[INTERNAL MEMO]
Guilt Isn't A Moral Compass
I wanted to share something fairly personal as I’m sure you will all be able to relate in some fashion.
About 1.5 years ago, I had a breakthrough. I realized a lot of what I was doing as a leader, I was only doing out of guilt.
I felt like I'd be a bad leader, a bad partner, a bad boss, whatever the label was, if I said no, held a line, or made a call that would disappoint/frustrate/annoy someone.
EVEN when it was the right call.
EVEN when saying yes wasn't a good use of my time or the company's.
Once I saw how much of a hold guilt had on me, I couldn't unsee it. My inability to tolerate guilt was shaping how I spent my time rather than my values and critical mind.
Since I decided to stop letting guilt run my leadership, I make faster decisions, hold higher standards, have more TIME and overall have more respect for MYSELF.
Guilt isn't a moral compass. It's just a feeling. And most leaders never separate the two.
Here's what I've seen (and experienced) happen when they don't:
You let an underperformer linger for months because letting them go FEELS bad. Meanwhile your best people watch you tolerate mediocrity and recalibrate what standard they actually need to hit.
You say yes to every meeting, every Slack ping, every "got a sec?" because saying no feels like you’re letting your team down. So you're insanely busy, your calendar isn't prioritized whatsoever, and the strategic work only you can do keeps getting pushed to 9pm or the weekend that realistically, never comes.
You avoid the hard feedback conversation because you're worried it'll make you look harsh or unlikable. So the person keeps making the same mistake, finds out too late, and asks you the question that should terrify every leader: "Why didn't you tell me sooner?"
Every one of these is guilt making the call instead of YOU.
So here's what I want to challenge you with this week:
1. Sit with the guilt instead of reacting to it.
When you feel that pang in your stomach after holding a line or saying no to your team, don't immediately soften the decision or over-explain yourself. Let the discomfort sit. It passes faster than you think, and every time you let it pass without caving, you prove to yourself the decision was sound. (Feelings pass whether you DO something or not, you shall see)
2. Separate the feeling from the facts.
Ask yourself, “Did I actually make a bad call, or do I just feel bad because someone's disappointed?” Write down the actual reasoning behind the decision. If it holds up, the guilt is noise, not a verdict on your leadership.
3. Practice holding the line on purpose, starting small.
Pick a low-stakes moment this week, decline a meeting, don't tip toe around a piece of feedback, hold a deadline, and let someone be mildly disappointed in you. The goal isn't to become a harder leader. It's to prove you can disappoint someone and still lead them well, so guilt stops running the decisions that actually matter, like who stays on your team and what standard you hold them to.
Guilt-tolerant leaders run their team. Guilt-avoidant leaders are run by whoever might be disappointed in them.
- Leila
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