The Scale-Up Guide to Upskilling Managers
The Scale-Up Guide to Upskilling Managers
For Founders, VPs, and Heads of People asking, “How do we better support our managers?” this is your guide. A step-by-step on supporting your managers as your organization looks to scale.
It’s time to grow up.
I don’t mean you personally — but rather your organization.
Your company has doubled in growth over the past few years. You’re a startup in spirit, but you know it’s now time to evolve as an organization into “scale-up” phase.
To grow out of the teenager years and move into adulthood.
This means supporting your team the best you can. Especially your frontline leaders.
Your managers are well-intentioned.... But they are hungry for support.
You know this because, aside from a few managers coming up to you and confiding in you that “they have no idea what they’re doing”, you’ve noticed the following:
Your managers worry about being "liked" as a manager and so wait too long to give difficult feedback.
Your managers do everything themselves instead of delegating (also known as “savior complex.”)
Your managers are not clear enough in setting + communicating expectations, so the team underperforms.
Not that you blame them of course! A good number of your frontline managers have been internally promoted and were immediately “thrown to the wolves” so to speak – and so it’s no surprise that they are acting of instinct rather than best practices.
While it’s sorta working okay for right now, you know this isn’t sustainable. The old adage “What got you here won’t get you there” comes to mind.
It’s time for your organization to take the next step. To evolve, scale-up, and fully support your leaders.
So the question is: How, exactly?
In this piece, based on our experience working with tens of thousands of leaders over the past decade, I’ll share the nitty gritty on exactly what to consider and how to best approach upskilling your leaders. Specifically:
How to gage your managers’ needs
How to analyze all the data and insights you receive
How to prioritize solution criteria
How to evaluate potential solutions & pros/cons of each
How to define success metric
How to get leadership buy-in
With this guide, you can thoughtfully cultivate the culture you’re looking for in the long run and help your organization grow and scale well.
Let’s dive in.
STEP 1: Gage your managers’ needs
You have heard through the grapevine certain sentiments (e.g., “I’d love help on navigating performance conversations”). But to truly make sure you’re meeting the needs of your team, I suggest two initial courses of action:
📈 Run a Leadership Skills Assessment
You’ll want to put together a survey that helps you understand the reality of where managers are at. How leaders see themselves and their skills, what kind of support they’re craving…
Here some Leadership Skills questions we recommend asking:
What might you say your #1 struggle is as a leader, currently?
How confident do you feel currently in your abilities as a leader?
How many years of experience do you have as a manager?
How would you rate your ability to give difficult feedback to a team member?
How would you rate your ability to coach an underperforming employee?
How would you rate your ability to share sensitive or difficult decisions with the team?
How would you rate your ability to communicate changes and decisions to your team?
For a more comprehensive in-depth 360 Skills Assessments of your leaders — that includes the perspectives of direct reports and the managers’ supervisors – you can deploy our 18-question Canopy Leadership Skills Assessment. It will take your leader less than 5 minutes to complete and can give you a holistic sense of opportunities for training for skills, outside of the more broad questions listed above.
Here’s an example of what taking the Leadership Skills Assessment in Canopy looks like:
And an example of the results:
👉 You can check our Leadership Skills Assessment here. Feel free to use it directly, or use our questions for inspiration or as a template to create your own.
🎧 Conduct a “Listen-and-Learn Tour”
There’s nothing quite like hearing from your leaders directly what’s on their mind and what kind of support they are seeking.
I recommend asking your managers in small groups of 3 - 6 folks who are interested in sharing their perspectives as a part of a “Listen-and-Learn Tour” where you ask the following questions…
Questions to ask Frontline Managers
To what degree would you desire more support from our organization, as a leader?
To what degree might you say continually learning as a leader is something you value?
What is the form of support that you might most desire from our organization? (For example: What is your preference for asynchronous/online vs. live vs. in-person?)
What time commitment would you be willing to spend each week to interact with and receive support?
