A client recently found herself up until 5am rewriting most sections of a tender. It was due at 3pm that day, and she still needed to hand it over in time for the budget owner to review the numbers before submission.
She hadn’t planned to rewrite it. She’d set aside time for a final read-through and minor changes. The work had been delegated. She’d been assured it was on track.
It wasn’t.
What had been submitted didn’t meet the brief. It showed a lack of understanding of what she’d read—and it became clear she hadn’t read all the documentation in the first place.
This leader had gone out of her way to support the team member responsible—offering flexibility, extending deadlines and checking in more often than usual. She knew they were struggling with their mental health. And they had confidently told her they were on top of it.
It turned out to be misplaced trust.
It wasn’t the first time she had to pick up the slack or give the benefit of the doubt. But this time, the cost was undeniable. Not just in lost sleep—but in realising that no matter how much slack she gave, it wasn’t going to help. Not her. Not the team. Not the person she was trying to support.
The Hidden Cost of Overcompensation
Leaders stepping into new roles often inherit people they didn’t choose. The instinct is to give them a chance. To keep an open mind. To lead with generosity.
And often, that’s exactly what’s needed.
Until it’s not.
You offer time, space, support. You assume things will improve.
But what if they don’t?
What if all that goodwill quietly becomes a burden you didn’t see coming?
It’s easy to say: Put them on a performance plan. Or mental health doesn’t excuse poor performance. But real leadership isn’t lived in absolutes. It’s lived in the grey.
Especially when you’re new.
You’re still earning trust. You don’t know the backstories. You don’t want to come in like a wrecking ball. So you listen. You hold back.
And sometimes, that’s exactly what’s needed.
Other times? It’s not.
Preventing the Breaking Point
It’s not always obvious when things are about to break. Especially if someone seems receptive, reassures you they’re on track and is facing genuine personal challenges.
So how do you tell?
You start looking beneath the surface. Instead of asking “Is everything okay?”, try:
- “Can you walk me through what you’ve done so far?”
- “How are you approaching this section?”
- “What’s still unclear or in progress?”
It’s not about micromanaging. It’s about surfacing the gaps early—before good intentions turn into late-night damage control.
You can also listen to yourself. Are you stepping in to double-check, rewrite or quietly fix things “just this once”? That’s a sign you’re over-functioning: doing their job and yours.
You don’t need everything documented—but you do need visibility.
Shared documents, live drafts, or even a simple project tracker can tell you more than a status update ever will.
If you can’t see how the work is unfolding, you’re guessing.
And guessing is what leads to 5am rewrites.
Finding the Line Between Support and Enabling
When someone’s not coping, the kindest thing isn’t to quietly carry the load for them. It’s to tell the truth.
That this isn’t working. That support doesn’t mean no accountability. That their wellbeing matters—and so does everyone else’s.
Including yours.
So how do you know what’s “reasonable”? When does understanding become enabling?
You look for patterns:
- Is this a one-off or a recurring theme?
- Have expectations been clear and consistent?
- Is there any real shift after feedback or support?
- What’s the impact on others—are they covering, withdrawing, burning out too?
And perhaps most importantly: what’s the impact on you?
Because here’s the part we often skip. Your capacity matters. Your time matters. Your nervous system matters.
You can’t lead well if you’re constantly compensating for someone else’s lack of reliability.
You can’t think clearly if you’re constantly firefighting.
You can’t lead strategically if you’re in survival mode.
And you can’t make sound decisions if you’re too tired to trust your own judgment.
At some point, trying to be fair to one person becomes deeply unfair to everyone else—including you.
Taking Clear Action Without Guilt
So, if you’re in that position—new in role, trying to lead well, but quietly starting to question what you’ve inherited—this is your permission slip.
You don’t have to be the hero.
You don’t have to fix it all.
And you don’t have to tolerate the intolerable in the name of being fair.
You can acknowledge complexity and still take clear action.
For leaders who can make personnel changes, this might look like a direct conversation where you outline specific examples of missed deliverables, presenting two paths forward: a time-bound improvement plan with clear milestones, or a supported transition out.
But what if you’re stuck with the situation? If you can’t remove the person due to organisational politics, tenure protections or family business dynamics?
In these cases, your strategy shifts from removal to containment:
- Restructure responsibilities – Move critical functions away from this person and toward your reliable team members, even if it means changing job descriptions.
- Create accountability systems – Institute checkpoints that don’t rely on trust alone: scheduled reviews, mandatory drafts or parallel verification processes.
- Set and enforce boundaries – Be explicit about what you will and won’t cover. “I won’t be available to review this after hours” or “If this isn’t completed by Thursday, we’ll need to pull someone else in.”
- Document consistently – Not to build a case, but to create clarity and prevent gaslighting about what was agreed upon.
- Focus on damage control – If improvement isn’t realistic, shift your energy to minimizing impact on clients, other team members, and yourself.
The clarity isn’t cold—it’s kind. Because whether someone stays or goes, everyone deserves to know where they stand.
Whatever your path, let it be one grounded in truth—not guilt.
Because real fairness includes you too.
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