Self-Compassion 101 for Engineering Managers

Gil Shklarski
Apr 19 · 7 min read

When I reflect on my first management job, I would have been lost without my manager’s relentless support and guidance. I have made every mistake in the book (and then some.) As I confronted new challenges, he would sit me down, offer empathy, and give advice that always helped.

Recently, I was asked which contribution of mine to Flatiron is my proudest. The answer came easily — it is the time I’ve gotten to spend emotionally supporting managers and coaching their growth. It’s a way for me to pay it forward, as I have been very fortunate to have excellent bosses and coaches guide me in my career.

My regret is that I will never have enough time to give to as many managers as I would like. It is my hope that some blog posts with tools I’ve learned over the years and insights I’ve gained from others can serve as a way to connect with more current and aspiring managers.

In this post, I focus on advice I find myself giving often to managers. While the scenarios are different, the thread is the same: promoting compassion, resilience and growth — for yourself and those you manage.

1: “It’s not about you.”

About 20 years ago, when I was a first-time manager, I received harsh feedback from some direct reports. I was running a technical team in the Israeli Defense Forces. My team had two core responsibilities: build foundational tools, and implement them within clients’ projects. The former was a task requiring research, creativity and flow; and the latter was detail-oriented project work.

During a routine review period, some of my reports said that I am too short-sighted because I wasn’t giving them enough time to invest in the long-term foundational work. They even went as far to say that my management was driving my team into the ground.

As a first-time manager, I took this feedback really hard — and really personally. In my view, I’d been accused of not running my shop well. But I was lucky because my manager had held my same role 20 years earlier. He knew the challenges surrounding the research work and understood why my reports were complaining.

He sat me down, offered me tea, and said, “Hot er gezogt.” In English, this roughly translates to, “So he said, so who cares?” He then gave me some of the most powerful advice I’ve ever gotten: “It’s not about you. Take yourself out of it, and look for the objective struggle.”

There was an objective struggle here. It is objectively hard to simultaneously achieve the flow that creative work demands while also balancing taxing, short-term project work. I now had an actual problem that I could address. The solution was to reorganize the cadence of my direct reports’ work so that they gained more uninterrupted blocks of time for the creative tasks.

Identifying the objective struggle and implementing a solution shifted the focus away from the harsh feedback. My bruised ego was healing. But my manager assured me this wouldn’t be the last time a direct report criticized me in a review (he was right.) He cautioned me never to internalize and personalize this kind of feedback, as it can cause a shame spiral. Or, worse, cause a manager to develop negative feelings about the direct report.

I’ve shared his advice countless times since with managers. For the sake of your relationship with team members, depersonalize any of their negative feedback and look for the objective issue they are grappling with. Once you know it, work to address or improve it.

Keep in mind that our work is hard and complicated. Sometimes when people are struggling with an aspect of their job, it’s normal for them to look for blame in the environment or a boss. When that blame gets pointed at you, take a deep breath and remember: it’s not about you.

2: “You will have this same struggle in any similar and reasonable company.”

Some years ago, I had an experience where I realized I wasn’t great at reading the room and influencing people. Or rather, my executive coach pointed this out to me. I had been in a meeting where one of our product managers and I pitched an idea, which got pushback from others at the table. I tried to sell the idea a little more while my partner stayed silent. I felt alone and frustrated that I was carrying all the weight.

As I was complaining about this to my coach, she asked me, “Gil, had your partner spoken up, would it have changed anything?” I had to admit that it wouldn’t have. As it turned out, he had read the room better than I had and realized our idea simply wasn’t going to happen. He made the calculation that it wasn’t worth risking the interpersonal capital to fight for this when we might want to fight for something more important down the line.

He was right. And I had to accept that I had a new area to work on and grow in. At first, I was resentful of that meeting, upset about the entire situation, asking myself whether I should find a different place, one without such hurdles. My coach helped me realize there was a learning opportunity there, to develop a skill that would come in handy later in my career — and I had many opportunities to practice it just where I was.

