Are middle managers being left behind in AI transformation?

Many senior leaders believe their organization is ready for AI, but the managers being asked to make it a reality are far less certain – and new research suggests the gap between those two views is a significant blind spot in workplaces.

Research published in August 2026 by Careerminds, a global workforce solutions provider, found that while 66 per cent of C-suite people managers in the US say they feel very ready to lead through AI-driven workplace change, only 42 per cent of senior and middle managers agree. The findings land against a backdrop in Canada where, according to KPMG in Canada's November 2025 Generative AI Adoption Index, 93 per cent of organizations report enterprise-level adoption – yet only two per cent are realizing measurable returns, and fewer than half of employees say they receive sufficient training to use AI effectively.

The disconnect reflects something structural, not incidental – and addressing it demands a more honest conversation about what managers are actually being asked to do, says Lee-Ann Reid, Vice President of Operations and Director of Human Resources at Vistek, a Toronto-based photography and video retailer.

"I think at the senior level, it's very high level, and they're looking at the potential for it at an enterprise level," says Reid. "Middle managers are often looking at it from an individual department or from a role perspective, and I think the worry level changes because of concern of how much it's going to impact the individual job – so perhaps skepticism comes into it at each of those levels."

The right AI tools and value for every level of the organization

Recent research from Capterra found that nearly three-quarters of middle managers are already under significant strain, and asking that cohort to lead AI transformation without preparation can compound it. Reid believes that every level of the organization needs to understand the right AI tool for them and its value not just the organization, but the individual as well.

The uncertainty around AI may linger underneath the executive confidence, according to Reid. "I once spoke at an HR conference on AI, and I started my talk by saying, I often get asked is AI good or bad, and my answer is always yes because we don't know what we don't know, and there's a lot about AI we don't know."

The ambiguity demands structure. "There's a lot of things we need to respect about security, intellectual property, and how AI is being used within your organization by your people and whether it's being used in a controlled environment," she says. "The genie's out of the bottle in many ways, and there are people within organizations putting their organizations at risk – not intentionally, but unintentionally."

AI as change management

Diana Kelly, Vice President and Chief Human Resources Officer at NAV CANADA in Ottawa, sees the problem from a different angle. Her concern is less about the gap itself and more about how HR professionals are framing AI.

"One thing I find right now is there's so much focus on AI. It's almost becoming a daunting thing that is then making people afraid of what it means, what's this change, and how will I be ready for it?" says Kelly. "I think as HR leaders, we share a responsibility in not making it such a daunting, frightening thing that we're approaching."

Kelly's organization has tackled the challenge through structural inclusion. NAV CANADA introduced a Shadow Board – 16 employees voted in by peers and tasked with advising the executive team on issues including technology change – and it has helped prevent the C-suite disconnect with middle management and employees that the Careerminds data shows elsewhere.

"There are ongoing discussions at all levels," Kelly says. "A topic like AI is the type of topic that they might select, and then they're giving us their perspectives, solutions, and ideas."

Embedding change readiness for managers before change

Rather than AI-specific training programs, Kelly's team embeds change readiness into existing leadership development. "We've been rolling kind of some of the concepts into our leadership training about this is what we need of our leaders, but it's not designed to focus on AI," she says. "It's designed for things – this is the evolution of organizations, and we need leaders who are prepared to work with people."

Her broader view challenges the assumption that AI readiness is a standalone competency. "Regardless of AI, we have an obligation to have a leadership team that’s up to date on what's going on in the world, is prepared to adapt to things, and has the ability to lead teams through change, whatever that might be."

Both leaders arrive at the same ground: preparing managers for AI isn’t primarily a technology problem – it requires building the conditions for candid conversation at every level.

Open communication and feedback to narrow the skills gap

Canada's AI skills gap sharpens the stakes. The 2026 TD AI Insights Report found only 37 per cent of Canadian workers say their employer has provided adequate AI training, and one in three admit to overstating their competency professionally.

Kelly frames the solution in terms of culture before capability. "With the advancement of technology or any other change, you need to have an environment that encourages candid discussion and you need to have leaders who are courageous enough to talk about issues that they want to see addressed, ideas they have, or change we need to have in a company," she says. "The biggest thing that we need is the environment that allows it and the leaders that are willing to do it – and then that cascades to their employees too. They have to create environments where their employees are talking to them about what's going on."

Reid believes that deliberate strategy around AI use must be established and communicated at every level, from senior management to middle management to frontline employees. "It's really having a strategy around how the tool is going to be used at each level of the organization, and then showing the value for each level of the organization and how to use it, and also educating on the important ways to protect the organization’s security and intellectual property at every level."

For HR leaders, the key to ensuring middle managers or anyone else aren’t left behind in transformation is being informed at the top, says Reid. "Educate yourself, collaborate with other HR professionals, and be informed – there's opportunity for risk if you're going into something naively without truly understanding, and then unleashing something in your organization without education guardrails and purpose," she says.

Without deliberate investment in the middle layer, Canada's AI ambitions around adoption and ROI risk stalling not at the strategy stage, but in execution – in the hands of the people organizations are relying on most to deliver it, says Reid. “It's starting to come, but – even at a governmental, national, and international level – they're still all trying to figure it out,” she says.