Leaders Need More Doubt - Advocate To Win

How do so many smart and savvy leaders become the victims of deception, and why does it matter? It matters because a leader’s job is to protect their stakeholders, their board, their employees and their money. In order to do their jobs, leaders need to learn to embrace and use their doubt.

Bill George recently wrote a wonderful piece for the Harvard Business School Working Knowledge publication asking “Have We Lost Sight of Integrity?” He argues that “leaders need to have integrity so that we can all agree on the truth”. He’s right that leaders must have integrity. But integrity must be balanced with doubt about others and their integrity. It’s not enough to tell the truth. Leaders must also be able to discern who’s lying. They need to know who to doubt, and what to do with that doubt.

Michael Smets, Professor or Management at Said Business School at the University of Oxford, has been an advocate for the power of self doubt. In his 2015 CEO Report: Embracing the Paradoxes of Leadership and the Power of Doubt, he argues that leaders should embrace doubt as a positive state. More recently, he’s said that “the better they doubt themselves in the decision making process, the more confidence they have in the outcome.” Smets’ work is focused on leaders admitting that they don’t know the answers, and this type of doubt is vital to build credibility. But leaders also have to admit that they have doubts about others in order to discern whether they’re being deceived.

For twenty years it was my job to capitalize on doubt. As a trial attorney, I made the jury doubt my opponent’s case and believe mine. I used doubt to win. I tapped into my psychology degree, my training and my experience to do so. Now I work with leaders and corporate partners, teaching them how to use the tools I used in the courtroom to make the case for their business, their teams, their ideas and themselves. One of those tools is doubt.

Here are three tools from the courtroom that leaders can learn to use their doubt and avoid being the victims of deception.

1. CURIOSITY

Ask questions. One of the most successful leaders I’ve ever coached learned to master questions in response to his doubts. When we first started working together, I was struck by his intuitive discernment. He’d hear something from a colleague or potential partner and he’d say “That doesn’t sound right to me.” His intuition was strong, and he knew what doubt was. He felt it in his gut.

But this leader didn’t always know what to do with his doubt. Just saying that something “doesn’t sound right to me” wasn’t enough to influence his board or his team. He had to go further, slow down and use curiosity to ask questions exploring the bases of his doubt. He had to get curious about it.

You’ll become a better leader if you get curious about your doubts. First, anytime you hear a pitch, a story or an explanation for a problem ask yourself “Does this sound right to me?” If not, ask yourself why. Why doesn’t this sound right to me? What about this sounds off, impossible or unlikely? Get curious about where things might be off, and ask questions. With each answer, check in again. Does that sound right to me?

Another great question for leaders to ask is “what am I missing?” Look for where the pieces don’t fit, or where a piece is completely missing. Explore the idea from all perspectives, and be willing to include stories or explanations that don’t make sense to you at first. Curiosity often leads to confusion before it leads to clarity.

Finally, get curious about anyone who’s critical of the choice you’re considering. Don’t shut them out or ignore their “negativity”. Ask yourself “were the naysayers right?” That one question could help you see the situation from a different and much more thorough perspective.

2. EVIDENCE

One of the best ways to discern whether someone is telling the truth is to look for inconsistencies. But in order to find inconsistencies, you need evidence to weigh a story or a claim against. If you’re accepting one story at face value, you don’t have enough to see inconsistencies may exist. You need evidence. Part of using your doubt is collecting and creating evidence to test it. Leaders must learn to use evidence to cross examine the things they doubt.

George Santos made hosts of claims that could have been easily disproved with a dive into the evidence, or lack thereof. He claimed to have worked with Goldman Sachs and Citigroup. A Google search or a telephone call could have discovered whether there was any evidence to support that claim. He claimed he graduated from Barch College, owned thirteen properties and ran an animal rescue group as a 501(c)(3). If any of these claims were true there’d be easily discoverable evidence to support them. It seems no one looked. Not one fellow politician or constituent seems to have cross examined him and asked him to explain inconsistencies. It may have been because they didn’t have time. But look at all of the time they’re spending on Santos now.

One of the reasons leaders often fail to use evidence to support their doubt is their impatience. CEOs move fast, and they make decisions quickly. In fact, in a ten year study of CEOs researchers found one of the things that high-performing CEOs make decisions earlier, faster and with greater conviction. That may not seem to leave much room for doubt. But when the stakes are high and the decisions are almost impossible to reverse, what Jeff Bezos calls “one way doors”, it’s worth taking the time to collect and weigh the evidence. It’s worth using your doubt to feed that process because it could save you time, money and reputation in the long run.

Collecting evidence is also something a leader can delegate. Have a team member engage in due diligence and collect evidence before those big decisions. Use the evidence to look for inconsistencies between the evidence and the story you’ve been asked to believe. Use your curiosity to ask more questions about those inconsistencies. A belief is a story you repeat and back up with evidence. If the evidence isn’t there, the story hasn’t earned your belief.

3. WIN / LOSE/ WEIRD

When I tried cases, I used my doubt to win. Sometimes it made my clients nervous. When I’d prepare them for cross examination, I’d do a mock cross exam myself. I’d challenge them with all of my doubts and dive into all of the evidence to find more doubts to explore. They didn’t always like it. I’ve been called “Chicken Little” before trial. But that same client tearfully thanked me after the trial, when we not only won the case but he handled his cross examination like a master advocate. I felt I’d done my job when my mock cross exam was tougher than my opposing counsel’s. You can’t win unless you know all of the ways that you can lose.

That’s why leaders need to use the Win/Lose/Weird process. My training and coaching clients have embraced this process and used it to win huge investments, important sales and important elections. It’s a simple way to strengthen your doubt and let it serve you.

Try the Win/Lose/Weird process the next time you’re weighing a decision. As you’re looking at a situation, consider all of the ways you could win. Collect the evidence that supports your win, and tell stories about that evidence. Build your own energy of belief. Then, look at all of the ways you could lose. Look for evidence that supports your competitor, or supports the antithesis of your argument. Consider where the evidence you thought supported your win could also support a loss. Be ruthless. Finally, look at the weird. Get creative about all of the weird things that could happen to change the variables in your equation. A hopeful congressman could make up his resume. That’s weird. When you’re prepared for the weird, nothing can shake your confidence.

Some say doubt kills dreams. They worry that if leaders allow themselves to doubt they’ll lose confidence in themselves and their decisions. I’ve found that the opposite happens. Mistakes kill dreams, and doubts kill mistakes. When I teach leaders how to cross examine a decision, and use their doubt to make better decisions they become more confident. They know they’re ready to handle anything that arises. They believe in themselves and their decisions.

We need to choose leaders for their integrity. But we also need to choose them for their willingness to feel and use their doubt. A leader who has both integrity and discernment is an asset to any organization.

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