Technology and typos: Keeping pace in the old world

When and how should you delegate tasks? This is probably one of our biggest business challenges
When and how should you delegate tasks and responsibilities? This is probably one of our biggest business challenges

In small businesses, “executives” certainly cannot spend all their time overseeing the business, leading, delegating and managing others to do the work. In fact, one of the biggest challenges in growth (and in tougher conditions, survival) relates to how, when and where to do the work independently, forget the job, delegate to employees, hire new employees, or contract the work out — and in contracting or employing, determining the best contractor/employee and how much you should pay.

It can be quite the juggling act, especially?for someone who arrives in business through trade or professional skills, which effectively define the business purpose. After all, a plumber will likely establish?a mechanical contracting business; or an engineer will set?up an independent civil engineering practice. However, a great engineer may not be skilled or interested in sales and business development and a talented plumber may know virtually nothing (and have almost no interest in) bookkeeping. And I’m quite confident that virtually no one in business starting from the trades or professional services has sought out or planned a career in marketing. (And those few who do, I’ve notice, almost immediately succeed to a far greater degree than their competitors.)

How do you resolve these issues?

One solution, advocated by several consultants,?is to think “systems” and develop a set of rules and processes, based on metrics and solid traditional business practices. These ideas work, to the degree that you implement them successfully and if you have habits in a more haphazard direction, once you successfully revise your habits and achieve a new standard.

The second solution, I fear (and maybe in some cases advocate), is to do what you love doing, and then check the boxes or simply find ways to reassign?the other tasks, presumably in order of time value and interest. ?If you hate doing something, and it consumes many hours, and the replacement services are relatively inexpensive and readily available, then you have a ‘no brainer’ delegation process, either to employees or contractors.

I remember discovering that I didn’t really need to keep the books myself — one of the first delegations — when I posted a small ad and received dozens of applications from people who claimed to have bookkeeping skills. ?Things worked really well until (this is true), her husband went crazy (literally), lost his job and then left his wife — taking the computer with our company records with him. We were able to rebuild from stored paper records and a new bookkeeper, but I really learned a lesson about backup there!

In practice, I think most business owners apply some of both models in solving their management and delegation problems.

For example, we ultimately hired our office manager/bookkeeper, through a systematic hiring model that I developed some time ago, which focuses less on resumes and interviews, and more on practical work exercises, evaluation tests and verifying references. When we faced economic challenges and our external bookkeeper decided to leave (fortunately this time in an orderly manner), the office manager took on the challenge to learn the basic bookkeeping skills and, with external software) both keeps the books and generates immediately accessible financial reports which I can review anywhere in the “cloud”.

Today, I’m testing the combination of self-reliance, systems and innovation in overcoming a problem with our email list management system. Internally, we don’t right now have an IT specialist, and by default that job has landed in my lap. Over the years, I’ve learned enough about CPanel, WordPress, mail servers and the like to be able to manage most routine tasks — jobs definitely not in my official job description.

Last night, in a fit of brilliant blundering, I managed to delete the entire email blacklist — the key file which determines the “do not mail” list and avoids spam complaints. The solution: call on the software developer for advice, ?and then implement the solution an offshore contractor in the Ukraine the last time I had a crisis in this area — and discovered the person’s incredible ability and support capacity through a lucky find on an online job board (

Have you experienced delegation experiences, challenges or solutions? Please feel free to share your observations through a comment below or by email to


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