Photo by Amelia Brown on Unsplash

My 10 Favorite (Quirky) Leadership Hacks — Illustrated Edition

Not long ago, the little tech company I started with a handful of employees and a maxed-out credit card officially turned 10 years old. In that time, we’ve gone from sharing a cramped workspace to having nearly 1,000 employees in offices around the world serving more than 17 million customers.

Along the way, I’ve learned a ton about leadership and building companies. Some of the lessons were deeply personal; others were all about fostering company culture and inspiring strong teams. And, with the benefit of hindsight I can definitely say that I got a lot of things dead wrong.

But here are the lessons that endured — the tips and hacks that helped us grow Hootsuite from a fledgling startup powered by passion (and lots of coffee) to a global enterprise. For other entrepreneurs and leaders out there, I hope these tips can help you on your journeys … so I’ve even included a few illustrations to make them easy to remember. These are ordered roughly chronologically — to trace my own trajectory and the trials faced at each stage.

The Impact-Effort Matrix

This principle seems dead obvious. Yet I see so many people — from entrepreneurs to C-Suite executives to managers — who just don’t get it.

You’ll always have a list of 100 things to do — I know we did when we were first getting off the ground in 2009. The reality is you’ll only ever have time to do a couple of them well. So how do you prioritize and sequence? By deadline? By cost? Do you pull an all-nighter and try to tick off your whole list?

The easy answer: just stick with the top right quadrant. Life is largely a quest to find those things that bring about the highest impact with the least effort. For an entrepreneur, this means less time tweaking your logo and more time finding an investor. For a manager, it’s fewer hours perfecting your PowerPoint and more time finding that all-star hire.

But it can sometimes be hard to tell the difference — which is where the Impact-Effort Meter comes in handy.

Commandos, Infantry and Police

Tech author Robert Cringley came up with this military analogy for the phases of startup life — something I turned to again and again as Hootsuite was scaling fast in its early years.

He points out that founders and founding team are a lot like commandos — the crazy soldiers who first parachute behind enemy lines. They work fast, cheap and recklessly … but they get the job done.

Once a perimeter is established, in come the infantry — front-line soldiers who impose order. In the startup world, these are the adventurous early employees who turn smart ideas into saleable products.

With time, things normalize — infantry are replaced by police who maintain the existing order. So it goes in business, where experienced professionals eventually come in to add scale and stability.

The most important thing: each of these three groups have very different personalities and goals. But all three are essential to building a successful business in the early stages. Learn to get along.

Laying Tracks In Front Of A Moving Train

The difference between being able to lead a growing company and getting overwhelmed? It comes down to the ability to lay tracks in front of a moving train — something that definitely came in handy as Hootsuite passed two million users and entered a period of hypergrowth in 2011.

Growth-minded leaders are always thinking, “What comes next?” They excel in their current role, but they’re also reaching out to mentors and figuring out the skills they’ll need next year … and the year after that.

It’s easy to get wrapped up in just “doing your job.” But if you focus too much on driving the train, you might not notice you’re running out of track. And sooner or later, you’re going to derail.

The Brown M&M Test

Rockers Van Halen used to include a unique clause in their concert contracts: no brown M&M’s backstage. Far from primadonna posturing, this was actually a clever quality assurance test. If promoters missed the clause, it was a sign they might be skipping over far more important staging stipulations.

This strategy works equally well in the workplace. Take job interviews. When Hootsuite was adding dozens of employees a month in 2012 after securing our Series A funding, we’d often throw an oddball question into the pre-interview paperwork, like, “Please list the three websites you visit most often.” Candidates who overlooked it generally weren’t worth interviewing.

But the Brown M&M Test can be applied anywhere. I’ve found the most effective employees are those who take the time to read the fine print. Keen attention to detail makes for incredible companies … not to mention killer rock shows.

The Elephant And The Rope

Baby elephants, the old story goes, are traditionally trained by tying one of their front legs to a stake in the ground. (This sounds terribly cruel, so let’s hope this is just an old legend.) Because the elephants are small, only a thin rope is required. But even as they grow, that same thin rope is all that’s needed to keep them secured. The elephants think the rope can still hold them, so they never try to break free.

This begs the question: In business (not to mention in life), what sorts of invisible mental ropes — flimsy and easily broken — might be holding us back? We reach a conclusion at one time, based on a specific set of conditions and data, then forget to revisit it after we’ve grown, evolved and have new information.

