A stab at building a better design leadership org

This article started as an answer to a task I did during my interview process for a company a while ago. While I can share the task I’ve adjusted the article to perform as a stand alone. Since then I’ve developed my ideas further and I’d love to hear your opinions.

I’d like to confront the challenge of scaling a design and product team in a startup. It’s a great challenge to have. Here are a bunch of things that can happen when you scale rapidly.

One of the things that makes startup products so amazing is that they start as extremely manual pieces of software. Doing stuff manually helps everyone in the startup to know all the funnels and cover them well enough MVP to make it work and profitable. But the past is not scalable and when you do hit a certain scale you run out of time to do stuff in the way you did it before. In the tech world it comes in the form of automation but in the product and design world, it comes through processes and more people. But both processes and new people create tension in the old system. Suddenly people who did many things find that other people are starting to do some of their jobs, the processes slow things down and there’s a lack of communication.

Once you start inserting seniors and experts into your team they will aspire to leave their mark and to raise the profile of their teams. In the aspect of design and product teams, you could end up with some of these more specific problems:

Comedy People GIF
  • Levels – The need to move from a flat hierarchy to levels, which in bigger organizations is supported by progression ladders. The tension between seniority and work experience is natural. In a flat hierarchy, everyone’s equal even if some do more or are better.
  • Employee growth – The introduction of new people and the fact that the company as a whole grows fuel self-confidence. But if rapid scaling makes everyone super busy, then assessment, nurturing, and growth opportunities could become an afterthought as managers are slammed with things to do.
  • Critique – Design critique is an integral part of the life of a designer, it is how we improve and do better. When the team grows a lot sometimes there’s not enough attention per project and designer.
  • Painful retrospectives – Let’s face it, retrospectives are usually painful, but when a team is growing and you have more ambitious people joining it they want to grow the power “of design”, for example, and to do that there have to be big changes.

Easing through processes and structure

A designer is not necessarily a generalist. We need to embrace these differences and use them to drive the team as a whole to succeed. In the design below you can see how a designer has extra training and a variety of improvement opportunities throughout a year.

Designer galaxy - Avi Ashkenazi
Designer galaxy

Company growth and output control

Switch and per – Moving designers around will create growth and levels for designers naturally. As a manager, you’ll be able to hear different people’s opinions on your designers and at the same time, you’ll create friendships. It is ideal for a designer to have the opportunity to switch teams every year. Switching meaning that the organization will work more closely together, more people will know each other and that the people who stay will have a lot of knowledge. This is also important when they onboard new-comers. If there is more than one designer per team it’ll allow the flexibility to make specific designers senior and allow them to lead the project rather than simply participate in it.

There is a natural tradeoff between being everywhere at the same time and doing a few things extremely well. As budget increases, design management can create better, more supportive design structures similar to Spotify and Google. In such big companies, there is usually more than one designer per team and there are function leads and product leads.

Design agile process - Avi Ashkenazi
Design agile process

Collaboration – In a fast-growing, well-funded startup there are new ideas springing up every second which will tempt design directors to put a designer in each project. Adopting a design-led approach everywhere will help promote positive growth with less waste of tech resources and it’ll keep the design team involved. But to be able to make the most of being design led it is ideal to have multiple designers working together on a product. Having just one designer per team creates a risk of inconsistency and mediocre results due to silos and lack of brain spurring.


Design org chart - Avi Ashkenazi
Design org chart

Design leadership should form a small yet powerful creative direction team which will include:

A system designer – to create reusable components and make them bulletproof so they don’t need to be broken by other designers (if it doesn’t fit their goal).

Guideline guardian – who will create guidelines and adapt them based on communication with the team (similar to the Material design team at Google).

DesignOps – a design producer who will make sure that everything is accessible, organized correctly and that will help to break barriers for designers.

Research coordinator – controls qual and quant researchers’ time and helps distribute them between different teams depending on the needs of the organization.

This can grow into even more specialized teams for illustrations, icons, typography, modules, grid etc. based on the organization’s needs.

Champion design – Designers should be encouraged to present their work within the company and promote the design team at any given opportunity. They should also be measured on these presentations, as Design is not just the act of designing but also the act of communicating it and advocating it.

These are all great opportunities to measure the designers and it’s also a positive way to push them to be better at all levels. Across these activities, it will be easy to grade designers and measure them against the progression ladders.


Incentives and extracurricular activities – To promote design within the organization and have projects and products be design-led, the designers must do more than just their day job. There need to be: design hackathons, writing, demos, research, and presentations. Many of these can find their way to Dribble, Behance and the company’s blog. Working and hitting social promotion goals and attracting other exciting designers to your company should be rewarded. It is quite common practice to offer financial incentives for recruitment but less so promotion and speaking at events. Raising your designers’ profiles will also raise the company’s profile and is fully supported in companies such as Google and Revolut.

Product goals should also be incentivized. For example, at iwoca, we have the rocket reward, which is money to buy cool things for the office and is based on our quarterly success in hitting the goals.

