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.

Comments in brackets [] are mine.

1. Julie Zhou – The Many Facets of Design Leadership.

[Note: I was disappointed design ethics did not come up at all, given her 14 year history at Facebook. It’s the toughest design leadership issue we have and her insight would be valuable. I looked but couldn’t find if she’d written about this before.]

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.

1. 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?
2. 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.
3. Intent. A passion for work that goes beyond money or status.
4. 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.
5. 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.
6. 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.
7. Communicating Openly. Collaboration is rooted in trust.
8. 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.
9. 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.
10. 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.
11. 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.
12. Take note of team members and partner communication styles. Help people feel like they have been seen and heard.
13. 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.
14. 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?
15. Get out of the fucking way. This is still a problem. How to balance facilitating without slowing things down.
16. Create a vision statement that is a north star. This helps people be autonomous and keeps the manager out of the way.
17. Check in on a regular basis. What is working? What isn’t? And where they need you to show up.
18. 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.
19. Manage our time well. If I’m in 15 meetings a day how can I possibly be there for my team?
20. Invest in our own personal development. He’s planning on watching all the other talks.
21. 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.
22. 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 a 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?

1. Know your maturity. How is your team partnering with the rest of the organization?
2. Design your Design org at all levels. Org health and team health are not the same. Org health is the environment and conditions.
3. Approach designing your org as you would any other initiative.
4. There is no “end state” to org design. it will always be evolving.
5. 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 opened 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.”

5. Jane Austin — Chief Design Officer, Flo Health Inc., The Three Ages Of Leadership

In the words of Cap Watkins: “Congratulations. You got promoted – now prepare to suck at a completely different job.”

She explained that every time she got promoted she made a new set of mistakes. And that helped her see that there were three ages or levels of management.

There is an emotional rollercoaster in doing this kind of work that from the outside seems expected but when it’s you can be hard to deal with. And that has led her to this talk, which is about how to suck less in these stages.

“Do you want to become a manager, or do you want to excel in your craft.” – Peter Merholz

She calls out how it’s uncommon for individual designers to continue to get rewarded as they become more senior, and they often leave to become freelancers. Some American companies are exceptions.

In deciding what level of management to pursue, she offered three ways to think about it.

• Heart: What gives you flow and excitement
• Tree: How do you want to grow professionally?
• Star: How do you like be rewarded in private or in public?

While there is status that comes with being higher in the org chart, that’s a bad reason for moving up. You might need some experience in management before you discover if it’s right for you and at what level.

“If opportunity doesn’t knock – build a door” – Milton Berle

She discovered (after making the mistake of waiting) that to move into management she had to volunteer to help with things like team retrospectives and speak at events to grow into a leadership status. It was hard to do all this without feeling like she was showing off (British humility). And this led to Age level one.

Being promoted over peers was a tough emotional shift. She can’t believe this now, but she apologized to them (which destroyed her credibility). She didn’t create the emotional distance and didn’t know about coaching. She was miserable.

What not to do: too hands on, micromanaging, being autocratic, working super hard (all aspects of keeping knowledge to yourself instead of teaching). Antonio Stradivari didn’t teach others what he knew, so he when he died his knowledge was lost.

What to do: she learned not to try to be perfect but to be better. She didn’t need all the answers but to ask good questions (including ones no one else was asking). She learned to coach instead of tell. And that everyone didn’t have to like her (as she didn’t like all of them!).

Paul Graham’s essay Maker time vs. Manager Time. A different way of framing the problem.

She explained how emotional intelligence is talked about but not often practiced. Yet it’s the reality of the culture around EQ that makes good work possible. It’s the managers job define a healthy culture. She joked about the three kinds of managers that don’t:

• Shit funnel – makes things bad
• Shit fan – makes bad things worse
• Shit umbrella – protects people from the other two

She shared a joke about being in an earthquake and tweeting about it. A designer responded and asked “Are you OK?” and a PM responded with “size?” which confirmed (in a joking way) that designers care about people but PMs care about metrics.

Biggest mistake as a director was underestimating her power. She didn’t realize that with the seat at the table she could disagree and change the conversation. If you make your case well you can shift important things that define the culture, something no one else in your organization can do.

6. D. Keith Robinson – Leading From The Middle, Lessons From The IC Track

Being a senior IC (Individual Contributor) can be squishy. What it’s shaped like will vary significantly. The role and the skills involve can vary depending on the kind of organization you are in.

