Featured in today's briefing:

  •  Takeaways from the Charter Workplace Summit.
  • Delegation skills in the age of AI. 
  • Why to write a weekly one-pager. 

AI and Work Radar

  • A new paper highlights a privacy risk posed by large language models (LLMs), finding that they can quickly and accurately infer Reddit users’ personal information from their posts, including location and income. “By scraping the entirety of a user’s online posts and feeding them to a pre-trained LLM, malicious actors can infer private information never intended to be disclosed by the users,” the authors warn. 
  • Financial-research firm Moody’s is now using generative AI to help workers quickly sift through reams of internal and public documents as they compile reports. “What could potentially have been a day’s long process is now literally five minutes,” chief product officer Nick Reed told Bloomberg.
  • A new LLM called Latimer aims to avoid the racial bias currently found in many AI tools. Named for the Black inventor Lewis Latimer, it was trained on materials from underrepresented communities, with the goal of providing users with more accurate and comprehensive answers around the experiences of marginalized racial groups. 
  • Feeding an AI tool structured prompts may yield less useful answers than simply chatting with it, a new study finds. The authors propose an alternative to prompting that they call “generative active task elicitation,” or GATE, in which AI platforms “elicit and infer user preferences through open-ended interaction… for example, by asking informative open-ended questions or generating edge cases for users to label.”

Focus on Takeaways from the Charter Workplace Summit

This week’s Charter Workplace Summit aimed to answer the question: How can leaders continue to advance a people-first approach in a new economic and social zeitgeist? Here are key ideas, tactics, and strategies that emerged over the course of the day: 

Ask yourself, “Should I do this, or should the machine do this?” Jared Spataro, corporate vice president of modern work and business applications at Microsoft, said this is the question he poses before every new task. Delegation will also become an increasingly valuable skill as workers learn how to effectively delegate tasks to AI with the right context and parameters, he said—one of many reasons why older workers, who tend to have more people-management experience, are often better prepared to work with AI than their younger colleagues. 

Set a “silent but unmuted” norm for meetings. A meeting facilitator’s task of building an environment of trust is more easily accomplished when they can hear participants’ in-the-moment reactions such as sighs or gasps, argued Priya Parker, author of The Art of Gathering. As one attendee noted, the practice also cuts down on the likelihood that meeting participants will be multitasking by removing their ability to mask telltale keyboard clacking. 

“Don’t run a focus group in your head.” In a conversation about best practices for remote and hybrid work, Kausik Rajgopal, EVP of people and sourcing at PayPal, warned against the common pitfall of leaders and managers assuming they know what their workers want and need. Listen to your employees and evolve, he added. 

Look for low-lift ways to introduce playfulness into daily work. Michelle Lee, partner and managing director at IDEO’s Play Lab, explained that even small tweaks such as a silly icebreaker to kick off a meeting (for example, competing for the goofiest, most elaborate Zoom high-five) help cultivate the three components of play, which also describe a healthy, effective working environment. The first, psychological safety, makes workers more willing “to propose wild ideas, to challenge the status quo,” she said. The second is a feeling of agency: “Can you change the game? Does your being there influence the outcome?” And the third is a sense of joy, she explained: “Without something that appeals to you on an emotional level, you can’t sustain what you’re doing.” 

Try speed mentoring. Around half of undergraduates say they’re more willing to apply to a job if they know that the employer has programs in place to support their learning and development, according to Handshake data shared by its chief impact officer Monne Williams. One attendee shared such a program from her own organization: mentor “coffee talks,” where younger workers can sign up for 30-minute sessions with a senior leader to seek guidance and advice. While the format is inherently low-commitment, those conversations also have the potential to evolve into longer-term relationships. 

Make sure you can articulate the “why” of an AI use case. Julia Stoyanovich, the director of NYU’s Center for Responsible AI, suggested a litmus test to help ensure the benefits outweigh the costs: “Is there a real social or business problem we think AI will help us solve?”

Train workers to productively disagree with one another. “A lot of us are feeling lonely and isolated, and we come to work and look to our leaders for community and conversation,” said Mita Mallick, head of inclusion, equity, and impact at Carta. Especially in the lead-up to the 2024 election, though, workplace discourse unrelated to work runs the risk of becoming fraught. Disagreeing with kindness and respect “requires skill,” she argued, and “we need to help people be skilled to have these conversations.”

