I was recently interviewed for Tom Scott's Verified newsletter which "covers the business of design through interviews and insights".

Hey Andy, what’s been your journey to design leadership?

I’m currently VP Design at Cleo, a chat-first AI financial advisor, building a world where money is no longer the number one cause of stress. Fintech but make it funny. I ended up ‘choosing’ design because it allowed me to cross two things that really excited me: my interest in graphics from growing up a huge music nerd, and being able to make things, both in print and on the early web. I’ve done most kinds of graphic and digital design over the years, worked in house, freelance, and in agency. In 2017 I got into design leadership at FanDuel, and the next 5 years there were a wild ride of hypergrowth and mergers leading to me eventually becoming VP UX & Design for FanDuel Group across our different brands. I joined Trustpilot as their first VP Design, as well as eventually becoming VP Product on the consumer side and co-leading one of our strategic company pillars. I’m currently half way through an interim role at Cleo, ending in early 2024. I also mentor design leaders and folks on the path to leadership in my spare time through ADPList as well as advising early stage startups.

In your view, what is the state of design leadership in 2023? 

I think the state leadership changes with industry maturity and even sub-industry maturity. In tech, engineering has been maturing for a few decades now, so the leadership practices and structures feel more robust and less challenged. Product design has only really been maturing for 10-15 years so it’s taken till the last ~5 years to really be a problem that a lot of organisations need to solve. We’re getting there within the design community, but there’s still a huge gap when it comes to non-designers in an organisation knowing what a good design leader looks like and what value they can bring. When it comes to brand and marketing design, it seems that leadership of the modern kind is a little further behind that.

What is your philosophy on hiring design teams? 

I have a few principles:

  • Hire as much for the 50% of the job that’s collaboration, as for the other half that’s execution

No one wants to work with a designer who doesn’t want to come to meetings and doesn’t want to be critiqued.

  • Get your team to a point where you can mostly hire junior people

Aim to develop the team over time so that everyone is growing, managers know what the aspirations of their reports are, and people are prepped and ready ahead of time to take on a bigger role when one becomes available. That way, most of the time you only have hire at the junior end of the levels which is: cheaper, faster, more diverse, less risky. You can develop a reputation in the community for being a team where smart people can grow their career. If you can get to that ideal world scenario, hiring takes care of itself.

  • Make your team visible

It’s not enough to work on an interesting product, or for a ‘cool’ company. Potential candidates have many different drivers for choosing a new role. Most of all, candidates are looking to work with good people. Getting your team out there, at events, on socials, on a blog will help to humanise what you do. It will let people see that you’re not the impossibly perfect AI hive mind that hides behind those cool graphics. You’re (hopefully) a diverse, fun, inclusive bunch of people who are always learning and often failing. That’s powerful. 

How have you found the best way to set out a hiring process?

The most effective way I’ve found to hire in general is a 4 step process: 

  1. Application review panel: get together a panel of 3-4 of your best designers, and have them independently review the application, from CV/resume to portfolio and/or case studies. This will allow for some diversity of thought and is especially helpful when a candidate doesn’t have a ‘straight forward’ career so far
  2. Phone screen with recruiter: short call to make sure the candidate’s time and the org’s time are not being wasted with mismatched expectations. Salary, working patterns, the specific role, and more. 
  3. Case study review: review a real world case study that shows the kind of work you expect in the role you’re hiring. That could be anything from assisting in a project as a graduate, to leading teams through hard problems as a Manager or above. There’s a long debate about having candidates complete a task for this and my belief is it depends. Ideally, and increasingly so, candidates will have one or two projects they can create a thorough case study from. If so, don’t ask them to do free work too. However, the Silicon Valley/London/New York view that everyone has a case study and therefore tasks are evil are missing the point a little. There are plenty of cases where I’ve hired great people who are transitioning in their career. They’ve only ever done heavily NDA’s work, or they’re coming from more of a brand design background, or they’re returning to work after caring responsibilities or a career break. If they show promise, offering them that change is not evil. It’s common sense. 
  4. Meet your peers outside design: I see a lot of designers being hired by the design team alone. That can be risky for two reasons: the candidate’s peers don’t feel as invested in their success, and you don’t get a cross functional view of the candidate. Having the candidate meet with two of their future peers will help to get a wider view of their collaboration approach, the experience they have working with similar peers, and more. In a common cross functional squad setup that might be the product manager and tech lead/engineering manager. At a leadership level it might be the same disciplines but at peer level for that role. In some organisations it will make more sense to meet a data scientist and a subject matter expert. 

How do you plan WHEN to hire and WHO to hire? 

