How Much Self-Compassion Can Your Leadership Afford?

“I Can’t Afford to Go Easy on Myself”

“I should have seen it earlier.”

Robert was talking about a decision he regretted.

It was not a disastrous decision. The company had dealt with the consequences, the team had adjusted, and business had moved on. After more than twenty years in senior management myself, I would probably have put it in the rather large category of decisions leaders make with incomplete information and later discover they would have made differently.

Robert was not prepared to put it there.

That made the executive coach in me curious.

There had been signs. One of his directors had raised concerns. Robert had listened, asked some questions and eventually decided to continue as planned. Three months later, those concerns proved justified.

“I knew enough to ask more questions,” he said. “I just didn’t.”

Then came the sentence that stayed with me.

“I am probably too hard on myself. People tell me that. But I don’t necessarily think it is a bad thing. At this level, I can’t afford to go easy on myself.”

Oh, I knew that sentence.

Not necessarily those exact words, but the thinking behind them.

It took me straight back to my first years as a Managing Director, when being demanding with myself seemed almost inseparable from being responsible. If something mattered, I had to take it seriously. And taking it seriously meant making sure I didn't let myself off the hook too easily.

Years later, I hear versions of the same thinking remarkably often in conversations with managers.

Self-compassion sounds good until you put it next to responsibility.

Then the doubts start.

"If I become more understanding with myself, will I lower my standards?"

"If I accept that I made the best decision I could at the time, will I stop examining what I got wrong?"

At what point does self-compassion become a very respectable name for letting myself off the hook?

I think these are good questions.

Because self-compassion and self-excusing can look surprisingly similar from a distance.

So can accountability and self-punishment.

What Are We Actually Being Compassionate About?

Take two reactions to the same mistake.

“I made a poor decision. I had information available, and I did not examine it carefully enough.”

And:

“How could I have missed something so obvious?”

For years, I might have considered the second response evidence of higher standards.

Today I am much less certain.

The first statement keeps the decision open for examination. What did I know? What did I assume? What did I dismiss? Was I rushing? Did somebody tell me something I did not want to hear?

The second does something else. Almost unnoticed, the subject changes. We are no longer examining the decision. We are examining ourselves. And this becomes particularly interesting at senior level.

After enough years of being valued for sound judgement, competence stops being only something you bring to work. It becomes part of how you see yourself and how you expect others to judge you.

So “I got this wrong” can become “I should have known.”

And “I should have known” can very quickly become “What does it say about me that I didn’t?”

This can feel like accountability. It certainly felt like it to me at times.

But there is a strange convenience in self-criticism.

Calling yourself stupid for ignoring a warning can be easier than admitting that you did not particularly trust, like or respect the person who gave it.

Telling yourself “I should have known better” can be easier than looking at the fact that you did know enough to stop, and chose speed instead.

The punishment is unpleasant, certainly. But it can also bring the examination to an end. You have been found guilty. You have suffered a little. The standard has been defended. Case closed.

Self-compassion, at least as I understand it today, does something rather different. It allows the case to remain open without requiring the person to become the accused.

Three Things I Used to Confuse

The first was high standards with being hard on myself.

They are not the same.

“This decision was below the standard I expect from myself” contains everything required to acknowledge a gap.

Adding “I cannot believe I did something so stupid” does not increase the standard.

It simply adds a judgement about the person who failed to meet it.

The second confusion is perhaps more dangerous because it sits on the other side.

Self-compassion can become an excellent explanation machine.

“I was under enormous pressure.”

“I did not have all the information.”

“The expectations were unrealistic.”

“I was exhausted.”

“I did the best I could under the circumstances.”

Maybe you did. Maybe I did.

But I have learned to be cautious with that last sentence.

There were moments in my management career when circumstances genuinely constrained what was possible. There were others when circumstances were only part of the story.

Perhaps I was under pressure and avoided a conversation.

Perhaps information was incomplete, and I did not look very hard for the information that might challenge my preferred decision.

Perhaps somebody was genuinely difficult to manage, and I tolerated the situation for longer because dealing with it would have created another problem.

Context explains a great deal.

It does not automatically remove our contribution.

The third confusion was believing that the ability to take criticism, including my own, was somehow evidence of strength.

Many senior leaders can take an extraordinary amount of criticism.

The more useful question, in my view, is what that criticism does to their judgement afterwards.

Does it make them more curious about what happened?

Or more determined never to be caught in that position again?

Does it make bad news easier to hear next time?

Or does it increase the need to be right before speaking?

Does it improve judgement?

Or simply make mistakes more personally expensive?

Being able to endure something for twenty years does not tell us whether those twenty years made it useful.

Self-Compassion Can Also Become Very Convenient

We can become extremely sophisticated at understanding ourselves.

There is always context. There is always pressure. There is always a reason.

And many times all those reasons are true.

Yet somewhere among them there may still be a sentence we would rather not say.

“I avoided that conversation.”

“I wanted this plan to succeed and became less interested in evidence suggesting it would not.”

“I knew this person was struggling, but replacing them would have created a problem I did not want at that moment.”

“I did not ask for help because I liked being the person who did not need it.”

Self-compassion that cannot tolerate these sentences is not particularly compassionate.

It is protective. It is a source of self-justifications leading to no personal development, a stall or even loss of our sense of being in control.

Relentless self-criticism is protective too, although in a different way.

One allows me to explain my behaviour until my responsibility becomes difficult to find.

The other allows me to punish myself instead of examining my behaviour with precision.

I have used both.

Neither helped me see myself particularly clearly.

So, How Much Can Leadership Afford?

Robert had dismissed a concern too quickly.

That was true.

He had also made many sound decisions before this one and would make many more afterwards.

That was equally true.

There was no reason for one fact to cancel the other.

He did not need to turn one poor decision into evidence that something was wrong with him.

But neither did he need to tell himself that he had simply “done the best he could with what he knew.”

Because, by his own admission, he knew enough to ask himself another question.

That is the part I find most interesting about self-compassion in leadership.

It asks for something considerably more demanding than being kind to ourselves.

Can I look directly at my contribution to a poor outcome without reducing myself to that contribution?

And can I remain respectful towards myself without editing the evidence to make myself more comfortable?

I no longer believe accountability requires punishment.

I also do not believe compassion requires acquittal.

Perhaps leadership can afford a great deal of self-compassion.

The real question is what happens when compassion meets the part of the story we would rather explain away.

How much truth can your self-compassion hold before it becomes self-protection?

How much truth can your accountability hold before it becomes self-punishment?

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The way you respond to your own mistakes influences much more than how you feel about them. It shapes what you are willing to examine, what you defend and what you learn from experience.

If you recognise the tension between holding yourself accountable and becoming unnecessarily hard on yourself or unnecessarily permissive with yourself, this is exactly the kind of leadership pattern we can explore in a 1:1 Executive Coaching conversation.

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