You’re reading an excerpt of Land Your Dream Design Job, a book by Dan Shilov. Filled with hard-won, personal insights, it is a comprehensive guide to landing a product design role in a startup, agency, or tech company, and covers the entire design interview process from beginning to end, for experienced and aspriring designers. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, commentary and future updates, and a high-quality PDF download.

During this phase, you’ll be in full-on learning mode. It might be tempting to start fixing things right away, but knowing the context, the system, and its people will help you push for change effectively later.

Key objectives for this phase include:

  1. Gather context.

  2. Set expectations with your design manager.

  3. Get to know your squad (product, engineering, data science, research, and so on).

  4. Meet the design team.

  5. Learn the product and design rituals.

  6. Learn your part of the system.

  7. Start designing.

Use Your Newcomer Advantage

Newcomers are usually given a lot of leeway. Don’t miss out on this opportunity to ask “stupid” questions. Your co-workers will feel valued sharing their knowledge, and you’ll gain their respect along the way. It’s too early to tell if things look good or bad. Outright criticism might even make you look foolish since you don’t yet know the full context of decision-making. But don’t lose your beginner’s mind. Ask questions to get to the root cause—how did we get here? As you collect info from various sources, start building your own model of the situation at hand.

Get to Know Your Manager

The first thing you want to do with your manager is agree on role expectations. You’ll need to drive this conversation with your manager to learn about their standards: what counts as underperforming, meeting the bar, and going above and beyond? Depending on your level, the standards will be different. This will be one of your crucial conversations this phase. It’s also good to cover these topics:

  • Advice on how to succeed in the role.

  • Organizational challenges to be aware of.

  • Tracking and documenting work performance.

  • Opportunities for support and training.

Beyond setting up regular one-on-ones with your manager (usually on a weekly basis), find out about their working style. What forms of communication do they prefer? When should they be called in for help? Understanding your manager’s style will help you broach serious topics and avoid missteps during difficult conversations later.

Bonus: If you’re up for it, share the 90-day plan (or a version of it that you’re comfortable with) with your manager to let them critique and identify gaps you might have missed.

Make the Most of One-on-Ones

One of the best ways to start building relationships with your co-workers is to schedule informal one-on-ones on their calendars. Use this as an opportunity to leave the building and get some fresh air while getting to know them. What makes them tick? Why are they excited about their role?

  • Learn what your team expects from you. Different engineers will have different expectations. Learn how your product manager’s experience has been shaped by other designers (not just at this company). How was research engaged? Understanding and setting realistic expectations with your team will help you commit to reasonable goals while giving you an opportunity to also go above and beyond.

  • How can design help? Not everyone understands design. Informing your team of your expertise will help them reach out to you in times of need. This isn’t just a one-time conversation. You’ll need to remind people about your skills, but the best reminder isn’t verbal—it’s doing the work itself.

  • Trust is built over time. There’s no easy way to take a relationship from 0 to 100, but you can start by understanding what’s personally important to a team member. What do they hope to achieve? Asking something as innocuous as “How can I help?” can also uncover deeper issues at hand.

Learn the Product and Design Rituals

As a designer, you’ll want to get up to speed on the process of doing the work. Here are some starter questions to bring up with the design team:

  • Where is the source of truth for design?

  • How is a project kicked off and by whom?

  • How are bugs or issues filed?

  • Is there a formal design review process?

  • How often do design critiques happen?

  • How is the design system used?

Don’t worry if you don’t have it all covered before you begin your first project. Doing the work will help you resolve many of these questions and potentially raise better-informed questions along the way.

Learn Your Part of the System

In addition to connecting with your team, you’ll want to learn about your part of the system. For example, if you’re joining an e-commerce company to do work on checkout, learn everything about that experience. Dig up the design and the documentation, and start formulating your own opinions and questions. What makes sense? What seems puzzling? Don’t rely solely on internal knowledge; be sure to also look at industry trends, patterns, and techniques that exist outside of your organization.

important To make sure you truly understand, I recommend creating a system flow or a concept diagram to capture the bigger picture as well as the details.

Reflect on Your Experience

You will now have a better sense of the company’s culture during this period by observing how people act. As you’re wrapping up your first phase, step back to reflect on your experience:

  • Beyond the work itself, how does it feel to be here?

  • What did you learn during this time?

  • What new info do you need to be learning?

  • Who are your go-to resources for help?

  • What support exists to help you get up to speed quickly?

As you’re reflecting on your experience, you might also want to update your plan to reflect your newfound information.

Phase 2: From Learning to Execution

This phase, you’ll start to shift toward execution.

Key objectives for this phase:

  • Learn about adjacent teams.

  • You’re reading a preview of an online book. Buy it now for lifetime access to expert knowledge, including future updates.
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