Delegating Wizardry and Why We Fail to Maximize It

Trevor Lim
6 min readApr 8, 2019

If we do a survey today and ask a hundred entrepreneurs, managers, and supervisors what they find the hardest to do, I wouldn’t be surprised if they would answer delegation as their toughest bout towards effective leadership.

Being a startup entrepreneur myself who came from an employee mindset and background, I could understand why delegating is such an ordeal for younger leaders and managers.

We are used to doing things ourselves. And why shouldn’t we? It’s our hard work, relentlessness, passion, and unwavering commitment to do our best that has led us to the success that we are enjoying now.

However, not being able to delegate well is as problematic and costly as any business or office mishap.

For one, you can’t really expect people to read your mind. So if you don’t properly communicate yourself, chances are things won’t get done or there will be redundancies in the work process. Either way, it’s inefficient and unproductive.

What are the reasons why we don’t delegate properly (or at all)?

Photo by Mimi Thian on Unsplash

We think we can do things better ourselves

Yes. For super proactive and obsessive-compulsive bosses and managers, their life motto is “If you want something done right, do it yourself.”

Maybe at some point that can be true. But not always! And certainly not in an environment that cultivates interdependence and collaboration.

Based on my experience, this kind of mindset is founded on one simple issue: lack of trust. The reason why we don’t want to delegate is that we don’t trust that the people in our team can do as much of a better job at a task as we can.

We underestimate the capacity of our subordinates or teammates. And this often results in discord and inefficiency. We think it would be better to do things ourselves. It’s a common trap most supervisors and managers make. And it’s certainly a stumbling block for most startup entrepreneurs.

The lack of trust in others could be a reflection of an even deeper issue: pride. We believe in ourselves too much to the point that we think we’re the only ones who can do a good job at something.

And while it’s not really wrong to have self-esteem and self-confidence — in fact, it’s quite healthy and much need — there’s definitely a need to work well with others.

It’s not humanly possible to work on your own, so don’t even attempt to do so. Otherwise, you’ll end up with a failed output and a sorry team of workers who might be hurt by your lack of trust in them.

We don’t know how to communicate

Sometimes we want to delegate but we just don’t know how to communicate it. This is a common problem, especially by younger or fresher leaders.

Learning to express yourself comes with the years of experience and making crucial mistakes along the way. And that is an acceptable way to learn.

However, we can also learn from the experiences of others. And reading resources such as the one you’re perusing now can definitely save you from the trouble.

So how do you communicate to someone that you are delegating work to them? Seah Ying Cong, CTO and Co-founder of Glint, says that there are stages to effectively delegate work. He adds, “Instead of rushing in and telling the employee what to do, just take them through the motions and have regular check-ins to ensure they’re on the same page as you.”

The o’l teach a man how to fish instead of giving him fish to eat. Leadership by example. Delegating by showing how the work should be properly done.

It’s also important to verbally communicate to someone that you are delegating work to them. The reason for most unmet expectations is that they aren’t really communicated at all.

If you aren’t confident with your communication skills, fret not. There are simple steps to take to prevent miscommunication between you and your team:

  1. Schedule time to actually talk about the work to be delegated. This alone already sets the proper tone that you are officially turning over stuff to do.
  2. Simple bullet points of the tasks to be delegated can already do the trick.
  3. Have a leveling off of understanding towards the end of your discussion just so you know that you’ve made your point across.
Photo by Kenny Luo on Unsplash

We’re afraid delegating will bother others

Okay, so this is probably more of a cultural thing more than anything else. Unlike our Western counterparts who are more frank and direct, we tend to beat around the bush with stuff like this.

Maybe it’s because of the notion that we grew up with that we have to take care of our own matters. This is how most of us were raised, to be self-sufficient enough to be successful in life. Of course, this is not without the usual and regular prodding from our parents, but in terms of accomplishing something in life, we take pride in doing things ourselves.

And we’ve managed to bring this to the workplace culture as well. In his book Outliers, Malcolm Gladwell outlines how Asians rank very high on the power distancing index (PDI). We are overly courteous to our superiors, and so when we reach that point of supervising and managing others, we inadvertently still bring with us this kind of mindset.

Delegating work to other people won’t be viewed as bothersome for them. In fact, they should expect it. As you climb higher on the corporate ladder up to the point that you’re leading and managing your own enterprise, you have to expect lesser legwork and more delegating. It’s not a hierarchy thing but rather a practicality and efficiency principle.

We lack the experience to delegate

The most acceptable reason for not being able to delegate is because you simply haven’t done it before. At all.

Maybe you’re a new manager, supervisor or entrepreneur. You’ve just put up your first enterprise and you know squat about tasking people with what they know. And you may end up just doing everything yourself.

Val Yap, founder of PolicyPal, has great advice that can be applied by first-time delegators: delegate based on skills and experience. It’s very practical, right? Why would you assign someone with an area of competency that he knows nothing about? As Val says it, “Pay attention to the people who enjoy taking on huge challenges and those who love going for small challenges.”

Wilson Tan, founder of Web Imp, also has an approach that could work wonders for first-time delegators. For him, startup founders mostly end up micromanaging. They want everything to be perfect because, after all, their enterprise is their “baby”. But as you grow, doing everything yourself just won’t cut it. As Wilson aptly puts it, “While it’s totally cool to value your work so deeply, there are just too many departments within an organization (even a startup) to fully handle on your own. Sooner or later, work delegation is inevitable.”

Photo by Mimi Thian on Unsplash

The beauty of delegating lies in these four words: do less, achieve more. By applying delegating wizardry, you will be able to maximize your output even with minimal input. More results with half the effort. Isn’t’ that the dream scenario for most leaders?

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Trevor Lim

I help liberate business owners by having more time and attention through team building and autonomy.