An ex-boss of mine and I were catching up a couple of weeks ago. We were meeting after years, and in the years that have passed us by, he had a mega-exit in his last startup, and after a brief gap he took to figure out what’s next, he is back in the driver’s seat. The startup is already making some waves and coupled with his previous success and trust investors have in him, they have raised decent capital in no time. As a result, hiring the right talent is not an issue. The problem, as he himself described, is coming with delegating the work.

The last team we built, it took everyone a while to understand my expectations, and while I was fortunate enough to find a bunch of great guys, the initial couple of years needed me to be on top of everything, figuring out what needs to be done, keeping track of those items, pushing everyone to get results. Unfortunately, I have to do it all again. We will get there again where people can work independently, without me having to drive everything, but it is going to take some time to get in the groove.

And this is the biggest challenge entrepreneurs face when delegating work to their teams. Entrepreneurs inherently love getting stuff done (and getting it done NOW), and they don’t mind getting their hands dirty to ensure it gets done right, and at the right time. The result? The idea of delegating work to others is often an uncomfortable thought, and they would always rather prefer to do it themselves.

Also, I believe I must note that this is not just a problem with new entrepreneurs who haven’t had much experience managing people. As we just saw in case of my ex-boss, no matter how seasoned an entrepreneur, the minute you put him in a new setup, in a new environment, with a new team and a blank slate, it is back to day 1. And with day 1 comes up all the challenges of day 1.

THE FRUSTRATION

It isn’t that entrepreneurs don’t try delegating the work. They do realize that if they are to truly grow at a neck-breaking speed, they need to be on the sidelines and not get dragged down to the nitty-gritty of every single thing.

So what goes wrong?

When they do delegate, it often results in frustration. They come to realize that the work they needed done hasn’t at all turned out the way they were expecting it to, or worse — not even close to completion by the time they could swear it should have been easily completed.

And from there it is a snowball effect. This failure weighs on their mind, and after some thinking, they jump to the age-old wisdom.

If you want something done right, you gotta do it yourself.

What they don’t often realize is that they are burning the candle at both ends, and it starts taking a toll on them, things start slipping through the cracks. Ultimately, both the entrepreneur and the business ends up paying the price.

SO, IS DELEGATING A MISTAKE? OR, ARE YOU MAKING A MISTAKE THE WAY YOU ARE DELEGATING?

The frustration we talked about results in us often coming to the conclusion that the business and the workforce isn’t mature enough to handle delegation. What we often don’t realize is that the problem exists with how we are delegating stuff.

You gotta delegate challenges, or better still, “results”, not items from a to-do list.

The most common way of delegating stuff around I have seen is the business leader making a long task list on a whiteboard, and then assigning various tasks to different stakeholders. This is the textbook definition of micromanaging, and the best resources you have will just hate that — they would rather solve a problem for you. And even your average resource who won’t hate being micromanaged, will just do exactly what you ask them to, and not a single action will be taken beyond what you have put on his plate.

Either way, it becomes counterproductive.

Just look at a simple example. Say I need to find a new office space for my team of ten people. I could ask someone in my team to contact all co-working spaces on XYZ Boulevard and get a quote from them. Before the week is up, I will have an email listing down the different co-working options available. Great.

Now imagine a scenario where I just put someone in charge of the fact that we need to change offices and ask him to look into it factoring in who we are as a business and how we have been growing. I may get an email that details out:

• not just co-working offices, but other options as well weighed on the benefits each option presents
• whether expanding our team would be a challenge in a location, and if so, they would be put on a separate ‘filtered out’ list
• options from different parts of the city, and not just a stretch of road as I had initially asked for. These options may be rated based on their connectivity from hubs of public transportation, distance from residential neighborhoods, availability of parking spaces, etc.
• other factors

You realize what I am talking about, right? In one case I am limiting my extremely capable resource’s bandwidth in doing a task. In the second case, I am putting him in charge of solving a challenge for the business and letting him decide of the things he feels we need to be mindful of while making the decision.

DELEGATING DOESN’T MEAN YOU WILL BE AN ABSENTEE

Delegating stuff around the right way helps you and your business achieve better results, and achieve them faster. It also frees up quite some bandwidth at your end that would otherwise be spent doing busy work. But, it, in no way, means you should be MIA. You need to now play the role of a mentor. You need to help them work their way through the challenge at hand and enable them in finding the solution — a solution that is both unique to them, and is found their way.

Take the office-space challenge we talked about earlier. The reason I would have gotten such a detailed mail when I delegated the problem instead of a task is that my team has been working with me for a while and they understand how I think and why I think that way. We have arrived at that understanding by me throwing them in the thick of things but always be there to help them figure a way out. Once they have been given a problem, we brainstorm on how they feel the problem needs to be approached and what would a good solution look like. In the case of the office-space, if we have a lot of employees commuting by public transport, it has got to be part of a good solution. Once they start dissecting the problem and figuring out what all should be a part of a good solution, they will solve the problem the right way, and they will do it all themselves — for this problem, and all future problems. Because they will always start at the basic building blocks of a good solution.

Oh, and most certainly, the second they start doing that, the first question they will ask — what are the reasons why we are looking for a new office-space to begin with? If you want them to challenge the status quo, they need to understand why the status quo needs to be challenged in the first place.

DELEGATION IS HARD, BUT AN INESCAPABLE NECESSITY

I love my ex-boss. There are a lot of things I learned from him. I have been fortunate enough to have worked with some of the sharpest, most passionate, dedicated and brilliant minds the Indian ecosystem has to offer, and they have all contributed to me being where I am today. He was one of the first, and he took a bet on me real early in my career. But I somehow feel he needs to challenge himself into getting to the delegation phase faster. They are onto something huge, and despite the fact that I know he will take the business to great heights, delegating things now and delegating them well could very well end up saving him a few years. :-)

If you want to truly scale your business, you do need to delegate, and not just delegate — delegate the right way. For a business to truly grow, the leader needs to stay on the periphery of things and not get in the thick of them. You need to be aware of what’s going on on a macro level, and enable people into growing into leaders who can handle the nuances of those individual challenges. And as your business grows, you need to encourage your leaders to inculcate that same behavior in their lieutenants.

Always remember, solving challenges for the business helps your employees take pride in their work while feeling more connected to the business on a deeper, more intricate level. And as we tend to prefer hiring people smarter than ourselves, the more you enable them into being control of the way they drive things forward, the more your business could benefit.

That’s it for today; see you tomorrow!