A CEO resigned after making remarks on Israel. He's a case study in failing to read the room.

• CEOs must tread a fine line when commenting on the Israel-Hamas war.
• Execs' statements are being closely and publicly analyzed for whom they seem to side with.

The recent fate of Web Summit's CEO might, perhaps, send chills down the spine of any business leader.

On October 13, six days after Hamas' terrorist attacks in Israel, the technology conference's leader, Paddy Cosgrave, posted his views on the ensuing conflict on X. In his first post on the subject, Cosgrave seemed to accuse Israel of war crimes. "I'm shocked at the rhetoric and actions of so many Western leaders & governments, with the exception in particular of Ireland's government, who for once are doing the right thing," he wrote. "War crimes are war crimes even when committed by allies, and should be called out for what they are."

After a week of backlash that saw attendees and major commercial partners including Intel pulling out of Web Summit, due to take place in Lisbon in November, Cosgrave apologized and eventually resigned as CEO.

The saga mirrors flare-ups on US college campuses, with companies rescinding job offers to students over student groups' statements on the war.

Cosgrave's departure illustrates the stakes for corporate executives when deciding whether or how to comment on any politically fraught subject. While students answer primarily to their school and any future employers, an executive's audience is more likely to include some combination of employees, shareholders, investors, and customers, often from multiple countries — all of whose views may differ.

Understand your audience

Cosgrave, who is Irish, may not have accounted for a culture clash. The US, the UK, and many European countries count Israel as a staunch ally. Ireland's government has condemned Hamas' terrorist attacks, but it was reported on October 7 that it had more explicitly urged a "proportionate" military response.

Ireland also has a long history of pro-Palestinian sentiment, much of it rooted in the country's relationship to the UK.

"The grassroots and the political elite are more pro-Palestinian than they are in the US," Bill Kissane, a politics professor at The London School of Economics and Political Science, told Insider. "This is for a number of factors. One is that historically the Irish regard themselves as having been a minority struggling against Britain, so they're more sympathetic to other anti-colonial or independent struggles — depending on what you regard the Palestinian cause to be."

Ireland was the first Western nation to recognize the Palestinian Liberation Organization as the "sole legitimate representative of the Palestinian people" in 1980, and in 2021 the Irish parliament accused Israel of the "de facto annexation" of Palestinian land. Palestinian flags and murals also frequent republican neighborhoods in Northern Ireland.

While Web Summit began in Ireland, its audience, speakers, attendees, and commercial sponsors are now international. Current and former commercial sponsors include Google, Microsoft, and Siemens, per its website. And American CEOs — including Google's — have mostly explicitly condemned Hamas and expressed support for Israel.

Cosgrave possibly "didn't really realize how big a deal it was given the diversity of his audience," said Paul Argenti, a corporate communications professor at Tuck School of Business.

For Cosgrave's critics, including VCs and founders, his comments lacked "moral clarity" by failing to explicitly condemn Hamas in the first instance, while also suggesting the potential for Israeli war crimes. (Cosgrave later did condemn Hamas.) But some of Cosgrave's Irish followers, including entrepreneurs and academics, supported his remarks or took similar stances on X.

Cosgrave did not immediately reply to Insider's request for comment.

"He might have been getting a lot of 'You're absolutely right' in Ireland," Argenti added. "But there's a push to be more pro-Israel in the US. No question about that."

Cosgrave may have also erred in U-turning, itself indicative that he didn't fully think through the consequences of taking a public position.

Proceed with caution

Many of the high-profile CEOs who have commented on the conflict so far have explicitly condemned Hamas and supported Israel.

Those who have yet to express an opinion may be mindful of previous blowback against corporate stances on topics such as LGBTQ+ rights and racial justice.

Argenti said it was important to remember that companies are not political entities and that the expectation for them to comment on issues outside their core business is a relatively new idea.

CEOs should consider whether commenting on a political topic issues is strategic, whether they can do anything practical to address the issues, and how much retaliation they might face either way, he added.

"If you have no connection to Israel, what is the point in mouthing off about political issues now?" he said. "Do we really want companies to become political entities is maybe an even better question."

"My main advice for companies is to be really careful," he continued. "Have a plan for how you want to deal with issues before they come up — not when somebody's pressuring you to say something — and then stick to your guns."