Questions CEOs and owners ask me

Usually because the people doing it are working from a different picture of the business than the people who wrote it.

Managers rarely fight a strategy head on. They're holding an older model of the business, one that made sense a few years ago. Measured against that, the new plan doesn't add up, so it quietly stalls. And it looks like poor execution.

Get the owners, then the leadership team, onto the same current picture first. Then write the plan. Then it holds.

Rarely because the strategy is bad. Mostly because the people meant to deliver it are working from a different picture of the business than the people who wrote it.

There are three usual causes, plus one that's newer. Sometimes the strategy needs work. More often, managers are still running the business in their heads the way it was a few years ago, so the plan doesn't add up for them. Or the leadership team won't put the real issues on the table. And now the picture drifts in months, not years, as markets move and AI changes what's worth doing. And even a good plan drifts after the strategy day: small differences compound, and nobody makes the small correction while it's still cheap. More in Learn, Unlearn, Relearn and Three Degrees Off.

Start one on one, before anyone is in the room. That's where you hear what's really going on.

Then build a clear, shared picture of where the business is going, together, and make it safe to name the issues everyone already knows about. Write down what was agreed in plain words, run it in short cycles (usually ninety days), and come back about a year later to recalibrate. More in Genetically Engineered for a Fast-Changing World.

Certain topics make the room go quiet. Decisions get agreed in the meeting and re-argued in the car park afterwards. And the plan stops landing.

Underneath it there's usually something everyone can see and nobody wants to name, often that the business has grown faster than some of its people. Leaders carrying the extra load get worn down, and good people further down start wondering who's actually in charge. More in Elephants Are Big, But Hard to See.

Usually they're not resisting it. They're measuring it against an older picture of the business, and against that picture it doesn't add up.

Every manager carries their own picture of how the business works, and nobody announces when theirs goes out of date. So a new plan looks like a people problem, or poor execution. Get everyone onto the same current picture first, out loud, in the room, and most of the resistance goes. More in Learn, Unlearn, Relearn.

Stop taking other people's problems off their hands. Every time you say "leave it with me", the problem jumps from their shoulder to yours.

Know your own priorities for the day and the week. Instead of taking the problem, set a time: "Come and see me at 3 with a couple of options." At that meeting, coach rather than fix. It takes more of your time at the start and saves heaps later. More in Not My Monkey (Not My Circus?).

It's worth it when you're carrying decisions you can't talk through with anyone inside the business, or when your leadership team isn't on the same page and you can't fix it from the inside.

It isn't worth it if you're looking for someone to hand you the answers with nothing changing on your side. The value is in an outside view, honest questions and someone who has seen a lot of leadership teams. A good test is a single session first. With me, that's a Position Session.

Plenty of them are. One well-known study found around 29% of entrepreneurs reported ADHD, against roughly 5% of adults generally.

The traits that come with it, like drive, big-picture thinking, spotting what others miss and running at it, are often the engine of a business. There's a shadow side too: the owner who's always out ahead and forgets the team hasn't seen what they've seen. Knowing how you're wired is what lets you work with it. I'm dyslexic myself. More in A Weird Menagerie of Misfits.

A facilitator runs the process so the team reaches its own answer. And owns it.

I don't turn up with the strategy in my back pocket. I design the sessions, ask the questions that get the different views into the open, keep things honest when it gets uncomfortable, and make sure what's agreed is written down in words everyone recognises. The hard part is moving people from an old frame of the business to a new one. A good day in the room is the easy bit. Making it stick on Monday is the work.

An advisor gives you an answer. A mentor tells you what they've seen from where they've been. A coach asks questions so you find the answer yourself.

All three are useful, just at different times. Urgent or specialist? You want an advisor. Facing something new? A mentor's experience is a map. When the real issue is how you're looking at the problem, coaching does more, because an answer you reach yourself sticks. I do all three, and I'll tell you which one I'm doing.

When you're carrying decisions you can't talk through with anyone inside the business.

Common moments: stepping into the role, leading through a restructure, a board or owners wanting something new, or a leadership team that isn't pulling together. A good mentor gives you somewhere confidential to think, an outside view, and the honesty that gets harder to find the higher up you go.

Yes. I work well with owners and leaders with ADHD and dyslexia. I'm dyslexic myself, so we tend to think the same way.

In practice that means big picture first, a live conversation rather than a long document, and getting to the point. It's how I work anyway.

It's a 360-degree leadership assessment. Your manager, peers, direct reports and others rate how you lead, and the results show where your leadership is creative and where it turns reactive.

