Investing in design strategy means investing in greater confidence

A talk with Ben Crothers, former principal design strategist at Atlassian, principal facilitator at Bright Pilots and an author of Presto Sketching: The Magic of Simple Drawing for Brilliant Product Thinking and Design.

Welcome to the [Design Talks] series. Here, you’ll find different perspectives and insights from my colleagues around the world. The goal? To learn and improve your design process!

This one is a bit longer than usual. It’s actually the first talk that demands its own table of contents! But it’s so worth it – I promise 🙂

Without further ado, here’s the design wisdom of Ben Crothers!

Who is Ben Crothers?

On Design Strategy

Design strategy translates the intent of a business into the experience of a business

Investing in design strategy means investing in greater confidence

A successful strategy is one that people use in their work

On Design Strategists

Don’t just look at the tree, connect it to the whole ecosystem

On Design Management

5 pillars of an effective design organization

An ideal design team brings diverse perspectives to the table

Good design managers set the right targets and the right constraints

Lead by presenting your team with a way forward

Create common ground for designers and non-designers to collaborate

On Business and Design

Design helps organizations to see and respond better

Use design as a competitive advantage

Innovation is about executing ideas

On Advice and Mistakes

Ben’s one piece of advice about quality

Fast is not best

Ben’s favorite failure: cardboard chairs

Ben’s Recommendations

Use design maturity as your success metric

You’ve already got all of the best tools

Ben’s favorite sources of knowledge and inspiration

The 3-bullet recap

Who is Ben Crothers?

Ben is a designer and facilitator who loves to draw, and helps others to think better and be more creative.

After finishing an Honours Science degree, he did what everyone did back then when they didn’t know what they wanted to do: he got a job in finance! He hated it, but interestingly enough, it’s where he first discovered design.

He ended up at the Department of the Treasury (Australia) and there he taught himself how to overhaul a website. Before he knew it, he’d moved into digital design. Funnily enough, it was only years later that he actually started to call himself a designer, as he hadn’t studied design formally or started at a design agency.

Maybe because of this, Ben always worked extra hard to speak the language of business whenever he was discussing aspects of design. He did all of the things that put him squarely in the camp of design strategy.

Through his very diverse career, he has had an enduring love of visual thinking, visual communication, and sketching, and the power of the latter to help people think and work better. He even wrote a book on the topic: Presto Sketching – The Magic of Simple Drawing for Brilliant Product Thinking and Design.

Ben’s passion for design probably stems from two big things.

From an early age, his father always involved him in fixing things and renovating whatever house they were living in at the time. This not only implanted him with an ‘itchiness’ to improve anything he could see that needed some extra love, but also an assumption that he probably already had the skills to do it!

He extends this to his firm belief in the democratization of design: anyone has the skills to improve the experience of products, services and systems, with a bit of bold intent, constant practice, and collaborative empathy.

The second thing is a love for anything relating to the Scandinavian blend of functional design and visual aesthetic. There is inherent beauty in anything that is devoted to its function.

Ben has just started his own visual facilitation business Bright Pilots, which is the culmination of his passion for helping people frame problems and generate better solutions.

On Design Strategy

Design strategy translates the intent of a business into the experience of its product or service

Ben is old-school when it comes to approaching strategy; this means that he wanders around with a big set of models in his head, but always starts with simple, smart questions before anything else.

Simple, smart questions are a gateway to a much richer strategic discussion. Questions like: Where in the market do we play? How do we win? What problem are we solving? How do we make the customer win? What’s our unfair advantage?

For Ben, design strategy is two things.

Firstly, it is a way of translating the intent of a business, product, or service into the experience of that business, product or service (and back again!). It’s the middle ground that’s often missing between what the business wants and what the people need.

This typically encompasses:

  • What success means (and for whom) and how to measure it,
  • The problem to be solved,
  • The unique value proposition,
  • A set of design principles.

If you think about it, any answer to any question that comes up in a design critique (What problem are we solving? Who are we trying to appeal to? Why is this website a one-pager and not multi-page?) should be expressed in the design strategy.

Secondly: design strategy is all about how we choose to design.