He sees that management can be a trap – when it’s the only way to get promoted people go into management for the wrong reasons. Or people leave when the way they want to grow as an IC isn’t rewarded.

Feeling Stuck. Common complaint. Leads to “how do I become a lead or manager?” as a result. You may have to let go being strictly a maker or crafter. As you take on more of a leadership role the skills are less tied to being able to make artifacts.

Expectations. When you have many years of experience, it’s harder to set expectations. You may need to lead the way in defining what your boss and others expect of you.

Partnering > Mentoring. As you become more senior people become closer to peers than to superiors or mentors. This is done by sharing goals and measures.

Managers often want senior ICs to have strategic impact. To be influential in how important decisions are made. But it’s difficult to be strategic when you are not in the conversation. Which means relationships and persuasion become more important. Including owning cross-functional relationships. A primary function is people influence and work with your manager to create opportunities.

“I like doing the work, you know? Not so much the meetings and all the talking.” This is probably not going to happen if you want more seniority. You’re going to be in more leadership situations which will be less about making artifacts. You’re going to have more relationships and more meetings.

Top complaint from Senior ICs is they don’t have enough time. This is about being overcommitted. But you have to learn how to say no to things and focus on what’s most important. Practice saying no so you can say yes.

You need to learn to think about scale. Your best work may be through other people by crafting a vision and helping others carry that work forward.

7. Temi Adeniyi —  Design Leadership For Imposters

She started with a personal story about feeling like an imposter since 1999. Her love for HTML/web design as kid and her love for NSYNC combined in leading her to make an ungodly number of fan websites. She developed her design and coding skills and that led to her studying it in school. Even as she succeeded she felt she was still so far behind. The term imposter syndrome actually helped her feel better as it gave a name to what she was feeling.

She refers to the Ira Glass’s gap between good taste and good ability. And how all go through this in our careers.

She was surprised to discover as she moved into leadership that it was really a different job. It’s scary to go from feeling secure as a senior to feeling low confidence. And impostor syndrome returns.

Part of the challenge is how different being a good leader can be depending on the situation you are in. It’s easy to feel like you don’t fit but that can be an illusion if your idea of what you should be doesn’t match what the team needs you to be (which may be much simpler).

The alternative is to trust in what you know. If you’re good at articulating design decisions, that translates well into articulating many things. Many design skills, like facilitation, have more value than we realize.

Imposter Thoughts:

• Wait – am I doing this right? Build relationships that help you get better data on how you’re doing (boss, mentor, coach). In getting feedback, ask about what you’re doing well in addition to where you need to make changes.
• Do people take me seriously? There are no shortcuts to credibility. Trust in your skills but accept that you will have to earn other’s trust.
• Am I good enough to be here? Embrace the way leadership looks to you. Find fellow works in progress and exchange experiences.

She closes that sometimes she still feels like an imposter. It is going to take awhile to get to where she wants and that’s OK.

8. Michael Yap, Mostly Clear, Partly Sunny: Creating the Conditions for Design to Flourish

He shared a personal story of unexpected management at Etsy. He never had a desire to be a people manager. His path was not a steady progression of promotion – he was actively trying to avoid it given how managers are often seen as out of practice and out of touch. He’d see this when he worked at a boutique agency. While there he did more and more recruiting and training. He hired many people with raw talent and trained them in his image. It didn’t scale. And the more people he hired the less time he spent doing the design work he loved.

When he joined Etsy he wanted to be solo again. He worked on signature initiatives. But the organization was looking to hire a VP of design for a long time. FUD, Fear, uncertainty and doubt become common. When he was asked to take the role he looked for someone else to do the job. He admits he was afraid of failing in a visible way. but eventually said yes out of duty.

At the time there were few resources on design leadership (that he could find). He felt he needed more than fortune cookie advice. The demand for design leaders has grown and the importance of design leadership knowledge has grown with it.

In 2019 McKinley surveyed design leaders and less than half felt that CEOs understood their role. 90% of CEOS didn’t regularly involve their design leaders in developing strategy [I don’t believe the report says how these numbers compare to other roles – so it could signify that CEOs only involve a handful of roles in strategy and is not specifically design exclusion].

He read from traditional business management texts and recognized how antiquated it was, based on command and control ideas.

Three basic questions:

1. How do good leaders conduct themselves towards others?
2. How do good leaders acquire, keep and apply power?
3. What personality traits must a good leader possess?

