Getting it right, Part 2

The tensions of leadership

Meg Lightheart, @megalightheart
Presentation skills & leadership coach and organisational culture gardener
Birmingham, UK

In my experience coaching thoughtful senior leaders, it seems to me that, when you move beyond just being someone who sorts finances and rotas and so on, a large part of being a leader is learning to exist within unresolvable or cyclical tensions. 

Here are four that seem particularly relevant for people starting to build a bigger team, grow their organisation or become more conscious as leaders.

The tension of power

As you develop as a leader, you tend to be comfortable with either direct, controlling power or space-holding, allowing power. Search your soul to see if you can find why you don’t like the other type. 

Practice the other style. Work on just having a small part of the truth and finding the rest of the truth through trusting others’ perspectives. Or work on being clearer about your own perspective if you find it tough to communicate what you think and stick to it. 

In addition, how are you moving towards mutual power, shared responsibility, distributed decision-making whilst holding enough structure for everyone in the business to function?

The tension of inclusion

You’re always going to be excluding some people. You decide if you’re excluding people who are more marginalised by society or people who are unwilling to drop their internalised dominance. Inclusion, equity, and justice aren’t about everyone being safe and valued, but the most marginalised in society being safe and valued. 

It’s not enough to be ‘nice.’ Educate yourself on aspects of identity where you are in the dominant narrative. If you’re white, educate yourself on white supremacy and racism. If you’re a non-trans man, educate yourself on misogyny and feminism. If you’re not trans, educate yourself on transphobia and the gender binary. If you’re not disabled (yet), educate yourself on disability rights, universal access and ableism. If you’re not LGBQ, educate yourself on LGBQ rights and heterocentrism. 

Your instincts aren’t enough. Unconscious bias is very real, but unconscious bias ‘training’ is 1% of what’s required to undo its lifelong effects.

Just google ‘[term] 101’ and read ten articles to start with. Or ‘[term] reading list’ and get (and read!) some books. Particularly read books and articles by Writers of Colour. Do that before you start asking people you know to educate you. 

Your instincts aren’t enough. Unconscious bias is very real, but unconscious bias ‘training’ is 1% of what’s required to undo its lifelong effects. 

Consider who’s in your leadership team and early hires. Those are the people who are going to significantly affect the makeup of your organisation. 

It’s fine that you and your organisation is working on breaking down your internalised programming, just be clear where on your journey you’re at, on your website, in your job ads and during your hiring process. If you’re hiring someone from a specific demographic and they’re the first, tell them that. They’ll probably already know.

Decide where your bottom line is in terms of code of conduct — what is totally not acceptable in terms of behaviour and what are the repercussions for breaking the Code of Conduct. Take a stand that is coherent with where you genuinely are. Make it public and it’ll attract some people and put off others.

The tension of values

There is a difference between aspirational ‘espoused’ values and values-in-action. This gap is just a fact of life. Don’t wait to be given feedback  on it — be the one who opens up a channel for candid dialogue. Stone and Heen, the authors of Thanks For The Feedback, say the one factor that most affects if an organisation is a learning organisation is the way the senior team receives feedback.

Model the values you want the team to live. Go there first. For example, don’t work 15 hour days and then lecture them about burnout. (This is the tension of care vs capitalism, I suppose.)

The tension of public and private leadership

Public leadership is presentations, meetings, conversations and so on. Private leadership is your awareness of timelines, patterns, empathy, power, your awareness of your own awareness itself.

Work on both. Sometimes one is more in your control than the other. Sometimes when what you’re doing feels out of your control, all you can do is to work out who you want to be today. 

Who do you want to be, by the way?

Old Team, New Leader

Randy J. Hunt, @randyjhunt
Head of Design, Grab

When a leader joins a new team, there’s a common phrase that’s used, “inheriting a team.” Inheritance is right...and wrong.

It’s right, in part, because the team is something someone else has built up before you, and now it’s transferred into your responsibility. It’s wrong because inheritance implies possession. Now you own it. This is a terrible frame of mind for someone joining a team. Which is precisely how I like to think about it at first: “joining the team.” The team leader is a member of the team.

