Spooky Software

Organizations that move our soul have a clear vision — a vision that elevates the mundane and repetitive into something exciting and life-giving.

— Chris Baca, on cultural fit in the workplace

As I gain more experience in the tech industry, I’ve been thinking more about what it means to be a leader. How does one lead well across the spectrum of roles — as staff engineer, tech lead, CEO, manager, or others? How does one do a good job, and what does success look like? Here are some “resume pieces” that I often encounter as characteristics of a good leader in technology:

• Intimate industry knowledge and domain expertise
• High degrees of technical proficiency
• Passion and drive
• Strong networking skills and industry connections
• Creative and unconventional thinking

These attributes are useful tools to have for any successful venture, but I think they also miss the point. I could possess all of these, yet they wouldn’t reveal whether or not I’m capable of leading work that matters. If we focus too much on the project’s technical soundness, operational efficiency, or even profitability, then we can become confused about what we’re doing and whom we are doing it for. Instead, we need leaders who possess qualities that inspire mission-driven work that is grounded ethically. A clearly defined ethical mission elevates work beyond simple TODOs and business milestones and ultimately, makes the project meaningful.

Parameters of Meaningful Work

Organizations can have a wide range of missions, and I don’t mean to prescribe what they should look like. We all should get the opportunity to choose what’s important to us. However, I think there are some boundaries that all mission statements should operate in. It is leadership’s primary responsibility to corral and shepherd the organization in the following ways.

First, ethically grounded work begins with transparency and excellent communication from leadership about the mission itself. Good leadership focuses deeply on answering the questions below for everyone on the project and assures that collaborators are on the same page, especially other leaders:

• What are the objectives of the organization?
• Why are those objectives valuable? And whom do they benefit?
• What methodologies are we choosing? Why did we choose them?

For the sake of safeguarding the mission, leaders embed open, transparent, and free-flowing discussion deep into the organization’s everyday practice. They call for regular, frequent feedback that is frictionlessly given and taken, with high degrees of psychological safety. They also offer training on how to dispense and receive feedback, so that collaborators can work independently with confidence and offer corrections when things get off-track. Good leaders recognize that open questioning ought to be tools for clarification and understanding of the mission and how work aligns with it.

Moreover, meaningful work requires leaders to treat colleagues with respect and consideration. I worry that we focus too much, for instance, on a director’s ability to promote growth in product delivery and not enough on their ability to promote growth in the people who build that product. Extraordinary leaders craft workplaces and cultures that motivate not just quality output, but also, more importantly, enable those involved to better themselves. Leaders advocate for, share with, and invest in those around them; they inspire and require professional growth. Successful leadership is where participants are more equipped than they were the day before and where they can have uninhibited access to the good life. Growth isn’t just for the business, external stakeholders, and customers, but also coworkers.

Finally, good leaders ensure inclusivity because it is paramount to successful and impactful work for everyone. Diverse perspectives and backgrounds help us to be smarter and more innovative. If someone is forgotten in the process, an organization is no longer entitled to the execution of its mission and is not meeting its full potential to enable its collaborators’ growth. To that end, leaders ensure their efforts to encourage diversity are not superficial. Tokenism cannot lead to meaningful work. Contributions can come in many shapes, sizes, and frequencies, and they may be fueled by differing reagents because, ultimately, meaningful work is about the beat that these contributions step to and the vision they service.

Markers of Success

What are the markers and measurements of good leadership? What are not? With a well established culture of open and regular feedback from all corners of the organization, leadership can critically reflect on their own performance and measure others’ trust in them. In particular, feedback should be used as a signal of whether collaborators feel that leadership is clearly communicating the mission and maintaining the relevant constraints on work.

In addition, leaders should find ways to measure, as directly as possible, how closely the organization’s actions align with its mission. For example, if the mission is to decrease the negative environmental effects of data center computing, leaders should prioritize measuring, say, the impact of the product on data center electrical usage, over tangential metrics such as “user engagement.” If leadership has spent enough effort assuring that everyone believes in the mission in the first place, then these direct metrics can also be a reflection of the meaningfulness of the work for employees.

