This post was originally published on the Dashing Leadership blog.

Startup leaders worry about many things and one of those is the question of whether their team is working hard enough. Usually, it's the CEO who brings this up, though no senior leader is immune from this thinking. In the leader's mind, they are working as hard as possible, throwing themselves into the work from 9am to past midnight, never leaving themselves a moment of respite. As heroes of their own story, they view their efforts as valiant and noble, setting an example for others to follow. But when they see their teammates working fewer hours than they do, they start to fret. Questions start to appear: "Why aren't the others around me working as hard as I am? Do they not care as much as I do? How do I get my team to work harder?"

This situation ironically causes the leader to anxiously spiral into spending more time worrying about this perceived productivity problem and less on doing actual work. What's going on here? And more importantly, how do we get ourselves out of this situation?

Using hours worked as a proxy for progress

We are taught that in the early days of a startup, we must put in very long hours to get the plane off the ground. There is truth to that idea; when we are creating something valuable out of nothing, we usually end up having to spend a lot of time turning over many rocks. In a universe of unknowns, it is extremely difficult to measure progress and so we end up using hours worked as a proxy.

But past the 0 to 1 days, when product-market fit has started to take shape, hours worked becomes a less useful measure of progress. At this point, two questions emerge: How do we measure progress? And how do we set the pace of progress?

One useful way to answer both questions is to implement the Objectives and Key Results (OKR) system. My friend Niket Desai wrote a fantastic summary on the topic here.

Many founders struggle to choose "the right set" of OKRs, especially in the very early days. For this, I like to point to the concept of a North Star metric. This is a number that meaningfully tells us how well we are delivering value to our customers. Amplitude goes into this concept in detail and Josh Elman has an excellent set of slides on the same topic.

When it comes to setting the pace, the key is to define goals on a time-bounded basis. Once the team has agreed to achieve a result within a certain amount of time, the pace of progress naturally follows and we can stop worrying so much about hours spent working. At this point, the concern becomes one of accountability for results.

Viewing people as objects

Another trap that CEOs often fall into is they end up viewing their team as objects rather than people. By this, I mean the leader sees their teammates as merely resources whose purpose is to deliver results. And though everyone agrees that results are important, that cannot come at the cost of failing to see others as human beings, with their own perspectives, needs, and concerns. Working in "crunch mode" may work in short bursts, but it will eventually breed resentment and poor performance if done chronically.

It may seem extreme to say the leader views others as objects. But this is in fact what is happening when we view our teammates' concerns as less important than our own. When we demand that people work more hours, we not only alienate ourselves from their humanity, but we also run counter to what fuels human motivation. The solution isn't to lament that people aren't working longer but to get curious about what motivates people in the first place.

According to Self-determination Theory, there are three important factors that fuel intrinsic motivation:

• Autonomy: the sense that we have control over our actions and that we have choices
• Competence: feeling effective and that our skill is growing over time
• Relatedness: connection to others and the knowledge that we are contributing to something greater than ourselves

Knowing this, leaders can do themselves a favor by taking these steps:

• Clearly articulate the company vision and why the team exists in the first place (relatedness).
• Draw a direct line between employees' efforts to the company's high level goals (relatedness and competence).
• Collaborate with teammates to define clear goals but leave it to them on how they execute (autonomy).
• Have regular 1:1s and show genuine care for them (relatedness).

The point is to shift away from a place of judgement to a place of curiosity. Instead of "My team isn't working hard enough", we go to "How can I better meet my employees' needs so they are motivated to work harder?"

Dealing with our own stuff

Finally, leaders who struggle with this question of team motivation must recognize that chronic anxiety around productivity is likely to backfire if left unaddressed. In a bid to get more done, faster, we are likely to burn out both ourselves and our employees. Decision making suffers, an endless cycle of firefighting emerges, and the business ultimately underperforms.

As mentioned at the beginning, it is common for leaders to fall into a cycle of worrying, leading to less output, which only feeds the anxiety further. Worse yet, sometimes our awareness of anxiety triggers harsh self-judgement, leading us to avoid these feelings. This may bring temporary relief but simply perpetuates the cycle.

A sense of urgency is important, but not everything is urgent.

The key to breaking the cycle is to develop our self-awareness so we can choose conscious action instead of relying on ingrained patterns. When you catch yourself in the automatic behavior loop, ask yourself these questions:

• "What am I feeling right now?" Name the feeling and honor what it is trying to tell you.
• "What is the story I'm telling myself right now?" For example, you may be thinking that if you don't push everyone, then you will fail.
• "What need might I be meeting by feeling this way?" Perhaps it's the need for safety. Or the need to be seen as virtuous and hard working. Whatever the case, your brain is trying to take care of you in some way and for that, you should thank it.
• "In what ways am I serving my team? How might I be hurting them?" Be brutally honest with how you are treating your people.
• "Is what I'm worried about truly urgent?" A sense of urgency is important, but not everything is urgent.

Depending on what emerges from this inquiry process, you may identify important actions to take with your team. But oftentimes, the result will be an understanding that the anxiety is a false positive. There may be no imminent danger, despite what your brain is telling you. In this case, helpful practices for regulating emotion include meditation, affect labeling, and talking to a trusted confidant (a friend, a therapist, or a coach).

Thank you to Elizabeth Wang, Nicholas Robinson, Colin Liepmann, and Pradeep Elankumaran for reviewing drafts of this post.

So why Credit Karma? There were several reasons. I’ll start with why I decided to make a move in the first place.

Career Direction

Venture capital is a services-oriented business, first and foremost. While the work of finding great companies and supporting founders is gratifying, I realized it’s not where I want to focus my energy right now. The more time I spent with founders, the more I realized how much I miss being in an operational role. There’s nothing quite like the feeling of putting in the hard work to build and ship a product, especially one that makes a big impact.

I also feared that my skills would start to get rusty the longer I was out of the game. But forget about rust, I knew there was so much left to learn when it came to building great products. So making the decision to get back to a product team was an easy one.

Mission

Finding a company on the right mission was high up on my list of priorities. At Fitocracy I spent several years working to help people take better care of their health & fitness, a longtime passion of mine. I understood that good health is foundational to a good life. I believe the same is true of personal finance.

We are a country full of people experiencing an economic crisis. The fact is, nearly half of Americans say they would struggle to come up with $400 in the case of an emergency. The average American household is only saving 5.3 of their income. Most people are walking around living paycheck to paycheck and the stress associated with that lifestyle is nearly guaranteed to perpetuate the poor decision-making that led to it in the first place. It’s a vicious circle.

Credit Karma is on a mission to help people improve their finances through technology and education that get people on the right track. The many parallels between health and personal finance, both in terms of importance and common behaviors associated with them, were not lost on me.

Team

As I spent time with a number of companies during my search, the key criteria for me was to find the best team, one that I would both learn from and enjoy being around. Everyone I met at Credit Karma during the process was sharp, accomplished, and importantly, easy to connect with. There was a wide variety of backgrounds and personalities, but the one thing they had in common was a shared desire to build something that matters. Just my kind of people.

Trajectory & Impact

If you’re offered a seat on a rocket ship, you don’t ask what seat. You just get on. — Eric Schmidt

Credit Karma has been growing at an amazing rate ever since its founding. And at 60M users, hundreds of employees, and a $3.5B valuation, it’s certainly not an early stage startup anymore. Yet all of this has been built on top of a simple product that’s merely the tip of the iceberg. There are so many more products and services Credit Karma is going to build to help better its users' financial wellbeing. I’m excited to be a part of that future.