Step Up, Take Risks, Lead with Confidence
How embracing risk transforms you into a confident leader with Elana Jacobs
Welcome to The Confident Product Leader! This week, we unpack how taking calculated risks can be a game-changer in building your confidence as a leader. Drawing insights from a conversation with Elana Jacobs, a seasoned product leader with an impressive journey across social impact organisations, we’ll explore how leaders can use bold moves to inspire growth in themselves and their teams.
Fear of Risk and its Impact on Leadership
Risk is often synonymous with fear—fear of failure, rejection, or criticism. For product leaders, this fear can manifest as hesitance to advocate for bold ideas or challenge decisions. Whether you're a seasoned leader or just stepping into management, this avoidance of risk can prevent you from being seen as a true change-maker.
Elana Jacobs reflected on her early career:
"I stayed quiet when I heard something that didn’t sit right... I was too timid. I largely implemented other people's ideas."
Does this sound familiar? Many leaders, particularly those still finding their footing, fall into the trap of playing it safe, waiting for validation rather than seizing opportunities.
Taking Risks to be Heard
Elana’s breakthrough came when she decided to trust her instincts. At Crisis Text Line, she began challenging the status quo and advocating for innovative ideas—even when the task seemed daunting.
"I started becoming less timid and spoke up and shared new ideas or new directions", she explained. "Sometimes, that meant telling the CEO, 'I don’t think this is a good idea.' Respectfully, of course."
The result? Her confidence grew, and she gained recognition as a leader invested in advancing the company’s mission.
Building Confidence Through Calculated Risks
Confidence isn’t something you’re born with—it’s built. And taking calculated risks is one of the most effective ways to build it. Elana emphasises the importance of being bold while staying rooted in respect, data, and clear communication:
"Approach disagreement or a different direction from a place of respect with whatever data or information you have at hand. The worst that can happen is they say no."
By sticking her neck out, she didn’t just contribute to better decisions. She also solidified her role as a trusted leader.
Key Steps for Leaders
For Growing Product Leaders (Directors, Heads of Product, VP Product):
Advocate for Bold Ideas: When you see an opportunity, speak up. Use data and insights to strengthen your case.
Challenge Respectfully: It’s okay to push back—senior leaders value those who think critically about the business’s direction.
Model Courage: Your team watches how you act. Show them that risks are opportunities, not threats.
For Emerging Product Leaders (Senior/Principal PMs):
Start Small: Test the waters with smaller risks, such as proposing a new feature or process improvement.
Lean on Data: Build confidence by grounding your ideas in evidence.
Embrace Discomfort: Speaking up is nerve-wracking, but every attempt makes the next one easier.
Common Mistakes to Avoid
Being Reckless: Risk-taking doesn’t mean charging ahead without preparation. Always evaluate potential outcomes.
Equating Boldness with Aggression: Confidence isn’t about being loud—it’s about being thoughtful and intentional.
Ignoring Feedback: Risk-taking includes listening and adapting based on what others share.
Confidence Grows with Every Risk
As Elana wisely pointed out, confidence comes from action. The more you step into discomfort and challenge norms, the more natural it will feel. Whether you’re advocating for a bold vision or respectfully challenging a decision, each risk you take strengthens your leadership muscle.
Remember, risk isn’t about recklessness—it’s about thoughtful, courageous action. So, take that leap. Your future confident self will thank you.