  • What is the mindset, skillset and toolset we choose (or default to) when it comes to designing something, and why?
  • What trade-offs are we willing to live with in order to get this thing out the door?
  • Should we only design for our customers, or with them as well?
  • When do we lean on our design system of patterns and templates, versus when do we create something completely new?
  • Should we tackle this problem with a design sprint, or break it up into several projects of research, ideation, prototyping and testing?

It’s very on-trend to talk about ‘what problem we are solving’ and yes, that is a crucial element of any design strategy.

But increasingly, Ben has found himself emphasizing another question too:

How do we make the customer win, more so than they are right now?

You can see this at play on the Value Proposition Canvas (popularised by Strategyzer). Customers win when our products and services create the gains they want and relieve the pains they have, in ways that are better than what they are doing right now (whether that’s a competitor’s product/service or not).

Investing in design strategy means investing in greater confidence

People seem to think of decision-making as a binary thing; some people are really led by their gut (intuition), while others are more ‘data-informed’. These two things are often in tension with one another.

Decisions in design (and in anything, really) are simply a game we play in order to reach our goals while minimizing risk. Sometimes it’s easy, especially if we just want to iteratively improve on what already exists.

For example, we can use the information from usability testing to determine whether one design is better than another.

Usually, though, it’s much harder, because we want to make something better that goes beyond iterative improvement. We want assurance from information or intuition that just isn’t there, because it doesn’t even exist yet.

Investing in design strategy means investing in greater confidence. By having a clear design strategy, you’ll have a much better idea of the value you want to create and for whom. You’ll also have an understanding of the risk that you’re willing to live with, and what you’re not.

This can actually be incredibly liberating for creativity, since the ‘borders of the sandpit’ (your constraints and targets) are clearly defined.

Design strategy, therefore, addresses the problem that a lot of organizations have in not being able to step out of the ‘hamster wheel’ of iterative build-measure-learn, and move into areas of greater innovation.

A successful strategy is one that people use in their work

The most important part of a successful strategy is that everyone who is meant to be involved in it (staff, management, etc.) can connect with it and use it in their work.

It goes without saying that any strategy should state a clear objective, something about the advantage over competition, and an idea about scope and time.

But something that lifts strategy beyond the ordinary is a reason to believe it.

What is it about your strategy that will make it truly resonant and relevant to those who are meant to execute it?

On Design Strategists

Don’t just look at the tree, connect it to the whole ecosystem

Good design strategists come from a variety of backgrounds. Ben has worked with some amazing strategists, all of whom have walked very different paths to his.

Despite this, Ben has noticed some common aspects that all of them share:

Seeing and thinking in terms of systems. It’s not enough to just see the tree; you need to ‘see’ the roots, the ground and the nutrients that have fed the tree, the forest around the tree, and the seasons that the tree has lived through.

Asking better questions. You can spot a good design strategist by the questions that they ask when critiquing a website. They’ll ask things like “Who is this website trying to appeal to?”, “How is this website supporting the business intent?” and “How will this website’s competition take it down?”.

Flexible conviction. Being able to take a robust position on something and argue compellingly for it, but still hold that conviction loosely enough that they can change it if new information comes along.

Connecting the dots. Being able to make sense of a lot of information fairly quickly (thanks to having a lot of experience in the job, which has allowed them to recognize patterns over time), spot insights, and help others make connections and notice gaps more effectively.

When it comes to good habits of design strategists, Ben thinks that these four are at the very top:

Be curious – foster and feed an appetite for how and why things work. Don’t settle for superficial appearance, but observe and listen more deeply, digging into the details. Collect conceptual models, which visually express how different systems work.

Be open – develop a broad diet of inspiration and inputs, rather than just the same feeds that everyone else is looking at. Seek out views and mindsets that are different from your own.

Be a synthetic thinker – cultivate experiences that involve you having to analyze, summarize, and play back information (like facilitation, and participation in collaborative workshops). Build your own set of questions that help you to critically analyze a lot of information, e.g. “What if…?”, “What does this mean for…?”, “Now what?”.

Be collaborative – actively seek out the opinions, experience and wisdom of others outside of your team. Not only does this help to increase your own relationship equity and hustle power within an organization, but you’ll also be exposed to a much more diverse range of perspectives and information.

Again, if the product solves the customer’s problems and resonates with them, it is more likely to be successful.

