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Wearing 500 Hats

Author: Larry Chester, President

“The 500 Hats of Bartholomew Cubbins” by Dr. Seuss was one of my favorite books as a youngster. It’s the story of a boy that tries to take off his hat when the king comes by, but another one just pops up in its place. He gets into trouble, as he keeps taking the hats off, and new ones appear on his head. Each one was grander than the one before, until the final one, which was the most glorious hat of all. Bartholomew is a bit like every entrepreneur I know.

As you start a business, you’ll be wearing 25 hats (a bit fewer than Bartholomew). Your first job is to get rid of as many hats as you can. Sometimes, taking off a hat means eliminating a useless activity. Sometimes it means that someone else is doing that job. Maybe they’re more skilled than you are and you’ll get additional benefit from hiring them. But at the very least, that task will be off your plate.

The obvious benefit is that you can concentrate on the critical tasks. What are these many hats that you – the Entrepreneur – have to wear? They include:

Human Resources, Finance, Accounting, IT, Engineering, Customer Service, Legal, Quality Control, Marketing, Manufacturing, Product Design, Strategic Planning, Operations, Reception, Secretarial and Office Maintenance, among others. Jobs that need to be done, but there’s nobody to do them but you. Plus, anything that you have someone else do, you have to pay for, whereas your time is free – or is it?

Like most entrepreneurs, I struggle to attain that work/life balance. With only so many hours in the day, I need to make sure that I get done as much as I can in the time allotted. In the balance are the hours left for sleeping and being with family. OK, I can always sleep less – well not really.

So, how do you take off those hats, trying to get to the most glorious hat of all, and make sure that the jobs are effectively handled?

  1. What is the ultimate job that you want to do?
    Is your strength product development, sales, finance, strategic planning or technology? Decide what it is that you want to end up doing. Just as each company changes over time, your desire to do particular jobs will change as well. There was a time when I most enjoyed working with clients and serving their needs. Now what I enjoy most is telling our story to the world. I’m a salesman. I’m not sure what I’ll be next year. What do you enjoy doing most in your company?
  2. What administrative tasks can you delegate to someone else?
    Probably the most impactful change I recently made was hiring an assistant. A virtual assistant who manages my calendar, keeps track of tasks that need to be done, and follows through with the administrative operations of my company. She’s part time, but once I pass off a task, it comes off my plate. I can worry about other things.
  3. What critical business operations can you delegate or hire out?
    It’s surprising how easy it is to find someone to do work to support your company. Many people hire outside marketing. But in the GIG economy, you can buy all kinds of skills on the street. Graphic design work, writing, publishing, HR, legal, technology. When there was just me, I only had a laptop and a desktop computer to worry about. I’m kind of a techie. I dig all this technology stuff, the cloud, processors, memory, SSD’s, wireless communication, etc. But is that the best use of my time, now? Is my time better spent developing more clients, or configuring a new laptop? It’s certainly a new expense, but now I don’t need to worry about it. Find yourself support staff to deal with chores you don’t want to take time to do.
  4. Off-load those repetitive chores.
    Get someone to take care of the activities that come up again and again. Doing the bookkeeping, bringing on new staff, adding new clients or vendors, managing your insurance. These are all things that need to be done properly. If you don’t create the structure to bring on new employees, clients or vendors, if you don’t find someone else to handle the day to day chores of invoicing, paying your bills, collecting your money or doing payroll, you will find your day filled with administrative tasks that are important, but don’t impact on your bottom line.
  5. Create a structure.
    Remember when you worked for a large company that had a form for everything? Remember the pain of filling out a form for everything you did? But those forms create a consistency that allows you to delegate the work that needs to be done. What are the critical pieces of information that you need when you hire a new employee? What are the items you need to know to add a new customer or vendor to your system? When you train someone, what are the things that you want them to know? How many times do you want to create that list all over again – from scratch. Create a structure, a form, a packet, a folder with the information for each of those tasks. Then when you need to do any of them, you’re ready to go. You don’t need to reinvent the wheel.

The key is that when you, like Bartholomew, can take off those hats, get those tasks delegated, bring on new resources, you will be left with the most glorious hat, that task that you really enjoy more than anything else. That’s what you started your company for. You didn’t create it to handle payroll, do your invoicing, or write manuals. You did it to sell, to deliver a service, to create new products. So, off-load those hats, those tasks, and proudly wear the most glorious hat that you wanted to wear all along.


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