Why Developing Managers Starts With Asking Better Questions
It’s time to move beyond training and get real about supporting managers.
Reconsidering the Default Response
So often, when an organisation recognises that managers are under pressure or not quite delivering, the answer is to send them on another training course. It’s usually well-meaning, with the idea of “equipping” people for the job. In my conversation with Dan Northover, CEO at Handcrafted, we took a step back from this quick-fix mentality. We looked more deeply at what managers actually need, and where the real difficulties often sit.
Slowing Down Before Stepping Up
What struck me most about working with Dan was his decision to consciously slow down and create space for managers to reflect. Before launching into yet more training, we asked four golden questions:
- What does your role actually require?
- What matters most to you about how you manage the people on your team?
- What can get in the way of your manager responsibilities?
- What helps you achieve your day-to-day managerial responsibilities?
These questions sound simple, but slowing down to answer them openly and honestly made all the difference. The reality is that, for many managers, the issues are less about missing knowledge and more about the hidden pressures and expectations that come with the role. Left unexamined, these build up until even the most dedicated people start to slip into exhaustion or self-doubt.
We also asked the people being managed a set of different golden questions to understand where there was alignment or a disconnect with what managers were doing, and which behaviours needed to be experienced less or more.
Data over Assumptions
One of the most powerful parts of our work together was looking at real feedback – not just what people thought was happening, but what was actually happening on the ground. When Dan and his team stepped back to survey both managers and their teams, the results were surprising. Whilst frontline teams reported that they were happy and well supported, it was the managers themselves who turned out to be carrying the greatest weight, and whose wellbeing was at risk.
This is a crucial reminder not to take things at face value. Good intentions can mask unseen stress, and even successful teams can be paying a hidden price. If you don’t dig deeper and challenge your assumptions, you risk missing where support is really needed.
Leadership and Management: Knowing the Difference
We also spent time unpicking the difference between leading and managing. It’s common for organisations to focus heavily on “leadership”, celebrating inspiration and vision. But technical management skills – setting clear expectations, holding people to account, managing workload – are equally important, yet so often overlooked. When the lines blur, managers try to wear every hat at once, which often leads to overwhelm or gaps in performance.
Equally important is self-leadership. Before you can support others, you must know how to set boundaries for yourself and recognise when you’re struggling. Being able to articulate and model this as a manager is not just about self-care, but about setting the tone for your entire team – for better or worse.
Feedback and Vulnerability: The Heart of Better Management
None of this works without honest feedback and a willingness to be vulnerable – especially from those at the top. When senior leaders show that they too are human, acknowledge their own limits, and genuinely listen to feedback from every level, they create permission for managers to do the same. That’s where a healthy, sustainable culture starts to take root.
The reality is that real development is not a tick-box exercise, or something you can fix in a single session. It’s about creating the conditions for everyone to thrive, and that’s ongoing, messy, and – ultimately – what makes the biggest difference.
If your managers are feeling the strain, let’s talk about how to create a culture where everyone can thrive.
Tune in to Beyond the Water Cooler to hear Dan Northover and I explore what effective manager development really looks like.
