Singapore’s $73 Billion Leadership Problem and the 10 Skills That Could Fix It

August 7, 2026

A picture of Marina Bay Sands in Singapore at night. Used to highlight the focus as Singapore for the article.

Singapore is one of the wealthiest, most highly educated economies on earth. It delivered 5% GDP growth in 2025 and its per capita GDP sits above US$107,000 at purchasing power parity.

And 86% of its workforce is disengaged.

That figure comes from the inaugural Singapore Workplace Report 2026, published by the Singapore Institute of Directors together with Gallup. Only 14% of Singapore employees are engaged at work, below the Southeast Asian average of 25% and below the global mean of 20%. We trail Malaysia (25%), Indonesia (27%) and Thailand (34%). The estimated cost is US$73.6 billion a year in lost productivity.

The number that should worry leadership teams most, though, isn’t the headline. It’s this: engagement in Singapore has been stuck at roughly this level since 2019. Six years of strong economic performance have not moved it. The report’s own warning is that chronically low engagement risks becoming a strategic liability for the country’s competitiveness.

So what actually moves it?

It’s a manager problem, and the data is unusually clear about that

Gallup’s long-running finding is that managers account for around 70% of the variance in team-level engagement. If you want a different number, you change what managers do.

In the Singapore report, business leaders were asked to rate their own organisations on the factors that drive engagement. On manager capability and effectiveness, they gave themselves 3.32 out of 5. They rated themselves similarly low on strengthening the leadership pipeline and preventing work overload. This isn’t a case of leaders being unaware of the gap, they’re naming it themselves.

Globally, the picture is worse than most organisations realise. Gallup’s State of the Global Workplace 2026 found that manager engagement fell from 31% in 2022 to 22% in 2025, with the sharpest single-year drop between 2024 and 2025. Individual contributor engagement, over the same period, barely moved. Managers used to enjoy what Gallup calls an “engagement premium”, they were meaningfully more engaged than the people they led. That premium has effectively disappeared.

DDI’s Global Leadership Forecast adds the human detail: 71% of leaders report increased stress, and 40% of those have considered stepping away from leadership altogether. Employee trust in immediate managers has fallen from 46% to 29%.

Meanwhile the job is getting structurally harder. Average span of control across organisations has climbed from around 8 direct reports in 2013 to roughly 12 in 2025, with projections pointing towards 25 by 2028 as AI absorbs coordination work and companies flatten. Korn Ferry found 41% of employees globally say their organisation has eliminated management layers.

Here’s the contradiction sitting at the centre of it. McKinsey’s work on managerial archetypes suggests a manager coordinating standardised work can handle 15 or more reports, but a manager doing genuine coaching, development and feedback tops out around six or seven. Organisations are asking managers to become coaches at precisely the moment they’re handing them coordinator-sized teams.

The ten skills below are the ones the 2026 research keeps returning to. They’re grouped into three clusters, because they’re not really ten separate things, they’re three shifts.

Cluster one: Leading AI-augmented work

1. Delegation to AI, and the judgment to know what not to delegate

    Microsoft’s 2026 Work Trend Index found that 49% of Copilot conversations now support cognitive work such as: analysis, problem-solving, strategic thinking and 58% of AI users say they’re producing work they couldn’t have produced a year earlier.

    The managerial skill here isn’t prompting. It’s deciding what leaves the human loop and what doesn’t. Notably, 86% of AI users say they treat AI output as a starting point rather than a final answer. Managers who model that distinction give their teams permission to think; managers who don’t, end up rubber-stamping.

    2. Modelling AI use rather than mandating it

      This is the most actionable finding in the 2026 research and the most widely ignored.

      In a Microsoft study of 1,800 workers, when managers actively modelled AI use themselves, employees reported a 17-point increase in the value they got from AI and a 30-point increase in trust in AI agents. Yet only one in four AI users said their organisation’s leaders were clearly aligned on AI at all.

      Microsoft’s broader analysis found organisational factors like AI culture, manager support, talent practices account for more than twice the impact of individual employee factors on whether AI actually delivers value. The bottleneck isn’t the technology. It’s whether the manager visibly uses it.

      Worth noting for Singapore specifically: DDI found frontline managers are three times more likely than senior leaders to have concerns about AI’s impact. The people expected to drive adoption are the most anxious about it, and rarely asked.

      3. Quality discernment

        Gartner named this one of its defining trends for 2026: an overwhelming push on AI adoption has produced what it calls work-slop (fast but poor-quality output), generated because employees are pressured to use AI for as many tasks as possible with no time or autonomy to judge whether the result is fit for purpose.

        Gartner’s guidance is to aim AI at the most arduous, friction-filled parts of work rather than the easy wins, and to use effort saved rather than time saved as the measure. That’s a judgment call a manager has to make deliberately, and most haven’t been asked to.

        Cluster two: Leading under structural strain

        4. Coaching at scale

        DDI found that employees whose managers are effective coaches are nine times more likely to trust them. With spans of control widening, though, coaching can no longer mean unstructured ad-hoc conversations whenever there’s time, because there won’t be. It means preparation: knowing how each person takes feedback, where friction will occur, what will land.

        5. Process redesign and systems thinking

        Gartner is direct that this beats technical AI skill. The organisations getting value in 2026 are prioritising people who can redesign whole processes rather than optimise individual tasks and Gartner recommends recruiting for AI judgment and critical thinking over technical fluency.

