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 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!
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
More detail on each below.
1) Long-term Strategic Thinking
This skill involves taking on large complex problems and finding a clear path to solving them. Examples of challenges Lenny gives (in a product management context) are: growth slowing on a marquee product, launching a critical new product from scratch, and building out a key piece of infrastructure. Developing your approach to addressing key business problems, including breaking them down into their core components, and defining solutions, is a crucial skill to step up to functional level. “The scope will be bigger, the stakes will be higher, and the number of people involved will be larger” says Lenny.
Part of stakeholder management that Lenny has written separately about is “managing up aka managing your manager, an essential skill at every level (even CEO)”. He argues that it enables you to do your best work, while also getting the recognition you deserve, and he offers these behaviours and tactics which have helped him:
Many of these translate well to managing other stakeholders (such as your peers and other leaders), including setting expectations, sharing trade-offs and updated priorities, and communicating regularly.
Given that Managers of Functions influence a large number of resources (people, budget, systems etc), they are expected to drive significant impact that “changes the trajectory of the business”. As you progress in your career, identify opportunities to demonstrate your impact. This includes priority calls, resource allocation, setting goals, selecting what to work on, and aligning your team(s) behind the right activities.
“Your ability to communicate clearly, concisely, and convincingly will be essential to being successful at every one of the above attributes”. Consider what tactics and techniques you’ve used to communicate with your team(s) and stakeholders, and how successful these have been – again reflect on examples of good and bad practice you’ve seen others use. Keeping your team(s) and stakeholders up-to-date is important, as is timely communication of bad news.
Helpful tips from Lenny on five key skills to practise and evidence on your path to managing a function. Please let us know in the comments if you agree or disagree, as well as other attributes you’ve seen successful Managers of Functions demonstrate.
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