The First 90 Days by Michael Watkins is often recommended reading for people taking on new roles: whether in the same company or in a new company. I’d never read it before my latest professional transition. I wish I had. It’s full of practical advice and frameworks for thinking about entering a new role and decreasing the timeline between you being a cost to you being a value-add to the organization. I particularly liked Watkins’s recommendations around accelerated learning and spotting blind spots.

I found quickly in my new role leading design at a 6.5 year-old start-up that the complex market environment, state of the team, and company priorities pulled me in many directions. Each direction was some pull away from my well-formed plan. Frameworks in a book and frameworks applied to daily work are two different things. It reminded me that the main value of planning is the act of planning itself. It’s not as much about sticking to the plan as it is having planned and then having the plan as a solid place to deviate from, as opposed to being pushed around by the winds, ungrounded. I’ve been thinking about this a lot, and have formed a talk about it that I’ll be presenting at Leading Design: London

This realization returned me to some other fundamentals, most strongly: setting expectations.

Expectation-setting is critical. Set expectations in a 90 day plan, in a statement of intent, in a vision essay, or in a hundred small conversations. Whatever you do, you have to set expectations. They should be inspiring (not necessarily in their ambition, I think that depends on the organizational context), but at minimum in their evolution beyond what existed before.

Getting it right

This post is the first in a series about successful business strategies and design team operations. I’m honored that the friends and colleagues who contributed made time to share their experiences and insights; it’s my hope that you, dear reader, find tremendous value in it, too. –Josh

Just Enough Process

Michelle Morrison, @michelephant
Sr. Design Program Manager, Dropbox
San Francisco, CA

Startups are motivated to move as fast as possible. Engineers, designers, and the people building the product get pressure from leadership who get pressure from their board and investors to get to market before anyone else does. This can lead to nimble building – or it can lead to organizational chaos. It’s difficult to prioritize a thoughtful approach when you’re building as fast as you can think. Under those conditions, process can be perceived as a bureaucratic impediment to innovation. 

On the other side of the same coin, just enough process can help a focused organization move in lock-step. Simplifying the process to get work done can help foster transparency, focus, and ownership that does lead to a productive design and build practice. When everyone has the same access to information and follows even a minimal process, teams stay in sync, priorities tend to be more clear, and motivated teams can move mountains together. 

It’s difficult to prioritize a thoughtful approach when you’re building as fast as you can think.

I saw this work really beautifully in my time at Square. You may have read Gokul Rajaram’s interview on using the SPADE framework. This was implemented a few years before the company went public. It brought a clear methodology for making and sharing decision to the organization, which kept the entire company informed. This prevented product clashes and lack of clarity, enabling all teams to move faster with more information. Everyone was empowered to use the framework, and it took the pain out of how to make decisions and forced you to focus on the what and why of a decision. 

As organizations become more complex, operations professionals – especially DesignOps practitioners – become key hires in developing these types of systems and frameworks. Ops becomes the strategic function for scaling the business. The more people involved in a process, the more you layer in training, optimizing, and scaling, which is a primary focus of the DesignOps practice. And thus, the business can move faster – with just enough process.

Tips for implementing just enough process: 

  1. Name the process – this will help people remember what they need to do and where to reference the process if they forget. 

  2. As few steps as possible – Keep it high level, with distinct steps that are clear and actionable. 

  3. Reinforce the process – Take each opportunity to use the process and communicate that you are doing so. Include a RACI matrix in your project doc, or use a SPADE framework in your wrap up notes. This will remind your colleagues that the process works! 

  4. Train your people – When introducing or changing any process, make sure that everyone on your team knows what they need to do and why it matters. Consider incorporating info into your wiki or new-hire on-boarding to ensure everyone knows what they need to do. 

  5. Iterate – Monitor how the process is working and make changes that increase the impact of each process. You’ll know that your process is broken if teams are slow to adopt or steps are difficult to remember. Treat your process like a product and seek feedback to help you iterate to keep teams nimble and process lean.

Team Structures vs Hierarchy

Dan Mall, @danmall
Founder, SuperFriendly
Philadelphia, PA

I’m a big believer in self-organizing, outcome-driven, autonomous teams, as most of my career has been either participating in or helping to create them. Science has my back here. Largely due to the Ringlemann Effect where people’s efforts tend to diminish as team size increases, my most successful teams have been in the range of 3–7 people. Miller’s Law says the average person can hold 7±2 objects in short term memory, so I find an additional level of hierarchy to be helpful after about 7–9 people. That’s the point where it’s been beneficial to split into multiple teams, and possibly with someone overseeing the teams.

