Your first 30 days when joining a new company can have you feeling simultaneously lost and found — you're generally confused but also excited to fit into your new tribe.

When joining as an engineering leader, sometimes these feelings are heightened with fears that you're not being productive as you want, you don't understand what success for your role looks like, and you don't have a complete understanding of the systems and architecture.

In December 2019, I happily accepted an offer to join Button as the Director of Applications, an engineering leadership position focused on supporting teams who build products to leverage Button's platform for our partners. This was the first time I joined a company at the director level, and I wasn't sure what to expect or what would be expected of me: Who do I meet with first? How can I help? What are the most important things to pay attention to? What should I definitely not do? With this post, I hope I can share my experience for others joining an engineering team in a senior leadership role, particularly on what went well at Button and what advice I would give others to focus on their role transition journey.

Button's Onboarding

30-60-90 Day Plan

By now most companies are probably doing some version of the "30-60-90 Day Plan," which, if you haven't seen that phrase before, refers to an document that identifies a list of tasks or achievements you should complete during your first 30, 60, and 90 days at a new company. These are really helpful because they give new hires clear guidance on what should have their focus, as well as a performance benchmark for the manager to ensure expectations for this new hire are clear. What made Button's use of this system stand out to me was how much care and thoughtfulness went into the plan, in the following ways:

1. It was written as a living document that I edit and update as I make progress. This seems simple, but I've seen many of these plans just be a hand-off without iterating and discussing it. As a small example, even the tasks were enumerated with checkboxes instead of bullets so I could it to update my completion status. I could also add comments and questions as I went, which are tracked and answered by my manager.

2. This plan also included language around themes and missions for each benchmark of time. So yes, I should meet with X, Y, and Z person as well as read docs A and B... but what does that add up to? In my case, my manager Jimmy made it clear:

...your role is to learn about Button - what our products are, who our customers are, and how we work together as a team to design and build new products. During this time you'll also build the foundational relationships - both within Engineering and between divisions - that will enable you to be successful in this role.

The impact of this kind of context meant I could reflect on my progress to that theme, and (going back to the first point) reach out to my manager when I didn't feel I fully achieved it with the tasks at hand. What about this person, will they also be on my team? How do I demo this product in staging? Where can I learn more about this project my teammate mentioned? In a start up environment, sometimes things are developing so fast that documentation can easily go out of date. Without having these thematic benchmarks, a set list of tasks might not fully incorporate what's required to get up to speed.

Onboarding Class

Another highlight of Button's onboarding process is the scheduled onboarding classes. For your first two weeks, peppered throughout your days, you meet with the same cohort of new hires to take various classes that cover everything about Button — from office/perk basics to a deep dive on marketing's organization and strategy. The idea is to equip each Button new hire with the tools to understand the company as a whole, and his/her/their unique place in it. I've previously been in onboarding classes that are grouped to one or two days, or happen (unfortunately) months after I actually started, but having cohort that you see regularly over two weeks is so helpful in establishing yourself at a new place. Everyone at Button is incredibly friendly, but having a few less strangers when you're just starting out is so nice.

Advice for your first 30 days

Outside of Button's wonderful onboarding, I also used a few of my own tricks (well, things I've picked up from others along the way) to find my fit in my new role. They mostly center on how to approach your team and position when joining a company as an engineering leader.

"What are you optimizing for?"

One of the first things I always try to remember when joining a new company, and things I tell my new hires, is that questions are not just welcome but expected when you're starting out. Don't be shy about asking someone to clarify what they mean in a meeting, or having a basic set of questions for each 1x1 like "What's working? How do we do X here?"

On top of that, I like to to use a question I picked up from Lara Hogan: "What are you optimizing for?" Like she describes, this 5-word question can unravel so much context and meaning because it asks a person to reflect on motivations, not just facts or outcomes. Apply it to anything you're confused about when you join a new company, and you'd be surprised at how much more information it can give you. For example, if you ask "Why did we prioritize this work?" you might hear "Because leadership gave us strong direction that this will impact the business" But if you asked, "What are we optimizing for with this project?" you might hear "We have a revenue target of x, and need the clearest path to shipping this to production. We've had problems with complication in the past, and needed the simplest solution." This suddenly gives you so much more context to understand where the tricky parts are, and where your influence as a leader can help unravel and move things in a better direction.

Embrace the ambiguity

One challenge when starting a new role as a senior engineering leader is that the expectations for that role differ from company to company. Depending on the team size, product maturation, or a variety of other factors, you might be asked to be on one side or the other of the hands-on-technical spectrum. Hopefully you sussed out the basic expectation during your interview process, but still when you start you'll be meeting with various teammates who are also unsure of how exactly you fit into their day-to-day.

My advice here is simply to accept that it's confusing, and embrace the ambiguity. Give yourself time to find out what exactly your team needs from you and how you can best help them. Sometimes they need someone who will review and edit architecture plans, or someone who can help clarify the product and align various leaders, or even someone who can fix their deployment pipeline because it's a huge pain point. Will Larson wrote an excellent piece on how to set your priorities and goals despite this ambiguity. I highly recommend giving it a read!

Be a shadow, not a ghost

My last piece of advice is more of an anti-goal, and a trap I found myself falling into few times during my first 30 days. When you're trying to understand something, you often calibrate it against your own past experiences and expectations. That's totally natural, but can also really color what you're seeing unless you reflect on those biases you have. For example, if you come from a company with a very rigid process and join a team that plays pretty loose, your first instinct when someone raises a frustration might be the blame the lack of process. Something like, "This issue didn't exist for us at the previous company, so it must be the lack of process that I'm used to here at the new company."

Be careful to check that assumption! Your first 30 days are to be a sponge and just absorb, to recalibrate your expectations and try to get the full picture of how your new team operates. Maybe the loose process is actually keeps them really agile, and the frustration is coming from a dependency issue from another team. Remember to be a shadow when you're attending meetings and learning, but don't be a ghost and let your previous experience haunt your new place.

While there are still exciting times to come in finishing up my 60 and 90 days at Button, I hope these sentiments help you as they helped me onboarding in an engineering leadership position. And of course if you're interested in learning more about Button and what your first 30 days could look like here, check out our jobs page and reach out. We'd love to hear from you.