Choosing, Choices + The Smart Spaces Between Them

Choosing, Choices + The Smart Spaces Between Them

Why you should care

Because we all have to do it — and there’s an alchemy to getting it right.

I was recently asked by a young entrepreneur how I have gone about making decisions to help build OZY and it made me ponder: How do we tackle life’s hard decisions — from work to family to relationships? Is it gut instinct? Careful analysis? Both, of course. Inevitably, the decisions that translate into action — whether the outbreak of war or growing a successful business, are individual stepping stones. But what entrepreneurship has taught me is to take the 360-degree approach — which, in itself, is a kind of decision-making plan – and to mine experience and experts alike for guidance.

This isn’t exactly what I told that young entrepreneur, but here’s what I’d tell someone now.

Learning how to make sound decisions is as imprecise an art as any — but when it’s done right and done consistently, the results can be immensely powerful. Take the Myers Briggs personality test, for instance. Years ago, when I first took the test (earning the “ESFP” label, meaning extroverted, sensing, feeling, and perceiving or, in sum, “the performer,” a title that the present Carlos might not even recognize in past Carlos), I learned that personality types can influence analytical and decision-making styles. In Myers Briggs terms, there are planners and reactors, dreamers and detailers. Which might not mean much until you’re stuck in a quagmire of indecision with a friend, colleague, boyfriend or girlfriend and think, Are we at a standoff because we come at decisions in fundamentally different ways?

That prompt made me want to dig deeper — and here’s what I learned and from whom:

Bill Clinton: Talk to everyone you know. Then get help processing the feedback.

Some of us fall into the “streamlined” camp — think Ronald Reagan, who favored single-page memos from his staff that presented clear recommendations. Others, like former President Clinton and current “secretary of ’splainin stuff,” prefer delving into the nuance of a matter, examining it from multiple perspectives and depths. (To my colleagues’ occasional chagrin, I have always been in the latter category.) Bill Clinton famously debated things with various people until the umpteenth hour, often diving in to make his own edits on everything from policy to speeches. Hillary has said many a time during Bill’s campaign that what it took to channel his energies was a planning strategy like hers: one that favored rigor, lists and systematic procedure. Blending the two different decision-making styles — one that took a high-level, curious, somewhat journalistic approach of asking tons and tons of people for feedback; the other that took a head down, straightforward, plow-ahead-with-procedure approach — seemed to get them a pretty successful campaign, if nothing else.

Lloyd Blankfein: Ask your middle management. Don’t just trust the top dogs.

When I worked at Goldman Sachs, CEO Lloyd Blankfein said that he found the most valuable information came not only from his senior team or other recognized experts but also from mid-level people he met in the mid-tiers of his finance departments. Why? Because they often are the most aware of how a company is spending and bringing in its money versus a hypothesis he might have come up with all on his own. Blankfein’s message: Your company’s people are more important than the prettied-up business plans that leaders tend to rely on.

In other words, look to your best people who spend their days in the trenches — from a salesperson to a campaign manager to a soldier; they’re a hugely valuable resource in terms of how to make decisions and knowing who to trust when you need the help.

Alan Greenspan: Research means talking to people on the street — and people in the ivory tower.

In a similar vein, former Federal Reserve chair Alan Greenspan used to extol the benefits of seeking out a number of sources — and making sure they were an eclectic mix of the classic and the unconventional. For him — and any smart journalist, entrepreneur, consultant or curious citizen — that might mean not only looking at unemployment data but also speaking to barbers, visiting a series of gas stations, and identifying the top employers for recent college grads. Greenspan used this alchemical process to guide the Fed in the 1990s, straight through America’s impressive boom. Looking back now, critics might say he did not look at all the relevant data — or he ignored some of it to the detriment of the global economy. Still, I think his practice of vigorously studying a wide range of factors before making complex decisions is a wise one.

As for me? Push back, and know your weaknesses.

What I would add isn’t as much a decisionmaking style as a flavor coating everything I do these days. Increasingly the hard-bitten entrepreneur in me looks at everything through a skeptic’s lens. I ask obsessively: Is that really true? If it’s not, then so what? Call it cynicism; I prefer realism: knowing that few things go as planned or as offered. So as I take in large amounts of information (from conventional and unconventional sources, from highbrow intellectual to the streets), I repeatedly push back, challenging what’s being asserted and why. One of the best and toughest moments during my early years as an entrepreneur was a sit-down with a potential investor, who, after I ran through a 90-minute business plan — one I’d primped and prepped and proffered with confidence — said he was “really disappointed.” I racked my brains. Why? ”You didn’t tell me what was going poorly,” he said. His point: Things are always an inch shy of perfect, and we do ourselves and our teams a great disservice by not being upfront about it.

My formula for success is not perfect. But whether we’re expanding our team, raising money, planning a marketing campaign or a million other things that go into running and building a business, my approach to decision making — developed from personal trial and error and lessons learned from those I admire — has made a difference. I can’t guarantee it is right for everyone, but for what it’s worth, try adding it to your mix and see where you come out. It could just be ahead.

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