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CASE STUDY: The Business Trip Didn't Fail Because of a Flight Delay. The Executive Assistant's Mistake Happened Three Days Earlier.
The flights were booked. The hotel was confirmed. The airport transfer was arranged. In the CEO's diary was the meeting that justified the entire trip.
Three days before departure, the Executive Assistant sent a message:
"Everything's sorted. The itinerary is confirmed and all the documents are in the folder."
But on the day of the negotiations, the CEO found himself at Amsterdam Schiphol while his onward flight was already preparing to depart.
The meeting was missed.
At first glance, the flight delay appeared to be the cause. But a closer examination revealed that the critical mistake had been made before the journey even began.
The assistant had checked that everything was booked. What they hadn't checked was whether the CEO could still reach the meeting if the schedule changed.
Let's examine the case as a professional investigation: reconstruct the timeline, identify the planning failures and explore how a capable Executive Assistant should manage these risks.
Three days before departure, the Executive Assistant sent a message:
"Everything's sorted. The itinerary is confirmed and all the documents are in the folder."
But on the day of the negotiations, the CEO found himself at Amsterdam Schiphol while his onward flight was already preparing to depart.
The meeting was missed.
At first glance, the flight delay appeared to be the cause. But a closer examination revealed that the critical mistake had been made before the journey even began.
The assistant had checked that everything was booked. What they hadn't checked was whether the CEO could still reach the meeting if the schedule changed.
Let's examine the case as a professional investigation: reconstruct the timeline, identify the planning failures and explore how a capable Executive Assistant should manage these risks.
1
🔎 Case File No. 1: The Copenhagen Meeting That Never Happened
A London-based business owner was due to fly to Copenhagen to meet a prospective commercial partner.
The negotiations were scheduled for 2 pm. The outcome would influence the next stage of a potential business relationship.
The CEO gave his assistant a straightforward instruction:
"Please arrange the trip. Ideally, I'd rather avoid staying overnight if we can do it in a day."
The EA found an itinerary connecting through Amsterdam.
On paper, everything looked reasonable:
✓ An early morning departure from London.
✓ Arrival in Amsterdam at 8.45 am local time.
✓ The onward flight departing at 10.05 am.
✓ Arrival in Copenhagen at 11.25 am.
✓ More than two and a half hours before the meeting.
✓ Two separate tickets costing less than a through-ticket alternative.
The assistant booked the flights, forwarded the confirmations and considered the task complete.
The CEO replied: "Thanks, looks good."
But one important detail was missing from the message: the flights had been booked separately.
This meant the journey wasn't a single protected connection. It consisted of two independent bookings.
If the first flight was delayed, the second airline wouldn't normally be responsible for arranging onward travel under the same conditions that may apply to a through-ticket.
That distinction would become crucial.
The negotiations were scheduled for 2 pm. The outcome would influence the next stage of a potential business relationship.
The CEO gave his assistant a straightforward instruction:
"Please arrange the trip. Ideally, I'd rather avoid staying overnight if we can do it in a day."
The EA found an itinerary connecting through Amsterdam.
On paper, everything looked reasonable:
✓ An early morning departure from London.
✓ Arrival in Amsterdam at 8.45 am local time.
✓ The onward flight departing at 10.05 am.
✓ Arrival in Copenhagen at 11.25 am.
✓ More than two and a half hours before the meeting.
✓ Two separate tickets costing less than a through-ticket alternative.
The assistant booked the flights, forwarded the confirmations and considered the task complete.
The CEO replied: "Thanks, looks good."
But one important detail was missing from the message: the flights had been booked separately.
This meant the journey wasn't a single protected connection. It consisted of two independent bookings.
If the first flight was delayed, the second airline wouldn't normally be responsible for arranging onward travel under the same conditions that may apply to a through-ticket.
That distinction would become crucial.
2
⏱ Reconstructing the Events, Minute by Minute
72 Hours Before Departure
The Executive Assistant completed the bookings.