What are the most critical skills you’d like to personally develop as a leader?
After participating in a leadership training / support program, what’s the main thing you’d like to be able to do differently?
What do you think is most important for us to consider as we look to put together a leadership training program and support you as leaders more?
What do you think might be the biggest barrier to a successful program to help support leaders?
Asking these questions is also a phenomenal way to encourage a growth mindset for your leaders and start to get their buy-in and engagement in the program as well.
You may also want to hear from your senior leaders, as well, as they may provide a helpful perspective on what skills they’d personally like to see their own direct reports who are managers level-up in. Specifically, you could ask them…
Questions to ask Senior Leaders
What are the most critical skills you’d like to see our frontline managers level-up in?
What do you think is most important for us to consider as we look to put together a leadership training program and support our frontline managers more?
What do you think might be the biggest barrier to a successful program to help support leaders?
Lastly, you will want to understand firsthand what direct reports of frontline managers are observing. They, after all, are the ones whose performance is directly being guided by and influenced by their direct manager. You can ask direct reports the following questions in a focus group…
Questions for Direct Reports of Frontline Managers
Ideally, what skill areas do you think your managers might benefit from being supported in the most?
What do you think might be most helpful for your managers as we look to put together a leadership training program?
STEP 2: Identify patterns in your managers’ needs
With all the data you gather during Step 1, you may initial feel you’re drinking from a firehose of information – but fear not.
There are several primary categories of patterns that will emerge and you’ll want to focus on identifying:
🎳 Skill Gaps
This will likely be the most obvious pattern you identify: What are the most important skills that you want your managers to level-up in?
You’ll want to create a list of roughly 5 - 10 skills, ideally ranked in terms of priority, based on the Assessment results and Listen-and-Learn Tour findings. I recommend taking a look at specifically:
What are the skills managers self-report as being least confident in, from the Skills Assessment?
Where are the biggest gaps between how managers perceive their skill level and how colleagues perceive their skill level, from the Skills Assessment?
What are the skills that managers unanimously seem to be asking for support in, during the Listen-and-Learn Tour?
What are the skills that both direct reports and senior leadership seem to agree are important for managers to level-up in, during the Listen-and-Learn Tour?
⛳️ Solution Preferences
From the Listen-and-Learn Tour specifically, you’ll want to take a look at the stated preferences that your managers expressed about their ideal solution. Examine answers for the following:
Do your managers prefer in-person live instruction, online live instruction, asynchronous online learning – or a mix of all?
How much time realistically did managers would want to spend in learning and upskilling? Thirty minutes? Ninety minutes? Per week? Per month?
How important to managers is it that they have continuous support throughout the year? Or do they prefer a one-and-done quick program?
🎩 Manager Archetypes
Least obvious and most overlooked – but quite important – is getting a sense of your “manager archetypes.” A manager archetype is a psychographic categorization to help capture the nuances of what kind of solution might be best for your leaders. Understanding the manager archetype helps you better answer the question: What is the kind of support your managers truly need?
To help determine this, there are typically 4 manager archetypes:
Novice and non-confident 🌱
Very green, new managers (with less than 3 years of experience) who’ve usually never participated in manager training. They are typically high achievers but feel like a fish out of water in their role and are craving as much hands-on support as possible.
Experienced and overwhelmed 🚌
More seasoned managers (more than 3 years of experience) whose top concern is that they are “time poor.” Often these folks are both “player and coach” and are wanting techniques and tactics to help them feel less stressed and manage the daunting number of deliverables they have.
Well-intentioned but oblivious 🛠️
Highly ambitious managers who were previously the top performing individual contributor on the team. They have good intentions, but out of a desire to “get things done” are not as self-aware or team-aware. This manifests in managers being perceived as “harsh” or “aggressive” because they have not yet developed the EQ and so-called “soft-skills” to finesse their leadership practices.
