Delegate like a Pro

Delegating is hard for a founder who deeply cares about his company. Once a company reaches a particular scale, a founder must embrace the inevitability of learning how to delegate. As a founder of Redwerk, I had to learn to delegate in order to overcome the company growth plateau.

Spoiler alert: it wasn’t easy.

Dealing with the Fear

The fear was real. I was paranoid about all the important things going wrong if I let anyone but myself do it. That’s why all the project management, customer communication, and sales functions for the first 8 years I did myself. For the freaking 8 years, I hired only engineers and testers while handling everything else myself. I reached a point of saturation and realized Redwerk hit the growth plateau when we had 10 customer accounts and hired 50 full-time employees. This was when I realized for Redwerk to become a big boy company, I had to learn to let go. To allow for growth, I needed to hire specialists such as marketing, HR, recruiters, project managers. I also needed to build and train a strong sales team.

I noticed that with the delegation for every role, I would stop worrying and would be able to delegate and let go once I clearly understood my own expectations for that role. Same like with engineers and testers, I clearly knew what to expect and what great work looks like.

Once I was able to clearly define a role and set expectations, I was able to delegate execution to others.

My job as the most senior leader in my company became to gain enough practical knowledge of processes to be able to set realistic expectations for the specialists I delegated to, who knew how to execute better. This way I knew that I’d be able to tell when things go well and when they don’t. If things didn’t go well, I’d be able to step in at least to fix it myself.

More Hours In — More Results Out

Like most, I only have 8 productive hours in a day. Sometimes I can stretch it to 12–16 maximum. If I multitask between 4+ roles, I’m only able to dedicate up to 2 hours to each. On the flip side, if a dedicated person is focusing on a specific role exclusively, it is full 8 hours, even if the work is done slowly.

Simple math — delegation increases the hours dedicated to specific areas of work and more work gets done this way.

Ready to Delegate?

So far, we’ve established that delegation is a virtue. However, you might be thinking, what’s the catch? If this is so good, why don’t I just delegate everything? There must be a downside, like being prepared to deal with subpar results compared to what you could’ve gotten by doing the job yourself. Well, yeah — you need to have criteria to decide what you can delegate safely. Here’s what I came up with.

Start with making a list of tasks for a business function you want to delegate. Literally, like that: open your laptop, login into the CRM, switch to the tab X, open the first record on the screen, etc. It has to be that detailed.

If some of the steps are vague or unknown, like in the South Park’s classic episode — “1. Steal socks. 2. ?. 3. Profit”, the business function is not ready for delegation.

It is not ready until you bridge that gap. If you don’t know what’s done precisely, you cannot delegate it. If the person you’re delegating to can fill in the gaps for you and knows the domain better than you — awesome, and congratulations. Once it is clear that you both know what to expect in terms of the execution and delivery, delegate away.

Let Learn, but Demand Results

When you delegate work, your employees get an opportunity to learn and grow. This opportunity comes with expectations of delivered results. While they will likely benefit from your coaching, it is critically important to communicate clear result expectations and deadlines. Accountability is a good demand in exchange for your trust. As far as delivery expectations, in software development, the logic is binary — one or zero. It is one when it is done. Otherwise, it is zero, even if the progress is 99%.

Delegate the Uncertainty

This is my favorite part.

Clearly, it’s easier to delegate what is well defined. A harder question is how to delegate something that requires creativity, involves a long-term effort, or consists of multiple steps. It’s even harder to delegate something that carries a high degree of uncertainty.

I like to start with decomposition, breaking it down into smaller, manageable tasks. Because these tasks are more apparent than the big problem, they can be delegated. Examples: gathering competition information into a spreadsheet, drafting up a presentation, or creating a template for marketing mass-mailing campaigns.

Instead of trying to solve this kind of projects entirely by yourself, try scoping out the first step and delegating it to someone. It’s much better for your business to have a result, whatever small than to let days, weeks, and months go by without any progress. I iterate quickly — once I define and write down the first version of a task scope, I pass it along. Subsequently, I expect a result, a draft, or a question that will help me refine the scope and repeat this process. This approach gets me results early and consistently, and this is good business.

Because most of the time perfectionism, paralysis by analysis and waiting for inspiration are simply procrastination in disguise.

And guess what, failure to delegate is just another excuse to procrastinate. Realize that early, tell your friends, don’t let this happen to you.

Best of luck!

Now I’d like to hear your stories: Was the struggle real? How did you embrace and master delegation? What did you learn along the way?