Principled Leadership

As organizations mature, it becomes increasingly challenging to optimize their operating model for scale while preserving the values which helped them succeed. The distance between leadership and front lines increases, urging us to be more explicit about the principles with which we operate the business. Here’s what I shared with my team as we grew from eight people to more than one hundred and twenty.


Over the course of the last two years, our team has grown from eight people to more than one hundred twenty. It’s been a sight to behold. But growth also brings its own challenges. Two years ago, we were in the trenches together day after day. We were close to the problems. The field of battle was concentrated. Today, the theater has sprawled. We have distinctly different businesses, different foci, and different skills. We have matured as an organization. And that maturity creates distance between each of our leaders and those on the front lines.

Distance is no reason to see a change in values. The same values that got us here will help our teams execute on a daily basis. Distance does require us to be more explicit about the principles with which we operate the business. Our team needs to understand how we prioritize our actions even if they aren’t learning that by everyday exposure.

The first step in sharing our operating principles is articulating how I think about leadership. I couldn’t be prouder of what we’ve built and believe that these principles have played a large role in enabling this environment.

My Five Leadership Principles:

Care Deeply.

Each person you’ve ever worked with or competed against has had great potential. The difference between those who excel and those who flounder is often found in how deeply they care about what they’re doing. When you are building product, caring deeply about your end users drives you to develop more delightful experiences. When you’re selling, caring deeply about your buyers causes you to understand their needs and bring them realistic solutions. When you are managing people, caring deeply about each individual causes you to take the extra time to coach and inspire them towards immense outcomes.
Caring deeply helps you achieve more. For leaders — people empowered with both authority and responsibility — caring deeply is critical. Care about your teams, the problems you’re solving, your customers, and your partners. Care in a way that brings out your best performance. And if you find yourself not caring — step aside to allow someone else to take the role. The individual that cares deeply will always outperform the individual that doesn’t.

Think Through Problems from Multiple Angles.

Every problem can be attacked from many angles. All too often leaders will arrive at a potential solution to a problem and adopt it. If that leader hasn’t thought critically about their proposal — if he hasn’t attacked the problem from multiple angles — often his decision will cause him to take the team on an untenable mission. Thinking critically is the solution to these types of problems.
This is not to suggest that we should overthink or over complicate our decisions. But we should challenge ourselves every day to find critical weaknesses in our thought processes. We must work to expose our unfounded heuristics and our subconscious biases. It is easy to find yourself on a foolish path if you fail to challenge your own assumptions and decision process. And that failure to think critically has negative consequences for the teams and customers that you should care so deeply about.

Know What to Prioritize Now.

With infinite time you could solve infinite problems in whatever order you choose. In life, you never have infinite time. In business, you never have infinite cash. Execution is a game of prioritization. Given the resources you’ve been awarded, every leader’s primary job is to prioritize the actions and efforts that are necessary. Make the right decisions in the wrong sequence and you risk abject failure.
For this reason, knowing what to prioritize now is critical. When you’re building a new product, that means prioritizing product over sales or the opposite. When you’re setting a strategy, that means prioritizing certain objectives at the expense of others. When you’re setting targets, that means thoughtfully identifying the drivers of your business that matter today. Knowing what to prioritize now also requires leaders to consistently revisit their actions and objectives and acknowledge whether they still hold true. Without a regular refresh of your priorities you risk allowing your team to stagnate with an objective that has long since been achieved or is no longer relevant to your long term success.

Empower Your Team.

Leverage is one of the most powerful concepts in life. In the software industry, leverage comes from writing a line of code and shipping it everywhere. In the finance industry, leverage comes from taking the same amount of time to make a purchase decision on 1 share of a company as it would to make the purchase decision on 1000 shares. In general management, leverage comes from your team. The more people you can trust to do great work on your behalf, the better off you’ll be for it.
The only way to successfully lead great teams at scale is to get leverage out of your incredible people. The only way to leverage incredible people is to trust them. No matter how smart you might be, you can’t be involved in every decision. If you are, you’ll just slow people down. You need to empower people to act; even when that action is contrary to what you’d desire. Your responsibility as a leader is to coach your team, to set direction, and to hire people into roles that you trust. Your job is not to micromanage them into obsolescence.

Make Tough Decisions.

A colleague at SAP once described to me the great compromise. Two individuals feel passionately about a topic. Each feels that they should be empowered to take action. The different strategies seem incongruent. However, choosing one will lead to losing one individual. The great compromise is to allow both to attempt their path forward… but in doing so, handicapping the chances either is successful. It’s a compromise that seems palatable at the point of the decision and seems foolish when both eventually fail. This isn’t just a problem of one organization. It’s pervasive. Humans naturally try to negotiate their ways out of situations where there are only bad options.
Ben Horowitz, the founder of Opsware and Andreessen Horowitz, famously wrote, “when you have to eat shit, don’t nibble.” As a leader you will end up in bad situations. You will be dealt a hand of cards that you simply can’t win with. And in those situations, it’s important make the tough call quickly and move onto the next hand. Don’t extend your losses by hoping for luck on the turn.
The worst part of these situations is that failing to make those tough calls might be easier on you. It is almost never, however, the fair or respectful option for your team. Avoiding a tough decision at the expense of your teams’ progress, career development, and general best interest flies in the face of caring deeply about your people.

Each of us is the cumulative set of our experiences. I’ve been lucky to learn from wonderful leaders who embodied these principles. I’ve seen the benefits of each. I don’t always execute flawlessly, but I always aspire to lead with respect to each of the above. To care deeply, think through problems from multiple angles, to know what to prioritize now, to empower my people, and to make the tough decisions.