But, a crucial part of this new level of reporting is that the person or people overseeing the teams see their role as better supporting the teams rather than telling people what to do. When “management” or “leadership” or whatever else you call it see their positions as a way to be helpful at scale, that’s where I’ve found that the teams – and more specifically, the people on those teams – thrive.

Rules to Work By: Guiding principles for products and teams

Tatiana Mac, @tatianatmac
Portland, OR

Question 1: If you were co-founding a company with the intent of building a digital product the world will use, what are a few core values you’d build the company around?

  1. Move intentionally and fix things.
    If how quickly you ship is your metric, you’re going to move like a bull in a china shop. You will break things and you will hurt people, sometimes with deathly consequence. We’ve broken enough things and people. It’s time we made an effort to fix the real issue: Dismantle the oppressive systems and build inclusive ones.

  2. Get comfortable with being uncomfortable.
    Comfort means never being challenged, which means you’re not growing. To test our own biases, expand our own world views, and perceive the vast world beyond our narrow experiences, we must spend time in places that are new, unfamiliar, and difficult to understand at first.

  3. Mistakes are necessary for growth. Learn how to make them gracefully.
    Spend less energy trying to avoid mistakes. Spend more energy responding to the impact – reflecting, learning, apologizing, and planning for next time.

  4. There is no best, worst, safe, secure – only better, worse, safer, and more secure.
    Removing superlatives allows us to see concepts more as a continuous spectrum. Perceiving the world this way makes us more open to we can continue to push for things to be better, safer, and more secure.

  5. Center the most vulnerable groups at your core.
    Maximize design experiences for the marginalized individuals and situations pushed to the edge. If they are considered and cared for, the centered will be fine. Test the capacity for your product to be used for harm. Don’t be caught saying you didn’t consider that bad actors would exist. Vulnerable groups have no such luxury.

Question 2: How would you configure your team to get it right the first time?

We’ll never get it perfectly right the first time (see 4 above). But we can configure our team to be healthy, safe, and productive.

  1. Cultivate a culture of radical kindness, thoughtful communication, and curiosity. Leave no room for hateful or abusive behavior, ego, or binary thinking. As a leader, I value the emotional and psychological safety of my team most. If they don’t feel safer expressing their concerns, we miss out on opportunities to identify vulnerabilities and points for harm. In the patriarchal work environment, non-men are told that to succeed we have to emulate men. (But spoiler: we still can’t because it’s not just emulating behavior.) Instead, we must subvert this approach by using anti-patriarchal methods grounded not in individualistic wins, but collective ones.

  2. Attract and retain a team with as few common demographic factors as possible. If you successfully create a culture in (1), you will have a much easier time accomplishing this. Instead of “equalizing” the gender ratio (which reinforces the binary), we need to be thinking of how we can find more folks all along the gender spectrum. Instead of finding two South Asian men to meet your quota and calling it a day, seek no racial repeats. Express representation across the full LGBTQIA+ spectrum. Ensure you have people with disabilities. People who grew up poor, not speaking English, with close immigrant roots, who have an atraditional family structure, who practice a non-Christian religion, who grew up somewhere other than here.

  3. Provide trust for your team with radical vulnerability and transparency.
    Trust is a two-way street. But all too often the individual contributors are expected to trust their employers without any indication or promise of trust in return. In fact, there is hella trickery baked into the relationship from the onset (at hiring), with deceptive salary discussions, etc. But if leadership can provide trust first, through openness – sharing their own fears, aspirations, finances, challenges, etc, – their teams will see that being human is not only acceptable, but demonstrated.

  4. Work with team members to set clearly-defined goals for the year, then accountable action plans to meet them weekly, monthly, and quarterly. Showing your investment in team members first will make them want to return your investment. To be successful, team members need to have a clear plan for to accomplish their life goals. By defining these together, you’re putting their fates in their own hands. Your job as leadership is to help remove all obstacles from their success and provide all the tools and accommodations that each team member needs. Sometimes those fates will mean leaving your company, which should be encouraged if it’s what’s right – it may seem weird, but if what you can offer doesn’t align with someone’s individual goals, then it’s time for them to find that elsewhere, and for you to give this opportunity to someone else.

