​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.

​Do you feel like you are micromanaged at work? Or, are you as a manager concerned that you might be crowding out the personal ingenuity of your team by giving directions that are too precise?

In this post, we set out suggestions on the topic of micromanagement, such as Lacy Schoen’s tips for handling a micromanager and advice for micromanagers themselves, as well as share an amusing TED talk by Chieh Huang called “Confessions of a Recovering Micromanager” where he describes his personal progression up the levels of management from start-up founder to managing others, to managing managers, and managing a business.

​Micromanagement is a topic that gets significant attention, with many saying they’ve worked for at least one micromanager in their careers. Superficial advice is often the knee-jerk reaction of quitting to get away from the misery of being constantly monitored and judged. One positive way though to view the experience is as a growth opportunity to learn what not to do when you gain a position of responsibility yourself. It can also teach you how to work with different types of people, a skill which will serve you well throughout your career. Read more to explore some of the nuances of micromanagement, including potential causes and how the employee might actually need close attention in the short-term.

Last month, William Hockey announced that he is taking a step back at the end of the quarter from the company he helped to build, handing over the reins to others. Together with Zach Perret, he co-founded Plaid, a Fintech platform that connects various applications with users’ bank accounts. William also served as the company’s president and Chief Technology Officer, and he refers to his announcement as “transitioning from my day-to-day role… to a solely board position”.

William shared on Medium the internal message he sent his team, as well as his thoughts on his transition, and we’re keen to share them with you given the self-insight and emotional maturity they demonstrate, while highlighting the importance of succession planning.

Read more to see excerpts from William’s post, as well as suggestions from Lolly Daskal (executive leadership coach and author) on succession planning.