They checked the passenger's name, travel dates, flight times, hotel address and transfer arrangements.
But three important questions remained unanswered:
✓ Was the connection protected under a single booking?
✓ How much time would remain if the first flight was delayed by 30–60 minutes?
✓ Was there an alternative route that would still allow the CEO to arrive before the negotiations?
The travel folder contained every confirmation.
What it didn't contain was a contingency plan.
Departure Day, 6.30 am
The first aircraft was scheduled to depart London.
But the flight was delayed.
Initially by 20 minutes, then by another 25. Eventually, the delay reached approximately an hour.
The assistant saw the updates but didn't initiate a review of the itinerary. The onward flight hadn't been cancelled, and the estimated arrival time was still being updated.
9.50 am — Amsterdam
The first aircraft arrived significantly later than scheduled.
Only 15 minutes remained before the onward flight's departure.
The CEO still needed to disembark, make his way to the correct gate and arrive before boarding closed.
In practical terms, the connection had already been missed.
10.05 am — The Flight Departs
The Copenhagen flight left without the CEO.
Only then did the search for alternatives begin.
But no suitable option remained that would get him to the negotiations on time.
The CEO contacted his prospective partner, explained the situation and requested a postponement.
A new meeting couldn't be arranged for the same day.
The trip had failed to achieve its primary objective, despite every booking having been made correctly.
The Executive Assistant completed the bookings.
They checked the passenger's name, travel dates, flight times, hotel address and transfer arrangements.
But three important questions remained unanswered:
✓ Was the connection protected under a single booking?
✓ How much time would remain if the first flight was delayed by 30–60 minutes?
✓ Was there an alternative route that would still allow the CEO to arrive before the negotiations?
The travel folder contained every confirmation.
What it didn't contain was a contingency plan.
Departure Day, 6.30 am
The first aircraft was scheduled to depart London.
But the flight was delayed.
Initially by 20 minutes, then by another 25. Eventually, the delay reached approximately an hour.
The assistant saw the updates but didn't initiate a review of the itinerary. The onward flight hadn't been cancelled, and the estimated arrival time was still being updated.
9.50 am — Amsterdam
The first aircraft arrived significantly later than scheduled.
Only 15 minutes remained before the onward flight's departure.
The CEO still needed to disembark, make his way to the correct gate and arrive before boarding closed.
In practical terms, the connection had already been missed.
10.05 am — The Flight Departs
The Copenhagen flight left without the CEO.
Only then did the search for alternatives begin.
But no suitable option remained that would get him to the negotiations on time.
The CEO contacted his prospective partner, explained the situation and requested a postponement.
A new meeting couldn't be arranged for the same day.
The trip had failed to achieve its primary objective, despite every booking having been made correctly.
3
Where Exactly Did the Executive Assistant Let the CEO Down?
Saying the assistant allowed too little time for the connection only explains part of the problem.
In reality, four separate planning failures contributed to the outcome.
Mistake No. 1: Cost Savings Took Priority Over the Purpose of the Trip
The assistant compared flights based on price, departure times and overall journey duration.
But the CEO didn't simply need flights.
He needed to be present at an important meeting at a specific time.
A cheaper itinerary can become the most expensive option if it causes a critical business meeting to be missed.
For an important business trip, priorities should be considered in this order:
Budget remains an important consideration, of course. But saving money shouldn't automatically take precedence over commercial risk.
Mistake No. 2: The Connection Was Assessed Against the Timetable, Not the Actual Process
There were 80 minutes between arrival in Amsterdam and the next departure.
But that didn't mean the passenger had 80 minutes of usable time.
Several factors needed to be considered:
✓ Time required to disembark.
✓ Distance between departure gates.
✓ Possible terminal changes.
✓ Additional check-in or security procedures, where applicable.
✓ Baggage arrangements.
✓ The boarding deadline for the onward flight.
