Decision-Making Roadblocks: Strategies for Common Challenges

6. How do I know when I’ve got enough options?

Advice: (1) Try to “fall in love twice.” Keep searching until you’ve got two really good options. (2) The purpose of multitracking is to let you easily compare and contrast options, which helps you map out the landscape of what’s possible. If incremental options aren’t helping you get smarter, you’ve probably done enough. Call off the search for more. (3) Be careful not to collect so many options that you don’t have the time or resources to “reality-test” them. (For example, the aspiring home buyer will need to limit her serious options to about 4 to 7 homes rather than 30, just because of logistical reality.) (4) If one of your options doesn’t have any advocates, drop it from contention. (Or, if it’s a personal decision, discard any option that never seems to cycle to the top of your mental wish list.)

7. We always go through the motions of exploring and analyzing decisions, but then ultimately the boss does what he wants to do.

Advice: (1) Consider the opposite: Maybe the boss is right. He may be considering a wider set of information than you. But if you’re still skeptical about your boss’s judgment, read on. (2) If your boss will inevitably make the final call based on his “gut,” then could you invest in training his gut? For instance, you could try to arrange a “close-up” for him—some kind of real-world visit (to a retail store, a customer site, a patient’s home, etc.) that would inform his intuition. (3) In meetings, find ways to remind the group of the organization’s core priorities. Surfacing those priorities might make it harder for your boss to go rogue. (4) Give up on today’s decision but start thinking about the next round: Try to get your boss on record about some tripwires. For example, what circumstances would convince him to reconsider the decision nine months down the road?

8. I have tried advising my son/daughter using ideas similar to these and they just won’t listen. They do what they want to do anyway.

Advice: (1) For kids of a certain age, parents are genetically disqualified as advisers. So find someone more “credible” whom they might trust. Perhaps you could get someone who has lived their choice to give your kid a realistic preview of what’s involved. (For example, a teen contemplating skipping college to pursue an acting career in NYC might benefit from hearing—from the mouth of an actual struggling actor—what that lifestyle will be like.) (2) Ask your kid, “If I let you make this choice, what am I going to see that will convince me that you’ve made the best possible choice?” (Sample answer for the aspiring NYC actor: “Mom, I just know this is going to make me happy and that I can live frugally enough to make it.”) Having these overconfident predictions on record will give you leverage when/if the claims prove false. (Or, conversely, they may help you to realize that your kid was right all along!)

9. We have too much information. A blizzard of customer data. To really process all of it would make our decisions take four times as long.

Advice: (1) Maybe you’re too zoomed in. Experts make better predictions when they zoom out and look at base rates rather than trying to predict based on the idiosyncrasies of individual cases. (2) You don’t need to predict when you can know. Is there a way you can ooch—run a small trial—and learn directly instead of continuing to speculate? (3) Could you be obsessing about a decision that just isn’t worth it? Try the 10/10/10 analysis: how will you feel about the decision in ten minutes, ten months, and ten years? Use that perspective to judge how much attention it deserves.

10. The culture here makes no one want to give up on a bad project or bad idea, because that means you have to admit failure. This silly persistence hurts us because it drains resources that could go to new projects. What should I do?

Advice: (1) Remember to toggle between the prevention and promotion mindsets, as did the companies who fared best after recessions. In your situation, the promotion mindset may help people reorient themselves toward seizing new opportunities rather than sticking with failed choices. (2) Try to insert some disconfirming views. Can you have people war-game what competitors or customers will do if the bad project persists? Better to admit failure now than face disaster in the future. (3) Andy Grove faced a similar situation with Intel’s memory business, which had begun as a tremendous success but slid slowly into trouble. The question “What would our successors do?” gave him the strength to declare defeat on memories—while doubling down on microprocessors. (4) Set up a tripwire in the form of a resource partition that forces re-evaluation at a specified time. (For example, “We are going to give this legacy project six more months, or $250,000 in additional investment, but if it doesn’t turn around by then, we’ll rethink it.”) That may make it easier and less political to change course.

11. I know what the right thing to do is, but I’m not sure I could ever sell it politically. So should I fight for the right thing or just resign myself to the “sausage factory”?

Advice: (1) Think “AND not OR”: Be careful not to frame the issue in black-and-white terms until you’ve made sure there are no solutions that would allow you to do the right thing AND satisfy your colleagues’ issues. (2) Be a devil’s advocate. Even if you don’t sway the final decision, you might still have an impact on the way the decision is implemented. (3) Appeal to core priorities. If the “right thing” is what’s most consistent with your organization’s stated values, then the burden should be on your colleagues to dispute those values, instead of arguing with you personally. (4) If the cause is lost, shift to bookending. Find ways to cap the potential harm you envision. In doing so, you’ll be protecting the organization—and also marking yourself as the one wise person who saw the harm coming. (5) And don’t forget to assume positive intent: Your colleagues may be wrong (or you may be), but chances are all of you want to do what’s best.