This is an AMA recap from On Deck Design.

‍David Hoang is a product designer and angel investor whose work focuses on scaling startups ranging from two-sided marketplaces to software development tools. He is currently Head of Product Design at Webflow and Design Partner at On Deck. Previously, he led design at One Medical, Black Pixel, and founded his own product consultancy. His skill set focuses on new product initiatives, recruiting and hiring, generative research, and product development.

‍

Before joining a company, what are some ways to evaluate whether the leadership "gets" design?

This is an interesting question! I guess the question I'd ask myself here is, "Does the company have to get design?" as it's our job to help them understand it.

For me, I try to get a sense of how design plays a role in the company when chatting with them. Is design viewed as a part of production in the product development process or is it part of their strategy in how they run the business?

The question I like to ask is "Why are you hiring for this role now?" to get a sense of why they didn't invest in design before.

There can be many reasons for it and varies across a company. If it's an early stage startup, or a startup that isn't stable yet, maybe they didn't have any funding to hire a designer.

I think it's more about the desire to invest in design vs. them getting it.

A question to ask yourself when joining a company:

Do you want to join a place where design is already mature or want to go to a place where you can establish it?

Do you have any exercises or frameworks for identifying how I should "optimize" my career? I keep hearing that I should have a career north star, but I don't know where to begin.

I like to view careers as odysseys and journeys. That's why I don't believe you necessarily have to have a north star. So much can change in what you want over the course of your career. If I would have mapped out my north star 15 years ago, management would never have been near that at all!

I like to find people I'm inspired by (career crushes) and see what aspects they've achieved inspire me—kind of like a career mood board. Once you have a sense of what that might look like, write down the skills and experiences you need to pursue that.

I can give you a personal example. One of my mentors works in venture capital, and I knew that space was compelling. However, I wasn't ready to quit my job and become an analyst at a VC firm. Instead, I toe dipped in angel investing to see if I'd like the work.

As a Senior IC I have struggled to balance maker time & meeting time. Are meeting interruptions something we just need to adapt to as we take on leadership responsibilities, or are there ways your team has addressed this issue to make time for uninterrupted IC work?

A mentor once told me, "As you progress in your career, it's less about heads down and more heads up."

That said, when you become more influential in your career, everyone is going to want to join your meetings. Naturally, as you get invited to meetings there might be a feeling that you're obligated to go.

Do a calendar audit every month and ask "Do I really need to be at this meeting?" What you'll find is a lot of times there are other people who can go to the meeting.

I do think as you get into senior leadership it'll be meetings all day :-)

How can I make sure that design is treated like a partner and not just an "internal agency"? I work closely with the product and marketing teams, but feel like I am reactive to their needs instead of being able to drive big things forward.

If you wait to be asked to do the work, you'll be treated as an internal agency.

Ways you can take a proactive approach is bringing bets you think the company should make and bring some evidence (customer feedback or data) on how you think the bet will move the needle at the company.

What makes design unique vs. other departments?

What makes us design unique is that a lot of our work is lateral - we have reach across the company.

We can come to leadership and say, "This is the problem I see the company trying to solve across all departments. Here's how we connect it together."

Can you talk through the responsibility difference between PM and Design? In my previous job, I lead both research and design so I am involved very early, in some cases even before PMs. In my current company, the PM feels they should be doing the discovery work. Any thoughts on how to approach this situation?

Great question! This may be a hot take and very much my own opinion, but I don't think there is a big difference between being a Product Manager and Designer.

The partnership in discovery should be together. Great product discovery work results in not being sure if the PM or the Designer led it.

One of my favorite books on this topic is Continuous Discovery Habits by Teresa Torres, the GOAT of Product Discovery.

I think at times, we have to be aggressive about inviting ourselves to things, coming in and saying, "I need to be involved in this."

The best PM/Design partnerships are the ones where you can play to each other's strengths and complement each other. Each pair is going to look a lot different depending on the team or company.

Do you have any tips or techniques for helping colleagues embrace more of a product thinking mentality?

I think the one thing that comes to mind for me is sharing with colleagues how product thinking can result in the longevity of what we build and invest in.

For example, when discussing features product and design are planning to build, taking a long lens on if this can be solved more systemically vs. shipping a bunch of features that end up being fragmented experiences or accruing even more tech debt.

How can I provide career growth opportunities for my team outside of job title progressions? Facing budget or headcount constraints and have limited flexibility when it comes to recognizing people through role upgrades.

Understandably so, we often associate career progression with promotions. However, promotion isn't the only way to grow. In fact, promotions should happen because you're continuously growing. I like to ask, what can we do to get people prepared for the next level or their next thing?

I once told my managers in the past that it was important for me to understand how executive teams work. She made an effort to bring me into exec meetings when relevant, and at times presenting. She didn't promote me to a VP willy nilly, instead gave me relevant experiences so when I'm ready I have experience already.

Would love to hear your advice on sourcing and recruiting new design hires, and understand your interview process. Portfolio review, specific questions, team chemistry?

Definitely check out our Recruiting & Hiring sessions from ODD's management track!