Poem, 8/11

the way he drove up the driveway, slowly,

unannounced, windows open, summer’s day

out of a blue green era

i pulled my bike up

to his window, smiling

susan and i

(his girlfriend post divorce,

sitting in the passenger seat,

to whom he is lovingly still attached)

susan and i

have decided that we are having a child

to make up for the mistakes your mom and i made raising you

is not unlike earth

and the colonization of mars.


there is only one of everything.


susan was an inspiration. 

she too is in ruins. 

Welcome to San Francisco

I am frequently asked for recommendations and local knowledge about the city I live in and love. I’ve put it all in one place – just for you!


  • Walking up and down Valencia St in the Mission is fillllllled with stuff to eat and buy and see.

  • Coit Tower is pretty, and you can get a great view from the adjoining park without paying to go up in the tower. But! the green space directly to the east of it, between it and Embarcadero, is like being in The Shire in the middle of the city. Magic!

  • Dolores Park, 20th/Dolores, the southwest corner has the best free view of downtown.

  • If you go to Dolo, because yolo, it’s fun to grab an ice cream sandwich at Bi-Rite – for which you do not have to wait in line because they are pre-made and since nobody is scooping a thing for you, you can avoid the wait & get the treat in yo mouth sooner.

  • Inside Golden Gate Park is the de Young (beautiful building, amazing viewing spot that’s free to get into, pretty cool modern art), close to the California Academy of Sciences (arts, sciences, fish), and the Japanese Tea Garden are all pretty cool.

  • If you walk out that way, the strip on Haight close to GG Park has some fun spots: Parada 22 and The Alembic are great for drink and food), and Free Gold Watch (actually on Waller, about 24 retro pinball games and a few old school arcade games).


Not fancy

  • Serrano’s Pizza in the Mission, 21/Lexington, is pretty amazing. They make each slice custom for you. Bigger than your average. I’m a fan of the Valencia.

  • Mau on Valencia is delish and affordable Vietnamese. Get the fried pork rolls with lettuce wraps, Cha Giao or similar. It could be a meal

  • Mama Ji’s in the Castro is dim sum and delicious and you can sit outside

  • El Metate has the best burrito in the mission, on 22/Bryant. Don’t come for me, bro, with any other place. They win on price, size, quality, and distribution of ingredients. Seriously, it’s not just a whole bite of beans and then a whole bite of vegetables. Oh, and get the vegetarian burrito – now with real vegetables!

  • Southern Pacific Brewing on 19/Treat. Lots of their beers, some other folks’ beers, pretty good grub. Recommend the garlic fries with any meal.

  • Crafty Fox, 13/Mission, another nice brewpub with a wide variety of taps, and a truly truly excellent fried chicken sando. Less excellent if it’s busy, though.

  • Tacolicious on 18/Valencia has pretty great cocktails and slightly pricey tacos, but the bottomless chips + salsa almost makes it worth it

  • Humphry Slocombe - very good, local, quirky & amazing flavors

  • Mitchell’s for ice cream. Especially the pistachio. Some crazy-ass flavors.

A little bit fancy

  • If you’re feeling a touch upscale, Starbelly is fun and has great cocktails and pizza and pasta. Plus a little patio in the back.

  • Tartine Bakery. For everything. An institution.

  • Kahnfections. If you don’t want to wait in line at Tartine and still want some quality baked goods.

  • Stable Café on 17/Folsom. Cool little joint, amazingly beautiful outdoor space.

  • Frog Hollow Farm Café in the Embarcadero Ferry Building has a risotto tartlet made with mascarpone, organic currant, and orange peel. That is all.

  • Mission Cheese – Wine! With cheese and snacks!

  • Beretta – Delicious modern italian in a lively setting

  • Bar Agricole – amazing cocktails, amazing environment, amazing food.


  • Heirloom Café is a delightful, delicious, comfortably upscale spot in the Mission that also has a terrific wine list. Their prix fixe with wine pairings is worth every dollar.

  • La Ciccia is the best Italian food in San Francisco. Be prepared to dine at an odd hour if you’re looking for reservations close to the day you’d like to experience it.

