Executive Fit Is Situational Not Universal | Rajesh Swaminathan

There is a particular kind of difficulty that comes with hiring at the very top. The higher the role, the fewer the comparable benchmarks, the more consequential the wrong call, and the harder the candidate is to evaluate on the tools designed for roles below them. Rajesh Swaminathan has spent his career working at exactly that level, helping organizations find, assess, and land the leaders who define what the next chapter of a company looks like.

He operates from Diligent Global, an executive search and leadership advisory firm with reach across Asia, the Middle East, Europe, and North America. In this episode #29 of Xobin Talks, Nikita Saini asked him what most organizations get wrong when they hire for leadership, what good executive assessment actually looks like, and how the landscape for global leadership hiring is changing in 2026.

What Do Most Organizations Still Get Wrong When They Hire for Leadership?

Rajesh's starting point is the wrong question. Most organizations, he observes, begin an executive search by asking: who is the best person available for this role?

Rajesh: "The question is not who is the best leader in the market. The question is who is the best leader for this organization at this moment in time. Those are very different questions. The first one is about the person. The second one is about the fit between the person and the context."

Why Context Is Everything

A turnaround specialist and a scale-up leader can both be exceptional, yet in the wrong context, both will fail. The executive who built a culture of rigorous process in a mature business may be exactly the wrong temperament for a startup that needs to move faster than its processes can keep up with.

Rajesh: "You cannot copy-paste leadership. The same person in two different organizations at two different moments will produce very different outcomes. Before you go looking for someone, you need to be very clear about what success actually looks like in the first 12, 18 months. Most organizations are not clear about this. They know the job title. They are not always clear on the job."

The implication is practical: a good leadership brief goes far beyond a job description. It includes the business context, the political landscape, the team the leader will inherit, the decisions they will face in the first quarter, and the constraints they will operate within.

What Makes Executive Assessment Different From Regular Hiring Assessment?

This is where Rajesh gets most precise, and where his perspective is sharpest. Standard hiring tools, psychometric profiles, competency interviews, reference checks, work reasonably well at the manager level. At the C-suite level, they tell you considerably less.

Rajesh: "At the leadership level, you are not assessing skills in the traditional sense. You are assessing judgment. You are assessing how someone thinks through complexity, how they hold ambiguity, what they do when there is no right answer. Most assessment tools are not designed for that. They are designed to tell you about personality and past behavior. Past behavior is a useful context. It is not a prediction."

The Track Record Trap

A strong track record at one organization tells you that the person performed well in that specific context, with that team, those resources, that market, that moment. It does not tell you what they will do in yours.

Rajesh: "Track record is a necessary condition. It is not sufficient on its own. The real question you need answered is: how did they do what they did? What was the situation? What choices did they make and why? What did they sacrifice to get the outcomes they got? A track record without that context is just a number."

In executive search, the best assessment happens through deep structured conversations, usually across multiple sessions, that go into the thinking behind decisions rather than the decisions themselves. The goal is to get beneath the polished executive narrative and access the actual reasoning.

How Can You Assess Cultural Intelligence in Global Leadership Candidates?

Rajesh works across markets that have genuinely different cultural operating environments: Asia, the Middle East, Europe, North America. In each one, what effective leadership looks like on the floor is genuinely different: communication styles, the distribution of decision-making authority, and the relationship between seniority and deference all vary significantly.

Rajesh: "You can have a brilliant executive who has succeeded in one part of the world and completely struggles in another. The issue isn't capability. It's the context around it. They misread the environment. They applied a mental model that worked at home and it did not translate. Cultural intelligence is not about cultural sensitivity training. It is about genuine curiosity, genuine humility and the ability to suspend your own model long enough to understand a different one."

How to Assess It

Rajesh's approach to evaluating cultural intelligence is not through a questionnaire but through how candidates talk about failures.

Rajesh: "I often ask candidates to share a real situation where they made a major mistake while working with people from different cultures. Their response can reveal a lot about how they lead. Do they own the mistake? Can they explain what went wrong? Most importantly, did they learn from it and change how they approach similar situations? If someone avoids taking responsibility or puts the entire blame on other people or circumstances, that also tells you something. It shows you how they deal with difficult situations when things don't go as planned."

Executive search practice is catching up, and the evidence supports the shift: leadership agility has overtaken tenure and industry pedigree as a primary selection criterion for many boards, with a particular focus on candidates who demonstrate the capacity to lead through transformation, not just manage through stability. Cultural intelligence is part of that agility.

What Does Good Candidate Engagement Look Like at the Executive Level?