✓ Potential delays to the first flight.
The assistant had identified the time between flights but hadn't assessed how much time the connection would actually require.
Mistake No. 3: The Booking Conditions Weren't Properly Assessed
Separate tickets and a single through-booking are not the same thing.
With a protected connection, a passenger who misses an onward flight because of a delay to the preceding flight may be entitled to assistance and alternative transport, depending on the applicable rules and circumstances.
With a self-transfer on separate bookings, those protections don't generally extend across the whole journey in the same way.
That doesn't mean the passenger has no rights in relation to the individual flights.
But the terms and consequences of a missed connection can be very different.
A professional Executive Assistant needs to understand not only the flight schedule but also the restrictions and protections associated with the booking.
Mistake No. 4: Action Was Taken Too Late
The assistant hadn't established in advance what level of delay should trigger a contingency response.
As a result, they continued monitoring the flight even as the likelihood of making the connection diminished.
A strong Executive Assistant doesn't wait until a problem becomes unavoidable. They know in advance which changes require action.
In reality, four separate planning failures contributed to the outcome.
Mistake No. 1: Cost Savings Took Priority Over the Purpose of the Trip
The assistant compared flights based on price, departure times and overall journey duration.
But the CEO didn't simply need flights.
He needed to be present at an important meeting at a specific time.
A cheaper itinerary can become the most expensive option if it causes a critical business meeting to be missed.
For an important business trip, priorities should be considered in this order:
- The ability to attend the critical meeting.
- The itinerary's resilience to disruption.
- The demands placed on the executive's time and energy.
- The overall cost.
Budget remains an important consideration, of course. But saving money shouldn't automatically take precedence over commercial risk.
Mistake No. 2: The Connection Was Assessed Against the Timetable, Not the Actual Process
There were 80 minutes between arrival in Amsterdam and the next departure.
But that didn't mean the passenger had 80 minutes of usable time.
Several factors needed to be considered:
✓ Time required to disembark.
✓ Distance between departure gates.
✓ Possible terminal changes.
✓ Additional check-in or security procedures, where applicable.
✓ Baggage arrangements.
✓ The boarding deadline for the onward flight.
✓ Potential delays to the first flight.
The assistant had identified the time between flights but hadn't assessed how much time the connection would actually require.
Mistake No. 3: The Booking Conditions Weren't Properly Assessed
Separate tickets and a single through-booking are not the same thing.
With a protected connection, a passenger who misses an onward flight because of a delay to the preceding flight may be entitled to assistance and alternative transport, depending on the applicable rules and circumstances.
With a self-transfer on separate bookings, those protections don't generally extend across the whole journey in the same way.
That doesn't mean the passenger has no rights in relation to the individual flights.
But the terms and consequences of a missed connection can be very different.
A professional Executive Assistant needs to understand not only the flight schedule but also the restrictions and protections associated with the booking.
Mistake No. 4: Action Was Taken Too Late
The assistant hadn't established in advance what level of delay should trigger a contingency response.
As a result, they continued monitoring the flight even as the likelihood of making the connection diminished.
A strong Executive Assistant doesn't wait until a problem becomes unavoidable. They know in advance which changes require action.
4
📊 What the Research Tells Us About Business Travel Risk
According to a forecast published by the Global Business Travel Association (GBTA) in 2025, global business travel spending was expected to reach $1.57 trillion that year.
This figure represents the scale of the business travel market, not the financial losses caused by disrupted journeys.
Source: GBTA — Business Travel Index Outlook.
According to SITA Baggage IT Insights 2026, approximately 24 million bags were mishandled worldwide in 2025, with associated industry costs estimated at $6.3 billion.
Source: SITA — Baggage IT Insights.
These figures don't establish how likely a particular business meeting is to be missed. However, they demonstrate that operational disruption remains a significant issue even within a highly developed aviation industry.
For business leaders, the consequences can extend well beyond the price of a ticket.
