15 months of reflection

We were raising our Series A round. It was 2015. An investor who had given us a term sheet took my co-founder, who also happens to be my husband, and me out to lunch in downtown Palo Alto.

Over tacos, he told us the story of why he’d first gotten into venture. “It was frankly my chance to live the American dream,” he told us, but especially my husband. “You know what venture is like — a bunch of undersexed, geeky guys holed up in their offices, with their super-hot assistants in high heels running around and making sure their every need is met.”

When we left that lunch, my husband and co-founder turned to me and said, “Guess they’re off the list, huh?”

I have so many of these stories that they’re frankly exhausting to relive and share. I’d like to say that my experience has been unique, but of course it hasn’t. As a younger woman in the industry, I experienced pregnancy discrimination, sexual harassment, and fell into the abrasiveness trap. My more recent experience — as a woman over 40 raising money with her husband as a co-founder — has its own character, and is different from what a 25-year-old single woman might experience. But for every superficial difference between our stories, every snowflake is just snow, in the end.

When we started Textio, it was with the idea of building a team where there were fewer of these stories — not just for women on our team, but for everyone who is accustomed to being on the outside. 2020 caused me to wonder whether we were succeeding. For me, the last 15 months have been a near-endless cycle of wondering about this.

I’ve been walking around the outside of this topic for many months now, trying to figure out how to say what I’d like to say. It feels both painful and inadequate. But after the Basecamp and Patreon announcements in the last couple of weeks, I decided to at least try.

Why aspire to something?

Most leaders will tell you that it’s important to establish shared cultural principles for a team. When principles and values are clear, they do two things. First, they let people decide whether they want to opt in to what you’re creating. Second, they become a touchstone that everyone can use to make and assess decisions.

At Textio, because we assumed that our core values were shared by everyone who chose to join the company, and because we talked about them often, we waited literal years too long to write these down. This was a significant leadership mistake.

Writing something down makes you get really clear really fast on what you believe. It also helps other people opt in or out of your mission, because not every organization has the same aspirations.

As a leader, the most honest thing you can do is share your aspirations clearly. It is a monumental amount of work to go from aspiration to reality. But starting with your true, clear aspirations lets other people decide whether or not they want to be part of what you’re aspiring to in the first place.

Coinbase did that a few months back. Basecamp did that a couple of weeks ago. I don’t share the cultural aspirations that those leaders articulated. But the aspirations themselves were certainly very clear. And as with any clear articulation of cultural values, people respond by sticking with you, leaving you, or joining you.

A controversial aspiration: Bringing emotion and identity to work

Before starting Textio, I had led teams at other companies. By and large, I enjoyed middle management. I felt close to the work and to the people doing the work. I built real connections with the people on my team. But by definition, my degrees of cultural freedom were limited. I inherited so much from the broader culture around me.

Starting a company of my own was a chance to define things intentionally from the beginning. I could build a team where real connection between coworkers was not simply the choice of any individual manager, but part of the cultural apparatus of the entire company. For those real connections to develop, I felt, and still feel, that people need to feel safe and comfortable to bring their real selves to work.

A few months ago, an engineer on our team wrote a document to all of Textio in which they asserted that our company believes that emotions belong at work. I have been thinking about their assertion ever since the engineer published it.

I felt gratified by the observation. I do believe that emotions belong at work. Perhaps relatedly, I also believe that identity belongs at work. Someone else may know how to build something meaningful without their emotion and identity at the center. However, I do not know how to build this way or lead this way.

When it’s functional, this way of working makes it possible for people to bring their honest views to work. In the best case, people not only bring their own perspectives, but stay genuinely curious about other perspectives too. This helps teams make better decisions, which is great. But making better decisions is not the biggest benefit of building a workplace where identity and emotion are central.

If I get where you are coming from as a person, if I see your humanity, I am much more likely to go the extra mile for you. I am more likely to hear your perspective with an open and curious mind. I am more likely to feel seen and heard by you in return. Above all else, we are just more connected to each other. Connected teams have an unfair advantage. They are force multipliers. They are more powerful than the sum of their individual parts.

But here’s the thing: When you acknowledge that people have a voice, and you ask them to use it, and they do use it, you are going to hear things you don’t like.

If people have different experiences from yours— and they do, whether on your team or in the outside world — you are going to hear a LOT of things you don’t like. You are going to hear things that you question, reject, feel defensive about or threatened by.

