How to Run Leadership Conversations That Change What Happens Next
Most leadership teams know their ways of working need to change. Fewer know how to have the conversation that actually shifts things. I was running a Ways of Working session with the leadership team of a large Asian electronics company, focused on lifting engagement, cutting turnover and tackling burnout as they moved into a new model of work. These were busy, clock-driven people with little appetite for open-ended discussion.
Then the right questions landed, and the room changed. What unlocked it was a simple discipline: getting genuinely curious through "How might we" questions. Below are the questions we used and what they surfaced.
Workspace: Giving Employees Ownership of Their Day
"How might we allow our employees to choose which part of their day is for them, which is for us and which is for recharging and reflection, and still get the best results for the business?"
Some companies talk about the work/life balance. Others work/life blend. The key is agreeing clear expectations with employees to create appropriate space in their lives to deliver to their accountabilities, and also encouraging them to create space for their lives during their work where there are important personal things that need to be done.
This means building trust to make work "work" for them whilst you are paying attention to burnout and wellbeing.
Workspace: Setting People Up for Success
"How might we provide the thing(s) our employees need to ensure they are as productive as possible wherever they choose to work?"
Second is the idea of setting people up for success with the equipment and facilities they need to do their best work. I will always remember talking to a GM in a large retailer who regaled me with the story of receiving a 28-inch monitor and the huge difference it made to her having been squinting at spreadsheets on a 13-inch laptop for years. Don't underestimate the power of creating an optimal workspace for your teams.
Are you the bottleneck?
Take the two-minute assessment and see exactly where work is queueing around you, and what to hand over first.
Workplace: Creating Connection Wherever People Work
"How can we facilitate allowing people to work from wherever they work best, and still create connection?"
A lot of businesses are discussing this right now. Where should our people work from? Should it be the office, should it be a co-working space, or should it be from home? Should it be a combination of those things? What I often hear is insecurity from leadership teams to let people continue working from home because of the opportunity for connection and performance management that in-person interactions traditionally create.
This is about being a better leader, not pulling people closer to you.
Workplace: Reducing Pace Through Honest Prioritisation
"How might we reduce the pace by stopping doing some things, slowing down some things, and doubling down on some things?"
The pace that people have been working at for the last two years is unsustainable. Leadership teams continue to demand continued results. Members of teams are resigning and not being replaced. Operational staff have been stripped out to save budgets, and people are trying to navigate new ways of working with varying levels of support. Most businesses have their people doing more with less when in reality, the opportunity here is actually a ballsy discussion about priorities.
Where is the friction in your team?
The Leadership Friction Finder pinpoints where effort is leaking, so you fix the cause rather than the symptom.
Workmates: Hiring, Developing, and Retaining the Right People
"How might we ensure we hire, develop and retain the right people into our teams for the future of our business?"
The people you work with and the manager you work for are the single biggest factors governing whether employees stay or leave. Making sure you get the right people in the right seats at the right time is essential to your business performance. Then ensuring they are growing their skills and experience to not only cope with the changing world around them but also to reach their career aspirations.
Nearly all of these ways of working factors can be greatly improved by having better conversations. That’s where the Ways of Working programme is really helping to create more sustainable, resilient teams.
If this sounds like your week
Your managers are not the problem. They are where the problem is stuck.
When your last leadership spend was signed off, did anyone go back to those managers' bosses and ask what changed? That question is the JBL Outcome Standard, and it is how I work.
- Find the friction. A short diagnostic that shows which decisions are stalling, and at what level.
- Am I the bottleneck? Ten questions on where your week is actually going.
- How I work with GMs. Six weeks, one hour a week, up to twelve of your managers, scored by their own bosses.
- Beat Burnout, Boost Performance. The book.
- The High Performance Leader podcast.
Managers I work with reclaim around four hours a week, and their bosses score the change 8.75 out of 10. Would it be a crazy idea to find out how we did this? Book a scoping call.
From the YouTube channel
Watch: more on this topic
A video from the JBL High Performance YouTube channel that goes deeper on the ideas in this article.
Most people conversations are prepared in a rush, run on gut feel, and forgotten by the following we
Start this week
Busy all day and still behind?
The Quick-Win Pack is five five-minute fixes for the overloaded leader, each built on a framework I use with paying clients. Every fix runs live on the page and hands you a finished, ready-to-use plan in minutes, with no AI account of your own needed. Just $19, and included free with AMPLIFY and the Six Week Reset.
Get the Quick-Win PackQuestions managers ask about this
How can I improve leadership conversations to change team outcomes?
Focus on asking curious questions that invite new thinking, such as 'How might we' questions. This approach encourages your team to explore different ways of working, identify priorities, and address challenges together. Leading with curiosity helps uncover insights that can shift behaviours and decisions, resulting in meaningful changes in how your team operates.
What questions help leaders address employee engagement and burnout?
Ask questions like 'How might we allow employees to balance work and personal time while meeting business goals?' and 'How might we reduce the pace by stopping or slowing some activities?' These questions help create trust, set clear expectations, and prioritise tasks to prevent burnout while maintaining performance.
How do I support my team’s productivity in different workspaces?
Ensure your team has the right equipment and environment to do their best work, whether at home, in the office, or elsewhere. Ask, 'How might we provide what employees need to be productive wherever they work?' Providing appropriate tools and flexibility boosts output and job satisfaction.
What is the best way to hire and retain the right people for future business needs?
Focus on hiring the right people for the right roles and invest in their development to meet changing business demands. Ask, 'How might we ensure we hire, develop, and retain the right people for our future?' This approach improves team stability and aligns skills with evolving organisational goals.
Explore this topic
Hear this discussed on the podcast
Episodes of The High Performance Leader that cover the same ground.
Jimmy Burroughes
FounderFormer British Army officer and corporate GM who has transformed nearly 3,500 managers into leaders across 30+ organisations. Creator of the Simplify to Amplify methodology, author of Beat Burnout, Ignite Performance, and two-time Global Recognition Award winner.
Keep exploring
Want to know where the drag really is?
Before you change anything, get an honest read on the friction slowing your team down. Take a short, free diagnostic and see exactly where the time is going.
