The skills new and developing leaders need.
The behaviours that make them stick.
Leading people, managing performance, the hard conversations and the numbers, built into a weekly rhythm you practise on the job, not just learn in a room.
David O’Sullivan · 20+ years helping leaders, teams and organisations perform at their best · charities, NGOs, not-for-profits, government and business
You were promoted. Leading a team is a different job.
You were good at the job, so you were given a team. Now you’re judged on people, performance and results. You may well have done the leadership training. Putting it into practice every week, under pressure, is the hard part.
Most leaders get pulled along by the day: the inbox, the urgent request, the next problem to solve. The things that build a high-performing team and a strong culture, like the one-to-one, clear expectations and time to coach, slip to tomorrow. And when the pressure is on, most new leaders fall back on what’s familiar: doing the work themselves.
Under pressure, you don’t rise to your intentions. You default to your habits.
HabitWell closes the gap between knowing what good leadership looks like and doing it, week in, week out.
When leaders are left to work it out, everyone pays.
Direction gets lost.
Pressure builds.
Gaps appear in communication, standards and follow-through.
Energy drains, from the leader and the team.
Good people leave.
Performance drops, and bad habits set in.
It’s rarely bad intent. Most managers step up without formal training (82%, CMI), and training alone rarely changes what happens on a busy Tuesday. It’s preventable, and prevention starts with how a leader runs their week.
The small things add up.
Leadership isn’t decided in the big moments. It’s decided in the rhythm of an ordinary week: how you start the day, whether the one-to-one happens, when you look at the numbers, how you walk into the hard conversation, and what your team sees you do when the pressure is on.
Get that rhythm right, and the right behaviours repeat until they’re simply how you lead. That’s what HabitWell builds.
Leadership, made practical.
Most leadership training changes what people know. HabitWell changes what they do, by turning the leader you want to be into practical changes to your working week.
What to change
The few behaviours that make the biggest difference to your team and results.
How to make it stick
Simple routines tied to cues in your day, repeated until they’re how you lead.
Where to change it
The moments your week already has: one-to-ones, meetings, the numbers. No time off the job.
When it matters
The moment before you walk in, where leaders usually slip under pressure.
The HabitWell model
Every lasting change follows the same path. A thought becomes an action. Repeated actions become habits. Habits that hold become behaviours, and over time your behaviours become who you are as a leader.
Why it works
Most of what we do each day runs on routine, not on decisions made in the moment. Habit research shows that repeated responses become easier and more automatic over time. Change the routine, and the behaviour follows.
Who's behind HabitWell
I’m David O’Sullivan. For more than 20 years I’ve helped people be at their best as leaders, building the actions, habits and behaviours that help teams and organisations succeed.
My experience spans employment services, disability, health and community services, working with charities, NGOs, not-for-profits, government and business across five countries. I’ve led teams and organisations myself, and I’ve spent much of my career developing and mentoring the leaders who run them.
HabitWell started at my own front door. Read my story →
What leaders say
“I did the 30-Day Reset because there were a few areas of my life that I knew weren’t working as well as they could. What I got wasn’t someone telling me how to live. David listened, asked questions and helped me work out where I could make a difference.”
— Scott F, State Manager
"The biggest change wasn't becoming more productive — it was becoming more intentional. I started catching my old habits and giving myself space to be different."
— Mark S, HR Director
“There wasn’t a huge breakthrough — more a series of small things adding together. Notice, choose, act, try again. That’s why this worked for me. I got to apply what I learned and try again, getting direction and insight every week.”
— Jessica C, Marketing
“Lasting change doesn’t come from inspiration. It happens on ordinary days — which means the leader you want to be is only one better day away.”
When leaders get it right, everyone gains.
Direction is clear, and everyone knows what good looks like.
Pressure is shared and managed, not passed down.
Gaps are spotted and closed early.
Energy stays high, for the leader and the team.
Good people stay, and grow into the best version of themselves.
Performance lifts, and good habits become the culture.
And you have energy left for yourself, your career, your life and the people closest to you.
Managers account for at least 70% of the difference in how engaged a team is (Gallup). Better leaders build better teams, and better teams build the culture an organisation runs on.
Getting started is simple.
Book a 20-minute call. Tell me about your leaders and what’s getting in the way.
Agree where to start: which leaders, the behaviours that matter most, and how you’ll know it’s working.
Start LeadWell, or a programme shaped to your organisation.
LeadWell
Six weeks for new and developing leaders.
Built around the four things every new leader has to get right: leading yourself and your day, leading your people, leading performance, and building the culture.
You leave with:
your own Leader’s Operating Rhythm
a weekly numbers review you’ll keep using
one real team challenge worked through
a sponsor review with your own manager
A$2,699 per leader.
Try it first: your organisation’s first leader is free when their manager acts as sponsor, so you see the difference in your own team before you commit.
Charities and not-for-profits: community rates are available. Ask when we talk.
Developing a group of leaders? Larger programmes are quoted to fit your organisation.
Not sure which route fits?
Want one-to-one support? 90-Day Leadership Coaching. Book a call →
Starting on your own? The 30-Day Reset, $495. Start the Reset →
A bigger challenge in your organisation? Consulting and bespoke projects. Explore Consulting →
Free guide: Design a Better Day
A free 7-day guide for busy leaders. Small, practical changes to how you design your day, built on the same method as the 30-Day Reset.
Coming early 2027: the HabitWell book for new leaders. Get the free guide and you’ll be first to hear when it’s out.