A delay may affect the executive's diary, preparation for negotiations, commercial relationships and the delivery of business commitments.
That's why effective business travel management requires more than making reservations.
It requires anticipating and managing risk.
This figure represents the scale of the business travel market, not the financial losses caused by disrupted journeys.
Source: GBTA — Business Travel Index Outlook.
According to SITA Baggage IT Insights 2026, approximately 24 million bags were mishandled worldwide in 2025, with associated industry costs estimated at $6.3 billion.
Source: SITA — Baggage IT Insights.
These figures don't establish how likely a particular business meeting is to be missed. However, they demonstrate that operational disruption remains a significant issue even within a highly developed aviation industry.
For business leaders, the consequences can extend well beyond the price of a ticket.
A delay may affect the executive's diary, preparation for negotiations, commercial relationships and the delivery of business commitments.
That's why effective business travel management requires more than making reservations.
It requires anticipating and managing risk.
6
How a Strong Executive Assistant Would Have Organised the Same Trip
Let's go back three days.
The CEO asks his assistant to arrange a trip to Copenhagen, preferably without an overnight stay.
What should happen next?
Before searching for flights, the assistant should clarify several points.
1. How Critical Is It to Arrive by 2 pm?
If the meeting can be moved without significant consequences, one level of risk may be acceptable.
If the negotiations would be difficult to rearrange, the itinerary needs to meet a higher standard of reliability.
2. Which Matters More: Avoiding an Overnight Stay or Having a Time Buffer?
The phrase "preferably without an overnight stay" doesn't mean arriving the previous evening is prohibited.
A professional assistant should distinguish between the executive's preferences and non-negotiable requirements.
3. What Happens if the First Flight Is Delayed by 30, 60 or 90 Minutes?
The aim isn't to predict the exact probability of a delay.
It's to assess the consequences.
If a one-hour delay would put the negotiations at risk, the itinerary needs reconsideration.
4. Is There a Viable Alternative?
For example:
✓ A direct flight arriving the previous evening.
✓ An itinerary with a longer connection.
✓ A through-booking with a protected connection.
✓ An alternative flight that would still allow the CEO to arrive on time.
Availability must be checked for the actual travel date and route.
What a Professional Recommendation Would Look Like
"I've prepared two options for Copenhagen.
Option A: Travel on the morning of the meeting. It's cheaper and avoids an overnight stay, but it involves a self-transfer. A significant delay to the first flight could mean missing the 2 pm meeting.
Option B: Arrive the previous evening. This requires an additional hotel night but provides a time buffer before the negotiations.
Given the importance of the meeting, I'd recommend Option B. If travelling on the day is essential, I suggest we agree the acceptable level of risk and check alternative routes."
In this example, the assistant isn't simply presenting flight options.
They're helping the CEO make an informed decision based on the potential consequences.
The CEO asks his assistant to arrange a trip to Copenhagen, preferably without an overnight stay.
What should happen next?
Before searching for flights, the assistant should clarify several points.
1. How Critical Is It to Arrive by 2 pm?
If the meeting can be moved without significant consequences, one level of risk may be acceptable.
If the negotiations would be difficult to rearrange, the itinerary needs to meet a higher standard of reliability.
2. Which Matters More: Avoiding an Overnight Stay or Having a Time Buffer?
The phrase "preferably without an overnight stay" doesn't mean arriving the previous evening is prohibited.
A professional assistant should distinguish between the executive's preferences and non-negotiable requirements.
3. What Happens if the First Flight Is Delayed by 30, 60 or 90 Minutes?
The aim isn't to predict the exact probability of a delay.
It's to assess the consequences.
If a one-hour delay would put the negotiations at risk, the itinerary needs reconsideration.
4. Is There a Viable Alternative?
For example:
✓ A direct flight arriving the previous evening.
✓ An itinerary with a longer connection.
✓ A through-booking with a protected connection.
✓ An alternative flight that would still allow the CEO to arrive on time.
