Joshua Sortino

Joshua Sortino

Design Director at Square

Design Director at Square, advisor, photographer. Previously Pivotus, Teespring and Disqus.

25 action items

Where to start as a new manager

    • Being a manager is a lot of work, and being a good manager is hard work. Be responsible and empathetic and you can become a great manager.

    • Find a good mentor

      How did you learn everything for your job today? Most likely, from others who have done it before. Finding a good mentor is essential.

    • Read

      Always be learning new ways you can approach problems.

    • Mimick or Avoid

      Look to the best managers you had in your career and emulate their best traits and avoid their worst.

    • Be Responsible

      Nobody likes an irresponsible manager. Stay on top of your duties. Take notes. Make lists. Attend meetings. Give a heads up when you’re going to fall short.

    • Keep Alignment

      Make sure everyone on your team is on the same page, and then make sure everyone else in the company is in agreement that the alignment is correct.

    • Shield

      Keep the bad, annoying, or tedious stuff away from your team. Your job is to make their job easy, even if that makes your job harder.

    • Empathize

      Put yourself in your team’s shoes. Try to look at the world through their eyes when making decisions.

    • Resolve Conflict

      When conflict arises, it’s your job to resolve it. Break through barriers or mend bridges together. Always hear both sides before making a decision or calling something out.

Measure the impact of a design system

    • Using the company’s business or financial goals is a very powerful tool for proving the value of a design system. Design systems offer some effective methods to optimize a design and engineering organization.

    • Calculate the amount of time designers spend creating elements from scratch and compare to how much time would be saved with a design system.

      Without a design system, designers must re-create every (or most) elements in their designs. This is time consuming. By showing the amount of time that could be saved with a design system, you are able to prove the value in terms of hours given back to the organization.... See more

    • Similarly, determine how much time engineers spend asking designers for specs and clarification.

      Engineers will often need the exact measurements of elements in a design. When no design system exists, they will need to re-ask these measurements every time. Additionally, other questions may frequently be repeated without a source of truth. Show how many hours would be saved if a design system existed.... See more

    • Track how long it takes to onboard a designer.

      When new designers join, how long does it take for them to understand your design language? Show the value of a design system by explaining how much faster designers could be on boarded.

Transition an individual contributor to a manager

    • Transitioning from an IC to a manager should usually feel like a natural, or at least logical step rather than a forced occurrence.

    • Are you already “managing” or influencing others without the title?

      Some of the strongest IC’s who have developed in-depth knowledge of the company they work at or the practice they work within often become the strongest influencers on others. In these cases, transitioning from IC to manager is very natural because in many ways, they are “managing” already.... See more

    • Is the company or product growing?

      As a product scales so will the team. In this instance, transitioning from IC to manager might be needed to help the company continue to grow.

Decide what roles to hire for

    • Building out a design organization can be thought of as building out a spectrum (or rainbow gradient). Each type of designer, whether visual, UI, UX, or research, brings a unique skill to the table. Each of those skills fill out a different “zone” in your gradient.

    • Make a list of each design practice your team is responsible for, and each practice you’d like your team to be responsible for.

      Understanding what you want your team to be accomplishing is the first step in determining what roles you will need to hire for.

    • Clearly understand the weakest points of your design process.

      Under each design practice falls a set of processes. For instance, UX design requires understanding the problem space, wire framing, and designing.

    • Identify and hire to stengthen your team’s weaknesses.

      Each designer on your team brings skills to the table. By understanding your weakest points of the design process, you will have a better understanding of your team’s weaknesses. Hiring for the areas you are weakest is often a good strategy for building our your team’s spectrum. (I.e. Your team may be strong in UX but weak in research. Hiring a Design Researcher may help your team improve its research capabilities.)... See more

Present work during a design critique

    • Before you prepare, put yourself in your audience's shoes. Who is critiquing the design? Is it product, design, engineering, business, or marketing? If you were in their role, what would you want to see addressed? Preface your presentation with the problem statement and personas effected, then demonstrate how the design solves the problem.

    • If you're presenting to business-minded individuals, present the work through a lens that highlights how the design solves for business needs.

      Show how the design drives value. Talk about the business needs which led to your design solution.

    • If you're presenting to marketers, show how the design impacts sales or increases brand awareness.

      Include ways that your design positively affects the marketing plan of the organization.

    • If you're presenting to product teams, focus on the original specifications for what the feature should be accomplishing.

      If there's a product specifications document, walk through the original feature requirements and show how the design meets those needs.

    • If you're presenting to engineers, hone-in on the complexities and specifics of the design.

      Mention what areas of the design may be difficult to engineer. Walk through the components, how they fit into your design and engineering guides, and any nuances developers should be aware of.

    • If you're presenting to designers, focus on the UX, interactions, and details.

      Designers will be most concerned with the experience of the design. Show how the design solves for the user's needs and does so in an easy, usable manner. Talk about the process of the design and the conclusions you made along the way.

Show the value of design to justify hiring more designers

    • Hiring should be dictated by need, rather than the selfish desires of a manager. If growing the design team truly is best for the company (and not out of selfishness), showing the value of design can help you justify hiring more designers. Every design team should be hosting weekly or monthly critique sessions and "show and tell" events. At these events, tie the design back to impact. Show what problems were identified and demonstrate how design approached those problems. By linking design solutions to success, the value of design is clearly associated with value and arguing for more resources is easier.

    • Understand the real problem a design is solving

      Designing for designers is a common mistake. Make sure your design is actually making an impact.

    • Be confident the design is making an impact

      After you've established the problem, evaluate the design is solving the problem. Use data to back up your original assumptions for the solution.

    • Demo the design in "show and tell" formats, with context and data that prove it made an impact

      Always preface your design with the problem before the design was introduced and how it addressed the problem.

    • Make a case to management for how many problems need to be solved and how few design resources exist.

      Once management sees design is generating value for the company, it becomes easier to present a strong argument for growing a design team.