The Compassionate Leader School Podcast
Aug 19, 2026 · 19 min · 6 segments
She lies down at 10 at night. At 1 in the morning she's still running scenarios. The rollout. The training schedule. Who's going to quit over this. Every one of those is getting the same grip, the…
Debbie LawrenceHost
She's a branch manager in Halifax for a professional services firm with its head office in Toronto.

The email that Juanita received said that the company was moving to yet another software system with the rollout starting this fall.

That implementation went badly enough that Juanita said to me, Debbie, people still talk about it.

There were the lost files, workarounds nobody documented, and a support line that she said it rang through this voicemail box that left her staff feeling frustrated when they couldn't get immediate help with yet another bug in the system.

By the time we got on a call, she'd been carrying her concerns about this new software implementation and the upcoming round of changes.

And she said to me, I keep running through the scenarios, the rollout, the training schedule, who's likely to quit over this, and whether they even consider the impact on anyone outside Toronto.

She said, I lie down at 10 o'clock at night and I'm still wide awake strategizing around everything at 1 a.m. She talked about how she'd been in the meeting where the proposed upgrade got discussed and she'd been asked for her input, which she readily provided.

And then the decision got made somewhere else by more senior people whose table she wasn't invited to join.

What she said next is very relevant to what I want to talk about in this week's newsletter.

Now, I said to her, you know what you you're running a full time second job in your head, it is an unpaid second job.

What was keeping her up at 1 a.m. was every possible version of the rollout running all at once with no way to sort one concern from another.

So the parts that we can act on today and the parts that were decided in Juanita's case in a boardroom, some 1200 kilometers away, get exactly the same amount of attention, the same 1 a.m. rehearsal, and the same tightness in the chest.

And what that means is that the things we could actually move get only a portion of the attention they deserve because the things that we can't move are eating into some of our focus, time, effort, energy, all of those things.

She's a branch manager in Halifax for a professional services firm with its head office in Toronto.

The email that Juanita received said that the company was moving to yet another software system with the rollout starting this fall.

That implementation went badly enough that Juanita said to me, Debbie, people still talk about it.

There were the lost files, workarounds nobody documented, and a support line that she said it rang through this voicemail box that left her staff feeling frustrated when they couldn't get immediate help with yet another bug in the system.

By the time we got on a call, she'd been carrying her concerns about this new software implementation and the upcoming round of changes.

And she said to me, I keep running through the scenarios, the rollout, the training schedule, who's likely to quit over this, and whether they even consider the impact on anyone outside Toronto.

She said, I lie down at 10 o'clock at night and I'm still wide awake strategizing around everything at 1 a.m. She talked about how she'd been in the meeting where the proposed upgrade got discussed and she'd been asked for her input, which she readily provided.

And then the decision got made somewhere else by more senior people whose table she wasn't invited to join.

What she said next is very relevant to what I want to talk about in this week's newsletter.

Now, I said to her, you know what you you're running a full time second job in your head, it is an unpaid second job.

What was keeping her up at 1 a.m. was every possible version of the rollout running all at once with no way to sort one concern from another.

So the parts that we can act on today and the parts that were decided in Juanita's case in a boardroom, some 1200 kilometers away, get exactly the same amount of attention, the same 1 a.m. rehearsal, and the same tightness in the chest.

And what that means is that the things we could actually move get only a portion of the attention they deserve because the things that we can't move are eating into some of our focus, time, effort, energy, all of those things.
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