Availability must be checked for the actual travel date and route.
What a Professional Recommendation Would Look Like
"I've prepared two options for Copenhagen.
Option A: Travel on the morning of the meeting. It's cheaper and avoids an overnight stay, but it involves a self-transfer. A significant delay to the first flight could mean missing the 2 pm meeting.
Option B: Arrive the previous evening. This requires an additional hotel night but provides a time buffer before the negotiations.
Given the importance of the meeting, I'd recommend Option B. If travelling on the day is essential, I suggest we agree the acceptable level of risk and check alternative routes."
In this example, the assistant isn't simply presenting flight options.
They're helping the CEO make an informed decision based on the potential consequences.
7
The T−72 / T−24 / T−3 Protocol: A Practical Approach to Business Travel Management
For trips involving critical meetings, a three-stage review can help identify risks before they escalate.
This is a practical executive support framework, not an official aviation standard.
T−72 Hours: Review the Itinerary
Three days before departure, the assistant should verify:
✓ The accuracy of all bookings.
✓ Whether connections are protected or self-transfers.
✓ Passport, visa and transit requirements.
✓ Check-in, boarding and baggage conditions.
✓ Realistic connection times.
✓ Travel time from the airport to the meeting venue.
✓ Available alternative routes.
✓ Ticket change and cancellation conditions.
✓ Airline, hotel and local contact details.
The objective: The assistant understands not just the itinerary, but its potential weaknesses.
T−24 Hours: Revalidate the Arrangements
The day before departure, confirm:
✓ Flight schedules and bookings remain unchanged.
✓ Check-in is available or has been completed.
✓ The hotel and transfer are confirmed.
✓ The meeting time and location are still correct.
✓ There are no significant airline or airport advisories.
✓ Contingency options remain available.
The objective isn't simply to open the tickets again.
It's to establish whether the original travel plan still makes sense.
T−3 Hours: Prepare for Disruption
Shortly before departure, review:
✓ Current flight status.
✓ Any changes to departure times.
✓ The potential impact of delays on connections.
✓ Communication arrangements with the executive.
✓ The conditions that would trigger a contingency response.
✓ Who will notify the meeting organiser if arrival is at risk.
For complex itineraries, monitoring may need to begin earlier.
The key is to agree not only what needs checking, but what should happen when something changes.
This is a practical executive support framework, not an official aviation standard.
T−72 Hours: Review the Itinerary
Three days before departure, the assistant should verify:
✓ The accuracy of all bookings.
✓ Whether connections are protected or self-transfers.
✓ Passport, visa and transit requirements.
✓ Check-in, boarding and baggage conditions.
✓ Realistic connection times.
✓ Travel time from the airport to the meeting venue.
✓ Available alternative routes.
✓ Ticket change and cancellation conditions.
✓ Airline, hotel and local contact details.
The objective: The assistant understands not just the itinerary, but its potential weaknesses.
T−24 Hours: Revalidate the Arrangements
The day before departure, confirm:
✓ Flight schedules and bookings remain unchanged.
✓ Check-in is available or has been completed.
✓ The hotel and transfer are confirmed.
✓ The meeting time and location are still correct.
✓ There are no significant airline or airport advisories.
✓ Contingency options remain available.
The objective isn't simply to open the tickets again.
It's to establish whether the original travel plan still makes sense.
T−3 Hours: Prepare for Disruption
Shortly before departure, review:
✓ Current flight status.
✓ Any changes to departure times.
✓ The potential impact of delays on connections.
✓ Communication arrangements with the executive.
✓ The conditions that would trigger a contingency response.
✓ Who will notify the meeting organiser if arrival is at risk.
For complex itineraries, monitoring may need to begin earlier.
The key is to agree not only what needs checking, but what should happen when something changes.
8
🚦 When Should an Executive Assistant Raise the Alarm?
One useful approach is to agree response thresholds in advance.
