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Everyone Is Asking the Wrong Questions About Dropbox. Here’s What They Should Be Asking Instead

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Taking a startup from zero to exit can be a long, unforgiving grind. Here is how you can help your team stay motivated and consistently perform at a high level.

Last week Dropbox held its Initial Public Offering (IPO) with great anticipation from the technology and financial industries. While most observers focused on the IPO’s financial performance, we couldn’t help but wonder what it took to deliver sustained high performance over the 11-year period since its inception.

What made it possible to weather the constant startup storms and consistently deliver at a high-level to create value for customers, shareholders, and team members?

We decided to ask this question of my own team to see what we might learn. We agreed we’d first have to define the characteristics of high-performance. There were a few things that jumped out based on our collective experience:

  • What we were working on was important to our business
  • Execution was fast and the quality of the result high
  • Team members had fun and enjoyed the experience, either during or after
  • There was little or no drama among team members
  • Teams worked harder than average by personal choice

Once agreed upon, we returned to our core question and discussed our own experiences. After sharing a dozen or so high-performance moments, the obvious conclusion was: “if we could experience ‘that’ most months, we’d be having fun, moving fast, and creating value even as our team grows.”

So, we took to organizing our thoughts, and what resulted was a neat and tidy framework for high-performance. From our team’s discussion, we decided that each initiative or project should have the following characteristics.

A well-defined goal with a purpose that matters to the team and the company.

It’s amazing how easily teams can embark on a project where the goals are ill-defined or have no measurable criteria for success. We always have to ask “what is it that we are trying to achieve?” Without this question, there is no success.

Having a defined goal isn’t enough, though. The goal must also matter to the company and the team. At Virta Health, we’ve been ruthless in improving our goal-setting process such that every goal, from those of small teams to high-level corporate objectives, aligns with our mission to reverse type 2 diabetes in 100 million people by 2025.

Preferably time-based (but not always).

Having a time-based effort cements your goal, creates a rallying tool, and gives you something tangible to work toward. It also provides a natural pause and a chance to reflect and create a plan for iteration to make something better.

Importantly, a deadline-driven goal can also prevent team members from feeling like they are part of a never-ending grind. Projects that go on forever can create the unnecessary feeling that things aren’t getting done. This is a recipe for causing discontent among team members.

A small team with few interdependencies and all members “pulling their weight.”

We’ve always been a believer in the power of small teams doing big things. Small teams are by definition more nimble and can simply move more quickly. People feel that their contribution matters, because to achieve a challenging goal requires that everyone delivers their best performance.

It is also important to remove as many of the dependencies on other teams as possible. Cross-team collaboration is a necessity of every environment, but too much of this slows down progress and worse, demoralizes a team.

Limited or no rules and restrictions with authority to make decisions.

There are often natural constraints — time, resources and money to name a few — in any situation. In fact, research that shows that some restrictions can lead to better creativity and more solutions. That said, it was clear from our discussions that having the freedom to think and act without guardrails is critical to high-performance. This also means as a company we must continually provide the culture and psychological safety required to “fail” and iterate.

This setup also clarifies where the decision-making power should reside. Our team indicated that the most rewarding experiences have little management intervention or oversight.

A hard challenge.

Maybe this shouldn’t be a surprise, but from our team it was clear that sustained high-performance always correlated with a challenging goal. Knocking off a bunch of easy things quickly leads to boredom. People want to be challenged, and as leaders it works to our benefit to give people the opportunity to rise to the occasion.

Once done with our framework, we pondered the opposite. Imagine a project with confusing goals that don’t matter, that goes on forever, that has team members “checking out,” that requires never-ending management check-ins and offers no decision-making ability, and presents no challenge whatsoever.

No one wants to be part of that.

Nothing guarantees that your company is the next Dropbox, but by applying these easy principles for high-performance, it takes you that much closer.

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Ayushman Pershad

Founder & CEO, Syntax

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