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Leadership lessons from Airbnb and Twitter

Morris Kaplan
Smarter Writer

Morris Kaplan is a former finance and venture capitalist who writes for entrepreneurs and professional services firms

Morris Kaplan
Smarter Writer

Morris Kaplan is a former finance and venture capitalist who writes for entrepreneurs and professional services firms

Airbnb and Twitter both can offer some brilliant lessons in scaling up to achieve global supremacy. Though as Morris Kaplan explains, leaders of fast-growth companies rarely get a smooth ride.

It’s almost a cliché that if you want to attract smart people to your fast-growth business, you need to give them a great place to work.

Certainly, the corporate headquarters of Twitter and Airbnb look like they’ve taken some cues from Google, with open-plan workspaces, kooky décor, games rooms and in-house dining. And like Google, these frenetic beehives are mostly populated by Millennials (people born since 1982).

While you don’t necessarily have to recalibrate your recruitment strategy to ensure no one is older than 37, it can pay to take on some of the cultural attitudes of Millennials.

Twitter Headquarters San Francisco Canteen

Attitude #1: Be tech-savvy – and willing to experiment

Both Airbnb and Twitter are founded and operated by Millennials who are obsessed with technology. Research has shown this generation is not only more tech-savvy, but many of its members have fewer family ties. Therefore these workers seem to have more bandwidth for challenging work and some are even prepared to postpone family life – for now.

So it would not be controversial to also suggest that Millennials have more energy and enthusiasm for innovation at this stage of their lives, and demand it from their bosses.

Attitude #2: Help workers grow up by up-skilling

Both companies have built workplace cultures that appeal to a broader base of values and not just money. Here are some big clues on how they’ve done it from recent surveys conducted by Deloitte and PwC:

  • More autonomy
  • More flexibility
  • More personal and professional development
  • More opportunities to multi-skill
  • More meaning – the work they do, and the contribution they make to the world

Since Millennials have a desire to grow and keep developing, prospective employers should find ways to offer these benefits – through the roles themselves – as well as through education and training opportunities that the business provides.

Attitude #3: Disrupt established markets

The founders of Airbnb made no secret that they’d settle for nothing less than shaking up the entire hotel industry to take a big slice of the $500 billion global market when they launched in 2008. In their view, competing hotels and other short-term accommodation providers were really only differentiated by price and luxury level – much like department stores are.\

Instead, Airbnb built a new source of supply in the market from ordinary people’s spare rooms and weekenders. When they started, the company had 13 employees working from a residential apartment in San Francisco. Their first listing was co-founders Brian Chesky and Joe Gebbia’s own apartment. Today, Airbnb is a global powerhouse with offices in 34 cities and more than 6 million housing listings around the world– a mainstream operator by any measure that has expanded the possibilities for private hotels and the plethora of individuals with property.

If you are a hotel or hospitality industry operator, Airbnb presents a case study in generational shift in buying behaviour.

Attitude #4: If you can’t do it, hire someone who can

Founders bring a certain set of skills to the venture which is critical at that startup point, but then those skills may not have the strategic operational talents to guide the business through massive growth while juggling the sometimes-competing needs of staff and stakeholders.   

In market circles, Twitter disappointed investors for some time. When the company went public its goal was to be the next Facebook, which meant growing its user base as fast as it could, and then figuring out how to turn users into revenue.

Most start-ups are focused on acquiring new customers, as it provides a strong value proposition for investors, but the need to develop ongoing relationships with those customers is an entirely different challenge.

Here, teamwork is vital. While acquiring customers is a sales job, and keeping them is an organisational effort, founder leaders may not be as skilled in building processes and leading teams as they are in their technical ability.

In 2010 Twitter’s xo-founder and then CEO Evan Williams announced he was taking a break for paternity leave and then wanted to focus on what he does best: product strategy. His replacement, Dick Costolo, is a man ten years his senior, who gained a reputation for strong operational leadership while driving several dotcom start-ups to acquisition by much bigger companies.

Hiring in a new CEO can be a bitter-sweet decision at a personal level. Even though Costolo was replaced as CEO in 2015 by another Twitter co-founder, Jack Dorsey, the scenario illustrates that a strategic leadership change can be a mandatory one to meet the challenges of a technology-driven world.

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Originally published December 24th 2014. Updated August 2nd 2019.

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