Strengthening judgment when stakes are high

The next generation of SEO • The rise of one-time CEOs • The fall of job perks -

July 15, 2025

The monday.com weekly

monday.com’s take on the latest work trends - sent on Tuesdays

Inside this issue

  • Workplace trends
  • The AI corner
  • Strengthening your judgment in high-stakes situations
  • Water cooler chatter
  • Question of the week
  • Just for laughs
  • Follow the monday.com weekly on LinkedIn

Workplace trends

Leadership

The one-and-done CEO trend reshaping executive careers

Corporate leadership is experiencing a fundamental shift as executives increasingly view the CEO role as a single-career pinnacle rather than a repeatable achievement. 85% of incoming chief executives in 2024 were first-time leaders, according to research from Russell Reynolds Associates, marking the seventh consecutive year that experienced CEOs made up a minority of new appointments. This trend reflects the evolving nature of executive leadership, where modern CEOs face unprecedented challenges including AI disruption, and heightened public scrutiny that can turn a single misstep into a career-ending crisis. Executive search experts note that many senior leaders are now declining CEO opportunities entirely, citing relentless pressure. This shift toward one-time leadership tenures is fundamentally changing how companies approach succession planning and talent development in the C-suite.

 

Culture

Tech's golden age of perks and job security comes to an end

The technology sector is experiencing a dramatic cultural shift as companies abandon the employee-friendly practices that once defined Silicon Valley workplaces. Major tech firms have eliminated beloved perks like free laundry, reduced cafe hours, and scaled back generous compensation packages while workers now face layoff fears and increased workloads from unfilled positions. This transformation is turning what were once considered the most desirable jobs in the economy into positions that increasingly resemble traditional corporate roles with standard pressures and limited job security.

The AI corner

Development

Startups rush to build the next generation of search optimization

A new wave of companies is capitalizing on the shift from traditional Google searches to AI chatbots, developing tools to help businesses optimize their content for platforms like ChatGPT and Perplexity. At least a dozen startups have raised millions to create what amounts to search engine optimization (SEO) for the AI era, with companies like Athena securing $2.2 million and Profound raising over $20 million from major venture firms. These platforms analyze how different AI models gather and present brand information, offering businesses insights into optimizing web content for chatbot searches that are typically longer and more complex than traditional queries. SEO consultant Cyrus Shepard reports that AI visibility work has grown from zero to 15% of his time this year and expects it could reach 50% by year-end. The emergence of this sector signals a fundamental transformation in how companies approach online visibility where consumers primarily interact with AI interfaces rather than browsing websites directly.

 

Data

Publishers fight back against AI companies scraping their content

Media companies are escalating efforts to block AI companies from freely harvesting their content, implementing technical barriers and legal strategies to protect intellectual property from chatbots that provide answers without driving traffic back to original sources. Publishers including The Atlantic and Dotdash Meredith are partnering with services like Cloudflare to create "toll booths" for AI scrapers, allowing them to control which companies can access their content as scraping activity jumped 18% in the past year. The escalating conflict has sparked legal battles, with Reddit suing Anthropic for scraping over 100,000 times despite promises to stop, while many publishers are simultaneously pursuing licensing deals with companies like OpenAI to monetize their content rather than lose revenue to unauthorized scraping.

Strengthening your judgment in high-stakes situations

A leader’s day is filled with decisions to make: which tools to purchase, which employees to promote, which strategies to pursue, which big bets to move on, and which risks are too high. In fact, leaders spend around 40% of their time making decisions, according to research by McKinsey – but unfortunately, many leaders feel that time investment is ineffective.

 

A 2023 study by Oracle found that 85% of business leaders experience decision distress, questioning or regretting the choices they’ve made. These doubts can easily spiral into burnout, making it even harder to lead with clarity. To strengthen their judgment, leaders need the right insights, sharp critical thinking skills, and reliable decision-making frameworks that help them see every angle clearly. Instead of acting on gut feelings alone, building a thoughtful decision-making approach can transform uncertainty into confidence and turn tough calls into powerful opportunities for growth.

 

So, how can you start sharpening your judgment and making better decisions?

 

Pause first

Being reflective may feel counterintuitive when you're working in a fast-paced and high-stakes environment, but doing so can make a huge difference in your decision-making. Deliberately pausing can help you recalibrate your thoughts and move to the next step with greater clarity and purpose. In fact, Harvard Business School research shows that leaders who engage in regular, structured reflection improve their performance and productivity by 23%. By pausing to consider options and implications, you make faster and more impactful choices in the long run.

