Love your business? Let it go

Delegating is one of the toughest skills for an entrepreneur to learn. But it’s the most important

 
CEO office with an empty chair
(Erik Dreyer/Image Bank/Getty)

Every once in a while, you’ll come across entrepreneurs whose efficiency and productivity seem to defy belief. They don’t fret about work-life balance. They don’t bail on family vacations to meet with investors. They’re never first to arrive at the office nor last to leave. They’re just so very together.

Yet these über-preneurs are no more talented or lucky than anyone else. They have simply mastered something so many others struggle with: the art of delegation.

There are a lot of reasons entrepreneurial types don’t often take naturally to delegating. For many, it’s sheer habit; if they started the business on their own (or with a bare-bones team), there’s a good chance they’re simply used to doing everything from answering the phone to cold-calling prospects themselves.

For others, personality gets in the way. Research has shown that entrepreneurs tend to be more egotistical, impatient and prone to micromanagement than the general population. These traits, so essential to the hustle of forging a successful venture, aren’t especially conducive to hands-off leadership.

Then there’s the uncomfortable reality that delegating takes work. It requires developing processes where once there were ad hoc solutions. It requires codifying and standardizing the ideas that once lived in one person’s head. And it requires documenting early experiences and mistakes that got discarded or forgotten on the road to success. Especially for entrepreneurial personalities whose natural instinct is often to eschew formality and convention, it all becomes uncomfortably bureaucratic.

It’s for these reasons that so many entrepreneurs are not just unable to delegate—they’re unwilling to do it. Yet do it they must, if they want to build something big while retaining a semblance of sanity. Every year, when we ask the CEOs of PROFIT 500 companies—who, as the leaders of the country’s fastest-growing businesses, have figured out what’s needed to scale up—to share the most valuable lesson they’ve learned, some variation of “I can’t do everything” is always a frequent response. Similarly, when we ask about the smartest thing these execs have done in growing their firms, the most common answers oscillate between “hired a good second-in-command” and “stopped working ‘in’ the business and started working ‘on’ it.”

This achievement can be revelatory. At the PROFIT/Chatelaine W100 Idea Exchange late last year, Grail Noble, head of award-winning Toronto marketing firm YellowHouse Events, spoke about the liberation she felt upon her recent discovery that her company can run without her hands-on involvement. The milestone was personally fulfilling, yes, but Noble also sees it as crucial to YellowHouse’s sustainability. And that is perhaps the best reason to let go: For the majority of investors, prospective customers and potential acquisitors, a leader’s inextricable involvement in a business’s operations is a liability, not an asset. What you might see as your indispensability, others see as a massive single point of risk.

There are plenty of tactics you can employ to disentangle yourself from the day-to-day. The most important are hiring capable people and, as mentioned earlier, developing internal systems and processes to capture all that brilliant lightning in your brain. Virgin founder Richard Branson has proved to be a master delegator—which is why he gets to spend so much of his time lazing in a hammock on his private island, dreaming up new business ideas, instead of being up to his elbows in cash-flow projections. His prescription is to assign people who have new ideas for the business with the responsibility of seeing those ideas through: “From those experiences, they will then have built the confidence to take on more, and you can take a further step back,” he says.

But none of that can happen without accepting the bittersweet truth that your own redundancy is ultimately a good thing. It’s the first step in becoming the kind of blithely proficient go-getter your peers will envy.

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