This was definitely the case for our company in 2013. We had grown to hundreds of employees and millions of users, but in some ways we were still thinking like a small company. For instance, weren’t identifying and pursuing the huge, complex customers that our larger competitors were targeting. But why not? The key, especially for growing companies, is to begin to see those ropes in the first place. Sometimes, all it takes is a nudge to snap them.

Eat Your Own Dogfood

Rumor has it that the managers at Microsoft popularized this phrase in the ’80s. They insisted that employees run the company on Microsoft software — placing ultimate faith in their product. (Why they called their platform “dogfood” — and not, say, filet mignon — is beyond me!)

But this approach is critical in any growing company. If you’re not confident enough to use your own tools, after all, what business do you have selling them to someone else?

Dogfooding has other benefits, as well. You get to stress-test your product with the most engaged user-base out there, i.e. your own team. (This approach proved especially helpful in 2015, as we tested out a brand new feature that enabled employees to “amplify” company social updates via their own accounts.) You convert employees into walking evangelists. And it creates strong incentive to improve features and sniff out bugs before they reach mass adoption with your customers.

Not to mention, you send a message to the market that you trust your product with the most precious thing going — your own livelihood.

The Quick And Dirty Growth-Profit Matrix

Growth or profit? For tech startups, it’s the million-dollar (and sometimes billion-dollar) question. How do you find that optimal balance between growth and burn?

Brad Feld’s famous “Rule of 40” says a successful SaaS startup’s growth rate plus profit should add up to 40%. (If you’re growing at 60%, you can afford to lose 20%, for instance.)

But I’m highly visual. Thinking about Hootsuite’s own trajectory, I find this super-simple chart — inspired by the Boston Consulting Group’s Growth-Share Matrix from the 1970s — to be helpful.

Bottom line: It’s OK to lose money if you’re growing, but at some point investors want to see a path to positive cash flow … no matter how groundbreaking your business idea is. This hit home for us in 2016, as we surpassed 15 million customers and became cash-flow positive.

The Three-Sentences Rule

For years, I’ve added a custom signature to my emails (adapted from http://three.sentenc.es/): “Sorry for the short response. I wish I could be more thorough, but it isn’t possible with the volume of emails I receive.” Far more than an email hack, this is a comms philosophy to live by. As Hootsuite continued to expand in 2017, and pressures on my time became even more intense, it proved more important than ever.

The approach — effectively treating all of my emails like short SMS text messages — has helped me manage the deluge of hundreds of messages I get each day. Instead of letting my inbox overflow, I get back to people with quick, pithy messages … right on the spot.

With time, I’ve trained myself to leave out the fluff and keep only the most essential points in an email. If I absolutely have to say more, I just pick up a phone or talk in person.

The People Movement Principle

Job hopping has created a lot of hand-wringing in the HR world. Millennials now expect to change their job every 2.5 years — double the rate of their Gen X predecessors.

But what if this isn’t a cause for alarm? What if it’s actually a strategic advantage for businesses?

The key is to enable people movement within your company. Each year, around one in five of our employees change their roles. Promotions, lateral moves and international transfers keep the staff in motion. As Hootsuite has grown to more than 1,000 employees, this tactic has proved absolutely invaluable.

The payoff? Employees learn new skills, stay engaged and stay longer. Institutional know-how is distributed across your org. Company silos break drown.

But it doesn’t happen by accident. Having a dedicated “stretch” or “bungee” program to help employees find new roles can make all the difference.

If You Can’t Draw It, You Can’t Explain It

So, you might be wondering about all these doodles I’ve been doing. As business (and life) has grown more complex, I’ve been thinking a lot about drawings. Basically, unless you can condense something to a simple sketch, you probably haven’t really “got it” yet. This was a brilliant insight I got from a former engineer on my team, Geordie Henderson, whose computer science professor forced his students to first answer a question with a sketch.

Whether we’re talking about complex technical processes, marketing and sales challenges or even leadership and culture issues, the ability to reduce things to a simple drawing is so important. It signals that you’ve wrestled with the complexities and distilled the issue down to its core elements. And only then are you ready to explain it to others, tackle it and find a solution

On that note, I’m hoping to share more business doodles in the weeks and months ahead. Follow me on Instagram for the latest. Personally, I’m a visual learner and find sketching things out to be really helpful. But I’m wondering if other people feel the same way. Are these sketches helpful? Would anyone be interested if I put together a whole collection of sketches on the experience of starting and scaling a business? Let me know.

What are your top leadership and growth hacks? Share them in the comments.