Eager but too nice 💖
Open-minded, growth-oriented managers who are eager to learn and do better. They embody high empathy and an intuitive sense for team dynamics, which is why they were promoted in the first place to a manager role. This has a trade-off though, as they can be too nice. They struggle with delivering effective performance feedback and have a habit of under-performers staying on the team for too long.
To be clear, your managers could absolutely fall into all 4 archetypes. But getting a sense of the distribution among the archetypes can help you with the next step, which is to…
STEP 3: Prioritize solution criteria
Now that you understand what your managers’ needs and preferences are, you want to start discerning a solution. What’s most important to solve for, given your managers’ needs?
Below are the criteria that you’ll want to consider. As you go through them, consider ranking them or assigning a number 1 - 5 of “Not important” to “Very important” for what you think your managers and organization care about most…
📚 Relevant, research-backed frameworks and content.
Based on the skill gaps you analyzed, how important is it that the content is up-to-date and delivered in a fast, engaging way? If you have managers in the “Experienced but overwhelmed” archetype mainly, this becomes even more important.
⚙️ Customized to your organization’s culture and values.
Consider what came up in the Listen-and-Learn Tour. Are there specific elements in your organization’s culture that you want to make sure are accounted for? If so, then the importance of customization may be much higher for you. Alternatively, if you have mainly “Novice and non-confident” manager archetype, then customization becomes less important, as you instead want to prioritize making sure foundational frameworks is shared with your managers as much as possible.
🍃 Lightweight and non-time intensive.
For most managers in a scale-up organization, your managers feel short on time. However, you may want to reflect on the findings from the Listen-and-Learn Tour on what “short on time” really means: Are folks willing to sit down to learn for an hour every week? Or is it every other month? Do they want to learn something in 1 hour? Or is more like 15 minutes? You’ll want to prioritize the time-intensive nature of the program, based on the salience of this to your managers.
👯♂️ Interactive and social.
Leaders of all 4 archetypes can benefit tremendously from hearing other leaders’ experiences. It helps validate their own experience and build confidence for leaders (especially for the “Novice and non-confident” folks) and encourages behavior change when you’re able to practice and discuss concepts (particularly for the “Well-intentioned but oblivious” and the “Eager but too nice” folks). However if you already have avenues for social learning in your organization (e.g., book club discussions, lunch and learns), you might prioritize this criteria less.
⏳ In-the-moment learning.
How important is it for your leaders to be able to quickly practice and get answers in-the-moment to the challenges they’re facing? You likely would have heard this surface in the Listen-and-Learn Tour, and will want to prioritize accordingly.
🔄 Continuous (not one-and-done).
To what degree are your leaders wanting continual support? Or, are they only support for a specific period of time? This is also something that would’ve come up in the Listen-and-Learn tour.
🌍 Scalable and flexible. Fast to roll-out, easy to add folks.
How quickly will you be hiring or promoting new managers in the upcoming year? If you’re projected to grow headcount significantly, a scalable solution is something you’ll want to highly prioritize.
💰 Budget conscious.
Of course, the budget is very important to all of us $$. But at this stage in your organization, what is the approximate budget expectation that your organization is ready to invest? Is this something that your organization sees as part of a learning & development budget for each person ($400 - $750 per person), or as a part of onboarding costs ($750 - $1,250 per person), or as a retention strategy ($1,250 - $2,000+ per person)? Understanding your organization’s budget expectations naturally plays a critical role in your solution decision.
With these criteria prioritized, below are a range of solutions to consider, with my recommendation around each…
STEP 4: Gather and evaluate options for solutions
How well do potential solutions address what you’ve prioritized, and what are the pros and cons around each?
Executive coaching 👩🏽🏫
PROS: The most personalized support that a manager can receive. Particularly effective for the “Experienced but overwhelmed” archetype who can make the most of the sessions because they can quickly pinpoint and ask for help on specific issues.
