What Happens When Managers Talk About Learning?
By Jonathan Yeo
Learning in the flow of work already has an infrastructure. It just needs to be enabled.
Same Workshop. Two Completely Different Outcomes.
Jordan and Priya work in the same organisation, at the same level, in adjacent teams. Last Tuesday, they attended a full-day communication skills workshop together. They heard the same concepts, engaged in the same activities, even gave the course the same positive rating. But one thing made their learning experience markedly different.
Last Friday, Jordan reminded his manager about the workshop, and the response was brief: “OK, just make sure you send me the latest Hendricks updates by Monday night.” Jordan did so, and returned to his desk on Wednesday after the workshop to a full inbox.
He remembered that one of the ideas from the day before was to remove unnecessary words in emails, so he decided to apply that to a response he had just drafted. He edited the email to make it more succinct, and sent it. The reply he received the next day didn’t give him any indication as to whether the shorter email was better or not. A week later, a colleague who was considering going to the same workshop asked him what stood out. Jordan struggled to remember.
Things unfolded differently for Priya. In her one-to-one with her manager the week before, she mentioned being unavailable on Tuesday due to the workshop. Her manager asked if she was looking forward to it (she was) and if she had an outline of the workshop.
Together they looked at the information she had received. Her manager highlighted part of the agenda: “I noticed this section on active listening — that could connect to what we discussed in your last review about being open to other perspectives. They might offer some practical suggestions. I’ll be interested to hear what you get out of it.” Priya wasn’t just attending a communications workshop anymore. She had a focus that connected to a development goal, and the promise (and accountability) of a follow-up conversation.
When Priya was back in the office following the workshop, her manager dropped by and asked about it: “How was the day? What stood out for you?” Priya explained what was shared on active listening, and the other ideas that resonated for her. Her manager asked her to think of an upcoming meeting or conversation where she could try out an active listening approach. Priya identified a project meeting in two days’ time where she felt there was some competitive tension with a cross functional partner, and thought it could be an opportunity to try an ask-and-restate approach with them. Her manager gave her the thumbs up: “I’ll be interested to hear how it goes.”
After the project meeting, Priya dropped by her manager’s office: “You know what? I think it worked. I just said ‘So let me make sure I’ve understood correctly …’ – it led to a deeper analysis, and I could see they felt more heard, and it felt like they became instantly less defensive.” Her manager congratulated her on trying the new approach and added: “You know, communication is something I continue to work on. One thing that has been really beneficial for me was learning to pause before I respond. Give myself the opportunity not to just say the first thing that comes to mind. Often the second thing is better.”
Learning Isn’t One Experience
This is the truth that we know intellectually, but often ignore operationally: for most workplace learning, the quality of the initial learning experience is not the primary driver of whether learning becomes behavioural change. It’s whether there is relevance to the work, and reinforcement over time. Managers are in the prime position to provide both of these.
Priya’s manager did three things that shifted a standalone learning experience into the flow of work, making it more impactful, memorable, and actionable. First, the manager primed Priya for the learning before it happened — connecting it to something real and observed, and gave her a concrete goal.
Second, the manager created space for exploration and application after the formal learning happened — not a tick-box check-in, but a genuinely curious conversation about what was learned and where it could be relevant. Third, the manager modelled something important: that development isn’t a skill gap remedy, it’s an ongoing practice that everyone should be engaged in.
The conversations between Priya and her manager were simple and straightforward, and required little to no preparation on the part of the manager. Each of them could have taken a couple of minutes at the most. A small investment for a big payoff.
The Manager as Learning Leader
Managers have two things no L&D professional can easily replicate: proximity and contextual awareness. They are already inside the work. They know the goals and the expectations. They see performance and behaviours in real situations and in real time. They have access to the learner’s daily experiences — the pressures, the patterns, the relationships, the moments where new capabilities could be tested or applied. When it comes to learning in the flow of work, the manager is not a nice-to-have. They are the key enabler.
There are two ways managers can activate this potential.
The first is delegation for development. Not delegating to get things off their plate, but delegating with the deliberate intent to stretch and develop a team member according to their needs and aspirations. This means thinking about what experiences would benefit an employee, weighing challenge against current capability, sequencing the steps to build confidence, and being explicit about the learning goal — not just the task goal. When a manager says, “I’m giving you this project because I think it will stretch you in a beneficial way,” they have just designed a learning experience – no classroom or LMS required.
The second is reflective conversation: the deliberate practice of talking with an employee about what they’ve experienced and what they’ve taken from it. If there’s a formal learning event, this looks like our example of Priya’s manager reviewing the workshop outline and co-creating a focus. After any significant task, project, or experience, it could sound like a manager asking: “What happened? What did you learn? What would you do differently? Where can you apply this?” These are not complex questions, and your managers don’t need training to ask them. They just need a prompt, and a reminder that it matters.
Together, these two practices — delegation for development and reflective conversation — turn the daily flow of work into a learning environment. They don’t need to be formal, or even scheduled. They should be continuous, real-time interactions between a manager and the people they lead.
Enabling the Conversations
Most managers do not see themselves as learning practitioners. The idea that they are responsible for the development of their people is usually understood, but the specific actions that contribute to that — the pre-brief, the debrief, the conscious use of stretch tasks and assignments, the modelling of their own ongoing development — are rarely made explicit, rarely practised, and almost never built into how managers are selected, developed, or evaluated.
L&D has a role to play in changing this. Not by adding another mandatory manager training program, but by repositioning manager enablement as a core learning lever. Here are four simple actions L&D practitioners can take to enable managers to be learning leaders for their teams:
- Advise them when their team members are attending learning experiences, what they’re learning, and how the manager can support the learning. Send pre- and post-experience reminders to the manager.
- Provide managers with simple daily learning questions to ask. Give them a cheat sheet, not a training.
- Include learning experience design, reflection and reinforcement as part of the expectations of manager success.
- Give them behavioural examples and role models – short videos of other leaders are a great scalable engagement tool for this.
From Workshop to Workflow
Jordan completed a workshop. Priya engaged in an opportunity to help her work.
They were both motivated to learn. But one manager understood — or had been equipped to understand — that they had the power to make the learning meaningful.
Learning in the flow of work is not, at its core, a design problem or an accessibility problem. It is a relationship-based opportunity. The most impactful learning leader is already paid, already in the room, and ready to work. They just need to be activated.
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About the Author: Jonathan Yeo
Jonathan is the founder of The Potential Space, a leadership and organisational development consultancy based in San Francisco. His experience includes ten years at Apple working on leadership and inclusive culture. He is a speaker, facilitator and coach, and is passionate about helping leaders and teams work productively with human complexity, not despite it. For more information, visit https://www.thepotential.space/ or https://www.linkedin.com/in/jonathanyeo/