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7 Questions on Leadership with Danielle Caldwell

Name: Danielle Caldwell

Title: Product Design Manager

Organisation: Open to new opportunities

Hi, there. I’m a Product Design Leader with 10 years of experience designing for global brands in industries such as health tech, retail, e-commerce, and legal. The majority of my work has been in B2B Enterprise SaaS applications but I've also led the design strategy and execution for B2C platforms.

I began my career as an industrial designer but eventually transitioned from designing in plastic to designing in pixels. Hello, UX design! About five years ago, I discovered that developing people became more satisfying to me than developing products - which is why I became a Product Design Manager. My favorite part of the job is working closely with others to overcome obstacles and get things done. I love building inclusive, highly collaborative teams where individuals feel safe, supported and inspired to do their best. I enjoy creating great work experiences for designers so they can create best-in-class product experiences for customers.

I have two professional goals 1) Get back into the health tech industry because it's truly meaningful work. 2) Start a personal coaching career because I enjoy helping people thrive.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Danielle's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

Mastering the art of situational leadership. I found it very difficult when I first became a people manager to delegate responsibilities to others especially when I knew I could do something faster, or more efficiently. I hated watching people struggle. I would want to do it for them to make their job easier.

Yet, being an effective leader means you have to assess the situation, and the skills of your team, and be able to flex your leadership style so that you can bring the best out of your people. Sometimes that means delegating, coaching, supporting, or directing. It's about meeting people where they are at and giving them the opportunity to develop and demonstrate important skills. It's also critical to show your team that you trust them while offering guardrails to protect them and/or the project from catastrophic failure.

2. How did you become a leader? Can you please briefly tell the story?

I was working in a large legal tech company with a tiny design team. When I wasn't delivering design work, I was advocating for design and building a business case for getting more design resources.

When the company I worked for was acquired, our new leadership tasked the product design team with creating a unified product experience across our entire portfolio of 12-15 products.

One afternoon my manager and his manager called me up and asked me if I would like to become the first-ever Product Design Manager in the organization. At first, I was unsure if people management was for me. I don't consider myself the "bossy" type. Then my manager explained to me that I was already doing 75% of the job by supporting my design peers and leading design.

I was most afraid of what my design peers would say when they learned that I was now their manager. Surprisingly, everyone was extremely supportive and happy to have a manager who truly understood their role and would be their biggest advocate. My team told me I was a natural leader, however, I was the last person to see it.

Now I realize that developing people is my favorite part and I'd struggle to go back to a role where that wasn't part of the job.

3. How do you structure your work days from waking up to going to sleep?

I'm currently seeking a new role so the majority of my days include being physically active - going to the gym or going for a walk, job searching, professional networking, and volunteering as a moderator with Never Search Alone, a mentor with ADPList and/or a store associate with Habitat for Humanity Restore.

Prior to that, my schedule often revolved around whatever project meetings I had that day - usually product development meetings or 1:1s with my design direct reports.

When I'm not doing work-related activities, I love cooking, home improvement projects, and making time to enjoy my favorite TV shows and board games with friends and family.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

This one isn't super recent but it's definitely shaped my leadership style.

Back when I was a design manager in an e-commerce company, one of my product development teams was assigned a new product manager who had a background in UX design. All three of the designers on his team complained to me that he was often extremely critical of their design work and was overall very difficult to work with. Thinking I could save the day, I went directly to the product manager's manager and shared the feedback. The situation escalated quickly from there.

By the time the product manager received the feedback from their manager, it was way too late to act on it. Furthermore, I realized I deprived my designers of learning how to navigate conflict and deliver critical feedback on their own. I learned that it's better to teach people how to develop the skills to navigate conflict on their own versus navigating it for them.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

The book "The Coaching Habit." Truthfully, I haven't finished reading the whole book yet. I discovered the book when I paired with another design manager to create a training session on coaching and I learned SO much from that experience. I used to think that coaching was about giving specific advice and instruction, like a coach yelling from the sidelines to their team out on the field. Yet, this book helped me realize that coaching is about listening and asking thoughtful questions to help people arrive at their own answers. It's often about being a sounding board, partnering with people to help them connect the dots or see a situation from a new perspective. I've taken that approach with my designers and mentees ever since and the feedback I receive is very positive.

6. If you could only give one piece of advice to a young leader, what would you say to them?

Wow, only one piece of advice? How tough!

There's a quote by Maya Angelou that goes something like this "Long after people forgot what you said, and forgot what you did, they'll remember how you made them feel."

I'm a true believer of this. As people leaders, we're often accountable to achieve results for an organization. There are many ways to do this. Do you want to be remembered as someone who achieved results through intimidation and tears or someone who achieved results through inspiration and collaboration? When we eventually leave our roles, there are only two things that we take with us; our results and our relationships. Don't sacrifice one for the other. You'll need both to be successful.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

One of the most underrated leadership skills is "listening" and it's a decidedly powerful tool. I had always envisioned leaders as the people who do all the talking but that's just not true. Here's how I used my listening skills to help a team resolve internal conflicts and start delivering features:

When I first joined as a design manager at an e-commerce company the product development org had just released the MVP platform but executive leadership had a fast-follow laundry list of features to add to the backlog. However, my product development team had come to a virtual halt. The engineers were complaining that there were no stories in the backlog. The product managers were complaining that the designs took too long and they didn’t know what the design team was working on. Design was complaining that they weren't included on product strategy discussions.

The first thing I did was start my listening tour. I met with product, design, engineering, and other stakeholders to understand the problem from their perspective and understand what they tried.

Then I implemented a cross-functional weekly design planning ceremony to give everyone input and equal visibility to the product development process. This created a forum for all disciplines in the team to raise concerns. We defined and assigned design work based on product strategy priorities. Engineering was thrilled to be engaged earlier in the process to provide feasibility.

Lastly, I facilitated a working agreement. This created alignment on how and where important decisions were made, captured, and communicated.

All of this resulted in increased collaboration, and more throughput of product development work, which delivered key platform enhancements that increased conversation rates. Most importantly, this resulted in a happy healthy team - and it all started with listening.

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