​In this post, we feature some career advice from Lenny Rachitsky (@lennysan), derived from answers he has given in his newsletter and shared on Twitter and elsewhere. We cover his advice on five skills needed to step up in your career to a “director-level” position, and advice on “managing up”.

Lenny’s background
Lenny began his career as a web developer and engineer after completing a Computer Science / Engineering degree at the University of California, San Diego. He ascended the ladder at Webmetrics (acquired by Neustar), becoming a Senior Manager of Engineering, and then Head of R&D. In 2010 he co-founded a location-based Q&A service called LocalMind, which was acquired by Airbnb in 2012. Lenny spent seven years at Airbnb, as a Product Manager, and then Product Lead. 

In his words: “Deciding to open your home to strangers is a complex decision. Over the course of the seven years that I spent at Airbnb, my work centered around helping people all over the world make this decision. As the number of homes on Airbnb scaled from around 100,000 in 2012 to over 6 million today, I led teams tackling everything from supply growth, to guest booking conversion, to marketplace quality.”

While most of his career has been spent in California, Lenny did spend time in Canada too while building and growing LocalMind.

Lenny is currently “tinkering” / working on something new, so we look forward to seeing what emerges! 

Career Advice 
Lenny has given speeches and blogged since early in his career (including while at Webmetrics). Earlier this year Lenny started answering inbound questions he receives on “driving growth, building product, and broad leadership skills” in his newsletter.

We find his leadership advice authentic, especially as he has himself grown through different levels in different organisations, and experienced leadership from different perspectives, including as CEO of a focused startup, and through leading change in a rapidly scaling business. 

While largely centred on product management in the technology sector specifically (given his own background, and the nature of his audience), his advice has broader applicability across many sectors, and we have generalised it below.

A terminology point: “manager” here refers to managers of people and teams, rather than a manager of products, services or projects (i.e. a “product manager” or “project manager” doesn’t necessarily manage people, and may be an individual contributor).

Lenny says that as you move up these management stages, “your gaze rises from the week-to-week, to months out, to years out. You’re increasingly looking further out into the horizon — laying ground-work, anticipating challenges, and working towards a long-term vision. You focus less on day-to-day execution and more on putting in place strong vision, strategy, and people.”

​Five critical traits to demonstrate if you’re looking to manage a function are:
1) Long-term Strategic Thinking
2) People Leadership
3) Stakeholder Management
4) Impact
5) Communication
More detail on each below.

​Perennial advice from Ian McAllister in this post about both proteges and mentors getting value out of their engagements, recognising that both parties invest energy and effort in building the relationship. 

Ian is Director of Amazon Day, and previous Director of Product at Airbnb. He’s had several mentors himself over his career, and mentors a number of professional colleagues and also start-up founders. 

He explains that the most successful mentor-protege relationships share these attributes:

• Mutually understood goals
• Protege-driven interactions
• A focus on approaches rather than tactics
• A focus on listening
• Transparency and feedback
• Appropriate dissolution when the interaction has run its course

Read more to explore these in additional detail.

​Adding mutual value in business relationships is a great way to build a network of people who can offer you information, resources and support to succeed over your career. In this article, we discuss networking and building business relationships, a topic our members ask about, whether as an ongoing process for career success, or specifically when they are joining a new organisation. We love that they, by asking, signal they are thinking of relationship-building in a strategic way while also appreciating that things get done through working with others.

Using ideas from Judy Robinett, we discuss the importance of building and sustaining your network. Judy grew up in a very small town in the US and “didn't know anyone of wealth, power or influence”, yet over her career she learnt lessons and built relationships such that today she has “such a broad and deep network that I’m connected to almost any resource you may need, so I’m having fun”. The term “networking” can have negative connotations, conjuring up images of schmoozing, manipulating others for self-serving ends, superficiality, or rigidly diarised followups. Read more to explore Judy’s tips to focus our relationship-building on adding value (including her "three golden questions"), learn more from a Harvard Business Review article on networking in a new job, and see Judy’s book about strategic networking and one of her TEDx talks.