        6. Change sense-making

        In 2025, 71% of companies said it had become more crucial for leaders to operate amid constant change, up from 58% the year before. The manager’s job is translation: turning strategy into priorities, and uncertainty into something a team can act on this week.

        Gartner pairs this with a warning about culture dissonance. Organisations asking more of employees without offering more in return, producing what it calls “regrettable retention,” where disengaged people simply stay put. For Singapore, where engagement has been flat for six years while performance expectations have risen, that description lands uncomfortably well.

        7. Self-regulation and energy management

          Research on 2026 leadership trends makes a point worth repeating: the limiting factor for most managers isn’t knowledge. They understand feedback models and decision frameworks perfectly well, and then default to reactivity under pressure. What’s missing is emotional capacity in the moments that actually matter.

          Gartner now frames this as an organisational responsibility rather than a personal one, arguing that managers must be equipped to recognise negative psychological effects of pervasive AI at work, including in themselves.

          Cluster three: Leading humans through difference

          8. Building psychological safety on purpose

            Microsoft found employees were 1.4 times more likely to be high-frequency users of agentic AI when their manager created psychological safety around experimentation. Psychological safety isn’t a wellbeing initiative, it’s the precondition for every other change an organisation is trying to make.

            SHRM’s State of the Workplace 2026 found 46% of CHROs name leadership and manager development as their top priority, for the second consecutive year. The intent is there. The delivery is the gap.

            9. Conflict navigation across genuine difference

              Workplace conflict is at record levels. UK conciliation service Acas found 44% of workers experienced conflict in the past year, with nearly a third of it involving line managers. Edelman’s 2026 Trust Barometer found 70% of people are unwilling or hesitant to trust someone with different values, problem-solving approaches or cultural background and 34% said they would put less effort into a project if the team leader held different political beliefs.

              For a workforce as culturally and generationally mixed as Singapore’s, this is not an abstract risk.

              10. Developing early-career talent when the rungs are missing

                Gartner’s 2026 talent research flags that the decline in entry-level roles is creating a fractured pathway into mid-level jobs. The middle rungs were where future leaders learned to lead, which means mentoring and succession now have to be designed deliberately rather than left to happen.

                Singapore’s generational data makes this urgent. Only 10% of employees under 35 are engaged, against 16% of those 35 and over. And 53% of younger employees report daily stress, compared with 37% of their older colleagues. The pipeline problem starts before anyone gets promoted.

                If You’re Responsible for Developing Managers, Start Here

                Ten skills is a list, not a plan. If you’re an HR, L&D or business leader deciding where next year’s development budget goes, three choices make the difference between spending it and actually moving your engagement number:

                Start with the managers, not the workforce. Gallup found that within best-practice organisations, 79% of managers are engaged, nearly four times the global average. These organisations span every region and industry. The common factor is treating engagement as business strategy rather than an HR programme.

                Pick two skills, not ten. The evidence points hardest at coaching capability and psychological safety, because most of the others depend on them. A manager who can’t create safety can’t coach, can’t surface conflict, and can’t get honest signal on whether AI output is any good.

                Build them somewhere with stakes but no consequences. This is the one most organisations get wrong. DDI’s research notes that leadership development commonly fails by teaching theory without giving people safe spaces to apply it. Managers don’t lack frameworks, they lack reps. Skills like conflict navigation, coaching and building psychological safety are behavioural, and behavioural skills change through practice under mild pressure, not through slides.

                That last point is why the strongest development work tends to happen outside the meeting room. Put a team into a shared challenge where the outcome genuinely depends on how they communicate, how they handle disagreement, and whether people feel able to speak up and you learn more about your managers in three hours than in three quarters of performance reviews.

                Singapore’s engagement number hasn’t moved since 2019. It won’t move because of another framework. It moves when managers get better at the human parts of the job, and get enough practice to make it stick under pressure.

                How Jambar Helps Managers Get the Reps

                Jambar Team Building has spent over a decade helping Singapore organisations turn team days into actual development. A few things we do that speak directly to the skills above:

                Facilitated programmes built around a debrief, not just an activity. Every Jambar Team Building for Growth event runs on the Jambar Loop (Frame → Pause → Commit). We name the focus before the activity starts, pause after each stage to connect what just happened to that focus, and close by turning it into committed actions captured in your Team Playbook. That structure is what makes coaching, conflict and psychological safety visible enough to work on. Without it, a team day is just a good day.

                DISC profiling and leadership training. The coaching-at-scale problem is that wider spans leave no room for guesswork. DISC gives managers concrete language for how each person takes feedback, where styles will clash, and what will actually land in a one-to-one, which is the difference between coaching six people well and coaching fifteen badly.

                AI-focused team experiences. Our AI challenge moves teams through stations using AI tools on real tasks like content creation, data analysis and problem solving. It’s a low-stakes way for managers to model AI use in front of their teams, which the Microsoft data suggests is the single highest-leverage thing they can do.

                Programmes sized to your team and calendar. Half-day, full-day, indoor, outdoor, at your office or a venue we arrange, plus larger formats when you need scale.

                If your managers need practice rather than another framework, get in touch and tell us what your team is working through. We’ll design the day around it.