CONS: Very pricey. Hard to do continuously because of the budget investment. Hard to scale to more managers as you grow, as a result. Not ideal for brand new managers who don’t know what they don’t know yet and would benefit more from foundational learning. It’s also not social learning — your leaders are only learning from one expert and not their peers.
MY RECOMMENDATION: A great option if you have either (1) a small number of managers and/or a manager group size will stay very stable over time, and/or (2) your leaders are all in the “Experienced by overwhelmed” bucket, and/or (3) you have access to an outsized budget to invest.
AI Coach 🤖
PROS: Cost-effective and scalable. Great especially for folks who are short on time and feeling the pressure of wanting to get answers as soon as possible.
CONS: The quality can vary on the actual responses, since it is AI generated and not a person. It also requires your leaders to have a specific problem that’s bothering them, which may not be relevant to all your managers. Your team would also need to be comfortable interacting with a AI Coach — it may feel “impersonal” to some for this to be the only solution or means of support. Lastly, it’s also not social learning — your leaders are only learning from one expert and not their peers.
MY RECOMMENDATION: I think this is ideal as a supplement to a broader program of support… But as the only form of support, it has real drawbacks.
👉 We in fact have an AI Assistant as a part of Canopy. If you’d like to try it out yourself you can sign-up for a free account at canopy.is and go to our “Coach” section in the app.
Create your own internal training program ✍️
PROS: You can customize this 100% to your organization’s culture, language, and values. You demonstrate the value and importance of leadership in the training being “homegrown.”
CONS: Will take a long time to create, and requires domain expertise. This is a full-time job and typically takes at least 6 months to 1 year to get off the ground. If you are scaling quickly and/or already have a significant number of managers, you’ll be leaving those managers waiting for your program for a while.
MY RECOMMENDATION: Wonderful if you have the team internal bandwidth and expertise to do, and if your organization has not yet scaled their manager population. If the organizational bandwidth and expertise to take this on, then this is a great option. If you are a People Team of one or a few, then this is not the most tenable option for you.
Work with a traditional training partner 🤝
PROS: In-person delivery, so it gives your team live social interaction and peer learning. Happens in a preset amount of time, and restricted to a certain timeframe and may not be overly intensive on managers’ time.
CONS: Tricky to scale. After the first cohort, there is a long ramp-up time and usually requires a manager-minimum in order to add more managers to train. This is also a one-and-done program (not continuous) – and so managers are often left wondering, “What’s next?”, and don’t feel supported the rest of the year after the program is over. Skill retention suffers as a result.
MY RECOMMENDATION: A solid choice if your organization is primarily all co-located and prefers to receive live in-person synchronous training. Also great if you’re looking to have your managers brush up in just a few skills in a certain timeframe, and are less concerned about continuous improvement or support. Works well too if you have a stable manager population size, and won’t be promoting or hiring new managers in the next few years.
Leverage a modern training partner: Canopy 💚
Yes, of course, I’d be remiss to not talk about what we do here at Canopy — we deliver lightweight leadership learning programs for organizations looking to scale. Here’s our take on what we do well and not-so-well…
PROS: A blend of live, customized training paired with an on-demand platform gives you best of both worlds: Interactive, live social learning PLUS in-the-moment, on-demand online learning. We’re fast and flexible to implement: You can get started in as soon as two weeks, depending on the level of customization you desire. And we have a range of options of programs to fit almost all budget expectations.
CONS: No in-person delivery options — all of the training is done online (via Zoom for live training, and our on-demand platform). We do offer deep customization abilities, but don’t “swap out” content in our on-demand platform for alternate content.
MY RECOMMENDATION: If you’re looking for both interactive live learning and on-demand learning that’s focused on high-growth, scaling companies (particularly in tech) we are a great fit. If you’re keen on on-site in-person delivery for training only, I’d recommend working with a traditional training partner.
