The Portfolio Leader

“Our executive recruiting firm loves to see the title ‘bartender’ under previous employment on a resume.”

I’m sorry, can you repeat that? I’m not sure I heard you correctly.

He did, and I had heard right. He went on to explain that his search firm gives successful bartenders special notice because of their ability to juggle multiple items while maintaining intense personal interactions. Translation: They can handle a high volume of tasks without abandoning their people skills.

Think about it. It makes sense.

What is a Portfolio Leader?

In recent years I’ve met more and more leaders attempting to master juggling skills in their own work lives, and I’ve started referring to them as “Portfolio Leaders.” These are leaders who have more than one work ball in the air. These are not simply leaders who juggle multiple tasks within one job. We all do that. No, these leaders add work or investment interests on top of a given occupation.

A doctor who manages real estate investments while remaining fully engaged in his or her medical practice. 

A seasoned executive who is also involved in a small start-up.

A pastor who writes and speaks…and maybe even builds a company on the side to house and support those items. 

A lawyer who takes on an equity stake in a new company in lieu of his typical fees and now juggles the daily work of a lawyer and evening work of a small business owner. 

Even the board member who balances her board duties with the responsibilities of her primary profession.

And surely I don’t need to introduce the serial entrepreneur who has his or her mind, wallet, or flesh divided among a half dozen ventures.

Juggling Well

If you know anything about juggling (and why wouldn’t you?) then you know that while there is certainly some inherent eye-hand coordination required, there are also some learned skills that must be practiced. Portfolio Leadership is the same. Some folks are built with greater than average capacity and are more innately wired to handle multiple items and responsibilities. These traits, however, are no more a guarantee of portfolio leadership success than eye-hand coordination is for a juggler. There are still skills that must be practiced and mastered. 

Questions to Answer, Skills to Master

1.  What is your motivation for being a Portfolio Leader?

One reason we’ve seen an increase in Portfolio Leaders is our inability to remain content, live simply, and stay focused. We live in an unsettled culture, jumping from one thing to the next without ever completing the first. We are accustomed to and thrive on over-stimulation. We switch interests and passions rapidly, just like we move from texts to calls to Twitter. Task stacking is second nature.

Because of this, we must be particularly honest regarding our motivations. Are they financial? Opportunistic? Boredom? A natural outflow of our calling? Some combination? 

2.  Clarify the swim lanes and expectations for all parties.

Before the starting gun even fires, be certain that you clearly understand your role and value-add. One of the most common obstacles that derail portfolio leaders is a misalignment of expectations between partners and ventures. Know your lanes and the lanes of all the other swimmers as well.

As a seasoned friend used to say to me, “Hope for the best but prepare in case it doesn’t.” 

Get things in print.  Outline the time, money, and any other contribution you are making. Make sure you understand them. Make sure your partners understand them. More communication, not less is the rule for a Portfolio Leader. 

3.  Establish and maintain sound personal ethics.

It is not uncommon for a Portfolio Leader to use money from the right pocket to fund the left. Employees from one venture often double up and pitch in on another. Intellectual property might not belong totally, purely to any one person or entity. All of these can be slippery slopes and require solid ethical footing. 

Whenever possible, establish right and wrong, acceptable and unacceptable ahead of time.  This will be invaluable as you navigate your portfolio and crises arise. Keep your ethical razor sharp. It can dull in a hurry.

4.  Budget and monitor success.

Ultimately, your sustained success will hinge, at least in part, on your ability to stay organized and manage your time well. It is hard for the unorganized and scatter-brained to succeed as a Portfolio Leader. That kind of person can do OK in a supporting role, or even a solo role, but to carry some of the strategic weight of the enterprise you will have to interface with effectiveness to maximize the ROI.

Make sure you are not letting crucial items fall to the ground. Keep your core business healthy and your key relationships intact.

Being a Portfolio Leader can be fun, rewarding, and productive. As you toss another ball into the air, just make sure the others are still in good position, and when necessary, don’t hesitate to remove one before adding another.