trust people enough; therefore, you are controlling. 

My view is entirely different: No one else possesses the full vision of how all the system’s parts connect. There is a fundamental difference between ‘good work’ and ‘suitable for the company at the moment.’

Did you ever wonder why it’s vital to keep the initial founders part of the company? Why it’s so hard to change an entrepreneur with an external CEO at the early stages? Why VCs invest not only in ideas but also in the people who build them?

The essence of startups (especially at the early stages) is transforming a vision into a reality—an up and running reality. It’s hard when the vision is unclear, perforated, or constantly changing. I feel that my involvement in the copy, product definition, and bug-fixing priorities is not an indication I’m any better than anyone. It’s because my role is to connect all the dots to create the exact experience I want our users to have. An experience built from so many components that only someone who has a 360-degree view can handle it.

I admit, there were times when I even underestimated managers who insisted on diving into the small details. Today, I understand that there’s a reason why the most distinguished CEOs were such ‘divers.’ It’s impossible to build a robust and innovative vision without being hands-on.

It doesn’t mean that I’m involved in every single detail at Oribi. Some areas operate perfectly without me, areas that are already established and connected to the vision enough. Others areas are less critical to the vision, and I’m less needed there.

Is ‘Letting Go’ Really Better for Your Reporting Employees?

The main reason I tried to ‘let go’ and give more independence to my employees was the prevailing perception that this is the proper practice for managing and nurturing people. This has led to constant tension: On the one hand, the product and the company were still not in a mature enough stage, and on the other, I really wanted to cultivate ownership and let the team lead.

Over the past few years, I’ve interviewed hundreds of candidates. One of the most-discussed issues on those interviews was their previous managers. The most esteemed managers were not the ones who ‘let go’ but rather those who led fiercely and paved a very distinct path. Working successfully under such a manager also requires immense faith in them and the vision they build. A manager who is involved in all the details can either be the best thing that has ever happened to an employee or their complete demise. Working with a manager who doesn’t ‘let go’ does not in any way mean that there’s no room to initiate and contribute.

On the contrary, now that I allow myself zero tolerance for projects that do not fit the vision, there’s a better understanding of the roadmap among the team. My attention to detail helps them to be synced with the big picture. Within borders, one can create and initiate a lot. 

During the past three months since I stopped ‘letting go,’ much of the features, microcopy, and company-culture decisions were led by the team and not by me. Insisting on adherence to our vision and being involved in the details gave rise to a better understanding of the company’s path and the creation of a true harmony - not the artificial kind that grows where fake ‘letting go’ is practiced.

And When’s the Right Time to ‘Let Go’?

We all have areas of expertise we feel are our forte. These are, almost always, the areas that bring us joy. For me, it’s marketing, the product’s roadmap, and finance. It is often hard to give them up. The biggest trap I see many executives fall into is holding on to a project or a position where they feel at their best rather than passing it on. This is a different ‘letting go’ than the one this post is about. It comes from fear of stepping out of one’s comfort zone or the dread of being replaced. If a team member accurately conveys the vision in a particular area, I let that area go (even if it’s my favorite thing to do in the world).

Another aspect is prioritizing. I believe that in order to build a stellar product, all the small details must be accounted for - from the features, through technical choices and even the team’s downtime. During the startup’s early stages, almost every aspect is instrumental (although there is still a hierarchy of importance). I have written quite a bit about focus in the past—the magic of building a startup is creating an entire world with a small team. At any given moment, the team and I know what matters the most, both within the micro and the macro. Some features are in higher priority than others; there are times when marketing is crucial, and times when it’s a nice-to-have, there are bugs that must be examined and fixed ASAP, and others that I am not even aware of.

So my mission for the past couple of months is to learn how to be ‘petty’ without feeling guilty. I guide the team on how all the dots connect and try to depict the vision that is forming in my mind as accurately as possible.