Literature on the importance of empathetic leadership is everywhere, especially in software engineering. You would be hard pressed to find anyone that doesn't use the language of empathy when describing their approach to management. Someone who eschews personal connection and empathy in the workplace entirely sounds like a caricature...a cartoon villain that couldn't possibly exist.

However, just because we now talk about things like relationships, emotions, trust, and authenticity at work does not mean that we have all magically become more empathetic. In fact, the situation is more complicated than ever. Sociopaths walk among us and now have a beautifully crafted Trojan horse to conceal their machinations within. Even well-meaning managers have to walk a fine line between outright manipulation and influence.

Empathetically Dishonest

We believe ourselves to be empathetic people, either as a natural facet of our personality or through practice and explicit effort. We read books like Radical Candor and Nonviolent Communication (both terrific, btw). In one-on-one's, we listen attentively and express deep, almost personal, concern for the other's feelings and experiences.

...and then we go right on ahead and manipulate them anyways. It was just a performance. What happened?

Intent is everything. An empathetic point of view enables you to feel someone else's pain, but that does not require you to act on those feelings of reciprocity. In practice, that means your personal goals and needs are still the driving motivator for all your actions. Without realizing it, you stop seeing people as people, and instead see them as tools to get what you want.

Consider the following incident, which (partially) prompted this entire article:

I was a rising manager at a growing company; we had recently hired engineer #14 and a formal org structure was emerging. I had not yet assumed management of all the teams, and for this team in particular I was just the project manager. Bob, my boss and CTO, was officially manager and technical lead of the product this team produced. Ryan was an individual contributor hired to replace Bob as the technical lead, due to his many years of experience with the underlying technology.

Bob and Ryan were not getting along. Ryan would submit code that was much more defensive than the norm for that product, and often structured his work in a way divergent from Bob's. It wasn't necessarily wrong, just different. Like anyone else, his code had gaps and flaws that Bob would point out in code review. Mixed in with the valid criticism were comments that boiled down to "this isn't how I would do it, therefore it is wrong, please do it my way instead."

After months of this, the relationship had degenerated into outright micromanagement. Ryan could not submit a line of code that was not close to, if not exactly, what Bob would write...even in cases where Ryan's code would have been more resilient. One severe occurrence of Bob overriding Ryan occurred over our team chat, and as the conversation unfolded I saw Ryan (who sat across from me) become physically agitated...he had clearly had enough. I asked him to take a walk with me.

Me: what's on your mind?
Ryan: I just can't work like this, he keeps forcing me to change my code at the last minute and I can't get anything done.
Me: it feels horrible when nothing we do is ever "good enough" and the other party can never articulate what they really want.
Ryan: I feel completely paralyzed, I want to do good work but every line of code I think "is this what Bob would do?" and get stuck.
Me: it would be a mistake for us to hire someone with your experience just to throw that all away by forcing you to work like Bob.

(the conversation proceeds back and forth, with me listening and reciprocating Ryan's feelings)

Ryan: I was worried about this before I got hired actually.
Me: oh?
Ryan: I didn't accept right away, citing concerns about not having the autonomy to really technically lead <the product>. In my past jobs this has been a big source of strife for me. Bob assured me this would not be an issue.
Me: yet here we are.
Ryan: yea...

(at this point I'm looking for a way forward, I know I can't fix Bob but I need to give Ryan hope for the future and get him solution-oriented rather than wallowing in the present situation)

Me: I can't make excuses for Bob, but I can conjecture what makes him act this way.
Ryan: oh? Tell me more, you've worked with him a lot longer than I have.
Me: he invented this product, which arguably is the reason our company is so successful, and now he has to hand it off to someone else to develop as his role has changed. This is something he hasn't really done before, and it's believable that he's being a little bit protective and clingy.
Ryan: sure...
Me: ...and so if what you want is the autonomy to lead your way, you'll first have to prove to Bob that he can trust you to take care of "his baby." That's what I had to do before he handed me control over <other team>.

(the apologetics are in full swing, I talk about different behaviors Bob respects and how Ryan can shape his personal workflow to include checkpoints with Bob to avoid late-stage blow ups and, hopefully, build trust)

Me: I know this doesn't "fix" the problem or make what happened any less harmful.
Ryan: Yes, but I feel like this is a problem I can handle now...and I really am in it for the long haul so I want to try my best to overcome this!
Me: that's great! This isn't the easiest place to work, but I respect your resilience. I'm here to support you any time you need.

In that story, did I help Ryan with his problem or manipulate him? All I wanted for him was a sense of autonomy, mastery and purpose—classic sources of motivation and self-actualization—and I knew the most plausible route to that would require gaining Bob's trust. I listened closely and came to understand (in my mind) what Ryan needed and gave him advice on how to get that. Seems fine, but let's talk about my intent.

As project manager, I had massive incentives to see work getting done on schedule (career growth, money). Whether or not I was explicitly, consciously thinking about that motivation, it still decided most of my actions. I knew Bob's micromanaging proclivities and had previously made attempts to fix the issue. Knowing the root cause was beyond my influence, I was "playing with the hand I was dealt." This blow up was just another hurdle between me and my ultimate goal of a happy team that finished projects on time...so how could I get Ryan to put this behind him (like I myself did previously) and get back to work?