 

Key question: “Where can you create space to reflect before deciding?”

 

Categorize decision types

Having too many decisions on your plate can lead to overwhelm and poor focus. To avoid this, try categorizing decisions by type, such as “High Risk” (your strategic big bets), “Operational” (team functions), and “Lower Priority” (smaller everyday tasks). Keep in mind that your energy should go toward pivotal, high-risk decisions that require deep research and critical thinking. Take inventory of your high-risk decisions and ask yourself which ones will have the biggest impact on your business goals. Then, rank them by urgency, so you can stay focused on what matters most.

 

Key question: “What categories do your decisions fall into, and which should you focus on personally?”

 

Delegate effectively

Empowering your team to make everyday decisions will help free you up to focus on more complicated or strategic ones. This does not happen overnight; you must build a structure around it. Start by ensuring all team members understand your strategy and that everybody knows who owns what, so they can act confidently when making a decision. Operational and lower-priority decisions are best assigned to team members closest to the work and who have been trained and empowered to act confidently. This way, you maintain your own focus while also strengthening your team's ownership of outcomes.

 

Key question: “How can you empower your team to make decisions confidently and independently?”

 

Seek diverse perspectives

Don't rely solely on your own perspective to make an important decision, no matter how well-versed you are on the subject matter. You could have blind spots that impair your judgment, so try to get a diverse set of opinions to help you understand the implications of a decision. Seek out experts from diverse backgrounds to weigh in – especially if they disagree with you! During your sessions with them, ask questions that get to the heart of the situation by inspiring everyone to think critically. For example, you might present a specific decision and ask everyone, "Will this decision hold up a year from now?" or "List the best and worst case scenarios if we go in this direction." Your goal is to understand all sides of the situation to make the strongest choice. The added bonus of bringing in others is that you're showing that their insights matter. When people feel included and respected, they’re more likely to rally behind the final decision.

 

Key question: “Who else’s perspective could help you make a stronger decision?”

 

Check for biases

Before finalizing a decision, ask yourself if you’re falling into common cognitive traps like confirmation bias (only seeking information supporting your beliefs) or herd mentality (aligning with the majority for safety). To challenge these biases, you might consider a “teardown” exercise. This is when you split into teams to analyze decisions from different angles, role-play scenarios, and test assumptions. Doing this can help you spot risks and make sure your choices are grounded in reality.

 

Key question: “What biases might be shaping your decision without realizing it?”

Water cooler chatter

OpenAI mandated a week-long vacation to stop Meta from poaching its talent. The talent war has reached fever pitch as Meta reportedly offers $100 million signing bonuses while OpenAI executives scramble to retain staff who often work 80-hour weeks. Internal memos reveal OpenAI leadership pleading with employees to resist Meta's recruitment efforts, with some researchers warning that Meta might intensify poaching during the forced vacation week.

"I feel a visceral feeling right now, as if someone has broken into our home and stolen something."

- Mark Chen, Chief Research Officer, OpenAI

Apple sued a former Vision Pro engineer for stealing trade secrets before joining Snap. The lawsuit claims Di Liu downloaded thousands of confidential files during his final two weeks at Apple, including project codenames and technology details that could benefit his new AR role at Snap. This marks Apple's latest legal action against former employees for taking company secrets.

"The overlap between Apple's Proprietary Information that Mr. Liu retained and Snap's AR products suggests that Mr. Liu intends to use Apple's Proprietary Information at Snap."

- Apple's Legal Filing

Question of the week

Last week’s answer: 38% of employees actually utilize their company’s mental health resources.

This week’s question: What percent of Gen Zers say they stream series and movies while working remote?

Just for laughs

“In the spirit of collaboration, I’m going to say I’m good with whatever and force everyone else to make decisions.”

To update your email notification settings, click here.

To stop receiving any marketing emails, unsubscribe here.

Want to manage your work on the go?

Download the monday.com mobile app.

Apple Google

© 2025 monday.com | 111 E 18th St NY, NY, 10003, USA

Comments

Popular posts from this blog

Make quick edits right in your PDF 📝

Strike the right chord with a PDF 🎵

Pitch perfect PDFs 💯