What if Leaders and Managers Weren’t Overwhelmed?

How increasingly powerful AI can relieve leaders from too many hybrid work responsibilities.

Dario De Santis
8 min readJan 28, 2024

According to Gartner, 75% of HR leaders say managers in their organization are overwhelmed by the growth of their job responsibilities [2023 Gartner, Building an Organization of Great Managers Manager].

As a result of the epic battle between decentralizing work-from-home forces and ineffective return-to-office directives (Only 26% of organizations report that their employees fully comply with on-site attendance requirements), every company is on its path to experimenting new ways of organizing their workforce, cascading the implementation to the individual managers.

New procedures and processes need to be socialized, agreed upon, implemented, executed, measured, reported to top leadership, all while dealing with the “firefight of the day” and geographically distributed team members that seem to be always busy and unreachable. In this challenging environment, 59% of managers report spending a significant amount of time on “work to do work”.

The tortuous path to sustainability

In a landscape characterized by productivity anxiety (nearly 50% of employees view their current performance as unsustainable) and mutual mistrust (only about 50% of employees trust their organization), the imperative is finding innovative solutions to boost everyone’s productivity and organizational efficiency, promote trust, and reduce the daily burden of overwhelmed managers and leaders.

How can HR leaders remove process hurdles, reduce workloads and make the work of leaders and managers more manageable?

Which AI will straighten the path?

More than 70% of HR leaders feel a strong sense of urgency to adopt Large Language Models (LLM), fueled by the fear of losing competitiveness. However, the decision to adopt an AI isn’t trivial, as it implies:

  • Understanding the relative impact of various Artificial Intelligence (AI) solutions — not only LLM,
  • Defining a roadmap that will allow the organization to tackle the issues on top of the agenda, thus maximizing the outcome.

The opportunity to lift the manager’s burden

To start, we’ll unpack the main factors that overwhelm managers and leaders, and we’ll isolate the impact that various AI solutions can have on those factors. We are going to build a meaningful framework from the HR point of view, focusing on aspects that HR leaders can (and must) control.

1. Productivity anxiety

The manager or leader role has never been easy, however, it got much harder due to the lack of in person interaction with team members and the request to implement experimental procedures and processes.

A logical candidate to overcome productivity anxiety is AI in the form of workflow automation and nudging.

Once the HR leadership decides to experiment with a new promising workflow, an AI operating system can implement the new workflow autonomously, nudging and incentivizing the employees to take the desired actions, without the involvement of managers and leaders.

As a consequence, managers and leaders will have their burden reduced.

2. Work to do work

To understand what this problem involves, we should consider a few compelling data points:

  • A 2022 Harvard Business Review article stated that enterprise managers spend, on average, 23 hours a week in meetings: 58% of their work-week.
  • A 2022 Tweelin survey pointed out that, on average, 37% of the meetings in any enterprise worker’s calendar are 1:1 scheduled meetings.
  • A 2022 ZoomInfo study reported that calling has less than 20% success rate.

We all know how important it is for a manager to communicate with their team members, as well as how hard it is to talk to someone, in general. Calling is no longer a viable option due to the low success rate, and scheduling meetings almost always implies cumbersome rules of engagement — texting “when-can-we-talk” back and forth, composing and sending invitations, reschedulings, cancellations etc. — all work to do work that can be avoided.

How did we get to this point?

While the answer to this question could be the subject of a long series of articles, it is important to point out that our society is stuck in a “work to do work vicious cycle”. Too many meetings make it almost impossible to have an impromptu conversation, and, ironically, the present solution is to schedule more meetings!

There is a clear opportunity to leverage AI to introduce new paradigms that minimize the rules of engagements and automate that minimized set of rules.

An AI can collect the intention of talking to a coworker, and automate the engagement to maximize the likelihood of being able to talk, whenever it is most convenient for everyone involved.

3. Mutual mistrust

How can an organization maximize the employee engagement and consequently the level of trust in their work ethics?

How can the organization establish a trustworthy relationship with disaffected employees that don’t trust the organization?

These are difficult questions to answer, however, a step in the direction of trust is, without a doubt, facilitating enterprise communications at any level.

