Wisdom//

My Company Just Hit Its 10-Year Anniversary. Here Are The 6 Biggest Leadership Lessons I’ve Learned As CEO During That Decade

A founder reflects on all the things he wishes he knew sooner.

patpitchaya/Shutterstock
patpitchaya/Shutterstock

My company, Skylum — previously known as Macphun — recently hit its 10-year anniversary.

As anyone who’s started a company knows, your 10-year anniversary is a reason for celebration. It’s hard work keeping a company alive — let alone guiding it to profitability — and it’s important to take some time to appreciate that. I know personally that my team has accomplished a lot over the last decade, including winning Apple’s Editors’ Choice Award, their App of the Year Award (six years running), and passing the two-million users mark.

But as much as your 10-year anniversary is a cause for celebration, it’s also an important moment for reflection. As a founder, you learn a lot about how to lead teams and drive progress over the course of 10 years, and the best way to put those lessons into action is to step back and think about why they’re important and how, moving forward, you can use your hard-won wisdom to keep getting better.

Here are the lessons that stand out to me as particularly important that I wish I knew a decade earlier.

1: The job of the CEO early on is to do two things: 1) keep your company growing, and 2) keep your team motivated to do great things together.

The role of the CEO is simple to explain, but difficult to execute — mostly because there are so many opportunities in your day-to-day for distraction.

To keep your company growing, for example, you have to focus on new business acquisition in addition to customer success, engineering excellence, and marketing. The success of every company vertical is, ultimately, your responsibility. And sometimes, no matter how big you are, it can feel like guaranteeing that success is a matter of you steering every process yourself.

To keep your team motivated, meanwhile, you have to sympathize with and cater your management techniques to a disparate array of learning styles, temperaments, and desired outcomes.

There are so many little internal details that fight every day for your attention, so it can sometimes feel like your job isn’t to build a company, but to instead juggle 100 different balls at once.

The only way to succeed, though, is to maintain a kind of hyper-focus on your two high-level goals — growth and motivation — and to not allow yourself to get lost in or overwhelmed by the daily minutiae. It took me a long time to so purposefully respect that bigger picture.

But we have been successful in doing so. Skylum was founded by just two people, but we’re now a team of 150 and have recently opened new offices in Bellevue and Tokyo. We started as a mobile apps development, and now we offer both B2C and B2B solutions for Mac and Windows. None of that could’ve happened if we didn’t keep our eye on the bigger picture.

2: What drives you as a CEO will be different from what drives your employees.

What also proved critical in learning how to motivate my teams was internalizing the fact that inspiration looks different to each individual. What inspires you won’t necessarily inspire your engineers or marketing team. Often, in fact, it’s the opposite.

That’s a mistake I made early on: assuming that I could inspire everyone on my team with a kind of one-size-fits-all solution, devised from my own personal preferences around how I like to be treated and how I self-motivate. The truth is, while you may be driven by increased company profits or industry respect, your employees likely prioritize job security, transparency, or an easy-to-understand incentivization system more.

There is something, however, that all employees desire and that is a kind of universal need: the sense that you and your leadership team are paying attention to them, and that you care about their well-being.

At Skylum, we employ people from all over the world, in different cultures and time zones, and so this proved particularly critical. Now we try to communicate with each other as much as possible and meet in person any time the opportunity arises. Teams work together and also motivate and educate each other.

3: As you scale, your role as a CEO will shift to more “big-picture stuff” as opposed to the day-to-day tasks.

At Skylum now, the internal mechanisms and systems I helped build — and often ran personally — early on are now largely run by themselves or under the stewardship of other department heads. That means the areas in which I can add the most value reside more definitively now in the realm of “big picture” thinking: less tactics, more scale.

A team of 20 people is inherently different and has different needs than a team of 150 people. At Skylum today, we have team leaders that are responsible for their teams. On a daily basis, I typically only interact with those team leaders.

More tangibly, if there’s a change that needs to be made to our website, for example, I know that’s something my digital team lead will handle.

My job instead is to think about how to grow awareness of our brand as a whole.

I’ve found it helpful to remind myself of this because, again, there are so many potential distractions that pop up during the day. If I don’t remain aware of what exactly I should be focusing on, I become less effective and less valuable to my team. The minor problems, although they seem major in the moment, are ultimately not emergencies.

That said, of course it remains important that I keep all my people in the proverbial loop, and that everyone on the team feels comfortable reaching out to each member of the company if they need to. To this end, I’m always willing to make myself available whenever there’s a team member in need.

4: Make sure you and your team are always working toward concrete goals.

To ensure your team remains effective and that your company as a whole remains productive, you must always set clear internal goals for folks to be working toward.

Just as you as the CEO will have your own concrete goals, your employees must understand what they’re working for and toward at all times. Otherwise, they won’t be able to work as purposefully as possible.

This means you as the CEO must set differentiated goals and targets both company-wide and team-by-team. These should be high-level — everyone should have an understanding of what the company is working toward 5 years from now — as well as granular; every team should know their key objectives each day, week, month, and quarter.

That’s how both you and your people will achieve long-term success: by breaking down those larger goals into more immediately achievable ones.

5: Realize everyone on your team can do much more than they think they can do.

I now understand this very clearly: every person in any given company can achieve more and perform higher than they think they can.

Time and time again over the years I’ve seen my employees obliterate their doubts and overcome their apprehensions. Shy employees charged with leading teams have produced great results. Engineers assigned tough deadlines have built great pieces of software in limited amounts of time.

Your people have that potential; you just need to help them realize it. Sometimes, as I’ve learned, it takes a bit of a push, a lot of confidence, and the right motivation. You have to believe in your employees. That way, they’ll believe in themselves.

6: It’s important to always be innovating rather than just copying someone else.

Finally, perhaps nothing else has served to set Skylum apart more than our commitment to innovation and our resolution, above all, to never settle for simply copying someone else.

A lot of startups build themselves upon the limited premise that what matters is making money, which sometimes means exploiting an already-proven niche.

But the truth is, what matters is solving problems with new, innovative solutions.

To provide customers with such innovative products and services, however, your company has to foster an ethos which prioritizes that. That starts with you as the company leader. You have to go out into the world and find out what people are clamoring for, and then you must commit to delivering it to them. To settle, in this sense, is to allow your company to look like every other company out there. You want the opposite: you want to stand out.

Sure, innovation is harder than copying what you already know. But many of the lessons I’ve learned as a CEO reflect that unavoidable truth: the harder choice is usually the better choice.

Originally published on Medium.

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