  • Central Kitchen – One of the most delicious places in the city, very upscale, beautiful, minimal, lots of smaller & medium plates with amazing nuance & variety


  • Atlas Café – great cafe with indoor & outdoor seating and a wide menu, plus free wifi (you have to renew it every few hours)

  • Coffee Bar – I know, I know, silly name. But if all coffee bars were like this one, you’d agree! Free wifi, delicious food, amazing indoor & outdoor setting

  • Haus – a minimal, quiet coffeeshop with a few pastries, great coffee, and beautiful yard

Getting around

  • Getaround – here’s $20 credit to use local cars owned by local people. Best for by the hour or a day. You need to tank the car up and pay for it before you return it.

  • Turo – here’s $25 credit to use local cars owned by local people. Best for the day or week. You need to tank the car up and pay for it before you return it.

  • Zipcar – local cars owned by a non-local business – but first to the market. They pay for the gas. Competitive pricing with the above two, once you compare multi-day.

  • Ford GoBike – ad-hoc bike by the hour, or by the day. Even better for those hills if you can get an electric bike. Don’t forget to turn it on!

What Actually Works

I’ve always been a fan of Milton Glaser’s maxim:

The solution to the problem is contained within the problem.

So when I saw on Twitter that Nathan Banshaw was starting a podcast and needed a name, I reflected back to him what I saw as the core of what they were talking about.

And, boom: they decided to call it What Actually Works.

Now, naming is hard. It’s rarely this easy. But this is a nice example of what decision-making can do in small teams.

Selling the story of your work

This is a story about creation.

This story is about your story. The story of the work you’ve been doing. The work you’re probably doing right now. And how to make that story clear and compelling, with a course of action.

I once took a public speaking class. It was my freshman year of college. In it, the teacher posited a simple framework: tell them what you’re going to tell them. Then, tell them. Finally, tell them what you’ve already told them.

Seems pretty easy, right? A simple way to embed a story within a story, maybe even to bulk up your own story.

But it’s totally wrong.

Nobody wants to be told, told again, then re-told. That’s literally being given a talking to – and lectures are rarely engaging. They are, by definition, one-way.

The way to establish an engaging story is to consider it selling.

Selling is not an inappropriate word in the context of design work. Even a design that is brilliant, timely, and original still needs to be contextualized with a little persuasion, a bit of unpacking about design decisions you made inside your head – in other words, selling. 

That public speaking professor was wrong, at least when it comes to design. Telling is not what you want to do. Telling is about you; selling is about the customer.

Telling is about features of your product or service – e.g., the fastest car, the best check-out flow. Telling is a bit cold and impersonal, and can sometimes differ based on who is doing the telling. When you tell a telling story, you are simply listing the facts.

By contrast, selling is about the benefits that your product or service conveys to the customer – e.g., the fastest car that helps you arrive safely in record time; the best check-out flow to make your purchase experience effortless.

Your customer will buy your product and sign up for your service based on what it does for them. They have a need, and you are suggesting that you can fulfill it. And once you capture their attention and interest – the promise of a better future, solved by you! – you will be able to establish trust.

And how do you do that? Start with why.

Why are you making this product or service? What motivates you to do this work? In what ways are you the perfect person to be solving this problem, fulfilling this need? This is a critical step that establishes your credibility, and requires you to be a bit vulnerable – especially since you will likely be in an environment focused around you and your content. Once you establish this credibility, though, it can be the basis for a wonderful, engaging story.

Here are seven elements of selling a successful story about your design:

  1. Start with why. It’s your central premise for doing this work. The passion you have about why you are doing this work conveys your credibility to solve this problem.

  2. Use clear, simple language that is easy to understand by anyone, with any job function – not just designers talking about design, or engineers talking with other engineers.

  3. Establish a great cadence of delivery. Speak at a comfortable pace – not too quickly, nor too slowly. And take breaths. The moment you pause, even for just one beat, you will (re)capture the room’s attention. Your body will thank you.

  4. Rehearse. Know your content, how it corresponds with your visuals, and practice selling the story over and over. You will want to rehearse so many times that you make it look easy.

  5. Sweep the room when you speak. Be inclusive, and make eye contact with everyone present. Don’t focus solely on the key decision-maker, your teachers, or your client; great input comes from everywhere.

  6. Be specific about what you want from the storytelling – is there an action to take or a decision to make? Is it due by a certain date? Would you like feedback on the whole thing, or a specific component? Knowing what you want out of the it before you go into it can influence the order of the narrative, or encourage you to highlight key points for a particular audience.