Imagine a self-transfer with an 80-minute connection.
🟢 Green — Proceed as Planned
The itinerary remains viable, with sufficient time for all necessary procedures.
The assistant continues monitoring.
🟡 Amber — Review the Alternatives
The available time buffer is shrinking, and there is a growing risk of missing the onward flight.
The assistant checks alternative arrangements and confirms the latest information with the airline.
🔴 Red — Activate the Contingency Plan
Continuing with the original itinerary is now highly likely to result in a missed flight or critical meeting.
The agreed response must be initiated immediately.
These thresholds shouldn't be tied to universal delay intervals.
They need to be calculated for each journey, taking account of the airport, boarding deadlines, connection procedures and available alternatives.
In our case, a delay of approximately an hour should already have prompted an urgent review.
But the assistant had no contingency plan.
As a result, the information about the delay never became a timely decision.
Imagine a self-transfer with an 80-minute connection.
🟢 Green — Proceed as Planned
The itinerary remains viable, with sufficient time for all necessary procedures.
The assistant continues monitoring.
🟡 Amber — Review the Alternatives
The available time buffer is shrinking, and there is a growing risk of missing the onward flight.
The assistant checks alternative arrangements and confirms the latest information with the airline.
🔴 Red — Activate the Contingency Plan
Continuing with the original itinerary is now highly likely to result in a missed flight or critical meeting.
The agreed response must be initiated immediately.
These thresholds shouldn't be tied to universal delay intervals.
They need to be calculated for each journey, taking account of the airport, boarding deadlines, connection procedures and available alternatives.
In our case, a delay of approximately an hour should already have prompted an urgent review.
But the assistant had no contingency plan.
As a result, the information about the delay never became a timely decision.
9
What Does a Failed Business Trip Really Cost?
A business travel budget usually includes the obvious expenses:
✓ Flights.
✓ Accommodation.
✓ Transfers.
✓ Additional costs arising from delays.
But important negotiations can carry other potential consequences:
✓ Lost executive time.
✓ Disruption to subsequent meetings.
✓ The need for a second trip.
✓ Delays to business projects.
✓ Potential damage to commercial relationships.
✓ Missed business opportunities.
Not all of these can be reliably expressed as a financial loss.
For example, it would be misleading to treat the full value of a potential contract as the loss caused by a missed meeting.
Nevertheless, these risks should inform the original travel decision.
If a more resilient itinerary costs an additional £250, that doesn't automatically make it poor value.
The additional expense needs to be considered alongside the potential consequences of disruption.
A good assistant knows how to manage a budget. A strong assistant knows when saving money creates disproportionate risk.
✓ Flights.
✓ Accommodation.
✓ Transfers.
✓ Additional costs arising from delays.
But important negotiations can carry other potential consequences:
✓ Lost executive time.
✓ Disruption to subsequent meetings.
✓ The need for a second trip.
✓ Delays to business projects.
✓ Potential damage to commercial relationships.
✓ Missed business opportunities.
Not all of these can be reliably expressed as a financial loss.
For example, it would be misleading to treat the full value of a potential contract as the loss caused by a missed meeting.
Nevertheless, these risks should inform the original travel decision.
If a more resilient itinerary costs an additional £250, that doesn't automatically make it poor value.
The additional expense needs to be considered alongside the potential consequences of disruption.
A good assistant knows how to manage a budget. A strong assistant knows when saving money creates disproportionate risk.
10
What Should an EA Do When Disruption Has Already Occurred?
Even a carefully planned trip can go wrong.
What matters then is how quickly the assistant can respond.
Step 1. Establish the Facts
Confirm the latest arrival time, the onward flight's status, booking conditions and available alternatives.
Step 2. Review the Options
Contact the airline or authorised travel agent, check available flights and clarify rebooking conditions.
Step 3. Assess the Impact on the Main Objective
Can the CEO still attend the negotiations? Could the route or meeting format be changed?
