How I Manage - Principles of Empathic Management

This is intended to be a primer on how I manage teams. It will be continually updated as my views evolve. Last edit @ Sun Jun 13 2021.

The reason I decided to write this is that I have seen what really poor management can do to a team and it unwinds a company faster than poor product or churn.

You may already be familiar with the tech bro, hustle culture workplace that has come into vogue over the last decade. In an industry fueled by VC money, bad culture can thrive even in growing companies so when managers leave a company during a hype cycle, they spread it throughout the relatively small startup world.

Here's my basic thesis for managing teams:

A happy team is a motivated team. Motivated teams do great work.

If you start using positive teamwork as the metric for success, you start to notice that teams that work together well tend to win together.

A few anecdotal examples:

• In Top Chef, it's usually the underdogs that win Restaurant Wars because they're united against the top players. Why? The top players are having ego battles that distract from service.
• In Ted Lasso, the American football coach takes a UK soccer coaching position, despite knowing nothing about the sport. As he calls out in the show, it's about the players and the team, not the sport.

A happy team is a well-functioning team. When a team works well together it moves all the metrics positively.

Unfortunately, most of the books on management teach how to optimize people for output.

If you follow this strategy, especially with a smaller team, you may find that you're eroding a team from the inside. It burns people out.

It can work for sprints, but if you let that culture become endemic, it moves through your company like a disease, sowing discourse and doubt.

For people working in teams like this already, it can be a shock to hear that work doesn't have to be like this, especially if they haven't experienced work any other way.

They've grown up from a pedigree of teachers optimizing towards SAT scores and graduated into an agency or corporation with direct managers that value the output more than the people creating the output.

I've had a mix of managers, some excellent, wise, and successful - and the other kind.

However, I've learned the most from the worst managers.

In this post, I'm going to run through the basic tenets of management I try to follow in my day-to-day work.

This is how I manage.

Identify and internalize the feeling of a negative power dynamic

While not everyone has the same life stories to draw from, I'm sure you can think of a few times that you've experienced a power dynamic that didn't feel right to you.

This is hard to pin down, but it's been my north star in management situations that are new to me.

If you're having trouble remembering a time when there was an imbalanced power dynamic, here's an exercise.

Think back to when you discussed with someone that was in a position of power that made you feel like less than you were.

This could be with a teacher, former boss, or a coach.

Maybe they dismissed an idea you had, minimized the work you put into something, or made a sweeping statement that unintentionally impacted you and it hurt at a level that was a bit deeper than normal because their opinion mattered to you. Those feelings tend to linger and build resentment that can last for weeks, months, or even years.

That feeling is also something you as a manager can inflict on those you speak with.

It comes from having the higher ground in the power dynamic and the power to wound, intentionally or not, the people you speak with.

Remember that feeling, then layer it with other times you may have felt helpless in a team dynamic.

Maybe you had imposter syndrome or you weren't sure you were doing well at work and thought you may be let go.

Those two feelings, being wounded by someone in a position of power and being helpless to do anything, should be internalized and reflected upon regularly so you don't forget them.

Why?

You now have the higher ground in the power dynamic and the power to impart those feelings upon those you speak with.

Therefore, if you can identify when others are starting to feel that way during a conversation, you can begin to take the steps towards righting that before the situation escalates and your team member becomes disenfranchised with their work.

A lack of work satisfaction can lead to anxiously sharing negative sentiments with the team or just outright leaving.

If you can right the ship as it starts rocking, you can prevent anyone from falling overboard. Learn to notice when other people react negatively to your words, try to clarify your position, and make you're not causing unintended damage.

This doesn't mean you can't offer critique. Offering critique is a necessary part of being a leader, but it doesn't mean you have to tear the other person down.

Projects, not KPI's

Have you ever been in a position where it felt like you were assigned a goal where you didn't control enough of the levers to move the needle?

That's one of the problems with traditional, metric-driven objectives. Often there are other facets of the business that affect your ability to accomplish the goals set forth if you aren't in a position to control enough of the levers to accomplish the task.

That leads to pointing fingers within the team or just taking the L. Neither is a good solution and both end with unnecessary turnover as employees get frustrated with an inefficient system.

But, at the same time, as a leader and people manager, you may have large business-driven goals that do need to be accomplished (eg converting 1000 new paying users a quarter, decreasing the response time in an app, increasing the positive close rates in customer support cases, etc.)

These goals are typically much larger and are set to the scale of your department whether it's marketing, product, engineering, customer success, or snacks.

