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Upskilling managers: Quiz, downloads, and reflection exercises

Updated: Oct 26, 2023

"Upskilling a manager" means providing the training, education, and development opportunities managers need to grow their existing skills, knowledge, and capabilities.

Equip managers with new competencies, tools, and insights to evolve along with the workplace. Your aim is to keep managers current and effective in their positions, enabling them to meet the changing demands of their roles and do it with resilience and optimism.

Reflect On This

  1. What resources do you have available to help support and uplevel managers at your company or org? Think: time, expertise, cash, and leadership support.

  2. How confident do you feel in your ability to support manager development? Do you need additional support to make this a reality?

  3. What impact would empowered, up-leveled, excellent management have on your organization? How does it feel to think about it?

Finding the tools you need for today

Look around at managers of today (the Modern Manager, if you will 😉), and you’ll see some stark differences compared to the best practices of 10 or 15 years ago.

Today’s employees expect coaching, leadership, psychological safety, career development and advocacy, and recognition.

A manager who delivers all this looks different from the command-and-control style managers dominating office spaces from the 80s into the 2010s.

This can be tricky for even the most dedicated employee to navigate

Imagine successfully executing throughout your first decade of work. You excitedly land your first management role, only to find that everything you’d learned about managing teams 10ish years ago is already outdated (counterproductive, even) in today’s workforce.

Beyond learning (and, in many cases, unlearning) to adapt to the ever-changing world of work, let’s not forget that management takes time, capacity and resourcing. It should be clear by now that great management deserves much more than a firm handshake and a “you’ll figure it out.”

Your managers need training

World-class management is a life-long aspiration – a skillset to be learned, developed, and finessed over time. World-class managers need baseline and ongoing access to resources informed by experts who distill ever-evolving better practices into effective learning experiences.

I’ve asked a lot of you over the last few weeks in our quest to uplevel your people managers.

You’ve distilled the right competencies for your culture. You’ve clarified expectations for leaders across your organization. Maybe you’ve even advocated for headcount or admin and ops support to free up your managers' time.

The reality is that unless you’re a learning and development whiz, training your managers to be the best they can be isn’t your bag. That’s okay! You’ve done enough to enable great leadership at your workplace.

I’m hooking you up with my favorite manager training resources so you can jump off from the point that best empowers you and your team.


Take the quiz: How well do you support your managers?

Pick the answer that most closely reflects your workplace, and we’ll let you know which of our favorite three learning and development resources could work best for you. Don't overthink it, and here we go:

1. What kind of facilitation chops does your organization have?

  • (A) We have an L&D team with strong experience in facilitation and training - we’re set.

  • (B) We have at least one team member with facilitation experience or someone eager to learn who could dedicate some time and energy.

  • (C) Our org doesn't have a single facilitation bone in its body.

2. Which statement most closely matches your company’s interest in bringing in outside support for personnel training?

  • (A) When it comes to People and Culture, we stick to internally driven programs and projects.

  • (B) We wouldn’t fully outsource something like this; a close partnership with outside support and expertise is the right balance for us.

  • (C) The more external support the better! We’d fully hand over end-to-end control of management training to outside experts.

3. How much time do you or your People org have on your hands to dedicate to this?

  • (A) Quite a bit, actually! This is a big time-blocked priority for us right now, and we can devote our focus if need be.

  • (B) Somewhere in the middle; we have some time to dedicate to this effort but certainly wouldn’t mind more.

  • (C) Time!? I don’t know her…

4. Let’s talk cash. How much budget are you able to dedicate to management training?

  • (A) We’ve got some in-house skill and some time, but what we don’t got is money. Our budget is zero, nominal at best.

  • (B) I don’t know the exact figures, but I know our team would be willing and able to invest in the right solution!

  • (C) Cash isn’t an issue for us.


A manager upskills with their team. Two people can be seen smiling in an office setting with a computer screen in the foreground. Manager upskilling is essential for the evolving workplace.

If you answered…

…mostly As: Check out Google re:Work

No budget? No problem! If you’re cash-light but time or scrappiness heavy, this free management training resource is a good place to start. Google re:Work is available for non-commercial use by any organization, and you can customize downloadable resources to fit your needs and culture.

  • Pros: It’s free, heavily research-backed, and available for immediate use.

  • Cons: Every piece of content needs to be learned and delivered internally; you’ll need strong facilitation and training skills on staff. Nothing is pre-recorded, meaning this manual lift will need to happen for every training session.

…mostly Bs: Give our Training For the Modern Manager a peek

Wish you had an internal curriculum you could use to train every current and future manager within your organization? Want to Work There (yes, that’s us!) has your back. Training for the Modern Manager is an evergreen curriculum you purchase once and use in perpetuity.

Grounded in modern management best practices like coaching, delivering feedback, and intentional culture building, the 12-week program ensures your managers have the skills they need to succeed.

Post-program resources, like the Feedback Planning Tool and Team Charter exercise, ensure your managers have the practical tools they need to handle real-life situations, as they come up.

  • Pros: Modern, interactive learning modules, a one-time flat cost, and multiple facilitation delivery options. Simple and quick implementation, making it easy to get your first training cohort up and running in less than a week.

  • Cons: The program requires ongoing internal facilitation and coaching support, as new managers go through the program.

…Mostly Cs? Take a look at Campfire

If you need to outsource the time, energy, and program management in the name of expertise and convenience (and you have the budget to support that), Campfire coaching is a great option. With a focus on coaching and connection, Campfire facilitators lead each session, giving managers of any experience level a ton to learn and implement.

  • Pros: The lift on your organization’s responsibilities is minimal, as all sessions are led by professional facilitators.

  • Cons: The per-person-per-month structure can be cost-prohibitive.

>Looking for more options? Check out the full guide to the best management trainings.

Final Thoughts

Perhaps you’ve found the right jump-off point to train managers at your company, but if you haven’t, fret not.

The world is full of creative thinkers, builders, facilitators, and leadership experts ready to help you uplevel the leadership and management experience at your workplace.

Feeling lost on where to go next? Give me a shout, I’d love to help.

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