How product and engineering managers can lead with empathy

The last few years have been marked by era-defining challenges of public health, market instability, and war. These have completely altered how we work, how we communicate, and what we value. Perhaps more than ever before, it’s up to leaders at organizations to create a culture where people know they will be supported in their work and career, regardless of the challenges that they may face.

An empathy-led organization is one which takes its employees’ macro and micro circumstances into account and cultivates a work environment where they can thrive professionally without sacrificing their authentic selves and personal lives.

At Pipe, we continuously work to ensure our values of empathy, safety, and sustainability percolate from leadership to our product and engineering teams, visibly impacting the way we work. We’ve found that while there is no single hotfix that alone builds an empathy-led organization, there are certain steps leaders can take to get started.

Building empathy requires a deliberate process to be put in place, which is open to iteration and improvement and tailored to the company’s culture and the people it hires.

Assess for culture fit at the hiring stage

Culture usually trickles down in the early stages of startups. The values that leadership brings to the table end up reverberating through the teams. Before hiring, leaders need to vibe-check themselves. To build an empathy-centric culture, leaders must first learn what that means. Only then can they identify candidates for empathy and culture fit.

Assess your current company culture for empathy.

Empathy is not a project you can ship—it’s a horizontal track that requires continuous improvement; therefore, it’s difficult to answer the question, “Does your organization lead with empathy?” The answer will never be a yes or no, but somewhere along a scale.

At Pipe, we regularly have check-ins and Kaizen (continuous improvement) meetings where we intentionally provide the space to focus on surfacing issues on a non-project, meta level. Check-ins can be between an entire group or team and their manager, or between a single team member and their lead or manager. Having a combination of meeting formats helps people voice concerns in whichever setting they feel most comfortable. Kaizen meetings prompt people to think about how processes, workflows, and communication practices are working for the product, engineering, and design teams as a collective.

Involve your team in the interviewing process.

Great leaders will involve the rest of the team in the hiring process. At the end of the day, it’s the team that will interact with the new hire on a daily basis and will have the most insight into whether the candidate is a good fit for the team’s dynamic and specific needs.

At Pipe, we enable leaders to figure out what culture fit means, not just for the organization but also specifically for their team. Based on this, the team can ask themselves, “Is our team missing someone fast and scrappy, or someone who can bring us greater process and structure?” Is it someone who works overtime to meet deadlines or someone who plans ahead to mitigate schedule conflicts? There is no right or wrong answer here. It’s whatever the team needs.

Help your team define what they are looking for, and teach them how to find it.

If the team is involved in the hiring process, it’s helpful for them to have a reference guide they can rely on to help them assess a potential candidate. The same guide may not work for every team, but it should at least cover a few basic questions and follow-ups that help them conduct interviews with potential hires.

At Pipe, we have an “Interview Tips” document, which helps guide interviewers through the screening process. This document covers our general evaluation criteria and some helpful questions you can ask, and also specifies topics to avoid, such as personal or biased questions.

Ask your team to choose an onboarding buddy.

An onboarding buddy is someone a new hire can go to with any question they may have about their role, the onboarding process, the product, or anything else without feeling like they are being a burden. The onboarding buddy is usually a member of the team the new hire is joining, and supports them for anywhere between 2 to 4 weeks.

At Pipe, every new hire has an onboarding buddy assigned to them. This person usually reaches out to the new hire even before their start date to introduce themselves and let the person know that they are being awaited. The onboarding buddy is also responsible for setting up the onboarding document for the new hire. Based on a template, this document covers topics such as account setup, learning about the product, information about ongoing projects, and more.)

The buddy also suggests a few different people the new hire should meet outside of their immediate team to help them learn about how Pipe functions as a whole. The onboarding buddy also makes sure the new hire has spin-up tasks in the backlog whenever they feel ready to dive into some light-weight work.

Make sure that the onboarding buddy is not always the same person, and that this responsibility is evenly distributed across the team. The buddy’s workload must be adjusted to account for this new responsibility they will be taking on.

For fully distributed companies, it helps if the onboarding buddy and new hire share similar backgrounds and time zones. It is much easier for a EU-based person to onboard another EU-based teammate—they will most probably be going through a very different HR process than a teammate from the US, and can be available to answer questions about this and more throughout the working day.

Adapt your communication style

Every person has a different communication style—some people thrive in large meetings and video calls, others prefer async Slack messages and deep focus work. Some people may be open to very candid and specific feedback, while others may prefer to be gently nudged in the right direction. As a leader, you first need to understand what your team member’s style is, then adapt your interactions based on that. This usually makes conversations more productive—people will focus more on the topic of discussion, rather than its delivery method.

Ask your teammates to write a guidebook for themselves.

This is a document that captures the basics of a person’s work and communication style. New hires are asked to create this document for themselves, and then share it with the rest of their team. They can also see the guidebooks for the members of the team they are joining.

At Pipe, we have “Working with X” documents. So, for example, the “Working with Sanja” document captures my preferred communication medium, what my work process looks like, how I usually like to collaborate with teammates, things I often do that may annoy people, and things that erode my trust. Writing such documents about yourself is a great exercise for people to go through, especially those who may never have thought about their preferred method of communication.

These documents can be as unique as people want, but there are a few key questions, shared in a guide, that your teammates should answer in order to cover the basics:

• What mediums of communication do you prefer? Some people prefer email, some prefer Slack, some like to hop on a Zoom to give you an update, and some live in Notion docs 24/7.

