"Asking the right questions the right way at the right time can often be more of a determinant of your success than being the person to raise their hand and come up with the answer." - Amy Radin Amy Radin is a pioneer in corporate innovation and strategic questioning. Amy shares her journey from the influence of her father's corner drugstore to becoming one of the world's first Chief Innovation Officers at Citi, and her roles at American Express, E-Trade, and more. The conversation delves into the importance of curiosity and questioning for personal growth, achieving corporate goals, the emotional and practical aspects of leading change, and the role of strategic questioning in innovation. Amy also discusses her experiences as an early-stage investor and advisor, highlighting the significance of asking the right questions to assess founders' pitches and provide guidance as they build their companies. Sign up for Amy's newsletter, Uncommonly Pragmatic, at her website amyradin.com. Amy is available for live or virtual keynotes and workshops. She can be easily reached through LinkedIn direct messages to collaborate on how to bring her expertise to positively impact your organization. This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Keep questioning!
"Asking the right questions the right way at the right time can often be more of a determinant of your success than being the person to raise their hand and come up with the answer." - Amy Radin
Amy Radin is a pioneer in corporate innovation and strategic questioning. Amy shares her journey from the influence of her father's corner drugstore to becoming one of the world's first Chief Innovation Officers at Citi, and her roles at American Express, E-Trade, and more.
The conversation delves into the importance of curiosity and questioning for personal growth, achieving corporate goals, the emotional and practical aspects of leading change, and the role of strategic questioning in innovation.
Amy also discusses her experiences as an early-stage investor and advisor, highlighting the significance of asking the right questions to assess founders' pitches and provide guidance as they build their companies.
Sign up for Amy's newsletter, Uncommonly Pragmatic, at her website amyradin.com.
Amy is available for live or virtual keynotes and workshops. She can be easily reached through LinkedIn direct messages to collaborate on how to bring her expertise to positively impact your organization.
This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.
Keep questioning!
Episode Notes
00:00 Introduction: The Power of Questions
01:28 Welcome to Curated Questions
02:06 Meet Amy Radin: A Pioneer in Innovation
04:01 Amy's Early Influences and Corporate Journey
05:13 Transition to Early Stage Investing
07:29 Understanding Founders Through Questions
10:51 The Importance of Diverse Expertise
17:16 Building a Personal Advisory Board
18:22 Handling Resistance with Questions
21:43 Effective Interview Questions
30:42 The Power of Asking Questions in Teams
36:10 Emotional Aspects of Change
40:49 Modern Change Management
43:46 Multi-Generational Workforce Challenges
46:14 Coalition Building for Change
48:07 Balancing Historical Knowledge and Innovation
50:37 Understanding Resistance and Fear
51:28 The Role of Experimentation
52:21 Digital Channels in Customer Acquisition
53:20 Designing Experiments with Skeptics
54:36 Financial Discipline and Digital Innovation
55:47 Customer Service and Digital Channels
56:12 Prioritizing Questions and Experiments
59:05 Becoming a Chief Innovation Officer
01:00:59 Challenging Assumptions with Questions
01:08:39 Qualitative Insight Gathering
01:12:28 The Emotional Side of Finances
01:16:33 Career Reflections and Resilience
01:21:23 Teaching and Strategic Advocacy
01:22:30 Celebrating Success and Staying Curious
01:23:46 Morning Walks and Creative Thinking
01:25:38 Final Thoughts and Places to Connect With Amy Radin
01:27:36 Closing Remarks and Takeaways
Resources Mentioned
The Change Maker's Playbook by Amy Radin
A More Beautiful Question by Warren Berger
Kotter's Eight Steps For Leading Change
Larry Keeley on LinkedIn
Amy Radin Website for the Uncommonly Pragmatic Newsletter
Amy Radin on LinkedIn
Questions Asked
When did you first understand the power of questions?
What am I gonna do with myself now?
My first question was, well, what's that?