  7. Enjoy it. Smile. This is your opportunity to share all the great work you've done and get feedback about it — which will ultimately improve your product, service, story, and storytelling ability. It gets easier to sell a story the more you do it.

And here are seven elements, highly tongue-in-cheekily described, of what not to do:

  1. Be bored and passionless, since you’ve sold this story a hundred times before. You’re not excited about it, so you don’t expect us to be. Yawn.

  2. Be inconsistent in your slide design. Mock-ups that jump and jitter are your specialty. Pixel perfection? Never heard of it.

  3. Bristle at feedback. Nah, it’s cool – I don’t want to learn from your expertise, thanks anyway.

  4. Use a quiet speaking voice, especially in a big space.

  5. Hide behind the podium / teleprompter / your notes.

  6. Use exclusionary words, such as obviously, so on and so forth, of course, and et cetera. Of these, “of course” is your favorite – what’s obvious to you is totally obvious to everyone else, right?

  7. Use effects to distract us, since there are so many awesome slide transitions built in.

So now that you know the difference between telling & selling, and elements of how to sell and not sell your story, let’s look at how to create that story!

My Jewish mother loves to make her mother’s matzoh ball soup recipe. Except that nearly every time she makes it, she’s prepared to throw the first batch of matzoh balls away. Why? Matzoh balls are a challenging mix of ingredients, and a successful outcome is subject to many variables – the heat of the pan, the ratio of cooking oil or fat, the quality and freshness of the matzoh meal, how long they are refrigerated for before being fried up. So many little things to consider, and adjust along the way.

Similarly, the creation process can be messy. You may have scrapped ideas, many idle or unproductive hours, and many more hours pursuing iteration upon iteration.

Document it. All of it.

Capture the beginning messy part of the process – and every subsequent part. Take photos, make notes. Step back from your work at a regular cadence – daily, weekly. By the time you are ready to sell the story you have been creating, you will want this content to look back upon, edit through, and coalesce. It shows where you’ve come from, the journey you’ve taken, the ideas and paths you pursued – and didn’t. Documenting your process provides more ingredients than you need to ensure the end product comes out deliciously.

So then: here are ten steps to creating a successful story:

  1. Hello / intro / what we’re here for – start with the basics and set our expectations, particularly how long you are going to be talking, if there’s a Q&A at the end, or if you prefer to answer questions along the way

  2. Why: the current status, how we have been living, how the situation got this way

  3. Opportunity: why is this unsatisfactory, sub-optimal, bad or wrong, broken. Set us up to think: how could we have we been living this way?!

  4. What: what’s the big idea? What will life be like in this new, more ideal future state?

  5. Who: I’m doing something about it, I’m qualified / my team’s qualified because…

  6. How: How will it work, in stages, over time? What’s the plan (for now)?

  7. Where: What was your journey like to get here? What pivots and a-ha moments did you have along the way? And what will it take to get to this new future state? Funding, advice, or simply more feedback? 

  8. Specifics: What are its benefits? What are the drawbacks?

  9. Now: what’s the call to action?

  10. And finally, my favorite: What question haven’t I asked that you’d like to talk about? This last point is an incredibly powerful way to open up questions, and get answers to important points that the audience may have been holding back on.

Many thanks to Simon Sinek and Barry Nalebuff for inspiration.

Ribbon Bed v1

Many years ago, for a bed design I created, I commissioned a sketch from an industrial designer and RISD grad Erik Askin. I told him of my inspirations and guiding principles, and he made some great suggestions about its structural integrity.

Cut to many years later when I found Green Piece Furniture, on Treasure Island, to work with me on its manufacture. The founder, Nick, developed a schematic drawing based on Erik's sketch. I visited his workshop a few times to see the work in progress, and to document the process of molding the plywood and adding the walnut veneer. 

Now that I have been sleeping on the v1 prototype since Summer 2016, and enjoy its smooth lines, I already have ideas about the v2... I’d be delighted to talk with a wholesaler about mass manufacture, wink.

The sketch.

The sketch.

The schematic.

The schematic.

One side of the mold.

One side of the mold.

So I think my floors are walnut, too…

So I think my floors are walnut, too…