The creative side covers things like relating, self-awareness, authenticity, systems awareness and achieving. The reactive side shows the habits that kick in under pressure: complying, protecting and controlling. Most of us have a favourite. Results are debriefed one to one by a certified practitioner, and the profile is for development, not performance reviews. Used across a leadership team, it gives everyone a shared language for how they work together.

It used to last years. These days, in my experience, it starts drifting within months.

Markets move, AI is changing what's worth doing, and businesses grow into being good at things they weren't before. Each of those makes the picture go out of date. That's why I come back about a year after the first piece of work to recalibrate. Not a new strategy. Help getting to grips with the one you've got, now it's real. More in Three Degrees Off.

Check position every ninety days, and recalibrate properly about once a year.

I like 90-day cycles: plan, do, review, adjust, go again. Then about a year later the leadership team comes back together. Not for a new strategy, but to get to grips with the one you've got, now it's actually happening. The point is to make the small corrections early, while they're still cheap. More in Three Degrees Off.

I talk to each person one on one beforehand, listening for the friction and tension that show where things are going wrong, and, if there's more than one owner, start with them. On the day we work live, in the room: we put the current picture of the business on the table, get the real issues out, agree where we're actually going and turn it into a plan people will act on. Afterwards there's a short written plan, a 90-day rhythm, and a recalibration about a year later.

Longer answer: Three Degrees Off.

Start before anyone's in the room. I talk to people one on one first, because that's where you hear what's really going on.

Then, in the room, the job is to make it safe to name the thing. Not to blame anyone. Just to say what everyone already knows. In the room, not in the car park afterwards. More in Elephants Are Big, But Hard to See.

Be honest about it. Sometimes an organisation leaves some of its people. Nobody did anything wrong. The business moved, and some roles moved beyond the people in them.

The leadership team's obligation is to say so, and to help those people through the transition, whatever that looks like. Avoiding the conversation might feel kind. It isn't. More in Elephants Are Big, But Hard to See.

Stop trying to predict it. Business used to be a track race. Now it's orienteering: you still know roughly where you're heading, but you stop at every checkpoint, read the map and pick the next leg.

In practice that means a clear, shared picture of the future you're working towards, pressure-tested together, and short cycles (usually ninety days) where you check you're all still heading for the same place. More in Genetically Engineered for a Fast-Changing World.

Before you launch a plan, imagine it's a year from now and it's failed. Badly. Then ask everyone: what went wrong?

It's not pessimism. It gives people permission to say the things they'd never say in a normal planning session. You find the landmines before you step on them, and you usually find out who's been sitting on a worry. More in Genetically Engineered for a Fast-Changing World.

For owners, business is personal. We know our people, their families, our suppliers and customers by name. And we eat last: owners get what's left over.

A lot of us are wired differently too. Plenty of owners have ADHD or dyslexia, and the big-picture, pattern-spotting, run-at-it traits that come with them are often the engine of the business. More in A Weird Menagerie of Misfits.

Noticing the urge to defend yourself, and asking a straight question: am I defending this because it's right, or because I don't want to be wrong?

It's a team discipline as much as a personal one. Every manager carries a picture of how the business works, and nobody announces when theirs goes out of date. Ask what lens you're using, and ask your team the same. Out loud. In the room. More in Learn, Unlearn, Relearn.

It's usually the first step: half a day in the room with the owners, then a one-page written position.

The page sets out where the business is exposed and where the openings are. One page. You'll actually read it. Start to finish takes about a week, and if you go ahead within 60 days the fee comes off whatever follows. It also means anything bigger gets scoped properly, not guessed.

No. Most owners won't read one. And the people who need to act on it definitely won't.

I work live, in the room, and what I write up afterwards is short: what we agreed, in plain words, and who's doing what. A lot of business owners think fast and want the shape of something before the detail. I'm the same.

Mostly privately held, owner-led New Zealand businesses, often professional and knowledge-based services. Plus the executive teams of larger organisations.

The common thread is a group of leaders who need to be on the same page and aren't quite there. I don't do rescue jobs for businesses in serious trouble. That's a different skill set.

Fixed fees, agreed up front, plus GST. Facilitation is $4,000 a day or $2,500 a half day.

A typical leadership-team engagement, with one-on-ones beforehand, the day itself and a short written plan everyone signs up to, usually comes to $5,000 to $12,000, depending on whether it's one day or two. Every piece of work starts with a Position Session ($2,500, credited if you go ahead). Coaching is per session, ongoing work is a fixed monthly retainer over twelve months, and bigger projects are priced after the Position Session, so the price matches the work.

I'm based in Auckland and work across New Zealand and the Pacific.

Facilitation happens in person. Coaching and mentoring can be in person or on a video call.