Spend enough time on LinkedIn and you'll come across all sorts of unconventional ways companies claim to assess cultural fit.

Some business take candidates to dinner to see how they treat waiting staff. Others pay close attention to how people interact with receptionists when they arrive for an interview. There are stories of interviewers looking out to see if a candidate offers to take their coffee cup back to the kitchen after an interview.

Duolingo even made headlines after revealing they sometimes ask taxi drivers for feedback on how candidates behaved during the journey to the interview.

Whether every story is true almost doesn't matter. They all point to the same idea - people often reveal more about themselves when they think they are no longer being assessed.

And whilst these informal observations can tell you something about humility and self-awareness, they only scratch the surface.

When we're helping clients appoint senior leaders, cultural fit isn't just about whether someone says "please" and "thank you" (although that certainly helps). It's about understanding how they naturally lead, make decisions, influence others, their values and whether those behaviours will help them succeed in a particular organisation.

Culture fit doesn't mean hiring people who are all the same

The phrase "culture fit" has developed a slightly bad reputation in recent years. No organisation benefits from recruiting people who all think alike.

The best leadership teams are diverse in their thinking, backgrounds and experiences.

What we're really assessing is whether someone's way of working, attitude and values complements the organisation they're joining.

Will this person be successful here?

The informal conversations often reveal the most

Many executive recruitment processes conclude with a "fireside chat".

Usually a final meeting with the CEO, Chair or founder. There's no structured competency framework or presentation to deliver. Instead, it's simply an honest conversation.

It's often during these relaxed conversations that candidates stop interviewing and start talking honestly about how they work.

Formal assessment should go deeper

Whilst chemistry is important, appointments at executive level should never rely on instinct alone.

The strongest hiring decisions combine conversation with structured assessment.

Personality profiling

Used well, personality profiling doesn't tell you whether someone is "good" or "bad".

It helps uncover leadership preferences.

Does someone naturally seek consensus before making decisions?

Are they comfortable challenging senior colleagues when they disagree?

Do they communicate directly or diplomatically?

These aren't pass or fail characteristics. They're simply indicators of how someone is likely to operate within a particular culture.

Understanding how someone manages up and down

A CV tells you what someone has achieved. Assessment should tell you how they achieved it.

How do they build relationships with their own teams?

How do they influence peers?

How comfortable are they challenging the status quo?

These behaviours often become far more important than technical competence once someone reaches executive level.

Cultural fit looks different in different organisations

One of the biggest misconceptions in executive recruitment is assuming every leadership role requires the same personality.

For contractors, cultural fit is often linked to the way projects are delivered.

A big consideration is whether a leader is comfortable working within a self-delivery model or whether their experience has predominantly been in a management contractor delivering through subcontractors. Leaders in self-delivery organisations need credibility with operational teams and must be as comfortable communicating on site as they are presenting in the boardroom.

We also explore how decisions are made under pressure, how visible leaders are on projects, and whether they naturally balance safety and commercial performance with operational delivery.

Leadership within consultancies often looks very different from other company types.

Many consultancies operate in matrix structures coordinating service lines, sectors and geographies where leaders rely on influencing colleagues rather than managing everyone directly. We therefore look beyond technical capability and assess how candidates collaborate across teams, build consensus and work with shared ownership of projects and clients.

Business development is another important consideration. In some consulting firms, work winning is everyone's responsibility; in others, it's led by a dedicated functional BD team. Understanding how candidates have operated within those environments helps determine whether they'll thrive within the firm's culture.

For client organisations, cultural fit is often about how leaders operate within complex stakeholder environments and ambiguity.

Major infrastructure programmes involve multiple stakeholders, governance processes and changing priorities.

Projects can also be subject to ambiguity around funding, regulatory approvals and shifting government priorities, often outside of a leader's control.

We also consider the wider organisational culture. Is the business PE owned? Is it family owned, with a very long-term outlook? Is it a listed organisation balancing commercial performance with shareholder expectations? Is it part of an international group where communication styles and decision-making may reflect different national cultures?

The strongest leaders are those who can adapt their approach to the environment they're working in whilst bringing others with them.

Great appointments happen when capability and culture align

At executive level, technical competence is usually a given.

The differentiator is whether someone can succeed within the way an organisation actually operates.

Assessing cultural fit isn't about finding people who are all alike.

It's about understanding behaviours, motivations, leadership style and working preferences - and matching those to an environment where they can genuinely thrive.

Getting cultural fit right isn't about instinct - it's about asking the right questions and understanding what success really looks like within your organisation.

If you're planning a senior appointment and would like to discuss how we assess leadership and organisational fit as part of our executive search process, we'd be delighted to share our approach.