The Tale of Two Leaders: Confidence in Action
This is the third article in a five-article series on the Tale of Two Leaders.
I reside in Calgary, Alberta. This time of year it means that we take off the business suits and dawn our favourite cowboy boots and hats during the Calgary Stampede. This year is no different. It also gives us the opportunity to connect, network, meet new people, and reconnect with folks we haven’t seen in a while. What I love most about this time of year is hearing the stories from business owners and leaders. I start to see and hear themes brew as I ask questions and listen. It also allows me to reflect on my journey as a business owner and leader.
One theme that has come up in several conversations over the past two weeks is how individuals show up confidently, or not, in these situations. I had a 30-minute conversation with a business owner whose wife is having a hard time building up confidence in her “sales pitch”. He asked me, “How is it you speak so confidently?” That question stopped me dead in my tracks. If I am being completely transparent, confidence is something I have 75% of the time. I have my own moments of self-doubt, timidness, shyness and questioning my decisions. I have learned over the years to quiet the noise.
Rather than telling you my story, let me unfold a tale of two leaders: one whose confidence is grounded and growing, and another who struggles with self-doubt and perfectionism. Then we’ll explore what helps build lasting confidence in leadership, and what happens when it runs amok.
Leader One: Sarah — Grounded and Clear
Sarah is confident but not cocky. She has been a leader for many years and was recognized as one during her adolescence and university years. She grew her leadership through action, not perfection. She realized early on that taking a learner mindset was more useful than focusing on perfection. This comes across in the way she communicates: with clarity and calm. She asks questions when things are uncertain. She openly shares her ideas without fear of being laughed at and takes feedback to adjust them. She doesn’t take things personally. She shares her ideas with her team, and she takes control of her schedule.
Behaviours Sarah demonstrates:
She believes, “I’m not 100% certain, yet. But here’s where I believe we are headed.”
She seeks feedback early, often. She takes feedback as a sign to course correct.
She has a process she follows when making decisions, big or small.
She understands her values and beliefs, and those of her business, which are aligned.
She permits others not to have all of the answers.
She communicates clearly and admits when she has made mistakes. She views them as a means to improve.
Her internal narrative is “Confidence is not about knowing it all. It’s about knowing enough to take the next step?”
Leader Two: Amelia — Doubting and Drifting
Amelia grew up equating credibility with certainty. Perfection ruled her school life, as she aimed for high marks and beat herself up when she didn’t achieve success. She admired leaders who appeared to have all of the answers; this belief led to her future struggles with imposter syndrome and seeking perfection of herself and others. That belief led her to perfectionism, impostor syndrome, and a fear of being wrong. As a result, her communication is hesitant and inconsistent. She delays messages until they’re airtight. She revises strategies so frequently that her team is often confused. She tends to change direction based on audience reactions and avoids speaking until things feel “just right.”
Behaviors Amelia demonstrates:
Overexplains to justify decisions or changes
Avoids sharing until things are “ready”
Flip-flops on directions depending on who her audience is at the moment.
Seeks reassurance, not just insight.
Delegates hesitantly, if at all.
Her internal narrative is: “I don’t want to say the wrong thing, so I’ll keep refining it just a little more.”
The Impacts of Two Approaches to Confidence
For Sarah:
Momentum: Decisions are made. Projects move forward. The team has direction, even if it’s imperfect.
Engagement: Others feel empowered to contribute, refine, and co-create.
Trust-building: Transparency in uncertainty builds credibility, not weakness.
Learning: Mistakes become part of the strategy, not a threat to it.
Mindset Anchor: Progress builds confidence. Motion reveals clarity. Leadership is learned in the doing.
“Perceived confidence in a leader positively affects group performance, especially under uncertainty.”
For Amelia:
Stalled execution: Projects get stuck in planning loops. Energy fades.
Confusion: The team senses hesitation and alignment slips.
Isolation: Leader carries the burden alone, afraid to share ‘unfinished’ ideas.
Erosion of trust: Inconsistency or silence creates doubt, even if intentions are good.
Mindset Anchor: Waiting for certainty often guarantees inaction. The cost is momentum and morale.
“Entrepreneurs and small business owners with low self-efficacy tend to underhire, underinvest, and resist scaling—citing fear of failure and uncertainty.”
How to Build Confidence if You Relate to Amelia
Let Go of Perfectionism “Perfectionistic self-presentation leads to chronic self-doubt.” - Hewitt & Flett, 1991. Letting go creates room for growth-based confidence and authentic connection.
Build Self-Compassion “Self-compassion is linked to higher confidence, resilience, and motivation.” - Kristin Neff, 2011. Compassion creates stable, realistic confidence that transcends performance.
Celebrate Progress, Not Perfection: “Realistic goals and small wins sustain momentum.” - Amabile & Kramer, 2011. Breaking it down makes growth feel achievable.
Take Action Early: “Mastery experiences, small wins, build self-efficacy.” - Bandura, 1997. You don’t need to feel ready. Doing builds belief.
Experiment Often: “Fear of failure stifles innovation.” - Shafran & Mansell, 2001. Test ideas in small ways. Adjust based on results.
How to Ensure Confidence Doesn’t Become Overconfidence
Stay Curious, Not Certain
Anchor in Feedback
Revisit Assumptions Regularly
Confidence is a learned skill.
Confidence is a learned skill, like many others. By embracing a learner mindset, being curious, focusing on progress rather than perfection, and being self-compassionate, you can build confidence and flourish.
Whether you’re a leader, a direct report, or an executive, the path is the same: sustainable, thriving leadership grounded in progress over perfection.
If you are looking for more practical tips, consider subscribing to The Wright Step Newsletter.