By making it easier and more frequent to communicate with colleagues, bosses and direct reports across any organizational hierarchy, companies can significantly speed up:

  • Collective decision making process
    Faster decisions generate higher business impact and less frustration, which in turn results in a more positive and trustworthy environment.
  • Creation of consensus and alignment among the employees
    Easier communications result in employees being able to talk to more people more frequently in exchange for the same amount of time invested. As a consequence, the likelihood that communications will happen across cohesive teams is higher, thinning the barriers among isolated teams (a real problem of the hybrid/remote work era) and increasing the alignment of workers towards a shared vision and goal. By enhancing the sense of belonging to the same organization, the overall level of trust is increased.
  • Diffusion of a healthy corporate culture
    It is no news that spreading the desired organizational culture in the post pandemic world became harder and harder, as people no longer congregate at the office, and online meetings don’t serve the purpose. So, the current best solution is to facilitate communications among individuals, no matter where they are. More communication inevitably results in better trustworthy relationships at any level, along with more occasions of discussing cultural achievements and cultural issues to be addressed.
  • The onboarding of new hires
    In many industries, new remote (sometimes local) hires don’t have the chance to grasp the company culture at the office. In addition, they aren’t exposed to the bosses and senior employees they can learn from, often by observing or imitating. Facilitating communication can help fill the gap.

All the previous points contribute to an overall healthier more trustworthy organization that requires less effort from managers and leaders.

Photo by Saad Chaudhry on Unsplash

Digital Serendipity: beyond the limitations of LLMs

I guess you will agree with me that we are in the middle of one of the most significant revolutions we’ll have the chance to experience in our lifetime; Large Language Models (LLM) have already had a profound impact on everyone’s life.

LLMs are amazing at making sense, and will get better and better. However, they require other technologies to be able to execute.

In terms of capability of execution in an organizational environment, the emerging paradigm that offers the highest potential is Digital Serendipity.

The idea behind Digital Serendipity is simple: workers implicitly or explicitly express their needs and the AI nudges them to do the most appropriate thing at the right time, according to a grand scheme that doesn’t need to be managed by the worker.

Digital Serendipity has the potential to free up workers from cumbersome rules of engagement, calendar management, task management and potentially many more mundane tasks and duties. These benefits are easily achievable by anyone, today.

Among the avoidable mundane tasks, which ones are the most impactful when eliminated or automated?

Let’s focus on the most measurable and impactful inefficiency currently making leaders and managers’ life miserable: communication barriers. Just consider that, according to a Reclaim.ai study (2021):

  • The average hybrid worker overtime is +7h/week.
  • The average hybrid worker amount of extra hours spent in meetings is +7.3h/week.

This means calendars are already oversaturated and people don’t have time to do the work during the day. To add insult to injury, when not in meetings, people are often distracted by playing the game of “calendar Tetris”.

How does Digital Serendipity break the communication barriers, and what is its relationship with the burden of leaders and managers?

Digital Serendipity applied to communications involves the automation of workflows — in this case rules of engagement — and nudging — suggesting the right moment and the right channel for a conversation to take place.

Productivity anxiety: alleviated

While there’s a potential to fully automate the experimentation of new ways of working, a quicker win is to streamline communications in general, including the ones related to the experiments. Easier communications free up managers and leaders’ resources, thus reducing their anxiety.

Work to do work: eliminated

Imagine if every meeting were serendipitous — as easy as bumping into someone on the street at the right time — and did not require any organization. In an ideal world, you would think that you need to talk to a certain person and the AI would connect you at the right moment through the right channel.

Managers and leaders wouldn’t have to manage their calendar or pay someone to do it. They would work on the daily tasks that matter according to their prioritized todo list, and communications would magically adapt to their priorities, without any user involvement.

No more coordination cost (or work to do work) to talk to colleagues and much more time to be productive and make an impact.

Mutual mistrust: reduced

Digital Serendipity makes it practically effortless talking to people. Managers and leaders can communicate upwards and downwards the hierarchy more frequently, strengthening their relationships with the rest of the organization, thus creating and nurturing higher levels of trust.

Photo by Brett Jordan on Unsplash

What you can do now

Simply put, look into Digital Serendipity as the solution to your most pressing HR issues.

Why?

  • Because the technology is available today, and it’s both proven and affordable.
  • Because, in the short term, you don’t need to deal with the huge burden of evaluating LLMs that come with uncomfortable biases, inaccurate results that look accurate, major security concerns, copyright issues, and a series of hard-to-evaluate potential integrations needed to automate tasks. Rather, with Digital Serendipity you can obtain an immediate impact with a modest adoption effort.

Interested in knowing how much you could save by adopting Digital Serendipity in your organization?

Get the Free Tweelin Value Calculator

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Dario De Santis

Long-termist visionary technology Entrepreneur and Product Leader, with a strong passion for improving people's productivity through innovative solutions.