White-glove security training closes executive vulnerability gap

Specific risks facing executives

A number of risks and attack vectors specifically target executives, often with great success. Some common attacks include the following:

• Business email compromise. BEC attacks involve a malicious hacker taking over or spoofing a business email account to impersonate a CEO or trusted supplier, which can lead to payment fraud, credential theft or data theft. In 2025, the FBI's Internet Crime Complaint Center reported more than $3 billion in BEC losses. Abnormal Security's "2026 Attack Landscape Report" found that more than 41% of internal impersonation BEC attacks targeting executives involved VIP impersonation.
• Targeted phishing. Security teams know how to address regular phishing attacks, but spear phishing and whaling take phishing to another level, building highly targeted attacks against senior executives.
• Voice and video impersonation. With deepfakes and vishing techniques, attackers can clone an executive's voice or likeness to deceive others. Only 30% of respondents to Ivanti's "2026 State of Cybersecurity Report" said their CEOs could definitely spot a deepfake if targeted, while 49% said they probably could.
• Personal exposure. Attackers target executives through their family members, home networks and personal accounts.

The pressures of executive roles also contribute to the risk.

"Executive attacks rarely succeed because leaders lack security awareness," said Ronald Lewis, director of cybersecurity governance at software security vendor Black Duck. "They succeed because leadership roles combine authority, access and urgency."

Executives might also make assumptions about their roles that pose a security risk.

"Some executives are complacent, believing their company isn't valuable enough or that attackers would never target them. Nothing is further from the truth," said Ira Winkler, CEO and program director of CruiseCon and former chief security architect at Walmart.

Why standard training falls short

Standard cybersecurity training is often targeted at employees and typically misses a few things that executives need.

"Standard awareness training teaches employees to look for bad grammar or fake domain names," said Muhammad Yahya Patel, virtual CISO and cybersecurity advisor at security company Huntress. "It completely fails against AI-enabled voice cloning and highly contextual multichannel social engineering."

Commonly taught best practices -- such as not opening an attachment or clicking on a suspicious link -- aren't enough, said Kelvin Lim, head of security engineering (APAC) at Black Duck. Neither does taking a simple phishing test to see if an executive will fall for an attack, nor finishing an annual training.

"I don't measure success by whether an executive has completed a training module," Lewis said. "I measure success by whether we've reduced their attack surface, improved their decision-making under pressure and put controls in place that still work when someone is having a very busy day."

What white-glove training includes

White-glove training is personalized in its purpose, assessment, delivery and content.

• The purpose. The approach is built on the individual, not the audience. "White glove, to me, just means the content is built off reconnaissance on that specific person," Gerry said. "Not a module everybody in the company clicks through in April."
• The assessment. The assessment starts with the executive's own exposure risks, including an evaluation of their homes and families for potential backdoors, Winkler said.
• The delivery. Delivery relies on practice instead of reading slides. Short, realistic simulations of payment fraud, executive impersonation or service disruption are more effective than generic presentations, Lim said.
• The content. Tailor content to the organization and the executive. Specific examples should reflect situations executives could realistically face and teach the procedures to follow when something looks suspicious, said Jordan Schoenherr, a cognitive psychologist and scientist at social engineering prevention company Humanix.

Components for the C-Suite and board

Experts' opinions vary on whether training threats and topics differ for the CEO, CFO and board members. Patel said that CEO training topics should focus on manipulation, impersonation and reputation, while CFO topics need to center on BEC, spoofing third-party suppliers, deepfake fraud and financial approvals. Topics for board members should emphasize communications and data handling, as well as how to verify information they receive and how to query highly sensitive requests through other channels, he added.

Winkler said that the nature of the training does not differ significantly for the parties in question. "With white-glove training, you are primarily dealing with the individual and the type of information they possess," he said.

Implementation best practices

Executive security training programs work best when they start with the individual and end with measured results.

• Start with each executive's risk assessment. The assessment precedes the creation of any white-glove training content. "Before carrying out training, it's important to carry out a risk assessment against the individual," Patel said.
• Rehearse the callback in the sessions. White-glove sessions should give staff a verification step to practice. "The mechanic that matters most is boring: a pre-agreed out-of-band verification for any financial or credential request, and practice using it," Gerry said. "A 26-year-old in accounts payable can tell the CEO, 'I'm going to call you back on your known number' without feeling like it's a career risk."
• Keep sessions short and repeat them. White-glove sessions best fit an executive's schedule when brief and spaced out. Five-minute exercises spread across several weeks, for example, are easier to fit into an executive's schedule, Schoenherr said.
• Present the program as support. Security teams should position a white-glove program as help for executives. It's important to be seen as a collaborative partner who supports and enables executives, said Javvad Malik, lead CISO advisor at security awareness training vendor KnowBe4.
• Measure results for each executive. Track how far the program has reduced an executive's personal threat profile -- and share that info with the executive. "I prefer to show them how the program lowered their personal threat profile and that of their family," Winkler said.

Remember, as with any security awareness program, white-glove training is not infallible. "The objective is not perfect detection," Lewis said. Rather, it's making sure there are safeguards in place in the event detection technologies fail.

Sean Michael Kerner is an IT consultant, technology enthusiast and tinkerer. He has pulled Token Ring, configured NetWare and been known to compile his own Linux kernel. He consults with industry and media organizations on technology issues.