Personal growth

In most big companies there are progression ladders. These progression ladders usually have two routes. Management and Individual contributor. By introducing a ladder, designers can measure themselves and see what they need to improve to grow and hit the next level. Such a structure encourages growth via skill development and initiative rather than just rewarding the amount of time someone spends in a company.

Progression Ladders Design - Avi Ashkenazi
Progression Ladders Design

In the progression ladder, there is a combination of soft and hard skills and the design management should have a course or a method to improve each of these skills. For example, for developing a designer’s skill to give constructive feedback you could build a curriculum that breaks down the psychological and technical aspects of feedback such as patience, active listening and constructing arguments. Whereas if a designer would like to improve in prototyping he can go to Kick festival in Belgrad and be in a few workshops there.

Skillset map - Avi Ashkenazi
Skillset map

This diagram represents an initial breakdown of skills that designers should be skilled at. It is divided into Soft skills, Leadership skills, and Contextual skills. If I had included all the technical skills here as well it would be a lot larger, as these can start at Telling a story and end in Pixel perfection or High fidelity prototyping.

Ranks on the ladder don’t have to be reflected in titles. Facebook has an interesting take on how to do that whilst keeping a flatter structure. In the end, it’s about the designer’s career progression and self-fulfillment. If the designer has enough responsibilities and they gain knowledge and feel that they are valued and nurtured they will be happy and grow. Landing new people from the outside can be a challenge sometimes but as long as they are thoughtful and they support this attitude the results can be amazing. In the end, designers are always happy when they have another person on their side especially if it helps them learn and do their job better.

Critique

A designer’s job is always criticized by everyone. Design is a social role and because it’s very visual it makes people who are not designers think that it’s easier than it is. In reality, it’s way easier to react to a piece of design compared to a class of code. We all have eyes and we all use the product.

Because designers get critique so often they should be better at communicating their design and also at defending it. Designers have a bullshit detector for comments like “make the logo bigger” or “my wife doesn’t like this color”.

What designers don’t have is a valuable, data-driven, researched constructive critique. By valuable I mean it’s actually helping them learn something new or look at their design in a different way. Data-driven and research are about the justifications for the critique. And constructive is about being able to make it actionable quickly without demoralizing them.

Fellow designers and design management are the best sources for such feedback. But such feedback takes time because you need to research it and you also need time to communicate it.

Design critiques are powerful rituals and for them to maintain their culty status they should be held at the same time for everyone. Even if it means splitting the team into groups so that it’ll be more efficient. In the design, leadership should shift between teams, to allow them to get to know everyone and for everyone to have a good scope of the projects and learn. This shuffling should not be random, it needs to be based on the stages and progress of the projects and the skills of the designers. Like every meeting, they should be prepared for it. If the designers are preparing their presentations and demos then management should prepare the shuffle and look at things in advance.

Good meetings are ones when you spend more time preparing than the actual meeting. Meetings should not be top-down (management giving information) or bottom-up (designers showing stuff to management). Meetings should be about discussions, critique, and learning for everyone. If the meeting has an agenda and an order of showing the demos there will be much less time wasted and far more valuable learnings. Everyone will feel more valued and everyone will know more about the products that are in the making. Looking at things in advance will also help the designers feel that management is less detached from them and that they care.

In every meeting, there should be a scribe (the Google way of saying note taker). People think differently and sending a summary of the meeting is a great opportunity to spark discussions again and flag up misunderstandings. There have been many times when I thought I understood one thing in a meeting, only to later realize I actually missed a very important point. Meeting summaries help everyone to be on the same page and give transparency.

Management distance

When an organization grows the employees will start feeling a detachment from management. Design management can be very demanding and very high-level focused while trusting the designers with the details. Good communication and a clear interface with the designers are all that is needed to bridge that gap.

In the communication between the two, there should be a mix of official and unofficial communications. It’s about being curious about your people, learning from the colleagues around them and really dedicating time to their needs. If you see a piece of inspiration that is linked to a specific designer then send them a link. It’s about helping them manage their time (one of the hardest things to do by oneself), and genuinely caring about their well being and their aspirations.

These are the things that set great leadership apart If you are passionate and are contagious in your positivity and growth mindset. If you are honest and communicative and don’t make things too political. And if you set an example and show that you care, personally and professionally.

Retrospectives

Retrospective comes from SCRUM, which is sometimes referred to as “the art of the possible”. It is very important to focus on things that can be improved rather than just a critique, especially in a team forum. When the latter happens, to me this signals that there is a communication problem and management should be proactive about it rather than reactive. In addition, it might mean that there is a facilitation problem in the session. In retrospectives, it is really important to let everyone speak. The facilitator should know in advance what some people want to say and that will allow them to divert towards other subjects and get different opinions. It’s also useful to timebox discussions on specific topics. Overall retrospectives are not the place for rants or rebellions, they are a forum for incremental improvement; if the story is too big, let’s break it down into something achievable within a sprint.
In addition, when there is shared accountability between designers, managers, and directors there is more mutual understanding and the chances of very negative retrospectives decrease as the team hopefully is continuously working to solve their problems.