👉 If you’re interested in learning more about Canopy for Teams, you can read about our program here. You can also reach out to me directly at claire@canopy.is with questions, and/or schedule a time to meet with myself and our team here.
STEP 5: Define the metric for success
In whichever solution you choose, you want to answer the key question:
How will you know this program will have been successful?
Ultimately, the reason we want to implement support our managers in the first place is to increase the performance of our team.
So really, it’s about asking ourselves:
What’s the degree to which the program you implement will increase performance?
The way we track this here at Canopy is by looking at measuring skill improvement: To what degree did managers’ skills improve before and after the program?
(We recommend deploying the Canopy Leadership Skills Assessment before and toward the end of the program to capture this — but you could absolutely run your own survey per whatever other solution you choose, as well.)
📐 For example: At Canopy, we’ve observed at least 20% increase in skills when enrolling in our Canopy for Teams program.
Let’s say we see 20% increase in skills for 15 managers. And let’s say each manager runs a business unit that generates $500,000 in revenue for the organization.
ROI = [Gain of learning - cost of learning] / [Cost of learning]
So that means each manager can generate $100K more for their business unit because of this increased skill capability. (Of course, this is assuming a 1:1 ratio of attribution between skill increase and revenue increase. In reality this could be less, or it could be more). With 15 managers under this assumption, that’s a $1.5MM revenue gain in learning. And if I estimate the program cost for 15 managers to be say $30K…
Then [ $1,500,000 - $30,000 ] / $30,000 = 49
This equals a return-on-investment of 49X. That’s significant.
This is of course only an example – and it’s only one way to calculate ROI. Improvement in performance though may mean something other than skill improvement to your organization…
Success may translate to retention rate or financial performance of the company as well. You may find those numbers are slightly harder to pinpoint the attribution solely to the leadership program you implement, but it’s nonetheless still helpful to have as lagging indicators.
STEP 6: Get buy-in from rest of leadership team
You’re in. You know the importance of giving your leaders support. And with this guide, you now have a process for figuring out exactly how to do so…
But, how can you get the rest of your leadership team onboard?
At the core, you want to focus your efforts on underlining the true purpose of this program: High performance. To set up the organization for long-term success. To enable the organization to scale to the next stage.
With that, you’ll want to frame your presentation or discussion with senior leadership around this primary aim. I recommend addressing the following points in some way:
🚀 Emphasis of purpose: The purpose of manager training and support is to increase likelihood of high performance and successful scaling of the company.
🔗 Link between overall org performance and manager performance: The importance of strong manager performance and how that impacts overall team performance. After all, managers account for 70% variance in employee engagement.
💸 Cost savings: Savings gained by upskilling internally vs. hiring new employees. It costs $4,000, beyond salary and wages, to hire an employee. Training an employee, on the other hand, costs U.S. companies an average of $1,111 per year, according to the 2020 Industry Training Report.
🏔️ Skill gaps in manager performance: The stated needs and skill gaps you discovered in the Skills Assessments and Listen-and-Learn Tour.
🧪 Solution criteria: What you’ve evaluated to be the most important criteria set in a solution to close these skill gaps.
⚡️ Solution recommendation: What solution you recommend and why.
📈 Expected ROI: What you can expect in terms of increase in skills and in what timeframe, and at what cost.
🙋🏻♀️ Next Steps: You’d love their input, feedback, and approval of the program.
You’ve now got a plan.
Take only what’s most relevant from this 6-step plan for supporting your managers, and run with it.
Of course, you’ll want to tweak and alter what I’ve shared here for your own organization. But I hope it’s a helpful starting point as you look to support your leaders in the best way possible.
I look forward to hearing how it goes for you!
-Claire
(CEO, Canopy)
💡 As you go through this process and think partnering with us here at Canopy might potentially be a good fit for your organization, please reach out to us here 📫 I’d love to learn more about your organization’s journey and current stage, and share more detailed recommendations on what solution might be best. Look forward to hopefully meeting you 💚