On Design Management

5 pillars of an effective design organization

Design can look and work very differently across organizations. Some places have designers spread amongst multi-disciplinary teams, while others operate in more of a ‘bureau’ style, where designers are centralized. Here are some qualities that Ben has found to help in any configuration:

Healthy onboarding – It’s great to set up all new starters for success (designers as well as anyone, really) by helping them to understand your organization’s approach to design and how design ties in with other disciplines. This includes the tools, processes and resources you use, and just generally who’s who in the zoo and how everything is connected. There have been countless occasions when Ben wishes he had experienced that when first joining an organization!

A common multi-disciplinary process and incentives – Here’s a great way to destroy a designer’s soul: have a product manager tell them that they have a month to do research and come up with a winning design, and then a week in, announce that they only have a week to go. Oh, and then tell them that the solution they have come up with won’t work and ask them to produce another solution tomorrow. In all seriousness though, effective design needs a common process and timeline that everyone agrees on and adheres to.

Good separation of discovery and delivery – A lot of organizations diminish the value that design (and designers) can bring by always placing them in a pressure-cooker environment. Good design – just like good products and services – requires time invested in discovery, not just delivery. This means having the ability to do some generative research (finding the unknown unknowns), producing some more diverse ideas, and trying and testing different concepts.

Really good design critique sessions – Design critique is an art and science all on its own, and design can thrive or fail depending on the quality of the conversations had in these sessions. It’s really important that the person asking for feedback is super clear about the type of feedback that they want, and it’s equally as important that everyone else gives the right type of response at the right time.

A robust design system – Whether it’s a simple style guide or a fully-fledged pattern library with a prototyping framework attached, it’s great to have a system that streamlines the work of design. This helps to economize everyone’s time and ensures that they’re not wasting hours trying to fix interface problems that have already been resolved.

This helps to economize everyone’s time and ensures that they’re not wasting hours trying to fix interface problems that have already been resolved.

An ideal design team brings diverse perspectives to the table

Ben’s best experience in a design team was at a small design studio in Surry Hills, Sydney.

Drawing from what he experienced, he believes that an ideal team of designers should have really diverse backgrounds and an array of ‘design diets’ and perspectives that they can bring to any client problem.

It would mean that designers spend a bit of time now and then solving problems that have nothing to do with client work (e.g. volunteering) to enhance their experience and creativity. It would also include having the time and space dedicated to thinking deeply about any given problem… with lots of natural light, great coffee and healthy snacks!

Good design managers set the right targets and the right constraints

Good design management style is all about setting really clear targets, then sheltering the team to give them the mental time and space to do their best work. This, for Ben, involves three things:

The right targets – working with the business to establish the right measures of success (according to both the business and its customers), and the metrics and targets that will indicate progression towards success. It’s helpful to ensure that if designers are held accountable to any targets, then others are held accountable too.

The right constraints – establishing sensible time and scope constraints according to the problem that needs to be solved or the impact that the design should make, and sticking to those constraints for the duration of the project (i.e. not caving in to the product manager when they get anxious about delivery).

The right quality culture – using every design critique session as an opportunity to reinforce the love of design together, and a way to always connect the customers’ needs to the work being done.

For Ben, every feedback session that has followed a ‘What’s the minimum quality of design we can do to fit this development schedule’ approach has gone on to cost the business a lot more. Why? Because of the costs needed to maintain and fix bad solutions that went live to customers.

Lead by presenting your team with a way forward

Ben has learned the hard way (i.e. through mistakes he has made) to always view people’s leadership, growth and management as a system of separate connected entities. For example, he finds the Situation-Behaviour-Impact Framework really helpful in giving and receiving feedback, staff guidance, and issue resolution.

It’s also important to see the person or the team or the meeting as the object of design.

What problem is this particular person (or team) going through? What’s the impact of that problem? What’s the root cause of it? How might he help in that?

Often, the right thing to do is not to solve a problem for someone else, but to equip them with a way forward. This is why Ben enjoys facilitation so much. He is a big fan of the GROW framework: What is the goal? What is the current reality? What are the options (or obstacles)? And what’s the way forward?

Create common ground for designers and non-designers to collaborate

It’s vital that there is some common ground for collaborative activity between the designers and anyone else on the team. Ben tends to break this down into three elements: common space, common language, and common customs.

Common space – this can be physical spaces (like a wall where designers can regularly share sketches and drafts for others to look at), as well as online spaces (such as Slack for shared conversations, or Mural for sharing work and collecting feedback remotely).

