Depending on the relative seniority of the level you’re hired at, and the company age/leadership experience, you may be called on to define answers to some of the questions below. Tread accordingly.

Information checklist

Culture

1. What separates great from good performance?
2. What might be the largest difference between two different engineering teams here?
3. What would be the biggest piece of advice all of you have for me?
4. What are the most common challenges faced by new team members here?
5. Which actions make new team members reach full productivity in weeks as opposed to months?
6. Are there any recent cultural changes I should be aware of?
7. Does the company have a documented history to help new team members understand how it has moved from inception to the present day?
8. What motivates teams/people to keep pushing through tricky situations?
9. Have any two cultural values ever come into conflict with each other?

Business

1. Who are the top-paying users/teams for our product? How many of them have started with us in the past 6 months?
2. Does our strategy to increase revenue focus on fewer larger teams, or many smaller ones?
3. What are the top reasons for user churn? Which ones are the least under our control today?
4. At the moment, do we want to differentiate ourselves from our closest competitor by target market, feature-richness, value pricing, support, or something else?
5. Which hypothetical announcement from Amazon/Microsoft/Meta would scare us the most?
6. Did the new(est) board members have any specific expectations around target markets/expansion strategy during the latest funding round?
7. How is the company structured today (more follow-up questions if this has changed recently)?
8. What does the business funnel/user-flywheel look like?
9. Which kind of user is the most difficult to serve today?

Priorities/Challenges

1. How are competing priorities and expectations balanced?
2. What is the current/next most important business outcome we’re looking to achieve?
3. Which early signs do we watch out for to re-prioritize work?
4. How are technology adoption decisions made here?
5. Which active risks need our immediate attention?

Product

1. What was the last big feature we shipped?
2. Do we have a publicly committed roadmap, or do we intend to have one soon?
3. What does our ideal user persona look like, and how does it differ from the typical user persona today?
4. What role does intra-team collaboration play in end-user experience today?
5. Which hurdles do new/existing users face during product onboarding/daily usage?
6. What is the biggest critique our users would offer us?
7. What is the one thing we wished we knew about how our users used the product?\
8. How do we discover/confirm new problems to be solved?
9. Is there a recent example of us having to reconsider a feature? What lessons did we learn from this?
10. What would we do if we had no worries about user retention / operating margins / funding runway?
11. What would we build/design from scratch if we could?
12. Are there any product features that were a surprise hit? Conversely, were there any surprises from product features that didn’t leave a desired mark?
13. Which use-case are we not going to build for anytime soon?
14. If we could change one thing about how our users behave, what would it be?

Team

1. What does success look like for the business / team / me?
2. What are the company/team’s needs from me?
3. What are the top 2-3 things others in the company depend on our team for?
4. What other skills/experience is the team/company on the lookout for?
5. Which people do I need to speak with within my first week?

Engineering/Technology

1. What are the key details I need to learn about our systems in the first month?
2. Which systems/practices slow us down the most?
3. What are the biggest pain points during development?
4. What troubles are we foreseeing with increasing scale?
5. What is the biggest hurdle to shipping new features quickly and confidently?

Targets

First week

Understand (and independently articulate):

1. Product roadmap
2. Business priorities
3. Team norms & processes
4. Stakeholders
5. Documentation/information/knowledge gap(s)

Meet 1-1 with the entire team, and with key partners outside the team.

First month

1. Fill in most/all identified information gaps for anyone to consume
2. Identify potential areas for long-term improvement, especially ones carrying low-effort.
3. Ship first small/mid-sized feature while demonstrating systems thinking
4. Show early signs of mentorship and cross-team influence

First quarter

1. Successfully lead/co-lead one business-relevant initiative to completion.
2. Show ownership of areas that are important but not always under your direct control (reliability, scalability, maintainability)
3. Demonstrate an ability to:
   • Proactively identify problems, voice them, and suggest + implment solutions to them.
   • Take initiative and ownership of ambiguous problems/situations to closure.
   • Make the rest of the team effective in their own way (and not just copies of yourself)
   • Make accurate, situational design tradeoffs on the road to consistent, measurable results.
4. Have a self-review matrix for what you've learned, contributed, and what you're going to do next across:
   • Product/team awareness
   • Tech depth
   • Cross-team collaboration, junior engineer mentorship.
   • Business acumen.

Tips

Awareness

1. Pay close attention to the contrast between your current and previous work environments. This is essential to understand what works generally across many SaaS product companies, and which ones are/were specific to your previous role.
2. Focus on expanding the breadth of context for the first 2-4 weeks, and then identify the top areas that will demand more depth from you for the next 1-3 months.
3. Do your homework: Shape your queries to coworkers as multiple-choice questions instead of open-ended ones, this shows you’ve done your homework and that you respect the time of everyone else around you.

Meticulousness

1. Document & organize all your learnings (no matter how big or small). This will help others at your level as the company/team grows.
2. Keep track of personal results and feedback, which makes building future promotion cases easier.
3. Even if you have the authority to, don’t try to change everything about your work surroundings from day 1, pick your battles. The reputation to do so and the eventual acceptance of your actions have to be built up over time.
4. Be prepared to have justification for what you’re doing, or not doing.

Behaviour(s)

1. A little humility goes a long way, no one appreciates the newcomer who wants to dump over everything that exists. There’s no faster way to tick your new coworkers off and shut them out from ever caring what you have to say, no matter how genuine it may be. In each interaction, always assume that the other side knows at least one thing that you don’t. Be open to learning by asking pointed questions.
2. Tune actions with the intent of making a part of your manager’s job easier. This includes sharing status updates regularly (the frequency will gradually decrease from daily to weekly, depending on your company environment)
3. A new company is the perfect chance to re-invent parts of your perceived work personality that you didn’t like but couldn’t alter because of inertia and the trouble with changing the minds of a large enough audience. Act accordingly from day 1, don’t let older behaviours drag you down in a new company.

Trust

https://www.atlassian.com/blog/productivity/build-trust-when-you-start-a-job