Becoming a manager and building successful teams with Derek Jones
Meet the members of DocuSign’s Product Experience team who are shaping the future of agreements
Hi Derek! Let’s start with the basics. What do you do at DocuSign?
I’m one of the Directors of Product Design here, managing the design for all of our eSignature products.
How did you get your start in Product Design?
I’m old. Like, dial-up modem, floppy disk, AOL old. I was in high school when the Internet went mainstream and, as a certified nerd, I was always first in line to jump on new technology. That usually meant playing the latest PC games. But in-between rounds of Quake, I would mess around with bootleg copies of design software (sorry, not sorry). Way before I knew what “product design” was, I would make small websites and animations for fun, and browse other sites for inspiration. That period was the foundation for my entire career. I developed fundamental skills, dabbled in coding, and cultivated my design taste.
My first few jobs were in Digital Advertising, and even though that meant delivering a mountain of banner ads and emails, I always tried to make the most of them — building simple Flash games, adding extra flourishes of animation, introducing interactivity to units that were typically static.
That experimentation and on-the-job training helped me eventually make the move to a team that specialized in experiential projects like large-scale touchscreen displays, motion-tracked interfaces, and AR mobile apps. It was my introduction to formalized product design and I was hooked. I’m mostly self-taught, and I think an “I can figure this out” spirit goes a long way in easing the transition to a new discipline. Also, building interfaces that get clicked on by millions of people is pretty damn satisfying and it’s why I still love doing this.
What made you decide to switch to management?
Seven years ago, I was adamant about never becoming a manager. From what I saw, managers lived in PowerPoint, went to meetings all day, and never ate lunch (turns out, that’s all pretty true 😉). So my path was much less deliberate: I organically started taking on more responsibility as a senior IC and realized how much I enjoyed mentoring and driving strategy. It was actually a helpful “trial period” that allowed me to get a feel for what would be expected of me, and to begin developing my own management style.
I’d like to hear more about your growth as a manager. What are some of your biggest learnings?
The hardest adjustment was learning to appreciate the unique impact managers can have. It’s like designing with boxing gloves on; you can nudge things in a general direction, but the fine details are out of your direct control. You’re dependent on your teams to bring thoughtful polish to the final product while you contribute in less tangible ways: providing clear feedback and long-term vision, encouraging collaboration, improving process, etc.
Learning takes a different form, too. Instead of sharpening hard skills and researching new tools, I’m constantly focused on how to better communicate, motivate, and persuade.
Management is ultimately a mix of preparation, experience, and improvisation. Books and articles can be helpful, but there’s no substitute for giving it your best shot, humbly learning from your mistakes, and getting a little better your next time up.
“[Management is] like designing with boxing gloves on; you can nudge things in a general direction, but the fine details are out of your direct control.”
As you’ve built your teams at DocuSign, what qualities do you look for when interviewing candidates?
We’ve been interviewing a ton of folks lately, which has helped us narrow in on what makes an impressive candidate and successful teammate:
Confident, concise storytelling
An interview is a perfect platform to show off storytelling skills: you have an hour to introduce yourself, define a problem space, describe your process, walk through designs, and field questions. Because of the tight time constraints, it’s important to provide just the right amount of context, carefully select essential details, and present it all in a casual, engaging way. Storytelling is one of those soft skills that never gets enough attention, but it’s legitimately as important as any hard design skill. It’s the primary “must-have” for all of our new hires, regardless of level.
Strong design fundamentals
DocuSign designers handle everything from initial whiteboard sketches to final polished pixels, so coming in with a strong understanding of basics like responsive grid, type hierarchy, and balanced layouts is critical. There’s always room for growth and learning, but as craftspeople, we all need to have a confident grasp of baseline skills on day one.
Adaptability
Nothing ever goes completely to plan. Honestly, most projects get pretty f*cked up at some point. So, while having a toolbox full of frameworks can be useful, being able to improvise and pivot when things go sideways is just as important. Just like a typical development cycle, interviews are almost guaranteed to include a few curveballs. We always appreciate when candidates can calmly navigate those hurdles and go “off script.”
“…while having a toolbox full of frameworks can be useful, being able to improvise and pivot when things go sideways is just as important.”
Why is storytelling an important part of being a successful designer?
Design reviews are tough. Product Managers are questioning your rationale. Engineers are scrutinizing feasibility. Everyone’s worried about the schedule. And their skepticism is understandable! You’re proposing a solution that will influence months of work for dozens of teammates with millions in revenue on the line.
Your team needs to be convinced.
This is a crucial — and often overlooked — step in the design process: selling your work. You need to be able to tell an easily-understood and convincing story of how your proposal will help point everyone in the right direction. A few things to aim for:
Brevity
Carefully crafting a concise, impactful narrative takes time, and it’s as important as ensuring our Figma files are pixel perfect. Attention spans are short. Zoom fatigue is real. Develop a habit of ruthlessly editing your presentations down to only the immediately-relevant bits. And keep the setup short! If you can’t explain the problem in under 30 seconds, you’re probably too deep in the details.
Simplicity
You’ve been working on a problem for weeks, but most audiences won’t be as intimately familiar as you. Break complex topics into smaller pieces. Focus on one small issue at a time. Avoid overly-technical language. Always strive for a tight, focused presentation that leaves your audience with one memorable takeaway and crystal clear next steps.
Relevance
Understand what motivates your audience. A design team critique is a great time to dig into interaction details and UI patterns. But a 5-minute deep dive on button corner radius will put a group of Engineers and Product Managers to sleep. Every good meeting has clear objectives and your presentation should always contribute directly to at least one of them.
Designers are the creative engine of any product team. Everyone is looking to us for inspiration and vision. And the unavoidable reality is that our presentation of that vision is as important as how beautifully crafted it is.
Want to learn more about Derek? Connect with him on LinkedIn
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