The Subtle Saboteur

“Why Am I Training My Boss?” and the Stories We Tell Ourselves

There’s a sentence I hear often in coaching conversations. It’s usually said quietly, sometimes with humor, sometimes with frustration.

“Why am I training my boss to do their job?”

On the surface, it sounds like a reasonable complaint. Underneath it, though, lives a story that can quietly undermine leadership, culture, and even our own credibility if we don’t examine it.

This is what I call the subtle saboteur.

Not a person.

A narrative.

Naming the irritation

Let’s be honest. Being asked to orient, onboard, or train someone who now sits above you can feel irritating. It can feel humbling. For some, it can even feel embarrassing.

Especially when:

• You’ve been with the organization for years
• You know the systems inside and out
• Others may assume you “should” have the role

Those feelings are human. They deserve acknowledgment.

But what we do with them matters.

What you are actually being asked to do

When a new manager, supervisor, or executive comes in from the outside, they are not being hired for their ability to run your specific system on day one.

They are hired for an umbrella role.

Leadership includes:

• Decision-making
• Strategy
• Accountability
• Managing humans
• Culture, morale, and trust
• Legal, ethical, and operational oversight

What you are teaching them is one rib of that umbrella.

Context. Nuance. How this organization works.

You are not training them to do their job.

You are orienting them to yours.

That distinction matters.

When resentment replaces curiosity

In many of these situations, one of two things is true.

Either the person did not apply for the role,

or they did apply and were passed over.

Both experiences can sting.

But resentment keeps us stuck. Curiosity moves us forward.

If you didn’t apply, it’s worth asking why.

If you did and were passed over, it’s worth understanding what the organization needed that went beyond technical expertise.

That information is data, not a verdict on your worth.

The toxic ripple (where leadership shows up without a title)

This is the part that often goes unnamed.

When a tenured employee voices resentment about “training their boss,” they are not just expressing a feeling. They are setting a tone.

Some people around them recognize the influence and weight they carry.

Others don’t consciously name it, but they feel it.

Either way, culture is being shaped in real time.

Influence can be used to:

• Steady a team
• Humanize a transition
• Create psychological safety

Or it can quietly sabotage it.

This is where the Golden Rule becomes a leadership practice, not a cliché.

If empathy replaced anger for a moment, the question would shift from:

“Why am I training them?”

To:

“If this were me walking into an unfamiliar system, how would I want to be received?”

Because first impressions ripple outward.

A leader can walk into a department already disliked, not because of who they are, but because resentment arrived before they did.

That is power.

And power deserves care.

Weaponizing influence, intentionally or not, rarely harms just the target. It damages trust, morale, and the very culture people say they want to protect.

Instead of:

“I’m training them to do their job.”

Try:

• “I’m helping them understand how this organization works.”
• “My knowledge is operational. Theirs is organizational.”
• “This is influence, not subordination.”

Sometimes the work isn’t fixing the situation.

It’s fixing the story we’re telling ourselves about it.

That’s leadership maturity.

With or without the title.

#LeadershipDevelopment #ProfessionalGrowth #OrganizationalCulture #Influence #EmotionalIntelligence #WomenInLeadership