It clashes with our instincts, but ambivalence in proposals often signal deeper thinking

In a previous article, In Praise of Doubt, we explored how our brains are seduced by those pitching recommendations with high confidence, presenting their proposals are clear-cut winners. We instinctively gravitate toward confident voices that comfort us in our uncertain world of business even though that kind of unwavering confidence often signals dangerous blind spots: failures to grasp real risks and nuances.

The moment when we truly need confidence is after the decision — when it’s time to execute. Before that? Healthy doubt (as opposed to paralyzing doubt) is crucial for making high quality decisions.

Research shows we tend to unconsciously penalize people who disclose their uncertainty. If someone says, “Our recommendation has its risk, but here’s why I think it’s worth considering ahead of other options,” we’re less likely to trust them. We unconsciously equate ambivalence to weakness and discount their competence — even though that candor reflects a deeper understanding of the landscape!

Ambivalence, then, is like dark chocolate. Kids hate it at first — too bitter, too weird. But as we mature, we come to appreciate the richness behind that complexity and it’s the same with ambivalence in decision-making. When we learn to embrace ambivalence — and encourage it within our organizations — we make smarter, more resilient, and ultimately more profitable choices.

So how do we rewire our brains to welcome and trust the ambivalent and to more wary of the over-confident?

1. Spot Healthy Ambivalence and Unhealthy Confidence

• Start by rating the balance of confidence versus ambivalence in the recommendations you hear. Don’t just react to how something feels — examine why it feels that way. Are you uncomfortable with a leader’s doubt? Pause and ask: Might that hesitation actually be a sign of deeper insight?
• On the flip side, if someone seems overly confident, challenge yourself to find what they’re likely missing. If you spot a gap right away, chances are there are more hiding beneath the surface.

2. Build Ambivalence into the Process

• Tweak your decision-making frameworks. Add steps that force teams to explore risks, uncertainties, and alternatives. Techniques like scenario planning, pre-mortems, and red teaming formalize this process — turning productive doubt into a standard operating procedure.
• Make it routine to raise competing priorities before finalizing a decision. Normalize the idea that few choices have an obvious winner – our world is too complex for it to be that cut and dried.

3. Get Comfortable with Being Uncomfortable

• Praise people who raise doubts or admit when a solution isn’t cut and dry. Make it clear: their honesty is a strength, not a liability.
• Also, push back on overconfidence letting people know it is hurting their credibility. When someone oversells a solution without proper risk analysis, send it back. That kind of accountability builds candor — and credibility.

4. Create a Culture of Collaborative Curiosity

• Ambivalent leaders — the ones who admit what they don’t know — often inspire their teams to think deeper, ask better questions, and break down silos.
• Make meetings safe spaces for challenge and dissent. When everyone agrees too easily, it’s usually a sign that not all voices have been heard.
  • A little disagreement is a healthy sign of engagement — and diversity of thought.

5. Enforce Learning

• Ensure reliable practices are in place and followed for regular review of major decisions
• Don’t just track outcomes — dig into the reasoning behind them: Were key risks properly surfaced? If projections missed the mark, why? Were those variances predictable — and if so, why weren’t they flagged?

Why This Matters

• It reduces bias. By slowing things down, ambivalence activates System 2 thinking — helping teams avoid traps like anchoring, overconfidence, and confirmation biases.
• It improves outcomes. Teams that acknowledge complexity explore more angles, land on better solutions, and take smart steps to mitigate risks.
• It boosts adaptability. Organizations that welcome uncertainty anticipate curve balls during implementation so change plans faster when the facts change.

Final Thoughts

Valuing ambivalence doesn’t mean encouraging indecision. It’s about creating space for thoughtful, bias-resistant, and adaptive leadership. By intentionally practicing — and institutionalizing — this mindset, ambivalence becomes one of our greatest assets.

“Declarations of high confidence mainly tell you that an individual has constructed a coherent story in his mind, not necessarily that the story is true.” Daniel Kahneman

 *For those of you who don’t enjoy dark chocolate, my sympathies go out to you.

© Dave Wittenberg