I can’t count the number of times that I have tried to minimize, or wanted to minimize, this messiness. After all, we are running a business! We have deliverables and deadlines! I am accountable for making things go up and to the right, and for keeping everyone employed! Can’t we just stay focused on what’s important?!

The problem, of course, is that when you don’t listen, the business you build doesn’t work that well. You make worse decisions, and you lose the power and potential of a connected team.

Early on at Textio, I met an investor who argued that aiming for diversity is a mistake in an early team. After all, he argued, if everyone shares a background and a way of thinking, it is a lot easier to reach consensus, make decisions, and move fast.

He’s not wrong about monocultures being able to move faster. When everyone shares an identity, discussions may be less informed, but they are also less messy. It’s easier to disagree with teammates when disagreement feels pragmatic rather than existential. You don’t have to work that hard at inclusion when no one is meaningfully different from anyone else.

But if you are committed to building a company that represents society as a whole — and it’s worth naming that not everyone is — then your team includes people who have different identities. And if people have different identities, running your team in a way that pretends they‘re all the same is a fast way to lose.

Reality bites

Unfortunately, your cultural aspirations aren’t enough on their own.

While cultural aspirations matter, I believe that the reality of someone’s experience at work is mostly about their everyday workplace. What is it like to work with your colleagues? How does your manager give you feedback? Do people commonly express contrary perspectives? What performance and behaviors get promoted, tolerated, or questioned? Who is held accountable, and for what?

In other words, your cultural aspirations are only as good as the systems that you build to encode them: the behaviors that get people hired, promoted, and fired; norms for making decisions; meeting cadences and procedures; the collaboration tools you use; how transparently you share financial information with the team. To define these nuts-and-bolts systems is to define your cultural reality.

For some businesses this is especially fraught. At Textio, like Basecamp as a matter of fact, we make tools for workplace communication — which means that there’s no clean way to separate the products that we make from our own team culture and cultural aspirations.

There are always gaps between aspiration and reality. When members of our team point out the gaps that they see, which happens on a fairly regular basis, it is like learning that the foundation of your beautiful house has termites.

It is excruciating. Who wants termites?

In a perfectly inclusive environment where showing identity and emotion were operating norms, everyone would feel equal comfort with expressing themselves. Not only that, they would also show equal openness to hearing their various teammates’ experiences and perspectives.

But what if everyone is aligned on the cultural aspiration, but reality still falls short? Because once you get past the Basecamps of the world that have explicitly set out different cultural aspirations, I think this is the state of many modern companies.

It is easy to look at the state of things and conclude that no one is really getting this right. Industry-wide, this is observably true. But if you’re committed to building an inclusive environment where everyone feels equal comfort bringing themselves to work, and you’re not all the way there yet, it doesn’t make you feel better that no one else has figured it out either.

It doesn’t make me feel better at all.

Principles matter, but systems matter more

In our first several years as a company, I approached disconnects between our cultural aspirations and people’s lived reality in a very hands-on way. If someone was having a bad experience, there was no meeting I would not take to try to understand it better. Once I became personally aware of it, there was no situation I would not wade into and try to micromanage to understanding and reconciliation. I thought, if I can just personally hear what is going on, I can address what is on people’s minds. I can hear people, and they will feel heard.

I felt, and feel, people’s stories extremely personally. The more personal time I spend on a situation trying to build understanding between people, the more painful it is when I fail. And as our team has grown, I have failed at this more often than I have succeeded.

I still believe that identity and emotion belong at work. I think this is a prerequisite to any meaningful work you aim to do on inclusion. I also think it is a prerequisite to building an ethical and impactful company.

However, one of my most painful lessons is that delivering on these aspirations must go beyond the purported empathy of any one particular leader or manager, even and maybe especially the CEO. I have often tried to micromanage miscommunications into shared understanding. I’ve discovered that not only does this fail much of the time, it also actively undermines any long-term chances of building genuine understanding within a team.

As a leader, you can’t be in every room. But more than that, you shouldn’t be in every room.

There are only two ways of handling this dissonance, and I’ll be honest, they are painful: You have to analyze and rebuild your systems, and you have to hold people accountable within those systems. Including managers, executives, investors, employees, and yourself.

(Re)building the system

When it comes to building inclusive environments where identity and emotion are at the center, it is tempting to adopt a binary mindset: An environment is either perfectly inclusive or it is terrible. But many, maybe most, environments are somewhere in between. Textio is.

