Last month I ran an executive planning session for a Canberra-based advice firm.
There were five in the executive team.
They have about forty staff, and we had a day for planning.
I start these sessions the same way.
Before any planning, any numbers, I ask each exec team member to share their professional and personal aspirations.
I call it the Why-Are-You-Working-So-Hard discussion.
I’m constantly amazed at how little thought and time advisers have spent thinking about this for themselves. Even more amazing is the surprise some exec team members have upon hearing their team members’ responses.
The point of starting here isn’t sentimental.
It’s strategic.
Until the exec team truly accepts their aspirations as the basis of their work, the rest of the day is just admin.
By mid-morning, this executive team hit the wall every busy advice firm hits.
Capacity.
Each of them had jobs they enjoyed and jobs they were doing purely because nobody else could. The plan was obvious on paper: hand off the second category, spend more time in the first.
Then reality turned up.
Their immediate delegates were either already stretched or not yet capable of doing the work well.
The conversation collapsed into the same conclusion I hear in almost every planning room.
“We just can’t make these changes right now.”
There you have it.
They are more comfortable with their current frustrations and misalignment to their own priorities than they are ready for the discomfort growth demands, particularly on firm leadership.
No one is ever ready for their best breakthroughs.
The problem in that room wasn’t a systems problem.
It wasn’t a training problem either, though both get blamed first because both are easier to fix than what’s actually going on.
The real problem was a prioritisation issue, and prioritisation is much harder to fix than a system or a skill gap.
It requires a paradigm shift.
A daily, deliberate awareness of why they are doing what they are doing, what they are working for, and an honest look at whether current systems, team structure, past promises, and past decisions are serving their “why” or actively working against it.
Most of what fills an exec team member’s day was probably once a good decision.
A client relationship worth protecting.
A colleague worth backing.
A project worth starting or continuing to support.
None of it was wrong at the time.
But priorities aren’t static, and neither are growing firms.
What deserved a yes three years or three months ago might now be sitting directly between the exec team and the future important to them.
True prioritisation, the kind that changes a business, often means going back on some of those past promises.
It means telling a long-standing client, a loyal team member, or a trusted alliance that something must change or stop.
It means dropping urgent projects in favour of important ones, even when the urgent ones seem most pressing.
That’s not a scheduling exercise.
That’s a courageous act.
I watch capable, successful exec teams constantly avoid this.
Not because they lack the ability, but because saying no to something urgent feels like letting someone down, going back on past commitments, failing to keep up with the latest system advances (particularly AI at present), or risking everything they have already built.
Deprioritising the why-are-you-working-so-hard responses in favour of yet another pressing issue may not feel like a significant step backwards.
It’s worse.
It’s more than a step backwards, it’s a tangential step, a deviation that will widen an expanding gap into a chasm between what they must do every day and what they hope to achieve one day.
Bigger isn’t better when bigger is less about why-are-you-working-so-hard and more about addressing everyone else’s priorities and pressing issues.
The firms that shift are the ones willing to sit with the discomfort of saying ‘no’, ‘sorry’, or ‘we have changed our mind’.
They stop, they drop, they disappoint some people in the short term, and they build something better for everyone in the long term, themselves included.
The exec team I sat with didn’t leave with a finished plan, as there is no such thing.
They left with something more useful: a commitment to a planning process prioritised on why they’re working so hard.