When to actually post job ads will depend on the organisation and budget. When to plan hiring is start yesterday. Look at the organisation goals. Look at the possible expansion of certain areas of the business. Scenario planning is never wasted effort. There’s a lot of value in being able to pull a plan out of your back pocket when decisions are made to expand/pivot/refocus. It allows you to be less reactive when you risk making hasty decisions or being left with only bad options. Also make sure your relationships with your peers and stakeholders are as strong and trusting as possible. Put time into them. You’re more likely to involved in those expansion/pivot/refocus discussions, and if you’re not then you’re more likely to be aware of what’s going on. Also think about always being passively open to hiring. Building connections with individuals and the community will allow you to hire more quickly and effectively when the time comes. 

Who to hire will depend on your organisation’s goals and scale. In a very early stage startup, someone with existing domain knowledge and startup experience may create the shorthand you need to go from 0-1 quickly. In a smallish to mid size team, it’s likely that all rounder product designers are effective hires because they can turn their hand to different projects and ask the right questions to get up to speed. It gives you options if priorities often change, if the org is expanding, or if you want to move people around teams for experience and growth. That being said, even non-specialist designers have situations that give them energy and those that don’t. It’s important to not treat designers as lines on a spreadsheet, interchangeable at all times. Make sure you have your most creative people who are comfortable with ambiguity and rough work out on your big hard problems and new bets. Make sure you have the folks who get energy from carving out small percentage point improvements through iteration and experimentation on those types of projects. 

Specialists can be extremely valuable at scale, or in situations where the organisation goals are very clear and specific. Some examples of the former as design systems designers, illustrators, research ops folks, content designers familiar with very specific regulations or similar. Examples of the latter are hiring growth designers when your org’s North Star is acquisition, futurist designers for rapidly researching, prototyping and testing brand new propositions.

Are you thinking about succession planning?

Tom: I’ve found designers rarely stay post 3 years.

Always. Average tenure in design is fairly short, but also things change as I talked about above. Even if you don’t have high attrition, if your organisation is changing rapidly through growth or changing market conditions, you don’t always know when you’ll need a new manager or lead or certain type of designer for a new team. The main thing is to make sure that the high performers you identify as capable of taking the next step have the support and training and opportunities for experience that will set them up for success when the time comes for them to step up. If you don’t have those people in your team and you have some time, you should be thinking about your next hires being people with the potential to take that step up in the future. Also scenario planning for succession planning. If this person was to leave, this would be the plan. If this other person leaves, this would the different plan. If someone leaves and there’s no natural successor, what’s the plan to find the right hire and the work with the people who may have felt that they were ready to be promoted. Al have you set clear expectations with them about where they really are and what they’ll need to do to progress into that role in the future. 

How do you educate stakeholders on budgets?

Tom: For example to build a top-tier team, you need to pay top salaries. 

There’s a lot been said of late about designers understanding the business/organisation better. Design leaders absolutely have to understand the business, it’s goals, and what it cares about as a whole. Educating stakeholders on budgets is about understanding what matters to those stakeholders and framing the ROI of more budget in those terms. It’s also normally about proving that out in small ways at first.. If the organisation cares about growth, having a product designer and/or content designer work on journey mapping and from that creating MVTs that show improvements in the journey, you can showcase that one person for X days created Y% increase in growth. You can extrapolate that to show what an extra designer could do for that growth. You could link that growth to revenue and present that a designer earning 50k or 100k could likely bring in Z% more revenue. If your organisation has built a lot of things that haven’t had the desired impact, putting together a proposal for hiring (more) user researchers can show that foundational research can make sure you’re building the right thing, before you build the thing right. If you have cross functional squads with shared OKRs, you can start to point to where the designer in each team contributed to those OKRs and therefore to company success.

Retention is just as important as net-new hires. How do you focus on retaining designers?

First, it’s really important to understand what motivates the people in your team. People are at different stages in their careers but also in their lives. There are some excellent designers out there who have things going on in their lives right now that mean they can turn up and do an excellent job but not have time or mental bandwidth for anything else right now. Do not try to push those folks to upskill unless it’s important for their role. For the folks who want to upskill there are a few tactics I use. First is to call out the achievements when someone has taken on work that they haven’t done before, or have levelled up on. Humans aren’t great at naturally recognising their own achievements all the time and often I find people who have grown a lot but feel they haven’t. Second is to make sure everyone has clear goals set for themselves. Ideally a mix of project related and professional development. It gives people the clarity on their project goals so they don’t spend time worrying or confused about that, and then gives them clarity on what to aim for in terms of growth, and how to get there. I’m always surprised how many people have never really set effective goals before, so guiding them through that process and helping them break down an objective into measurable results, and then actions to achieve those results is so important for many. It also sets clear expectations between you and your report, which is often lacking.