Managers will often tell me that a report is really frustrated about something — so much so that the manager is worried this valuable person might quit. What I have learned is what I suggest to managers: Flatiron is a big, ambitious, complicated endeavor. It is the nature of working in an environment like ours to hit roadblocks. It’s up to us to turn them into opportunities for growth.

I then tell managers to reframe the issue to help the report see that if they move to another big, complicated endeavor, they will confront the same frustrations. Normalizing certain realities of work helps give people the energy they need to push through the challenging moment. It allows them to see the frustration from a new angle: Do I want the skills and abilities to be able to overcome such challenges? Do I want to develop these skills here, where I know the product and the people? Or do I want to confront it in a new company, where I have a steep learning curve?

More often than not, it’s much easier to develop a new skill in the environment we already know.

3: “How much can you actually help this person?”

Many years ago, I had come to lead a group of people who each managed a team. One of these managers was eager to advance from managing one team to two. He was aware of the skill deficits that were holding him back from promotion, which made me that much more invested in helping him. Over months, I found myself giving this person a disproportionate amount of my time and energy to help him develop certain skills. Yet, he continued to struggle, as I grew exhausted and frustrated with the sunk cost.

My boss pulled me aside one day and said, “Gil, you’re a good manager. But you’re not a magician.” I was taken aback by this. But, I also knew he was right. At this point in this young manager’s career, he wasn’t ready for more responsibility. Shortly after, he moved to another organization, where I trust he continued to learn and grow in new ways.

Everyone is on his or her path. Sometimes this means that, for whatever reason, they are not ready for the responsibility they tell you they want. I believe everyone is capable of unlimited growth, and I’ve come to see that sometimes it’s not on the timeline we want. Or the circumstances are not quite right for us. As managers, we have to know our limits in mentoring people. And we have to accept that sometimes another person’s limits are beyond our reach.

Caring for and investing emotionally in your team is work that takes a lot of energy. Learning to manage how much energy we give each member of our team is vital to ensure we don’t run out of it.

The common actionable thread

In general, each of these scenarios can be approached similarly:

  • Identify the objective problem or tension: Complaints, insults, and frustrations mask an objective problem for which there is a solution.
  • Depersonalize the situation: Ruminating on the personal will keep you stuck. Shift your focus to developing the skill you need or the plan you must devise to solve the problem.
  • Be thoughtful about your energy: Ruminating on the personal will also drain your energy. As will complaining and continuing to invest your time in goals that are unlikely to pan out or people who aren’t yet ready for more responsibility.

The common human thread

Managing humans is hard work. On our worst days, we might feel regret, doubt or even shame. But on our best days, we are a positive influence on the lives and careers of the people we manage and the company we work for. On our best days, we connect deeply with the reward of our work.

I’ve learned that compassion — to self and to others — is the secret to creating more ‘best’ days. When we approach ourselves and others with compassion, we separate from our frustration or our shame and can then take productive action. We become empowered.

As you manage, carry these rules with you every day:

  • Choose self-kindness vs. self-judgment: You will make mistakes. Accept that you, too, are always learning and growing.
  • Choose common humanity vs. isolation: Remind others they are not alone in their struggle, nor are they the first to experience it. Remind yourself of this, too.
  • Choose mindfulness vs. over-identification: Acknowledge the pain when you make mistakes, but don’t get stuck in it. After all, mistakes are opportunities for growth and resilience.

Research shows that those who practice self-compassion are more compassionate to others. Research also shows that receiving compassion can make a person more likely to give it. As managers, we can be vectors of compassion, resilience, and growth — or not. The choice is ours.

Flatiron Engineering

Thoughts from the Engineering team at Flatiron Health.

Flatiron Engineering

Thoughts from the Engineering team at Flatiron Health. We're building technology that enables cancer researchers and care providers to learn from the experience of every patient.

Gil Shklarski

Written by

Startup advisor, mentor, and investor. Formerly, CTO at Flatiron Health (acq. by Roche) from inception to a thriving culture of 350 technologists.

Flatiron Engineering

Thoughts from the Engineering team at Flatiron Health. We're building technology that enables cancer researchers and care providers to learn from the experience of every patient.

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