Step 4. Present a Recommendation
Don't simply report that the flight is delayed.
Explain what the delay means and propose realistic options.
Step 5. Coordinate Communication
Where appropriate, suggest postponing the meeting, joining remotely, changing the order of discussions or involving another representative.
This is where professional judgement becomes essential.
Not every disruption can be prevented. But the time between recognising a problem and responding to it can be reduced.
What matters then is how quickly the assistant can respond.
Step 1. Establish the Facts
Confirm the latest arrival time, the onward flight's status, booking conditions and available alternatives.
Step 2. Review the Options
Contact the airline or authorised travel agent, check available flights and clarify rebooking conditions.
Step 3. Assess the Impact on the Main Objective
Can the CEO still attend the negotiations? Could the route or meeting format be changed?
Step 4. Present a Recommendation
Don't simply report that the flight is delayed.
Explain what the delay means and propose realistic options.
Step 5. Coordinate Communication
Where appropriate, suggest postponing the meeting, joining remotely, changing the order of discussions or involving another representative.
This is where professional judgement becomes essential.
Not every disruption can be prevented. But the time between recognising a problem and responding to it can be reduced.
11
Three Questions That Reveal Whether Your EA Can Handle the Unexpected
If your Executive Assistant regularly organises business travel, give them this scenario:
"I have a meeting abroad at 2 pm. You've found a cheaper itinerary with a connection that gets me there two and a half hours beforehand."
Ask three questions.
1. Under what circumstances would you reject this itinerary, even if it were cheaper?
This tests risk assessment.
2. What would you check before booking?
This tests their understanding of booking conditions, connections, travel documents and alternatives.
3. What would you do if the first flight were delayed by an hour?
This tests contingency planning, independence and the ability to escalate appropriately.
If your EA struggles to answer, it doesn't necessarily mean they lack experience in booking travel.
They may need to develop stronger risk management and decision-making skills.
And those capabilities are particularly important when supporting senior business leaders.
"I have a meeting abroad at 2 pm. You've found a cheaper itinerary with a connection that gets me there two and a half hours beforehand."
Ask three questions.
1. Under what circumstances would you reject this itinerary, even if it were cheaper?
This tests risk assessment.
2. What would you check before booking?
This tests their understanding of booking conditions, connections, travel documents and alternatives.
3. What would you do if the first flight were delayed by an hour?
This tests contingency planning, independence and the ability to escalate appropriately.
If your EA struggles to answer, it doesn't necessarily mean they lack experience in booking travel.
They may need to develop stronger risk management and decision-making skills.
And those capabilities are particularly important when supporting senior business leaders.
Do You Need a New Executive Assistant — or a More Capable One?
When an assistant makes a serious mistake, the natural reaction is to consider hiring someone more experienced.
But before beginning a new recruitment process, it's worth identifying what actually went wrong.
If an employee repeatedly fails to check basic documents, disregards agreed procedures or conceals problems, that raises one set of concerns.
If they're reliable, understand the business and manage routine responsibilities well but struggle when circumstances change, that's a different situation.
The skills that may need developing include:
✓ Scenario planning.
✓ Risk assessment.
✓ Prioritisation.
✓ Information analysis.
✓ Preparing recommendations.
✓ Responding to changing circumstances.
If you need an EA who can think ahead, years of experience alone aren't enough. You need to assess how they think.
But before beginning a new recruitment process, it's worth identifying what actually went wrong.
If an employee repeatedly fails to check basic documents, disregards agreed procedures or conceals problems, that raises one set of concerns.
If they're reliable, understand the business and manage routine responsibilities well but struggle when circumstances change, that's a different situation.
The skills that may need developing include:
✓ Scenario planning.
✓ Risk assessment.
✓ Prioritisation.
✓ Information analysis.
✓ Preparing recommendations.
✓ Responding to changing circumstances.
If you need an EA who can think ahead, years of experience alone aren't enough. You need to assess how they think.
