Leading Design Festival 2021 – Live Notes
Here are my notes from Leading Design Festival 2021, liveblogged (recorded in real time and updated as I go). My notes from the 2016 LD event can be found here.
1. Julie Zhou – The Many Facets of Design Leadership.
[Note: I was disappointed design ethics did not come up at all, given her history at Facebook. It’s the toughest design leadership issue we have and her insight would be valuable]
What she thought would make her a great design leader was just being a great designer. If you don’t know what good design looks like, how can you know who to hire? While it’s great to keep your skills sharp. the flavor of what it means to be great at design changes. it’s not your execution skills, but how good your eye is. It’s the difference between being a creator and an editor.
She referred to the book No Hard Feelings, and this diagram.

Which she redesigned to be about design.

She offered that design is still a growing profession. It’s at a place where the industry knows they need more designers, but they may not understand design or how to empower it in their organization.
Designers aren’t helping in our jargon world. We discuss abstract topics, but our peers, engineers and others, often don’t understand us. Great design leaders need to translate their concepts into words others understand. She’d get huffy about it and get frustrated. And they’d stare at her blankly. She’d point fingers at the environment and say “is this place hostile to design?” She didn’t have control over the environment, but she could learn to talk in analogies. “stop talking about clutter and space, and talk about the impact on other people”.
Too much clutter = lets reduce choices people have to make.
Catch yourself with jargon and remember to translate. Translation is different from good communication skills. It’s more targeted and specialized.
Excuses stop mattering. She referred to a story about Steve Jobs: Somewhere between the janitor and the CEO reasons stop mattering (why is this a mess? Is not something you can blame on others). And that’s where you are as a design leader. As you become more senior this expectation rises. The heart of it is the business: how will this organization be viable in the long run? What keeps the CEO up at night? The business is the context. Designers get a seat at the table because they understand the wider context of the company and how design can solve those problems.
Diagnose with data. Treat with design. It’s great that we have more information about what people actually do with our products. It’s also a way to keep us honest that our intuitions have the results we expect them to. If I showed you data that said 20% growth year over year, is it a great product? Great is subjective. Great compared to what? To last year? To our competitors?
Team process is design. How do you consistently get great design outcomes? It’s a kind of design problem. There is no formula. But look at poker. There are patterns and habits you can learn. You can’t just wait for a great hand. Move from design, to creating environments so others can design well. What is the meeting cadence? What is the psychological feeling the team has? It’s up to design leaders to decide and to help their teams win more hands.
Andy Budd asked “How to balance a company’s desire to a/b test everything?” Zhou replied that instincts are good for finding gaps with particular designs and good for novel ideas. In the v0 to v1 phase you have to start from first principles. But in second phase, after product market fit, it’s about optimizing. And that’s where instincts start to fail and a/b tests surprise designers (micro-levels). But always trust your instincts even when some data shows improvement, but you suspect it may create other problems. It’s a sign you’re past the point of low hanging fruit and should move on to bigger objectives. [Andy pointed out that a designer’s intuition improves by comparing it regularly against the data, insead of being afraid of it].
How to bond teams while remote? Have 5/10 minutes time at start of meetings where people play simple games (someone suggested https://skribbl.io/). We’ve lost the natural fun that happens between things and need to put it back in.
Question on personal growth. Start by asking how individual want to grow? Build out from that conversation to discover what kind of help they need and what can be discussed in one on ones.
Don’t forget about yourself. It’s easy to get lost in exclusively serving others. The role is about helping others, but still make investments in yourself, in mentors and network, and time to reflect for yourself.
2. Up next. Aaron Irizarry Leading Successfully Through Ourselves.
In order to help our teams, he suggests sometimes we have to learn first ourselves.

Leadership is not about being in charge, but taking care of those in your charge.” Simon Sinek
We need to get better about EQ.
- Self-Awareness. How do I show up? How do I recognize and manage my moods? What is my ritual for getting into a mental space where I can manage and lead?
- Self-Regulation. How do I control or redirect disruptive impulses or moods. He has used note taking as a way to keep in control of his thoughts before he acts on them.
- Intent. A passion for work that goes beyond money or status.
- Empathy. It’s a buzzword, but the ability to understand the emotional makeup of a person or situation makes us observant and more productive. If we don’t have empathy for our teammates and partners first, we’re kidding ourselves.
- Social Skills. Introverts sometimes have better social skills as they’re more measured. It’s not about extrovert/introvert, but more about how to read the room and find ways to connect. This should be modeleld behavior.
- Lead with vulnerability and transparency. Not assumption driven thinking, but with clarity and candor. So people feel like they know where we are going. Show your team you trust them enough to share their concerns. It’s a balance to not overwhelm people with being too transparent, but not being too closed that they’re not connected.
- Communicating Openly. Collaboration is rooted in trust.
- Adapt our communication styles and leadership approaches. Everyone is different with different needs. There are foundational things, like meeting cadence, but as he engages he tries to be contextual.
- Make an effort to recognize how communication style impacts other people. I’m a high strunk guy. I always engaged and I talk too much. I work with others who may not work that way and want me to slow down.
- Take the time to consider how different perspectives affect perception. I’m in so many meetings and the vibe at the end of one meeting carries over into the next. It impacts everyone especially when they are back to back.
- Be intentional in planning for ambiguity or confusion. When he is in partner meetings with his reports, it can be confusing about how things are messages or what is nailed down or still up in the air. Be an agent for clarity.
- Take note of team members and partner communication styles. Help people feel like they have been seen and heard.
- Lead through autonomy and enablement. He tends to be a hands-off leader until he isn’t. He has set up guidelines for free space and put your imprint on it. Other times he’s more open about assignments. It’s a balancing act and sometimes he gets it wrong. And he wants to get better at it.
- Model an autonomous working style. How much does he need from his boss? When does he ask for clarification and when does he pave the way?
- Get out of the fucking way. This is still a problem. How to balance facilitating without slowing things down.
- Create a vision statement that is a north star. This helps people be autonomous and keeps the manager out of the way.
- Check in on a regular basis. What is working? What isn’t? And where they need you to show up.
- Establish personal norms. Our vibe sets the tone. Imagine how not sleeping, being too tired, spread too thin, so the vibe is off. How he shows up sets a tone for their day and their ability to show up. Sometimes it’s just how it is, but he wants to be mindful of it.
- Manage our time well. If I’m in 15 meetings a day how can I possibly be there for my team?
- Invest in our own personal development. He’s planning on watching all the other talks.
- Establish healthy routines. He realized his choices at events like this weren’t always great. But that the he needed to make adjustments so he’s refreshed and recharged when he needs to be.
- Get a therapist. If he has someone he can talk to on a regular basis about whatever is going on he does much better. Get a personal board of directors (but that’s more business focused).
“I’m a leader struggling to lead my people. This is a good community. Reach out”
3. Kristin Skinner — Co-author, Org Design for Design Orgs, Founder & GSD
[Kristin went fast with dense slides. There were are few references that went by too fast to catch.]
How teams work is as important as what they make. She told the story about how the Golden State Warriors basketball team transformed over years to be a balance of talent and good management.
Three key areas define effective teams:
- Foundation
- Output
- Management