Perhaps, to some extent, all metrics are false shepherds. Here are some commonly employed, but misleading, measurements of successful leadership:

A leader should be careful when prioritizing “consistency” for its own sake. I often witness leaders give too much weight to some sense of stability within an organization. Just because the team was building one kind of product yesterday doesn’t mean that they need to continue to build the same one today. One becomes blind to new insights if they mistakenly see persistence as more valuable than realizing the mission itself. A leader’s commitment is to cohesion in messaging of vision and clarity in communication — not to particular implementations of that mission statement. Changing directions is not a marker of failure, but can be an indicator of growth in leadership and the organization.

Additionally, being an exceptional leader is not the same thing as being omnipotent. Leaders should avoid measuring their skills against the skills of their coworkers. They don’t need to be the best at every skill the organization needs or know exactly the best way to implement everything. An engineering manager doesn’t need to know how to turn the database inside out, the exact details of making an inclusive and accessible web interface, or what the best sales strategy is. Good leaders enact guardrails, philosophy, and high-level constraints; they don’t draw maps or dictate exactly how it all happens in practice. If leaders foster institutions where experimentation is freely granted and respected, then they can be force multipliers for those they lead. It’s the employee’s job to be amazing at what they do, grow, and execute on the shared mission in the best way they know how.

Building Teams

It’s important for leaders to recognize how crucial hiring and retention practices are to executing on a mission. Conventional thinking about how to manage personnel can handicap leadership’s responsibility to enforce accountability to the mission. For example, especially for new and small organizations, it can be tempting to hire anyone who’s willing to work on the project at all. However, just because someone is an old college buddy doesn’t mean they care about the vision; you need allies for the mission, not friends. As another example, high employee retention rate is commonly seen as a marker of strong leadership, but retention for retention’s sake disables one’s ability to let someone go who isn’t on the same page. I would advise that one be more picky and ensure that hires are truly for the right reasons, instead of falling for romantic ideals of “making it work as we go” or “sticking it out.” Missteps here are an outright disservice and a drain on both parties’ time and energy. I would say if no one is ever leaving or even, occasionally, being dismissed, the organization is not actually encouraging growth in its members.

When recruiting, leaders should evaluate candidates for alignment with the mission, not just expertise, technical know-how, and experience. This may mean skipping the coding exercises, especially for more senior candidates, and instead, looking to other modes of assessment, like essay writing or interviews about the candidate’s values, perspective, and philosophy. Candidates should be required to answer mission alignment questions such as “What attracted you to this position?” Leaders can also ensure that the candidate has enough time (not the “last 10 minutes”) to ask questions that demonstrate motivations, aspirations, and values. I could go on and on about how wasteful and exclusionary whiteboarding interviews are, but it’s also massively draining on the organization later when there’s a sudden surprise that a new employee feels very differently about goals and vision. Leaders should reject candidates for misalignment as easily as they reject someone for lack of technical competence. An engineer with 20 years of experience may be an attractive hire but still not belong on the team if they don’t agree with the mission.

I recognize that “cultural fit” has been used in unacceptably discriminatory ways — actively excluding women, people of color, and others from the technology industry. But I believe that with ongoing, critical reflection and willingness to engage in anti-racist, anti-sexist practice, we can still be discriminating in ethical, equitable ways and avoid exclusionary or cultish environments. Hiring processes should include specific and aggressive diversity goals, but relevant values and mission alignment are not dimensions of diversity one should be aiming for.

Being More

I acknowledge that the perspective presented here on meaningful work and effective leadership comes from a position of privilege, especially in the technology industry, which enjoys a particularly cushy existence. The opportunity to see labor beyond a monetary transaction is not equally available to everyone. However, this is precisely why I am appealing to leaders in technology and calling for action: leaders in this space can afford to break the status quo and provide this privilege to their colleagues.

Technological “innovation,” industry “disruption,” and “crushing it” are themselves never the goals; the organization has a deeper mission that leadership defines and focuses their collaborators’ efforts on. It is the primary objective of a good leader to heighten work to be more than software specs, more than quarterly financials, more than product milestones, and even, more than employee paychecks. C-Suite executives, tech leads, hiring managers, staff and principal engineers, and other leaders should drive efforts toward a mission in order to elevate work to be more meaningful.