Read more about the summit here, and look out for our forthcoming playbook with takeaways from event speakers and attendees. 

Read our past interviews with Charter Workplace Summit speakers Jared Spataro, Priya Parker, and Michelle Lee

What Else You Need to Know

Close to nine in 10 CEOs plan to reward employees who choose to work on-site, according to KPMG’s recent CEO Outlook survey, which asked about leaders’ intention to give “favorable assignments, raises, or promotions.” 

  • At the same time, 66% of respondents reported that diversity, equity, and inclusion progress is moving too slowly. 
  • The two statements seem to be in conflict, as underrepresented and marginalized groups like workers with disabilities or caregiving responsibilities show strong preferences for remote and hybrid work. 

Employers are increasingly offering menopause benefits to retain older, female workers. Organizations including Microsoft, Palantir, and the NBA have started offering additional services to workers who may be experiencing menopause, including access to specialists and hormone therapy, dedicated education resources, wellness coaching, and sick time for managing menopause symptoms. 

  • The overall number of companies offering menopause benefits remains low. Benefits consultancy NFP found that just 4% of employers that offer sick leave provide additional menopause-related benefits. 

The racial wealth gap has narrowed during the post-Covid economic recovery. While previous recessions have widened the racial wealth gap between white workers and workers of color, the period from 2019 to 2022 saw the median net worth of Black and Hispanic families rise by 60% and 47%, respectively, compared to a 31% rise for white families, according to a new Treasury Department report

  • Similarly, the gap between white and Black unemployment rates reached a record low in April of this year, and the gap between the white and Hispanic unemployment rate was at a record low in November 2022. 
  • The narrowing gap in economic outcomes for different racial groups led the report’s authors to dub the current economic recovery “the most equitable in recent history.” 

Recent research finds a direct link between worker wellbeing and a firm’s financial performance. In a report from Oxford’s Wellbeing Research Centre, economists analyzed worker-provided data for more than 1,600 organizations on the job-search platform indeed, including self-reported measures of happiness and stress. 

  • Comparing these measures to the organizations’ finances, they found that “wellbeing is associated with firm profitability and that companies with the highest levels of wellbeing also subsequently outperform standard benchmarks in the stock market. “
  • Just under half of workers now believe that their employer cares about their wellbeing, down from 60% in 2021, according to a new Aflac survey spanning more than 2,000 workers and 1,200 employers.
  • Some 57% of those surveyed said they’re at least moderately burned out, while 74% said they experience at least moderate workplace stress. 

Here are some of the best tips and insights from the past week for managing yourself and your team:

  • Create space for dissenting opinions. Avoid team groupthink by prompting disagreement and dissent by asking questions such as, “What risks or blindspots remain unaddressed?”, “What objections might this plan raise for potential stakeholders?”, and “What are potential points of failure, and how might we avoid them?” 
  • Prepare a weekly one-pager for your manager. Keep potentially overbearing or anxious managers at bay by writing a weekly memo on the status of each of your workflows and projects. Detail any progress, setbacks, and upcoming deadlines. Then, link to past editions of the one-pager so they can track progress.
  • Normalize skill profiles. Have all workers prepare “skill profiles” that detail areas where an individual has significant experience, training, or knowledge. Then, encourage colleagues across teams to reach out for upskilling, guidance, or help in a specific skill area. 
  • Set up passkeys for your personal tech. Passkey logins are slowly overtaking traditional passwords on many sites, like Amazon and Google. Rather than having users type in a password, passkeys allow individuals to use password manager tools to sign in with a single click, making sign-ins both more secure and more efficient. 


A chilly reception. The newest—and literally coolest—trendy networking activity: the cold plunge, where participants submerge themselves in icy water in the name of team bonding or deal-closing. 

  • “You get a better deal,” one enthusiast told The Wall Street Journal. “People’s hearts are more open, and they’re more receptive.” 

LLM: Looking like a model. AI image generators have a tendency to feature exceptionally good-looking people in their outputs, even when the initial prompts don’t specify anything about attractiveness, a pattern one Atlantic writer recently dubbed “the hotness problem.” 

  • One possible reason is the generators’ training material includes celebrity photos and the flattering photos people tend to post online.

The handbook for this new era of business doesn’t exist. We’re all drafting our own as we go along—and now we’d like to start doing so together. You can sign up here to receive this briefing by email.