• What is your preferred work schedule? An easy way to automate this is to set up your working hours in your calendar and use an intelligent calendar system to set your preference around meeting hours, focus time, lunch, etc.

• What is your thinking and working process? Some people like to jump straight into execution, some need to take a step back and look at the bigger picture.

• What is your collaboration style? Forcing someone into a specific collaboration style is a fast track to emotional burnout.

• What things do you do that may unintentionally annoy others? Mine are overusing emoji and gif replies 😅.

• What are some things that erode your trust in others? Different people approach trust differently, but it’s far easier to build trust when you have an explicit guide of what not to do in your work relationship with a person.

• How do you like to receive feedback? Some people prefer radical candor, others like gentle nudges. Some prefer you give them specific examples of areas for improvement, others prefer more general coaching.

• How do you measure success? You’d be surprised how many different ways of measuring success different people have. Some people thrive on velocity and shipping fast, some are fulfilled seeing their team succeed, and some like to see their metrics improve.

Supercharge your meetings

While meetings are essential to working together, they need not follow an expected structure—synchronous, weekly, hands-on—to be effective. The types of meetings that a leader or team holds can be thoughtfully tailored to the agenda, team members’ communication styles, time zones, and more.

Hold project check-ins in the format that works best for your team.

Project check-ins and status updates are necessary to keep teammates on the correct course, provide guidance where needed, and identify potential issues early. A lot of managers tend to fall back to a one-on-one meeting structure for these, however, there are plenty of other mediums that are effective.

At Pipe, we encourage teams to do project check-ins in whichever way they prefer. Some teams have weekly team calls where they go over the status of all projects and share achievements, blockers, and give shoutouts to other teammates. Other teams have scheduled Slack bots that ping them to share asynchronously instead.

Keep mental notes on your team members.

Noticing how a team member is doing at work and, if they bring this up themselves, in their personal life, can help you ensure you’re supporting them in the best way possible. The kinds of things to notice can include a variety of things:

• What are some important occasions in their lives? It might be good to suggest they take a day off on birthdays, other special occasions, and local holidays. This is particularly relevant to note in distributed companies, where company-wide holidays may not cover important dates in their region.

• Is there a struggle in their personal life with which they require help? If people bring up personal challenges, think about how you can best support them—whether that is offering them time off, additional HR resources, etc.

• What kind of work “charges their batteries”? Do they show interest in a certain area within the organization? Do they give best results when working with a specific team? Do they like to explore innovative solutions or nail down execution? This helps chart their career growth at the company.

• What kind of help with work processes do they need from you? Is it having a stronger voice in the room to shield their decisions? Do they need additional members on their team? Do they need more time or help to make a difficult decision?

• How much ownership do they prefer? Do they appreciate having someone to lean on every step of the way, or do they like to take full ownership of their work?

• What are they currently working on or participating in? Do they have too many things on their plate which are not obvious or clearly visible in issue tracking software? If it seems like they are taking on too many things at once, think about whether there is something you can help them reprioritise or reassign to someone else.

Build a framework for your one-on-ones.

One-on-ones should be structured in a way that enables your teammates to not only share what they’re working on and any blockers they’re facing, but also to grow personally and professionally.

Structure your one-on-one meetings in a way that makes it very easy to check in on all of the above—your mental notes will help you cover what seem to be the most important aspects of their personal and professional life. Filter the meeting topics based on your insight into their work and life. Focus on motivating them and enabling them to grow, rather than micromanaging their work.

At Pipe, we use an intelligent calendar system to help us schedule flexible one-on-ones. This system moves one-on-one meetings automatically to enable people to have more focus time, have their lunch break, or resolve schedule conflicts.

Create a safe space for people to work in

Feeling safe and working in a positive environment is a must. Particularly for fully distributed companies where people rarely meet and do not have cues like body language to rely on—furrowed brows to indicate they’re having a tough time or conversations over lunch to share personal news. Remote communication has less fidelity and people sometimes fill in the gaps with negative information, so it’s important to provide less opportunities for miscommunication and misunderstanding.

Encourage “watercooler talk” in a way that it’s not forced. Creating spaces to encourage people to chat about non-work related topics is a great way to build camaraderie and team cohesion. People can share what they did over the weekend, their hobbies and interests, their grandma’s best recipes, and more—the possibilities are endless.

At Pipe, we have a #watercooler Slack channel for non-work related chit-chat. We also schedule weekly watercooler events on the product, design, and engineering calendars, which rotate the event time so that they can involve people in all time zones. These are held as a huddle call on the #watercooler channel and everyone is welcome to join.

Encourage and mandate time off. “Unlimited time off” seems to be a common selling point on many job listings these days, but people almost always take less time off than they need. A vague leave policy can lead to insecurity and anxiety when it comes to requesting PTO. Ultimately, it’s up to managers to keep an eye on whether employees are taking sufficient time off, and proactively suggest they do so in order to avoid burnout from creeping in.

At Pipe, leaders pay close attention to their teammates. They stay on top of their workload, and also their PTO. If people seem to be overworking themselves—say, if they’re working on weekends instead of logging off—they are encouraged (and sometimes mandated) to take time off.

At Pipe, we have Summer Fridays, which is an annual practice of making 5-6 Fridays during summer a non-working day. It mandates people to take the day off and enjoy the sun.

Conclusion

Creating an empathy-driven culture is hard work—it requires as much thought and effort as building a product. And it’s never done in one shot, with reflections and iterations being necessary to the process. Leaders not only have to choose empathy as a core value, but thoughtfully work to refine practices that help it seep through every team and aspect of their company.