Don Quixote And The Quest For Management Support

Rather than default to managers as the primary vehicle for getting people to apply what they learn, maybe it’s time to redirect the quest for this seemingly out-of-reach ideal and find other ways to conquer the windmill.

As a talent development professional, it’s gratifying to know organizations are investing more in learning. Companies are spending billions of dollars on training in the United States alone (see Training’s 2018 Industry Report). Quantity, however, too frequently does not translate into quality. Return on investment studies reveal disappointing behavior change and bottom-line results. Lack of management support often is cited as the root cause of people not applying what they learn to their jobs. “It takes more than footing a bigger bill for training. If only managers would get engaged and do their part,” has become a common lament. Enter Don Quixote.

“Don Quixote” is a timeless saga by Miguel de Cervantes. Quixote loses his grip on reality and embarks on an obsessive quest to revive chivalry. On his journey, he spies a bank of windmills on the horizon. Perceiving the windmills as his enemies, Quixote engages them in an intense yet fruitless battle, leading nowhere. “Tilting at windmills” has come to mean the vigorous chasing of an ideal while ignoring information that calls for different action.

It’s easy for dedicated Learning and Development (L&D) professionals to embrace a Quixote-esque quest as we search for the ideal strategy to engage managers in their employees’ learning. Have managers become the windmills in the training results story, enemies to be battled rather than collaborative partners? Are you— like Don Quixote—tilting at windmills?

Here’s the reality:

  • Time-starved managers struggle to address a fraction of what’s expected of them each day.
  • Leaders appreciate the importance of learning; however, when it comes to allocating time, issues and priorities they associate with a more direct business impact always come first.
  • Many managers may have the will but simply don’t have the skill to fully support learning and change.

So rather than default to managers as the primary vehicle for getting people to apply what they learn, maybe it’s time to redirect the quest for this seemingly out-of-reach ideal and find other ways to conquer the windmill.


Traditionally, managers have been instructed that their learning support role should involve attending management support sessions and even employee courses, engaging in pre-and post-training conversations with employees, coaching to new skills, recognizing effort and modeling the skills being taught, and even becoming course instructors. While these expectations are valuable and could drive remarkable return on investment, let’s get real. Multiply each action by the average number of direct reports and it’s easy to understand why this hasn’t happened.

So let’s dramatically hack back the manager’s learning support role. Concentrate on just three focus areas (we call them the 3As) with high-impact “asks” of managers and the tools that make it easy for them to step up.











We’ve said for some time that learners must own their own learning. And we’ve even given them control in many cases over the what, when, and where of the experience. But have we really enabled learners to go from passive consumers of training services to actively leading the effort to translate information and insights into performance and results on the job? Too frequently, the answer is “No.”

If we are going to stop “tilting” at management expectations relative to training support, we have to set learners up for greater self-sufficiency. That means putting greater emphasis on such things as:

  • Context: We have to be considerably more explicit about how and under what circumstances knowledge and skills should be activated so the learners can coach themselves into action.
  • Reflection and action planning: We can no longer think of this as a perfunctory add-on to the learning experience; it must become central. Learners need a clear, actionable, and self-driven plan to put what they’ve learned into immediate practice.
  • Setback anticipation and recovery strategies: Knowing managers may not be able to support and coach learners as they stumble and struggle with new skills, we must help people anticipate what might go wrong in advance. When they’re prepared with specific triggers and strategies, learners can pick themselves up, coach themselves through failure, and plan for greater future success on their own.
  • Coaching pairs, trios, or cohorts: In the absence of active management support, individuals can reinforce and support each other to put new skills and knowledge to productive work. And the process of coaching others increases the informal coach’s knowledge, fluency, and buy-in for the information.


Systems that support learning are getting smarter and more sophisticated daily. The key is staying abreast of what’s possible and making non-human resources work as hard as possible for you and your learners. Best-in-class organizations are figuring out how to shift the support burden in a variety of technology-enabled ways by:

  • Turning the learning management system (LMS) into a reinforcement partner. Supplementing “pull” content access methods with smart “push” strategies can enhance memory and accountability while establishing a cadence of follow-up with scheduled reminders, success stories, additional micro-moments of content, and even individual learner commitments and intentions.
  • Incorporating new skills into the performance management system. Upon completion of learning, the newly acquired competencies or outcomes can be loaded into an employee’s profile or development plan. This highlights learning that has been completed and prompts at least one manager-employee conversation each year on the subject.
  • Leveraging chat-bots for learning support. The rise of the electronic coach offers an interesting and less laborious alternative to some of what traditionally has been expected of managers. These coach-bots can be set up by L&D professionals to automatically offer reminders, inspire reflection, and simulate some elements of a coaching conversation. And as artificial intelligence (AI) continues to advance, it’s not hard to imagine this capability quickly expanding to include the ability to offer context-specific cues, tips, and even feedback about the extent to which employees are putting new skills and learning plans into practice.


Quixote’s quest, like the quest for manager support of learning, sprang from noble beginnings. In the end, however, Quixote, beaten and battered, abandons all the chivalric truths he followed. Don’t follow that same dismal path. Take a step back and look at what you’re trying to achieve.

Manager support for learning has always been a means to an end, not the end game. What is your quest...really? What do you want to achieve? Behavior change? Transfer of learning? Measurable training results? It’s time to plot an alternate path.

  • Make the managers’ role count by suggesting only high-impact and easy-to-implement actions.
  • Set learners up for greater self-support by providing greater context and strategies to make learning stick.
  • Activate connection and reinforcement through the sensible use of technology tools.

Try this and, unlike Quixote, we might keep at least some of our sanity and live to fight other winnable battles facing L&D.

Julie Winkle Giulioni (left) works with organizations worldwide to improve performance through learning. Named one of Inc. Magazine’s top 100 leadership speakers, Winkle Giulioni is the co-author of “Help Them Grow or Watch Them Go: Career Conversations Employees Want” due out in its second edition in January 2019. Contact her at

Karen Voloshin is a learning designer and team and individual effectiveness coach. Together with Winkle Giulioni, she leads bicoastal learning design and coaching firm DesignArounds. Voloshin has authored thousands of hours of customized learning.


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