1. Can your leadership team recite your core values from memory?
Not “they’re on the wall.”
Not “they’re in the handbook.”
From memory. Right now.
If your leaders cannot say them out loud without looking, those values are décor. They are branding. They are not behavioural standards.
In a family business, this matters even more. The overlap between family & business is emotional. If values are unclear, decisions default to personality, hierarchy or history.
When values are clear & lived, they become the filter for hiring, firing, rewarding & resolving conflict.
If they are fuzzy, you get politics.
2. Does everyone on your leadership team own a number?
A real number.
Updated weekly.
With clear accountability.
Not a vague “I’m responsible for operations.”
A measurable.
If scorecards are inconsistent or optional, you are driving at speed with no dashboard.
In the Harvard 3 Circle model, this is where the Business circle needs to stand on its own two feet. The business has to operate professionally, regardless of family dynamics.
Clarity of numbers reduces emotion. It replaces opinion with data.
And data is calmer than a family debate.
3. When was your last quarterly planning session?
Not “sometime last year.”
Last quarter.
With clear 90-day priorities that every leader can name without checking their laptop.
I recently spoke with a business owner who had not set a single clear company priority in 27 years. Twenty-seven. They were busy. Profitable. Stressed. Reactive.
Busyness is not traction.
If your priorities change every few weeks, you do not have agility. You have organisational whiplash.
Consistency creates stability. Stability creates growth.
4. Do your weekly leadership meetings actually happen every week?
Same day.
Same time.
Same agenda.
No drift. No skipping. No “we’ll just cancel this week.”
Your meeting pulse is the heartbeat of your business.
When meetings slide, accountability slides. When accountability slides, results slide.
This is where I get quite direct with teams. Structure does not kill entrepreneurial spirit. It channels it.
Mark’s Visionary book explains this beautifully. Visionaries need space to create, but they also need a consistent drumbeat that turns ideas into outcomes. Without rhythm, you just have noise.
5. When someone has an issue, do they know exactly where to raise it?
There should be one answer.
Not three.
Not “depends who’s involved.”
Not “we’ll talk about it later.”
If issues float around corridors, WhatsApp threads or family dinners, they get buried. They do not get solved.
Healthy teams have a clear forum for solving real problems. They do not gossip. They do not triangulate. They surface & solve.
In family businesses especially, this is gold. The Family circle & Business circle need different forums. Mixing them creates confusion & resentment.
Clarity reduces drama.
Here’s What Nobody Says Out Loud
Most operating systems fail because leadership never fully committed to installing them properly.
They liked the idea.
They liked the language.
They liked the tools.
But they did not commit to the discipline.
An operating system is not a motivational poster. It is a behavioural contract.
If you answered “no” to more than two of those questions, your system is not running your business. It is window dressing.
And here’s the good news.
This is fixable.
It does not require genius. It requires commitment, consistency & courage.
Courage to hold each other accountable.
Courage to prioritise properly.
Courage to separate family emotion from business decision-making.
Mark Winters’ work on the Visionary role is powerful because it shines a light on where leadership often unintentionally sabotages installation. Visionaries love ideas. Installation loves discipline. Both are essential.
Which question hit you hardest?
If you are honest, you probably know exactly where the wobble is.
And once you see it, you can fix it.