When Recruitment Is the Right Decision
Hiring a new Executive Assistant may be appropriate when the existing employee's capabilities consistently fall short of the role's requirements and development hasn't produced the necessary improvement.
But recruitment should assess professional judgement, not just previous job titles.
Instead of asking, "How many business trips have you arranged?", present a scenario:
"The CEO has an important meeting abroad. One itinerary is cheaper but involves a short connection. Another costs more but arrives the previous evening. How would you decide?"
The candidate's reasoning may reveal far more than the number of years on their CV.
At SMART AND TALENTED, we approach Executive Assistant recruitment by considering how a candidate's capabilities align with the actual demands of the executive and the business.
Finding someone who can book travel is only part of the challenge.
The greater value lies in finding someone who understands the consequences of their decisions and can protect the CEO's priorities.
But recruitment should assess professional judgement, not just previous job titles.
Instead of asking, "How many business trips have you arranged?", present a scenario:
"The CEO has an important meeting abroad. One itinerary is cheaper but involves a short connection. Another costs more but arrives the previous evening. How would you decide?"
The candidate's reasoning may reveal far more than the number of years on their CV.
At SMART AND TALENTED, we approach Executive Assistant recruitment by considering how a candidate's capabilities align with the actual demands of the executive and the business.
Finding someone who can book travel is only part of the challenge.
The greater value lies in finding someone who understands the consequences of their decisions and can protect the CEO's priorities.
Why Even Experienced Executive Assistants Make These Mistakes
Having organised hundreds of business trips doesn't necessarily mean someone is confident managing unusual situations.
If most journeys have gone smoothly, an assistant may become accustomed to a familiar process:
Receive the dates → Find flights → Agree the budget → Book → Send confirmations.
As long as circumstances remain predictable, the process works.
But executive support requires more than following a sequence of tasks.
It requires anticipating consequences, understanding priorities, preparing alternatives and communicating risks early.
These are skills that can be developed.
And if an existing EA already knows the executive and the business well, investing in their development may be more sensible than starting recruitment again.
If most journeys have gone smoothly, an assistant may become accustomed to a familiar process:
Receive the dates → Find flights → Agree the budget → Book → Send confirmations.
As long as circumstances remain predictable, the process works.
But executive support requires more than following a sequence of tasks.
It requires anticipating consequences, understanding priorities, preparing alternatives and communicating risks early.
These are skills that can be developed.
And if an existing EA already knows the executive and the business well, investing in their development may be more sensible than starting recruitment again.
Developing an Executive Assistant Who Can Anticipate Problems
SMART AND TALENTED Academy offers the “Ассистент на миллион. Новое поколение” (Next Generation Executive Assistant) programme, focused on developing the professional capabilities required in modern executive support.
An important part of the training involves managing complex tasks, analysing information, setting priorities and making decisions within clearly defined responsibilities.
Participants also explore the practical application of artificial intelligence to information analysis, document preparation and workflow improvement.
AI, however, cannot replace professional judgement.
For example, an AI tool can help structure a business travel risk checklist, but live flight availability, visa requirements and booking conditions must still be verified through official and reliable sources.
The practical project “90 Days with the Principal” involves working through a sequence of professional scenarios in which circumstances change, new tasks emerge and earlier decisions have consequences.
This approach helps develop the judgement needed to support senior executives.
An important part of the training involves managing complex tasks, analysing information, setting priorities and making decisions within clearly defined responsibilities.
Participants also explore the practical application of artificial intelligence to information analysis, document preparation and workflow improvement.
AI, however, cannot replace professional judgement.
For example, an AI tool can help structure a business travel risk checklist, but live flight availability, visa requirements and booking conditions must still be verified through official and reliable sources.
The practical project “90 Days with the Principal” involves working through a sequence of professional scenarios in which circumstances change, new tasks emerge and earlier decisions have consequences.
This approach helps develop the judgement needed to support senior executives.