Finding an executive is only half the problem; getting them to the table is the other half. Most of the best executives in any field are not actively looking for a new role. They are running something, building something, or being asked to stay somewhere.

Rajesh: "You won't often find great leaders actively searching for new jobs. So, don't wait for a position to open before you start meeting people. Build those relationships early. Stay connected, have real conversations, and get to know good talent before you need to hire. Then, when a role opens up, you already have people you can reach out to who know you, trust you, and understand your company."

What Actually Gets a Great Executive's Attention

Rajesh: "Senior leaders often plan their next career move instead of waiting for the right opportunity to find them. They want to know what they'll be building, which problems they'll get to solve, and who they'll be working with. So, if the first thing you talk about is salary, you may lose interest before the real conversation begins. Start by talking about the business challenge instead. What are you trying to achieve? Where is the team struggling? What would a great outcome look like? Those are the questions that can grab the attention of leaders who have plenty of choices."

This is a meaningful shift from how most organizations brief their search partners. Most organizations instinctively lead with why the company is great. At this level, the more effective approach is to lead with what is genuinely difficult and why solving it matters.

How Is AI Changing Executive Search, and Where Does It Still Fall Short?

This question generates Rajesh's most nuanced answer.

Rajesh: "AI is genuinely useful in executive search in a few specific ways. Market mapping, understanding who is in the relevant talent pool globally, is significantly faster and more complete with AI than without it. Name generation for a long list is better. Removing certain categories of early-stage bias, if the model is built right, is also something AI can help with."

Where AI Cannot Go

Rajesh: "AI can support the process, but human judgment still matters when assessing candidates. It cannot tell you how someone performs under pressure in a board meeting when the numbers are bad and the room is divided. It cannot tell you whether the candidate in front of you has the political intelligence to manage a complex stakeholder environment. It cannot tell you whether the humility is genuine or performed. Those require a human in the room."

At the C-suite level, where a wrong hire can cost an organization far more than the search fee, the reliance on human judgment is not reluctance to adopt technology. It is a recognition that some of the most important variables in executive fit are not legible to an algorithm, at least not yet. AI can structure data efficiently, but the assessment of genuine leadership presence, political intelligence, and cultural fit still depends on human judgment that no current model can fully replicate.

The Right Model Is Augmentation, Not Replacement

Rajesh: "AI can take a lot of work off a search consultant's plate and help them move faster. But relying on it to run the whole search can mean missing things that matter. The best results come when consultants use AI for what it does well and bring their own judgment to the parts that need a human touch."

How Do You Think Global Leadership Hiring Will Change in the Next Three Years?

Rajesh closes with a view that is both optimistic and sobering.

The Talent Pool Is Getting Harder to Navigate, Not Easier

Rajesh: "There are more leaders in more markets than there used to be. Ten years ago, the pool for a truly global executive role was much smaller. Now you can find exceptional leaders in markets that were not on the radar for global searches in the past, Southeast Asia, the Gulf, certain parts of Africa. The pool is broader. But assessing across that pool requires capability that a lot of search processes do not yet have."

Boards and organizations are facing a leadership environment defined by volatility, accelerating technology shifts, and rising expectations, and they are moving away from traditional markers like degrees, titles, and linear career paths toward demonstrated skills, experiences, and actual outcomes. That shift makes the search harder before it makes it better, because the shorthand markers that used to simplify evaluation no longer carry the same weight.

The Speed-Quality Tension Is Getting Worse

Rajesh: "The pressure on search timelines has increased significantly. Boards want roles filled faster. The market does not necessarily produce great candidates faster. The tension between speed and quality is one of the defining challenges of executive search right now. A quick fill that does not work is far more expensive than a slower fill that does."

What Organizations Can Do Right Now

Rajesh: "Build succession pipelines before you need them. Have real conversations with potential future leaders before there is a role. Know the market. When you need to move, move fast, but move from a position of preparation, not panic. The organizations that do leadership hiring well do not treat it as a crisis response. They treat it as an ongoing strategic activity."

About Rajesh Swaminathan

Rajesh Swaminathan leads global leadership hiring at Diligent Global, an executive search and leadership advisory firm operating across Asia, the Middle East, Europe, and North America. With a multi-decade career at the C-suite and board level of talent, he has helped organizations across industries identify, assess, and land leaders at moments that matter, transitions, transformations, scale-ups, and turnarounds. His practice is built on a conviction that leadership hiring is not a procurement exercise. It is a strategic function, and when done well, it shapes the trajectory of organizations in ways that almost nothing else can.

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