Starting Your Job Strong

15 minutes, 2 links


Updated October 11, 2023
Land Your Dream Design Job

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.

In tech jobs, two-year stints are becoming the norm. If you started working at 21 and retired at 65, that’s potentially 22 jobs and 22 different onboardings. This number may be higher if you’ve worked for startups, since some companies don’t even make it past the first year. Regardless of the company, ramping up to a new role poses unique challenges. Although companies usually have an onboarding process in place, many of them are short and aren’t role-specific. Don’t leave this crucial part of the process to chance. By structuring your own onboarding, you’ll be able to build strong relationships, avoid pitfalls, and create momentum toward great work and your next promotion.

important Every onboarding will be different. Depending on the size of the company some phases may take about a month each. Some phases may be a quick affair while others may drag a little as you get into the details. In a small startup your onboarding may be compressed to a week or even a few hours. So take these as a starting point and be sure to adjust them to your context.

Before You Start

It may come as a surprise, but your onboarding starts with your first interview. Treat it as an opportunity to ask questions as if it’s your first day working at the company. Of course, you won’t learn everything here, so be sure to follow up with interviews of your own after you get the offer. When you accept the role, ask your manager if there’s anything you should study ahead of time. Even if there isn’t, this shows initiative on your part to get going fast. You want to be sure to do two things before you dive in:

  • Close the previous chapter. When you’re transitioning to a new role, take the time to rest and reflect. Even a small break will give you enough distance to close out the previous work chapter and savor the future possibilities of your new role. Don’t make the mistake of jumping right in without proper recovery—you won’t be able to start off as strong, and you may even burn out in the long run.

  • Create your learning plan. After a period of rest, plan what you need to learn and accomplish by the end of day one, week one, month one and so on. Adjust your plan as you gain new knowledge, of course, but planning now will help you keep your career priorities in mind, especially when you hit the inevitable snags. Even if there are none, this shows initiative on your part to hit the ground running.

Phase 1: Be a Sponge

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.

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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.

  • Continue building relationships with your immediate team.

  • Learn how your part of the system interacts with the larger whole.

  • Wrap up and retro your first project.

Learn Adjacent Parts of the System and Their People

As a product designer, your top priority is to create a seamless experience for the customer, not ship the org chart. This means you’ll have to signal to other teams where their work breaks in your part of the flow or where you see potential collisions occurring.

  • Full customer journey. In the first phase, you got to know your part of the system. Now it’s time to dive into the customer journey from beginning to end. Consider mapping out this experience by looking at the system from different perspectives: How does the experience look for new users? What about for intermediates or power users? If your product is on multiple platforms, consider capturing those as well.

  • Collision resolution. As you learn the system, you’ll encounter various problems and collisions in the experience itself. What process is in place today to get them resolved? Does the current organizational structure hinder or support cross-functional work? How can this be improved?

Develop Your Existing Relationships and Handle Conflict

In phase one, you kicked off relationships using the one-on-one format. Now’s the time to continue building relationships as you do the work.

  • Design partnership. As you dive into doing the work, you’ll play different roles, from leading and facilitation to coaching and support. Be on the lookout for how you can help support partners in research, data science, and engineering. Getting into the details of the work will help you pave the way for smoother projects and make everyone feel like they’re treated fairly.

  • Handling conflict well. It’s natural to encounter signs of conflict at some point, such as a teammate who disagrees with you and fights for their opinion or a PM who’s unwilling to let go of their pet idea. These are all par for the course. The earlier you get to your first conflict, the faster you’ll advance the relationship.

By focusing on first principles and understanding the problem, you can help drive productive discussions and turn conflict into a positive force. This way, you’ll consider different perspectives and make a well-informed decision.

Ship Your First Win and Do a Retro

When you wrap up your first feature, do a mini retro. What problems did you encounter? What did you wish you’d known when you started? By this point, you may be already working on another project. Apply the lessons learned from your first project here.

Phase 3: Accelerate Impact

By the end of this phase, you’ll be a trustworthy, well-versed insider who’s up to speed on process, team, and the inner workings of the organization. Your challenge will be to keep this momentum going.

Key objectives for this phase:

  • Become efficient.

  • Amplify impact.

  • Reflect on your onboarding.

Become Efficient and Amplify Impact

As you’re working on projects and collaborating with your team and other teams, you’ll start to understand the best way to communicate (maybe it’s Slack or informal desk chats) and when to share the work. Continue finding, noting, and removing barriers that slow you (and the team) down.

  • Beyond efficiency, look to be effective. To make an impact, you’ll need to uncover the spirit of the intent (the true business need and the customer value), consistently deliver on the work, and amplify impact across the entire organization. Proper problem framing and understanding the full context of the situation will be key.

  • Learn company priorities. How far does the company plan? How does the organization react to bugs? By documenting and bringing up issues, you can get a better sense of how the company makes decisions, which in turn will help you properly frame your ideas.

  • Build allies. Lastly, don’t forget to continue building your relationships. Whether it’s informal coffee chats with your peers or skip-level meetings with your manager’s manager, understanding the struggles they’re facing and helping them will make you more successful.

Reflecting on Your Onboarding

As your third phase nears the end, do a final reflection:

  • How do you feel?

  • What went well?

  • What didn’t work as well as you expected?

Don’t forget to give onboarding feedback and help set the next designer up for success. This will make everyone’s experience so much better. Good luck on your first days on the job and beyond!

Additional Resources

If you’re interested in learning more, take a look at The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter by Michael Watkins. It was the original inspiration for this section and covers onboarding in depth. While it generally gives advice to set up managers for success when transitioning, many of the strategies are useful for individual contributors as well.

Land Well and Own Your Career8 minutes, 2 links

By now, you should know the nuts and bolts of how to land your dream role. From taking stock of your various skills, building your identity, structuring your portfolio, and navigating the various interview types, to reflecting on the feedback and wrapping things up with negotiation and a strong start.

As we know, design is never a linear process from A to B, and often there’s a big, messy middle. Knowing how to get to your dream role comes with an understanding of what skills you bring to the table and how to properly communicate them in various stages of the process. Reflecting on your experience throughout these stages is key, as usually new information comes in to help us steer our job search in a favorable direction. While each journey is unique, having a destination in mind makes navigation easier.

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