It is hard work to look critically at your own system. Even and especially if it has a lot of elements that are working well. It is important to honor the things that are working, which can and do coexist alongside the things that are not working. It’s also important to look with clear eyes at the things that are broken. Both things can be true at the same time.

Over the last year, we chose a few specific investments to focus on in order to help us do better at living our cultural aspirations. I won’t pretend that we know how well all of these investments are working yet. What I can say is that we chose them with consideration.

We have changed so much about how we work over the last 15 months. The current climate has highlighted existing disparate social realities and created some new ones. 18 months ago, our team was nearly entirely colocated in our Seattle HQ. That was a principled stance on our part as a company, based on the belief that we generally build stronger relationships with people with whom we share a space.

Today, we have team members working in seven states, and no intention of returning to the way we were. We miss some of the advantages that we got with full colocation, but we have also created new ones. People have much more flexibility, both in location and schedule. We have access to new talent communities. But above all, we have had to find new ways to collaborate. When “let’s get lunch” isn’t a shortcut, we have to face different perspectives and disagreements head-on.

Because we’re mostly working from home, we’ve also found it harder to take a real break. After all, I’m sitting on the same couch whether I’m working or watching TV. My daughter’s bedroom doubles as my home office. To help us find a sustainable rhythm, we have introduced several additional Shared Days Off for our team, in addition to our regular holidays and PTO. When we all take a break together, we don’t have to fear the digital onslaught of piled up notifications when we get back online.

Every person has a different work situation and a different residential situation. How can someone not bring it to work when their family has come down with COVID? How can someone not bring it to work when they feel personally threatened by law enforcement? How can someone not bring it to work when their desk is right next to their baby’s crib? Identity has to be at the center of work because it is at the center of life. Our ways of working need to respect that.

We have also done a major overhaul of how we pay for work. 18 months ago, we had descriptive career maps and company-standard pay ranges for roles. But we didn’t publish these ranges to our whole team, and it was hard for any individual person to know where they stood relative to their peer group.

This past year we undertook a major revision of our pay system. This included working with a third party firm to research fair pay ranges for our market so we could update the ranges we were using. We mapped these ranges onto our career journey documents and published the whole thing to our team. Every person on the team has clear visibility as to where they are within their range and how it relates to their level and performance.

In addition, we significantly revamped our system for issuing stock options. We formalized and published standard option grants for every role and level in the company. Each new hire receives the standard grant for their role and level, and team members receive totally programmatic refresh grants on a predictable schedule.

After all this, we retained an external labor economist to review our full set of compensation data, pay range by pay range and employee by employee, to make sure there were no equity gaps in our decisions.

Our goals in defining our pay system were to be both programmatic and transparent. In the past, we’ve been programmatic. But we haven’t been transparent. In system where identity is central, people rightfully expect both.

One other internal area where we’ve made major investments is in getting our team members additional resources for coaching and support. If you believe that emotions belong at work, then it also stands to reason that people need support expressing and managing them. We invested in a Bravely partnership, where anyone at Textio has access to confidential coaching from Bravely professionals, in a safe and confidential space outside our team.

Finally, we’ve taken a look at our team’s organizational structures in light of all of the above. In some cases, we’ve made significant personnel changes or updates to reflect our beliefs that identity and expression are hallmarks of an inclusive team. If cultural aspirations are only as good as the system that encodes them, then the system is only as effective as the people who work within it.

Many of these projects deserve more detailed conversations of their own. And while things like Shared Days Off and supporting external coaching for all employees have been clear wins, the truth is that the jury is still out on several of these efforts. What I do know is that we’re trying things, and we will keep trying things. Because while the process starts with setting out cultural intentions, reality shows up most clearly in our everyday systems and interactions.

This process never stops. When I shared this post with our team internally before publishing it broadly, they correctly pointed out that our current written principles need to be more explicit about how we think about identity, emotion, and inclusion at work. If you’re doing it honestly, the flywheel that connects your cultural aspirations, your reality, and your systems keeps on going. Identifying and closing the gaps is continuous hard work.

In my view, it is worth it to resist the binary: the belief that an environment is either perfect, or it is terrible. The binary lets you off the hook from doing any real work.

The work to set clear cultural aspirations is impactful, but it is just the start. The work to understand where your aspirations are falling short is harder and more painful. But the work to build systems that stay accountable to your aspirations, and to staff those systems with people who are committed to that accountability, makes or breaks your company.