How to Wear the Right Hat for the Task

Do you sometimes feel trapped by all the different roles you play in your small business? Do you love going out and schmooze it up, build relationships and get that new client? Do you hate being locked up in your office and concentrate on juggling cash flow? Or, are you bored or uncomfortable dealing with employee issues? Yet you’re a small business owner growing your business and cannot afford, yet, to hire people to take on some of these responsibilities.

Wearing different “hats” can actually be a positive experience as long as you and your people are clear on which one you’re wearing at any given time. Rather than approaching it as a burden try to look at it as an opportunity to experience your business through a different lens depending on what role you’re finding yourself in. In the long run this approach will greatly benefit you as you grow your business and start removing yourself out of the roles you don’t want to play.


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“What is it that you like doing?  If you don’t like it, get out of it, because you’ll be lousy at it.”

Lee Iacocca



How to Wear the Right “Hat” for the Task  


The term “wearing a lot of hats” is virtually synonymous with being a small-business person or entrepreneur. The expression comes from a time when a craftsman’s hat signified unmistakably what he did for a living—welder, miner, baker, butcher, banker and so on. But the luxury of wearing a single hat for a career is long gone. For most of us these days, wearing a lot of hats is what we do for a living. And at any given activity, there may be multiple of those “hats” that have to be firmly on our heads.


For the most part, this is a good thing. One of the advantages of wearing a lot of hats is that you can show up at a meeting or tackle a problem from various perspectives. If you are in a sales meeting, your production manager “hat” can keep you from giving away the store in order to get a customer. In a procurement decision, your sales “hat” can keep you from paying too much for materials. And through it all, wearing your CFO hat can keep your business solvent. Some even argue that wearing a lot of hats enhances the creative process. At best, you are cross-pollinating each of your tasks with a little wisdom and experience from other fields, which makes you better at all your “hats.”


But successfully wearing many hats, like effectively multi-tasking, isn’t necessarily a skill you are born with. It is, however, a skill you can learn and refine. Since there is no way to escape it, you might as well enjoy it—without becoming schizophrenic. Here are some tips:


Inventory your hat rack. In his classic The Seven Habits of Highly Effective People, Steven Covey explains how to consciously define and nourish each of the roles you play in life. The same logic applies within your business life. Don’t just think of yourself as “entrepreneur” or “business owner,” but delineate all the separate roles and think through how you approach and perform in each.


Pick the right hat(s) for the task. This is especially important if you are engaging with someone who has the luxury of being focused on a specific task. First, you have to meet them where they are. If it’s a production issue, you’ve got to show up in your COO or production manager hat. But then try to imagine who else on your virtual “team” you would bring to the meeting. The head of marketing? The CFO? Take a few moments and look at the forthcoming meeting from that perspective. What are you watching out for? When would you insert a comment? When would you kick yourself in the shin for saying the wrong thing? It’s a simple mental exercise that can bring tremendous leverage to meeting preparations.


Know when to fold ’em. If you really detest a task, or you’re just not very good at it, then hire it out. Wearing many hats may be good for your brain, but you naturally are going to be better at some—or enjoy some—more than others. Don’t sacrifice your performance or the results of your business by clinging to tasks that you shouldn’t be doing. Leverage what you do best—that may be two hats or it may be 10—but then hire out the rest.



Ellen van den Berg, founder and owner of NEXUS Consulting works with small business owners who are the victim to their own success – overbooked, understaffed and unable to grow because everything depends on them. Ellen helps her clients reconnect with their passion, align the business with their life and change unproductive behaviors. The result is a productive, profitable business that can mostly run itself and provide more joy and freedom for the business owner.

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