When I was 13, I cut off most of my hair in an attempt at a pixie cut. Disappointingly (albeit, inevitably) I ended up looking more middle-aged Bev than pixie. This experience – and every other awkward teenage moment that followed – instilled a deep fear in me of anything adolescence related. Learning how to be big while still being relatively small, the uncertainty of doing everything for the first time and the general unpleasantness for anyone involved.

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As much as I fear adolescence and actual teenagers, the teen years are my metaphor of choice to prepare founding teams for the growing pains that come with trying to scale a startup.

"There is nothing natural about being a founder of a company and trying to scale it up… That learning curve – whether it's at Atlassian size or any founder going through that journey – is just unnaturally steep. If you can just hold on with your white knuckles and get through it, I think everyone should be pretty proud of that." — Scott Farquhar, Co-Founder, Atlassian.

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When do the teen years start?

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{{big-quote}}

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Like human teenagers, there's no hard and fast cutover point. But in general, it's around the 100+ employee mark that makes everyone a little cranky. At this point you're managing more complexity, informal systems break down and the organizational challenges of scale become more obvious.

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Based on the Dunbar number, 150 is the cognitive limit to how many meaningful relationships humans can juggle without forgetting who's who in the office. Bill Gore (of Gore-tex fame, whose company Gore Associates is a go-to case study for its organizational approach and ability to innovate) keeps its factories to 150 because beyond that size "things get difficult."

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Flying-by-the-seat-of-your-pants when you're a scrappy startup is fine because you're small enough to make it work and things tend to happen by osmosis. But once you're growing, you need structure. Suddenly, people are joining who don't know the founding stories or inside jokes. And your once-perfect little startup culture starts developing on its own. Meanwhile, the poor HR manager is drowning while desperately trying to hire enough people to keep up with ambitious growth plans. (Hello HR pals at scale-ups – I see you.)

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So how do you make these teenage years less painful?

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1. Make it easy to share information

If you've ever tried talking to a teenager in real life, you'll understand the challenges that come with communication. Sometimes information flows, sometimes it doesn't. The best way to prepare is to create consistency so everyone knows what to expect and feels like they have a way to share what they think.

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This is the kind of stuff people assume will happen by default. Except it doesn't. You need a consistent way for information to flow down from leadership and more importantly, to flow back up. And in general, you need to communicate more than you think you need to. On the rare chance someone comes to you and says 'please stop telling me what's going on around here' then you can pull back.

Start here:

• Leadership updates: How are you updating everyone on the big picture? Is there a regular drumbeat that's working or do you need to tweak how often you're getting together?
• Feedback loops: Where do people go to share what they really think? The interesting questions always happen ‘after hours’, just after the meeting, in the kitchen or at the bar. So find multiple ways for people to share their feedback and let them know you’re listening.
• A single point of reference: Where do people go to find answers about the business? Make sure this is up to date and assign team members to their respective sections so it stays that way.

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In the real world: Canva's season openers are standard quarterly business updates on steroids. Each team presents what they achieved in the last three months and then presents their next big goal. The one I read about had circus performers. Circus performers are not mandatory, but I think some level of creativity is.

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2. Make it easy to be new

Otherwise known as onboarding, this is something a lot of big corporates still do a pretty crap job at for various reasons but they get away with it because they're giant. Startups don't have that luxury because of two reasons. 

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One is time - the faster they find their feet, the quicker they ramp up and the less people problems you'll have to deal with down the line. 

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And two is culture. Even if you're following the advice to 'hire for culture, train for skills', when you bring in a bunch of new people all at once, you risk diluting your startup's culture, which is generally something you want to avoid. So you need to help new starters drink the cool-aid from day one rather than them slowly figuring it out themselves.

Start here:

• Be good to HR - a good principle in general but especially important right now given the amount of pain they'll be enduring at this growth stage.
• Create an onboarding process (here's a simple checklist from our Founder's Handbook to get started).
• Meet new hires within their first month then refine the onboarding process based on their feedback. What would have made it easier for them when they started?

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In the real world: Zapier onboards new hires in cohorts to create a sense of community from day one. They also get new employees, including executives, to spend time handling customer support tickets to deeply understand user needs. This approach has helped them maintain their customer-first culture while scaling from 20 to over 500 employees across 30+ countries.

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3. Stay weird

Don't be the teenager that morphs into a clone of their friends to avoid standing out from the crowd. Nobody joins a startup dreaming of ending up in a soul-crushing corporate environment with mandatory fun days and corporate cheese. Yet somehow, that's where many companies drift as they grow.

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Figure out what actually makes your culture special beyond the ping pong table and free snacks. Is it radical transparency? Customer obsession? The freedom to experiment and fail? Whatever it is, bake it into everything: your hiring, your meetings, your decisions.

And keep your weirdness. Corporate-speak is where personality goes to die.

Start here:

• Re-read your values. Are they meaningful and do they help people make decisions? Compare your values to the way we actually work, do they align? If not, what needs to change?
• Involve your team - this is not an HR thing, it's a leadership thing.
• Set aside time to preserve what keeps your culture strong

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In the real world: Atlassian has kept its ‘ShipIt Days’, which started out as a casual 24-hour hackathon for employees in one location and has since scaled to become a global event with thousands of employees across multiple countries. Teams at every level take part and work on anything from product features to office improvements to charity projects. 

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Bonus tip

Keep your finger on the pulse as you grow. For every teenager there's a little brother or sister who will tell you what's really going on. As a leader, you need at least one of these people who will tell it like it is without sugar coating it so you can stay in touch and anticipate issues before they're issues.

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Growing up is hard for teenagers and startups alike. But by managing your own expectations and intentionally nurturing your people through these awkward years you’ll get through without completely losing what made you special in the first place. Plus, unlike actual teenagers, your company won't slam the door and tell you it never wants to talk to you again.

Remember: Teenage years are painful, there’s no silver bullet - you just need to see this ship out. Start simple, get feedback early, and evolve as you grow.

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