Common language – this is such a big one! All too often, there’s friction between different teams because they try to use their own discipline’s lexicon and jargon on everyone else. People don’t want to look dumb, so they play along and don’t ask questions… which makes shared understanding really tricky!

It’s useful to have some common language that unites the voices of the customer (research), design (desirability), business (viability) and technology (feasibility), e.g. common goals and metrics framework, product design principles, and user stories or job stories.

Common customs – ensure that all disciplines are present together at some common time, e.g. in standups, retrospectives, work-in-progress meetings, and planning sessions.

On Business and Design

Design helps organizations to see and respond better

When you think about it, any organization is just trying to make an impact in the world through its products and services, and it needs to connect with people so that they pay for and use what the organization is offering.

It’s like a conversation: organizations need to see and hear effectively, then respond clearly.

With this in mind, Ben thinks that design’s role in business is to help the organization see better.

This means using data visualization and opportunity framing to allow them to improve the way that they look into the future. Making use of visuals and storytelling can also help them to learn about customers in more authentic ways and frame (or reframe) problems in a more beneficial manner.

It also means using the design skillset and toolset to visually bring a business’ vision to life, so that everyone in the organization can, quite literally, be on the same page.

Design’s role is also about helping the business respond better to their audience by making sure that the products and services connect with what matters to customers as best as they can.

To achieve the best outcomes, companies need to combine several things: they should conduct research into customers’ needs and problems; they must create brand personalities, communications and interfaces that make customers win, and they should support design processes for the things that go on around the product/service, such as evaluation, support, and advocacy.

Use design as a competitive advantage

Design becomes a competitive advantage when it comes from the top, rather than being an ‘add-on’ to what’s already in place. If you have a design mindset at the executive level – one that encompasses curiosity, empathy and people-centric problem-solving – then your organization will exceed.

What this looks like (in Ben’s experience) is keeping customer satisfaction at the core of an organization’s strategy. Show him a strategy consisting of a bunch of goals around increasing market share, and he doubts that they’ll be able to ‘move the dial’ very much. But show him a strategy that is genuinely concerned about increasing customer effectiveness, and he will probably buy shares in that organization!

Having customer satisfaction at the heart of operations acts as a forcing function for the whole organization, encouraging them to invest in finding out what actually matters to their customers and what will make them more effective, and therefore more satisfied.

Innovation is about executing ideas

For me, innovation is as much about building the habit of executing ideas as it is about generating innovative ideas in the first place.

In general, designers tend to nurture innovation with healthy doses of empathy and curiosity for people and what matters to them.

Designers are also usually the best at bringing ideas – anyone’s ideas – to life through sketches, prototypes, journey maps and storyboards. But where Ben finds design can really shine (and design strategy comes into play here) is when designers help to create the processes and workshops needed to build that ‘execution machine’. It means that those ideas can get properly tested, proved, and eventually shipped.

On Advice and Mistakes

Ben’s one piece of advice about quality

This advice is probably aimed at more seasoned designers, and it’s this:

Don’t let your quality work be compromised.

Firstly, this is not a call to be arrogant or inflexible while working with others. We’re going to assume that you understand the meaning of ‘quality work’ here.

Ultimately, it means doing the research and doing your homework. It means involving other people’s expertise and feedback. It means iterating and testing, and sweating the details. So, if you’ve done all of the above and created a quality result that will make your customers win, then it’s just not right to let that positive result be dampened by unreasonable production deadlines or inappropriate technical implementations.

What this doesn’t mean is that you can toss your solution to others and absolve yourself of all responsibility.

The implementation of your solution can indeed become your new object of design.

Help the rest of the team to figure it out. But don’t compromise on the quality that will end up in the hands of your customers. You’re better off working elsewhere, where convenience doesn’t trump quality. If it works for Apple, it’ll work for you. The world is groaning under the weight of too much mediocre design as it is.

What does this mean for Ben? He knows that real magic can happen in a room where people get together and visually explore a strategy, a problem space, and come up with solutions face-to-face. In the past, people have asked him to facilitate workshops in which some people are in the room and others are remote. He said no. It’s just not a quality experience, and the result is compromised when we optimize for convenience.