The TLDR is:

• Create a rubric on what you're evaluating for using Job Descriptions and attributes of what makes a good designer (make sure this is clear!)
• Build interview questions to get signal on that. For example, if you want to understand a manager's ability to resolve conflicts, ask a situational question like "Tell me about a time there as a conflict between one of your direct reports and a cross functional partner. How did you evaluate the problem based on hear-say from two people? What was the outcome?"

Any advice you would give to expand one's network remotely beside ODD?

It's important to understand the goals of why you want to expand your network and optimize for that. Are you looking for new career opportunities in the future, trying to mentor, etc.?

I keep a list of 10 people I'd like to connect with and see if there is anyone I know who can connect me with that person.

Cold emails can be scary and intimidating for some and that's where getting someone to help make an intro can expand your network.

Do you think there's a risk of designers being commoditized? It seems like tech is moving in this direction, Canva, Squarespace, Webflow and maybe even DALL-E will eventually be able to design things. Would love to hear your thoughts on the future of our discipline. thanks.

You might get a bit of a biased answer here as someone who works at Webflow :-)

I see these tools as more of an outcome provided through design. One of the questions I get a lot is how I view developers since Webflow is no-code. Are developers going away? Absolutely not. There will always be new challenges such as AI and other complex challenges engineering will need to solve, and this is the same with design. I'm not concerned about design ever being commoditized as there will be new technology and paradigms that will need design—what we work on might change.

As the company grows, how do you get colleagues to embrace design culture/principles and have them screen for it in further hiring/growth that you may not be part of?

This has to come from the top in the leader setting the culture and also has to align with everyone on the team. This is why I think continually having your principles and core values memorable and repeatable is so important in order for it to scale in the areas of the org you don't see.

Remote work can be very screen time intensive, and I am observing how it is causing fatigue for a lot of designers. How has this been discussed or addressed on your team?

One thing I've tried is making some meetings optional for video or audio only. For example, some 1:1s can be audio so you can go on a walk or look away at the screen while continuing to be fully engaged.

Another thing I've been doing is trying to do as much work as possible on pen and paper.

Instead of having to look at Figma all day I can upload thoughts there later. Even shaving off that time to not be in front of a screen has been a godsend for my eyes!

How do you balance design intuition and relying on feedback or data? Our leadership team is composed of people with engineering background, and while we don't have the "50 shades of blue" mentality like Google, sometimes it can get exhausting trying to rationalize design decisions.

I think data and insights should be built on the foundation of core intuition. It's a slippery slope if you optimize for one over the other and it should be a balance.

Start with what the hypothesis or bet is, and from there, look at data that informs that.

On the flip side, don't use data as a way to validate your bias. We have an Insights team at Webflow which I like to think of as the neutral arbiter of research and data so we don't get biased by our own personal motivations.

The layers of data that's important for an org is:

• Business Intelligence
• Insights
• Embedded research

What is your strategy for building cross-functional relationships? Particularly with a cross-functional leadership team. Any tactical guidance or approach?

I think cross-functional partners appreciate it when design feels invested in their problem or their lens. For me, when I meet new partners I like to ask them, "What are the challenges your org is facing?" to understand what their goals are. From there I carve out time for design to invest in helping out. This shows design is invested in the company's problems.

Could you tell us some examples, whether from your own personal experience or from what you've seen, where a design lead successfully advocated for more resources? How did they do it?

I find those who successfully do it frame the opportunity proactively vs. reactively. For example, if your case is "we're under-resourced" it's very reactive and there are multiple ways to solve it. Is it under-resourced or is your team not effective enough?

Consider framing it like, "If we could add another designer for X, the impact on our team can be Y."

This is how I was able to get a much larger headcount on User Research.

I pitched it, "Product Designers can do user research. However, it results in a lot of administrative work to schedule the interviews, synthesize the findings, and as a result there is less time to do design work. If we bring on a User Research Coordinator and four researchers, they can amplify the quality of research without taking time away from the product designers."

Contrary to popular belief, the execs don't want to solve all the problems or have time! So when you bring a problem, also bring a recommendation on how you can solve it.

If you can get to the point where an exec only needs to approve or disapprove, that's a great place to be in!

How do you keep up with design trends, and how do you stay inspired or find inspiration?

This is very hard in a leadership position but important. I think leaders need to be relevant in where trends are happening.

I block out 30m a week for reading time on this and think it's an important practice, otherwise you'll drown in all the work that needs to get done.

I think many may be familiar with Bill Gates' "Think Week" and it's important to block that time.

One of my favorite newsletters is The Profile by Polina Marinova: https://theprofile.substack.com

It has nothing to do with design but I find it refreshing to read about profiles of people across all industries and sectors.

What would be your advice for someone who does not know what to do next in their career? What can you do to figure it out?

The question I'd ask is, "How important is it to figure it out right now?" 

There is a lot of pressure to continue growing in your career or having it figured out, and it's okay to be like "I have no effing clue what I want to do!"

If you're enjoying what you're doing now, time might uncover what you want to do next.

If it's something you want to figure out, I would look for a career coach and sign up for some sessions with them. It can help you uncover some nuggets of where to go next.

What are the most gratifying things you have experienced so far in ODD?

When I go to the #-04-small-wins-big-wins channel I get the most gratification from that. ODDs value is truly because of the fellows and I am so happy to see how you all show up helping each other out. Reading all the wins you all are making makes me so happy.

* * *

Learn more about On Deck Design here.