1. Before the incident, accrue an empathetic persona. Speak frequently on the importance of building relationships and the "human" side of making software.
2. After the incident, make the offended party feel heard and respected. Ask questions, give them space to say their piece, and display active listening with the likes of "agree, build, compare."
3. Use the subtle cues and view points you hear from the other person to steer the conversation. Plant the idea in their head that what they desire (and why this incident was so inflammatory for them) is autonomy, and that the environment is as much to blame for the lack of it as the person.
4. Leverage the trust you've accrued and the existing power dynamic to offer "sage" advice on how to get autonomy: prove you can be trusted to execute tasks superlatively and can handle direct feedback when needed.

That was quite the song and dance to basically say "suck it up and get back to work...it'll (hopefully) work out eventually." Viewed through the lens of my own personal goals and intent, I didn't just commiserate and advise...I actively manipulated; it was just cloaked in the language of empathy and understanding.

Self Deception is a Defense Mechanism

Was this just a case of what Radical Candor calls "manipulative insincerity?" At no point during the exchange above was I plotting to get what I wanted (work getting done, no drama). I thought I was focused on Ryan and how to help him make the best out of the situation.

Therein lies the self-deception: I knew even in the heat of the moment that what was really needed was fixing Bob's micromanagement issues—one way or another—or else issues like this would multiply. Saying I was just helping Ryan understand his situation and find a way forward is how I justified to myself the original betrayal of leaving the hard problem untouched (Bob) and focusing on the more pliable person (Ryan).

My ego needed that excuse, otherwise I would have to confront either the limits of my efficacy (I knew I couldn't fix Bob) or my self-preservation instinct (I need this work done, which means I need this problem to go away).

True empathy requires the ability to consistently remove the self from consideration...but how?

Insights from Esther Perel

Esther Perel is a therapist whose podcast "Where Should We Begin?" features recordings of couples undergoing therapy; clips were featured on This American Life 617: Fermi's Paradox, Act Two. What was just some idle background noise while I was at the gym turned out to be the key insight in answering this question.

In the episode, Esther is counseling a couple where the wife discovered her husband had been cheating on her "widely, and compulsively" for decades. She wanted to stay together if at all possible, and keep all the good things in their life: kids, grandkids, etc. Turns out that being lied to for decades makes it hard to move forward.

The session was going around in circles, when Esther figures out exactly what to focus on: "she needs a degree of accountability and recognition about the pain that he caused her. But now, he's so busy with his own pain that he has a hard time owning the hurt that he caused her. So he feels so bad about himself that he can't feel bed for her."

From that point forward the whole session is about getting the husband to actually acknowledge the pain his wife is feeling, without talking about himself. There are flashes where he seems to understand this, but then lapses into talking about himself and what he did.

It was in that I realized one of the ways to solve my problem was to check my language. When speaking in a supposedly empathetic situation, can I say what I need to say without invoking myself: the way I feel, my actions, or my experiences? For example, if I am trying to communicate "I understand" by sharing my own past experiences (as a sort of conversational compare-and-contrast), then I may be slipping into the empathy-as-influencing-tool trap.

Keeping Yourself Honest

When empathy is used as a tool, it becomes the vehicle by which you create an emotional context ripe for manipulation and abuse. This is a feature, not a bug. In a normal relationship between equals, the closer you become the more vulnerable you are...the more each can inflict great pain or great joy upon the other. It can be a wonderful experience with the right intentions.

As much as I am agonizing over this issue, and trying to get you to do the same, there is truth in the quip "a spoonful of sugar makes the medicine go down." As a manager you will need to influence your team to do things that may not be their first instinct or their most preferred path forward. Your job is to find the intersection of what each individual needs and what the company needs.

The intimacy you breed will ultimately conceal the power dynamics underlying your influence...from your reports as well as yourself. It is a slippery slope from a well-meaning and emotionally aware leader to manipulative sociopath. If you fear this down slide as much as I do, consider adding some self-checks to your personal event loop:

1. The Esther Perel Check: after one-on-ones, take a moment to reflect on the conversation and whether the focus was primarily on you and your experiences or the other person in the room...was that focus reflected in the language?
2. The Crucial Conversations Check: before an important meeting or conversation, ask yourself "what do I want? How would I act if that was truly what I am after?"
3. The Peer Check: find someone removed from your workplace (a mentor or even a therapist) to talk through tricky situations or replay important conversations. It takes a really honest friend to say "lol, are you a sociopath?" but a dispassionate professional can easily gut-check these things.

The proliferation of self-help and people management literature aimed at improving EQ has democratized access to very effective tools for influencing others. Intent makes all the difference; make sure you use your super powers for good.

If this article spoke to you, consider reading Leadership and Self-Deception. Ultimately what I described here is the act of "getting out of the box" from that book, and it wasn't until after I started writing this post and doing background research that I found this gem...it could have saved me quite a lot of pain.