One way to answer is what styles to adopt. In his research he found some foundational references:

• Lewin’s Leadership style: Autocratic, Democratic, Lassez–faire
• Mouton’s Leadership Grid: Country Club, Team, Impoverished, Product or Perish
• Primal Leadership: Visionary, Coaching, Affiliative, Democratic, Pacesetting, Commanding

Each style prescribes certain characteristics. The problem is that character isn’t something people can just put on when they get dressed for work. He turned to design ways ways of thinking, seeing and making. In particular, systems thinking.

He suggests thinking about leading design orgs, and orgs in general, as self-regulating systems. That have feedback loops. They work on a loop of Sensing, Comparing and Acting. These systems are everywhere, like in thermostats.

[Note: for the rest of the talk he presented interesting concepts individually, but I was lost on how they tied together, or how they should be be applied to the challenges of managing. I did my best with what I could understand].

You can think of design as series of three nested loops. The user interacts with an object in a loop of acting with and responding to. And the next loop of the designer has a similar loop with both the sign and the user. And then there is a meta loop for the meta-designer who interacts with all the conditions [I looked for a paper from Dubberly that this references, but I couldn’t find it].

[I think he was implying that there are similar loops for managing organizations]. If we think of management in terms of conditions, he offers that there are five to consider: people, tools, process, operations and environment. The bulk of leadership literature is focused on people conditions. What’s less clear is process at scale. How to design at an organizational level.

It’s not hard for him to recall when the double diamond was a foreign concept at Etsy. And that it took time for it to be accepted.

Think for a moment of your design org. How do you prioritize and focus on people, tools, process, operations and environment? This is one useful way to think about what managers do.

He is no longer head of design at Etsy. And some of the work he does as an IC is investmenting in process.

9. Christine Pizzo — Mythbusting Millennial Management

[Update. She gave a thoughtful apology in the event chat room. ]

[This talk was problematic with some unfortunate commentary about millennials. but there was generation bashing here and I imagine any Millennial would be upset by it. She did not offer context/research from experts on generations to support or contextualize her opinions]

She compares Millenials to flowers. Environment matters. You need to talk to them quite often. They have a different level of needing to be heard [compared to?] and they’re going to give you opinions whether you like them or not.

She offered this shit list about designers:

• I don’t know shit
• Scared shitless
• Don’t give a shit
• Want to be the shit
• They’re good shit

She offered that whatever your list is, there is no one size fits all. You have to tailor who you are since you can not approach each scenario in the same way.

Myth: they want trophies for minimal work. This is just everyone, she suggests. But they do need outward recognition.

Her organization provides a skills matrix and levels documents to help them understand how to grow.

She offered that growth and promotions are probably the number 1 misalignment. Three years in their first job the want promotion to senior. The maturity to separate technical skills growth vs. pure time and experience is often lacking. “The definition of 5 years or 10k hours is the definition of mastery” is something she heard at a past Leading Design event and she felt this helped frame the goal for Millenials.

Myth: Obsessed with social. They are passionate and stand firm about the brands they follow. They are a generation that utilizes technology to the best around them. She referred to selfless collaboration. How the platforms like github, youtube, Dribble, Creative Market, are free and they see as a ‘right’ to use. These tools and crowdsourcing platforms are assumed to be useful and they’re surprised when they’re not used.

Myth: so many feelings. It can be hard to explain to them why they are given certain assignments or not. She explained that it can take effort to help them understand certain decisions that are about the og and business.

Passion=engagement. They get bored quickly. You will quickly know how they feel about the work they are doing.

The best way to get them more maturity is to give them mentorship roles for someone else. They start to see what it’s like to be responsible for someone else and generate some self-reflection.

Her summational advice was to buddy up, motivate their world, and get ’em working.

She closed offering a note about how “If you give a millennial even an inch they are going to take it 20 miles (!?) or they are going to use it for the next 5 years.” Which I wasn’t sure how to take.

10. Abi Jones — The Manager’s Guide To 1:1’s

She has done 1000s of 1-on-1s and her advice is based on that experience (which will also be a forthcoming book).

She’s quick to point out that 1-on-1s are not a panacea and that she lives in California and has a west coast bias – YMMV given how different cultures can be.

Last year during the storms in CA there were lightning storms near her home. Over the week the sky turned orange and it was scary. And it was not clear how to stay safe. They heard bulldozers and other equipment not far away setting up fire barriers. Eventually they got personal door to door information about what was going on. And that made a difference.

She reported a staistc about how employees respond to confliting information. And that 1-on-1s is one way to ensure people hear things directly from you.