Set goals that scale with the capacity of the person to make change. If you're working with a writer, the goal shouldn't be "driving new user signups". It should be completing an article, something they can directly impact.

As a side note, sales folks are typically one of the only roles in a smaller organization that can actually drive impactful metric driven work at individual levels.

People first, company second

It's a shame that this is a controversial statement.

It's important to make this clear at the org level, so your team members don't feel like they need to make up excuses or balance potential health priorities to keep their job.

If you make it clear you care about them more than the hours they clock, you've already made positive changes in your organization.

A few examples where this can be put into practice:

• If someone lets slip that family they haven't seen in ages is visiting from out of town and they wished they had more time to spend with them, offer to let them take a few days to fully enjoy the experience. They'll come back in a better mood, more energized, and happy with their work-life balance.
• Surgery or health concerns. Just give them an extra day, no questions asked.
• If you're sensing burnout, encourage them to take time and reboot.

Let knowledge flow upwards

If you're not learning from your team, you're making a mistake. Hire people that are experts in their craft or hungry to become experts, then let them experiment, make mistakes and improve.

Take the learnings that they've gained, then make sure they get the recognition they deserve, while also sharing the learnings with the team.

Do public "post mortems", so that everyone understands what the outcome of the sprint was. This can be a presentation or just a simple bullet point list of what went into the project, what was learned, and the end result.

Post mortems also add a sense of completion that helps curb burnout.

Celebrate your team

A win for a person is a win for the team, but ultimately, the individual still needs to feel good about their achievement.

If a team member accomplishes something outstanding, yes it should go into your notes for the exec team or company all hands, but that person should also have the opportunity to take credit for their own achievement.

A quick example. If you're working in a remote team and your team member crushes their goals, let them share it in Slack. Then, you can call it out later in front of a smaller group or an all-hands, but let them have then individual win. They deserve it and will be walking on air after.

Output, not hours

Similar to the "projects, not KPI's" guideline, think about how you can reward people based on their pacing towards the goal. Not everything can be quantified in terms of hours spent with a green active icon in Slack.

Personally, some of my best ideas and tactics come to me when I'm on a walk or working outside. Separation from the constant notifications and a change of pace can jog loose a problem you've worked on for days.

Assess the work people have accomplished, not the amount of time they've spent working. If they're able to complete their work in 20 hours instead of 40, that's a good thing. You hired a smart, talented person. Don't bog them down with busy work just to fill their time.

Let the quiet voices be heard

I love async work.

It's one of the best measures of work output and quality because it's hard to fake. Ineffective managers tend to despise working remotely and asynchronously because they have no idea how to manage people without interrupting them face to face and dragging them into spontaneous meetings.

But if you encourage deep uninterrupted stretches of work and recording your thoughts in Notion or a similar wiki tool, then everyone has the same volume of voice. Those introverts that have great things to share are in the same doc as the extroverts on your team and the work can be judged equally.

Acknowledge ambition, reward competency

One of the best squad leaders I've ever had the pleasure of working with didn't want to manage a team. Hated the idea of admin work, more responsibility, etc. At the same time, they had a natural knack for creating smooth systems and processes. I had to try 3 times to promote them from an operator with no direct reports.

It was still one of the best management decisions I've ever made, but while this was happening, I was trying to work with someone who wanted to move up but had trouble keeping their work organized.

I did my best to acknowledge their desire to move into a management role and work with them to get them there. It took two years but it happened. The other person took 6 months and didn't have any desire. They're both excellent managers today.

Treat others as you'd like to be treated

Simple right? You may remember this adage from your childhood. Ultimately, it is one of the core pillars of my management style. Just to make sure I don't just leave you with a platitude, here are a few ways this can be applied:

• On 1:1's, try not to check your phone, notifications, or multi-task. If it feels like you're too jammed up, either shorten the call and devote all of that time to the other person or reschedule to a time when you can give them the attention you would expect in their shoes.
• In slack or email, use responses that would have trouble being conveyed incorrectly. This can be hard and might sound a bit excessive, but I had a younger team member confess that they spent an entire afternoon worrying about being let go because I responded "k" to a message.

Wrapping up

This management style may not be for everyone but it's inherently simple at its core. Treat your people well and the work will improve. Inverse negative feelings and be aware of the power you have, then try not to take advantage of it. Reward strong performers and initiative. Care about the end result and not how long it took to get there.

Managing doesn't have to be difficult, but if you don't have some type of developed principles around it, the learning period can be rough, not only for you but for those that work with you.

Hopefully, this post helps guide you in the direction of positive leadership.

Resources

The Netflix style of leadership and culture helped inspire this.