As a Lebanese-born entrepreneur, I am preloaded with software that is driven by one overriding factor: The world will constantly surprise you. It’s an outlook that deals in real-time risk — you’ve got to think fast and adapt quickly. When my family fled civil war in the mid-1970s, we didn’t have time to strategize. The world was on fire all around us in Lebanon. We just needed to go. We’d figure the rest out once we got there. Ever since we left (all 18 of us) and emigrated to America, I’ve been conditioned to think and act in the moment — that is, to work with real-time risk.
Today, as a business owner and leader, I’m obsessed with risk. I attribute this to a few factors:
- My dad loved to bet on ball games.
- The Lebanese worldview is summed up as follows: The world is an inherently risky place, so you better get your act together quickly.
- My Lebanese parents’ worldview, one driven by a single tenet, is this: Never do nothing. Give it some thought, but don’t think too hard.
But all risk is not created equal. Risk manifests itself in two ways. The first kind is what I call future potential risk. It’s the harder of the two types to truly assess because it’s not real. The other is real-time risk. This is the risk you face when you’re no longer planning in the war room — you’re out on the battlefield and the facts on the ground are changing constantly.
Future potential risk: The Queen’s Gambit
Putting aside speed chess, the game of chess is a lot of future potential risk planning, thinking ahead as to what can go wrong for minutes on end. Recently, while watching The Queen’s Gambit, a beautifully shot and acted Netflix drama, I was reminded that I actually hate chess. I’ve thought a lot about why I hate chess. The game, with its millions of possible paths, should draw me in. But it doesn’t. I think my lack of enjoyment of chess is because it favors thinking over doing — a practice that will paralyze you in the world of risk management in business. Maybe it’s the Lebanese in me, but paralysis equals giving up.
When you have time to think and plan, part of that thought process is spinning up risky scenarios and navigating through them. This is fictional risk or future potential risk. Future potential risk crops up when you’re plotting and planning. If you haven’t yet embarked on an effort (or in the case of chess: the next move), you’re going to do a lot of thinking about what could go wrong. You usually see it in scenarios or models you draw up in your mind or on a spreadsheet.
It’s a frustrating form of risk because, depending on your mood, you can dial up or down the variables to increase or decrease risk. Even worse, you can dial up or down your perception of the exact same level of quantifiable risk at any given moment. The exact same set of facts can feel great one day and utterly demoralizing the next.
The exercise of evaluating future potential risk is a good investment — it’s important to find that path of least peril, as long as that path is a path forward. In chess, you still have to make your moves (you can’t stall the game entirely), but the game prioritizes analyzing over doing, and it does so in an environment unrealistic for business. There is no pause button on the battlefield — or in client meetings. That’s only in chess.
Real-time risk: Total Annihilation (1997)
The lack of real-time risk is why chess is boring (send angry reactions to email@example.com). I need the added stakes of watching shit blow up. Enter the world of real-time strategy (RTS) gaming.
I still remember my first introduction to RTS. The year is 1997, and the game is Total Annihilation. It wasn’t as big a hit as RTS blockbusters like Command & Conquer or Starcraft, but it was this ambitious attempt at 3D back then and it was incredibly fun.
I associate RTS with the second type of risk: real-time risk. You’re no longer planning in the war room. Now you’re out on the battlefield, and the facts on the ground are changing constantly.
Watching the action unfold in real time in RTS games is just part of the fun. The real fun is injecting your directives into the chaos as the action is unfolding. Chess is turn-based. With RTS, it challenges you to assess a constantly changing environment, plot out your next steps, assess the risks associated with those actions, then execute them. Doing nothing and thinking too long equals total annihilation. You have to make good decisions quickly. A requirement of RTS games: Hitting pause hides the battlefield. The muscle you’re exercising is real-time planning, thinking, and doing. Hitting pause and just thinking for long stretches at a time? That’s chess. With risk in business, you must do something, now. The luxury of pondering a move is gone.
Some advice on dealing with risk in business and software
What does all of this have to do with business? It turns out that both flavors of risk are very much present in the world of business and software. It takes experience to build out the antennas that pick up credible risk, whether future potential or real time. Software is unusual in that you can’t blueprint away all the unknowns at the outset. Computer code and humans are full of surprises. There will always be risk. The key is to hone that risk-sensing skill and pair it with an openness to adapt and change. Here are a few of the things I’ve learned:
- Make the leap into real-time risk. Take your time, think through all those probabilities, and weave the path of least peril before you head out on your journey. This is a valuable part of the process. But once you do come up with that plan, recognize and acknowledge the shift from theoretical to real time. Once you’re in motion, don’t hesitate. Trust your strategy. Execute aggressively, with confidence. Your team will need to see that confidence as they (and you) deal with adversity.
- Don’t solve risk with more work. I’ve never been involved in a software effort that didn’t shift and change over time. When you’re presented with real-time risk, avoid solving it with more software, or in blunter terms: more work. More means more paths to friction and more opportunity for new problems to crop up. When in doubt, do less.
- The smaller the team, the better your ability to react in real time. Team size is often associated with output, and in calm waters well-organized big teams can ship a ton. But when faced with adversity, it’s hard to quickly turn a big lumbering ship. Big teams can get more done (maybe), but when you’re presented with an unforeseen challenge, it’s much easier to react and adjust with a smaller team.
- Real-time risk is always there — but sometimes you have to look for it. As a manager, you’ll rarely witness risk first-hand. It often shows up when either a) someone on the team shares something, or b) it’s too late and you’ve already slammed into the iceberg. Sometimes it surfaces casually in a meeting or email. But more often it has to get teased out. Just as you try to foresee future potential risk when planning, seek out real-time risk by fishing for weak links and vulnerabilities. The challenge is to do this without undermining or second-guessing your team. Be inquisitive but supportive.
Over time, I’ve come to appreciate the value of taking the time to run future potential risk scenarios. My frustration with chess is probably driven by an allergy to inaction that I’ve cultivated over the years. It’s the antsy Lebanese side of me, constantly wondering how I’m about to be blindsided. But I’ve come to learn the inherent value of failing in your head instead of failing in real life.