Commentary: Lessons in executive decision-making from a chief strategist
BY SHANNON WOODS, GUEST CONTRIBUTOR
I’m paid to make difficult decisions. Some come with multimillion-dollar risk or reward. Other choices influence people’s daily lives and their futures. As a chief legal, compliance and strategy leader, I’m energized by opportunities to make a recognizable impact. As a woman in my field, I recognize my determinations come under gender-specific scrutiny.
My decision-making process has evolved over the past 25 years of my career. Early on, I believed that if I overprepared and waited just a bit longer for more information, clarity would arrive. As my responsibilities grew, I learned “lightbulb moments” are more myth than heuristic. Now, I’m on a mission to help other women strategize more successfully; at work, and in life.
Navigating major decision-making moments
Complex decision-making doesn’t just happen in a corporate setting. It’s choosing a care plan for your kid or an aging parent. (Sometimes both, simultaneously.) It’s whether to try for a baby or go for a master’s degree. (Those decisions are not mutually exclusive.) It’s opting out of a volunteer role someone else thinks you’d be perfect for or taking on a career stretch that you suspect will challenge you beyond anything you’ve tried before. Pressure to make “the right choice” can feel almost paralyzing. While you crunch the numbers and pro/con list yourself into a corner, your opportunity window closes.
Stepping into male-dominated industries while advising construction companies, spearheading union negotiations and navigating corporate environments short on female executives, I thought data, consensus and a deliberate plan determined good leadership. The reality is: Most consequential decisions are made with incomplete information, complicating the task. Urgency shifts. Regulations move. Goals change. And yet, you are asked to decide anyway.
Some of the most pivotal moments in my life and career came when I didn’t have absolute clarity around what to do. I had experience, judgment and direction but not certainty. Waiting would have felt safer, but delayed decision-making would have diminished my credibility. That’s not an acceptable outcome for me.
My decades of executive leadership taught me: Decisiveness doesn’t mean confidence without doubt. It’s confidence alongside doubt.
Combatting ‘role congruity’ with confidence
For women, the experience of making big decisions may come with a narrower margin for error. The “role congruity theory” says that when men make decisive calls that fail, they are seen as taking smart risks. But when women do the same, they are more likely to be labeled as impulsive or unprepared.
And yet, I’ve found that leadership rarely grants opportunities to learn decision-making skills slowly. Nor are we likely to have a mentor who models how to move forward in the moment. If I can learn decisiveness, you can. And thankfully, you don’t need 25 years of experience or a perfect set of facts. You simply need to build confidence. We are taught, subtly and explicitly, to think again before we step forward. Research shows women are more likely to wait until we meet nearly all qualifications before pursuing a role, while men are more comfortable acting with partial readiness. The difference is not capability but instead, permission to use your own instincts.
Let me be clear, you will never eliminate doubt. But you can grant yourself the grace to acknowledge your uncertainty and move through it. You won’t always have flawless execution, and nobody does. After all, in professional baseball, even the elite players get a hit in only 30% of their at-bats. Even Caitlin Clark’s career field goal percentage is under 50%. Through consistent, thoughtful action, you will grow stronger in your confidence to make challenging decisions. It’s those decisions that open the door to true impact.
Seizing opportunities to say ‘yes’
During law school, I learned to boil decisions down to a “yes” or “no.” Moving from private practice into corporate compliance in highly regulated industries, “no” was the easiest answer. (Legal and compliance teams are known as the “fear filter,” thanks to a reputation for killing ideas.) I’ve seen “no”’ shut down innovation and stifle growth opportunities.
My goal in driving businesses forward is finding a way to “yes” while staying compliant with regulations. Naming uncertainties out loud gives me strength. I often say, “Here’s what we know, here’s what we don’t, here’s what the risks are and here’s why I’m comfortable recommending we move forward anyway.” That framing turns decisiveness into thoughtful leadership rather than unchecked confidence. In environments where women’s authority may be questioned more quickly, transparency builds trust.
Fearless leadership isn’t about eliminating uncertainty or waiting for perfect clarity. It’s about recognizing the risks, weighing the tradeoffs and choosing to move forward anyway, fully aware of what’s at stake. It means accepting accountability in real time and making decisions before all the answers are in. Especially in environments where women’s authority may be questioned more quickly, courage often looks like trusting your judgment even when doubt is still present. The goal isn’t to silence fear but to lead effectively in spite of it.
Shannon Woods is a veteran C-suite legal and strategic executive known for leading highly regulated organizations through complex compliance environments, growth initiatives, and mergers and acquisitions. Woods serves as chief legal officer and chief compliance officer at the Mutual Group and is open to corporate board opportunities.