Job embeddedness: the totality of how we feel about our workplace and why we stay. How connected they feel with their team and the larger organization.

1-on-1s help you understand embeddedness. The links, fit and sacrifice they feel about your organization.

1-on-1s are also an early warning system. This include turnover shocks. events that make people say “should is stay here?” These events are why people leave – it’s usually triggered. For example: spouse gets a great opportunity, a person gets passed over for a promotion, or a pandemic transforms people’s lives.

1-on-1s should be early warnings to you team. Communicate shock in advance and create/maintain a direct channel. Create clear invitations to your team about why these matter and how they can best use the time.

“Students least likely to go to office hours are the students who would benefit the most” – Anthony Jack

Preparation, Attention, Curiosity and Takeaways. Only 50% of people report knowing what to do at work. Setting expectations is the manager’s job and we should tell the truth. Make clear why it’s important and what can be covered.

She listed a set of challenge questions, and radical questions. The specifics don’t matter it’s about make sure the right context is set. She creates a 1-on-1 doc in advance that’s driven by the employee. Abi believes just the act of writing it out itself helps people think more clearly.

Preparation: set expectations, share a thinking space, be positive. Be ready to help and listen.

She challenged the audience to consider how many tabs they had open. And how distracted out attention was. And how bad a habit it is during a one on one to have divided attention. Walking 1-on-1s, or any context that is passively active but allows full attention is a great habit to keep attention. Doing audio only can help too as it does actually increase focus (since you’re not obligated to awkwardly stare at each other). Turn your phone off.

Curiosity: She recommends Humble Inquiry, by Edgar H. Schein. It teaches a better way to think about questions and how to use them. Moving from ! to ? First step is you are a manager, not a forensic investigator. You’re job is to ask question to help them realize the solutions to their problems. That’s more valuable than telling them answers. Best way is to stop problem solving, and shift into being curious.

The goal is to have clarity after a 1-on-1. That both people are clear on how they other person feels and what their opinions are. They don’t have to agree. She believes in takeaways. When 5 minutes left, ask “What are you taking with you as we wrap up? Or what are your priorities for this week?”

40-80% of information given by doctors to patients is forgotten (missed attribution). Imagine what is forgotten after 1-on-1s?

11. Timothy Yeo —  Design Leadership For Introverts (Iso-Edition)

As an introvert, he finds too much social interaction exhausting, even if it’s something he likes.

Introversion != Shy. Instead it’s about how you tend to respond to social stimulation. It’s also true that introvert vs. extrovert is not binary. There is a spectrum of tendencies, including ambiverts who depending on the context have different preferences.

he talked about Susan Cain and the cultural stereotype that leaders needed to be extroverts. He asks how can an introverted design leader succeed?

Being more extroverted is not the answer. He tried it and it doesn’t work. Instead he asks how can we use our introverted ways as a superpower?

Remote work has been a challenge for him. He felt he was good at reading people and rooms in person, but will that work in this new world? The answer is yes, with some caveats.

He recommends arriving at virtual meetings early. You get to meet the other punctual people and talk to them one on one or in small groups. The small talk is easier and people speak more freely. It’s an opportunity to connect at a more human level and you get information you might not get otherwise.

Not everything has to be a meeting. So many other ways to communicate and express a message. You can record a message on your own time and share it. It’s the same amount of time for others but you gain more control over your message [as long as you keep it short].

Respond on your own time. You don’t have to respond to every Slack message immediately. Schedule messages to be sent. Asynchronous communication is much better for everyone.

High stakes meetings are often pre-decided. Senior leaders often arrive already knowing their opinion. You need to influence them beforehand. Try to engage with them before their minds are made up. A containership takes a long time to change direction – you have to start early.

It’s good to hire butterflies. People who are natural connectors and communicators. This helps introverted leaders. It doesn’t absolve your responsibilities, but it helps balance the social load.

He referenced a study by [will find reference later] about how it can be a contrast of styles that works best. So if you get the chance to choose who plays management roles, the best mix might be not what you think.

He sees social media as a gift from the introvert gods. You have access to respected people and can engage with them in a way you can control.

Networking combines all of the things introverts do not enjoy. But remot events can make it easier. You have more control over who you interact with and what you can learn about them first (see what they posted last on social media as a way to start a conversation), as opposed to awkward impromptu conversations a conference events.

Trick: pretend networking is user research. Who are these people? Why are they here? Small talk questions through this lens are much easier. Just don’t go to far and make it an interrogation.