What were some of those right questions to be able to get a little bit deeper?
What questions am I gonna ask?
Can you tell me more about that? How did you figure that out? Or I'd love to understand that better. Can you dig in a little more?
Do we wanna go to the next step?
Have there been some particularly insightful questions that founders have asked of your team that have resonated with you?
What else do they bring to the table?
I would ask tell me a little bit about some of your recent experiences working with some of your other portfolio companies and how you've helped them out. Tell me about a situation when another portfolio founder when the market changed and they almost had the rug pulled out from under them, what was your reaction and were you able to step in and help them?
Tell me a story, not what would you do?
Has there been anything this new venture has taught you about questions that all of your other previous experience hadn't taught you?
What do you think might be a personal bootcamp that somebody could do that could help build that experience?
Ask, wow, I'd love to understand more where you're coming from. Could we walk through it? Because I wanna appreciate what you're trying to do and why you're uncomfortable with this. So, can you help me understand your perspective better?
How did I do? Did I do this three times?
What do you think makes for a good question?
What are the key requirements? What do I really need from this person? What would you do about X, Y, Z?
Help me understand what you did. What you felt and what you thought, and how did you actually handle that situation?
What metrics should we consider that would be appropriate to helping us understand the potential for this idea that would make us feel good about this tiny little investment you wanna make for prototype?
How can they bring the entire questioning game in the conversation up another level,
What do I really wanna understand better about this opportunity?
What do I really wanna understand better about working with these investors?
Do I wanna use the opportunity of this call/pitch session/diligence to ask them their advice about something? And can I be candid about?
Why can't you...? How might you...?
How do you think about that feeling or that component of us and bringing that into the workplace?
How is this change going to affect my career and what happens to me and my ability to pay my mortgage and send my child to college?
How do you feel?
Why does Sally seem so upset at the meetings?
As you are engaging with a company and helping them think through change, how do questions play a role in that process?
Who's gonna be there? What's their mindset about learning? Is it a curious organization? How would you describe the culture?
What role do questions play in change?
How do I really accomplish this change?
How does fostering curiosity and questions play a role in coalition building?
How do you get that tipping point?
What role can digital channels be effective to attract new customers?
What aspects do we think that innovating around the digital experience could favorably impact those aspects, those financial drivers of the business?
What role could digital channels play in customer service that could improve the customer relationship, lower costs, improve customer satisfaction, reduce attrition, and increase people's usage of the card?
What role does digital technology play in our business to benefit customers and shareholders?
How did you become a chief innovation officer?
What's that?
What do you think about specifically on questions in challenging assumptions?
Why are we doing it like this?
Where did that assumption come from?
When people go online, what happens to call volume?
What do we measure?
How do you see questions playing a role in sparking insights?
How are people managing their financial lives in the context of dealing with all the fallout from the financial crisis?
Are things filed, or is it a big mess in a paper stack? Why is it set up like that?
What are all the things that I could do?
You had mentioned early on about not being the cookie-cutter person, and wanting to be out there on the edges a little bit and mixing things up. How has that served you?
What can we do about this?
Would you be interested in teaching this Strategic Advocacy course? What the hell is that?
What do you need to do next?
What are your right now questions or question that you're working with?
I'm wondering why some of my best questions seem to come to me when I'm talking to my dog?
Are there any areas of questions that we didn't touch on that you were hoping to or excited to be able to touch on?
Where is this the best place for folks to track you down and see the things that you're working on and the things that you're excited about?
How would your career trajectory change if you spent the next year becoming known for asking brilliant questions rather than providing quick answers?
Can you identify three times over the coming week when you could practice asking "Help me understand your perspective" instead of explaining why someone is wrong?
Who are the people in your network who know what you don't know, and how could you formally invite skeptical perspectives into your most important decisions?
What would happen if you designated a regular meeting as question-only, where solutions are forbidden and curiosity is the only currency?