How to Run Leadership Conversations That Change What Happens Next

Picture the scenario. I’m running a “Ways of Working” session with the leadership team of a large Asian electronics company, utterly fascinated by the moments of insight happening about how they operate versus how they might. We were talking about maximizing engagement in their people, with a secondary focus on reducing turnover and burnout, as they transition to a future of work scenario.
This was a team used to running meetings by the clock and with limited flexibility the way they do anything; when suddenly, things started to change. I’ll share some of the questions which were asked to provoke insights. The key in these sessions is getting curious using “How might we” questions.
First, we talked about Workspace:
– “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/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 2:
– “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 (workspace) 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.
The next conversation was Workplace:
– “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. Hint – this is about being a better leader, not pulling people closer to you.
The third conversation was Workplace:
– “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 out 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.
The final discussion in our workshop was Workmates:
– “How might 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 and that’s where the Ways of Working (WoW) program 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.
#waysofworking #blog
Questions 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.
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 3,000+ 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.
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