Fast is not best

Fast is best – it’s a phrase that seems to crop up a lot. Ben feels like we’ve all bought into the lie that if we ship the bare minimum faster, then we’ll learn faster, and therefore we’ll improve things faster. This might be reasonable advice for a brand-new fledgling product, but it’s horrible guidance for any product that’s already been established.

Why? Because if speed always beats quality, you’ll see diminishing value from all of that effort over time, creating more and more technical and design debt down the road. Always remember that every shortcut you take now is something that another team has to pay for at a later stage.

This fast is best mantra is made even worse when it involves constantly shipping rapid changes to your customers. It treats your customers like unwitting guinea pigs, disrupting their experience all of the time and hoping that they will politely inform you if and when their experience improves.

Ben’s favorite failure: cardboard chairs

A few years back, Ben got to overhaul a meeting room at Atlassian to create more of a ‘design workshop’ space. He replaced the existing table with several smaller whiteboard tables on casters. That part worked well. But he also replaced the chairs with some stools made out of recycled cardboard.

They looked amazing on the Italian product manufacturer’s website… but once they started to use them, the cardboard buckled and broke. They looked awful, and they were just as awful to sit on!

This taught him not to be lured in by looks alone. Just because something has attractive features (these stools could be combined into larger formations with magnets), it doesn’t mean that they’ll be the right ones for you or your customers!

Ben’s Recommendations

Use design maturity as your success metric

Design maturity in an organization equates to how design is being adopted and the impact it has. Design tends to have to earn its position on the curve, with increasing return and impact. The metrics of success go from being more tactical and short-term, to more strategic and long-term. It could break down like this:

Design Success Metric

Design as a service – Better interface design, visual design, and task flow design. Success looks like: fewer error rates, more efficient task completion, higher customer satisfaction (CSAT) scores.

Design as a facilitator – Better problem definition, better value proposition definition, a greater range of ideas generated, decisions made more efficiently.

Design as a partner – Better translation of business success metrics (e.g. revenue, staff retention, NPS) and product success metrics (e.g. activation, retention, CSAT) into lower-level cascading metrics that each team can actually affect (e.g. getting evaluators to that ‘moment of value’ and conversion to purchase more often). Success looks like: design being an active partner in coming up with better metrics to be tracked by the organization.

Design as a navigator – Better translation of market research and user research insights into risk factors and opportunities for the business to pay attention to.

You’ve already got all of the best tools

As you’ve probably noticed, Ben is a huge fan of visual thinking and visual communication. With that said, he says that our best tools are our brains for thinking, our hearts for empathy and our hands for drawing. Digital tools come and go, but our own brains, hearts and hands will always be our best instruments.

Keep cultivating your critical thinking and analysis skills; you need those more than ever! Continue to ask smart questions. Keep developing your empathy and curiosity for others. And be sure to utilize your drawing skills. Everyone can draw… remember that we were all drawing and mark-making before we could write!

You don’t have to be an artist or a virtuoso, and you certainly don’t need to draw to impress people or get likes on Instagram. You just have to have the guts to draw your ideas in a neat, simple way. You’ll be amazed at the clarity it will bring to your own thinking and communication, as well as your team’s!

Ben’s favorite sources of knowledge and inspiration

Ben firmly believes that all problems have already been solved by nature. He is always turning to natural characteristics and systems for inspiration – anything from permaculture and the branching patterns in leaves to river delta formation, photosynthesis and immunology.

He is constantly referring to the work of people like Charles and Ray Eames, Piet Mondrian, Dieter Rams and Milton Glaser.

Ben is always on the lookout for anyone’s work that helps us to see familiar things in unfamiliar ways, which is why he really digs abstract art. If there’s one book from which he keeps drawing inspiration and affirmation, it’s Orbiting the Giant Hairball by Gordon MacKenzie. Read that, and you’ll understand a lot about Ben!

The 3-bullet recap

Holy cow, Ben, I don’t know how to thank you for this fantastic interview! It’s truly a feast for thought!

Let’s try to end this with our usual 3-bullet recap. I don’t think it will do justice to this talk, but still, here we go!

  1. Create a design strategy that people will actually use, as well as one that will help your customer win more than they are right now.
  2. Reinforce the love of the craft of design any time you get the chance.
  3. Don’t let your quality work be compromised.

Reach out to Ben



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