She identified a list of common problems.

This means we need continually redesign our organization. And you can use these lists to help score and rank the issues that people experience. Which helps everyone feel responsible for identifying and dealing with change.
Common goals to strive for:
- realize investment in design
- attract talent
- plan for growth
- and find roadmap detectives
“People spend 60% of their time on what they call the work about the work – trying to figure out who’s doing what, when and why” – Chris Fainacci, COO Asana
Common issues design teams face (from survey she did?):
- Limited time or resources
- Involving the right people or teams
- Lack of proven value
She referred to a Harvard Business article about the value of metrics and measuring outcomes. Then she explain how this translates into what designers can do.

The Design Management Framework: People, Practice and Platforms. A framework like this helps make sure you have happier designers, better designers and more effective teams.
Organizations change every 30 days. It’s always shifting in different ways. And many efforts to do deliberate change (she offered three models of change but too quickly for me to catch).
She offered a stat about how 90% of organizations (from the McKinley survey?) about design leadership expressed that it had little impact on design maturity growth in those organizations.
What can leaders do?
- Know your maturity. How is your team partnering with the rest of the organization?
- Design your Design org at all levels. Org health and team health are not the same. Org health is the environment and conditions.
- Approach designing your org as you would any other initiative.
- There is no “end state” to org design. it will always be evolving.
- How will you know you if you’re successful? You need some measurements to track and compare over time.
Talks continue tomorrow.
4. Doug Powell: Sketchbooks over Spreadsheets: Designers as Leaders In A Complex World
He opens with a story about how Randy Hunt wrote a simple diagram during a meeting explaining, in a passed sketch to the CEO, how the organization currently worked. It helped the CEO to understand how things were working and suggested how things could change. Powell considers this an act of clarity, alignment and velocity.

He then referred to a talk Kate Aronowitz gave where she reported that there were 66,000 open executive design jobs [I think he misspoke and its design leadership, not strictly executive roles, as she explained in this article – he didn’t provide a link so this is the best I could find. Also without comparison to how many engineering, marketing or other unfilled leadership roles there are it’s hard to frame if this is unique to design or not.]
Who are the people who are going to fill these roles? What skills do they gave? Will they be ready? The demand for people to fill these roles has exploded. What are the missing skills required to effectively play senior business leadership roles in complex organizations, and how to designers acquire them in the middle of our careers?
From a summary paper from MIT Sloan management school (which I had to dig up since he didn’t have a reference. He had other unreferenced quotes From Harvard Business and Forbes). Only 12% strongly agree that their leaders have the right mindsets to lead them forward. [Note: w/o context of how many moderately agreed it’s not really clear how big a problem this is. And the summary paper does not share the complete survey results, I looked, which is always concerning.]
He suggests chasing after the established methods of current business school methods, which he believes are behind the times, is not what we should be doing. But instead think about what we need for the present and the future.
He refers back to the summary of the MIT Sloan study, which says:
“we identified a number of leadership teams that are embracing new ways of working and leading. For example, many of them are increasing transparency, demonstrating authenticity, and emphasizing collaboration and empathy.”
He argues that most designers actually possess the skills to effectively lead in this transformative era. Leading to a reframing of his core question: How do we retain, enhance, and maximize unique differentiating skills as designers?
He returns to the opening story. Randy knew his CEO responded to simple and direct messages. He quickly made a prototype and delivered it in a way Anthony could consume. He considers this a design act.
He shared a story from Raquel Bretenitz, head of Aperture Health, who noticed “We were sitting in the same office, but the design, data, tech, and social media teams were completely siloed.” And she led her team to pick up their stuff and moved to the dev team’s workspace. It was cramped but it made a huge difference. He sees this as a a use of her design skills.
He sees that there are surprisingly simple skills designers have that have greater value than we think. We can turn business challenges into design problems.

In his role he facilitates meetings between design leaders and the senior business leaders, or GMs. They’re called design program reviews and they happen annually. He’s found it’s good to approach these meetings as a UX design problem with the GM as the primary user. They know GMs are: busy, data-driven, opinionated, competitive and no BS
This informs a 6 slide review deck template used in these program reviews. He believes it works, and quoted an anonymous GM – “This review has helped me understand the need for design resources… We can double this design team with no problem.”