28 OCTOBER 2026 · GENERAL EDITION
Who is supporting your managers?
An AI readiness gap, a financial wellbeing blind spot, and three small moves to try.
👋 Welcome
New tools. New expectations. Who is helping your managers explain it all? Korn Ferry's new research highlights a leadership readiness gap as AI changes work.[1]
This week, a practical question: what can you make clearer or easier for your team before adding anything else?
— Emma Olie
📊 This Week in Workplace Data
6% 🧭
Leadership readiness is scarce.
Korn Ferry's 22 October report found only 6% of 1,300+ talent and senior leaders across 75+ countries said senior leaders were fully prepared for AI transformation.[1]
66% 💪
Physical thriving is up.
WTW's 2 October findings report this employee self-assessment across 31 markets, up from 55% in 2019. Financial wellbeing, however, deteriorated over the past two years.[2]
56% 🛠️
The operational majority needs a route in.
PwC's 29 September survey calls this group the "engine room": workers with less scarce skills and fewer reported AI advantages. The survey covered 48 countries and regions.[3]
🌍 Workplace Headlines
1Managers are being asked to absorb uncertainty
In Korn Ferry's survey, 66% of respondents expect managers to spend more time guiding teams through change than managing day-to-day work. That is an expectation for 2027, not an observed workload measure. Give managers clear context before asking them to explain the change.[1]
💡 TRY THIS
Share what is known, what is not, and the one answer you will find. Invite one question you cannot answer yet.
2Financial wellbeing can hide behind improving signals
WTW finds physical thriving rising while financial wellbeing has deteriorated amid cost-of-living pressure. Do not demand personal disclosures. Make existing guidance and support easy to find when life feels expensive.[2]
💡 TRY THIS
Send an optional note with three plain-language links: benefits guidance, financial education and confidential help.
3The AI divide is also a work-design divide
PwC's "engine room" keeps delivery moving but reports less AI, learning and opportunity. Access alone is not development. Learning lands better when someone can practise on a real task and judge whether it helps.[3]
💡 TRY THIS
Protect practice time for one high-volume task. Scale only what the worker can explain and verify.
🌎 Around the World
🇺🇸 United States Payroll check
Form 941 for third-quarter 2026 is due 2 November, because 31 October is a Saturday. The 10 November filing date applies only to employers with timely, proper and complete deposits.[4]
🇬🇧 United Kingdom Prepare now
HMRC's 21 October bulletin confirms Phase 1 mandatory benefits payrolling is scheduled for 6 April 2027. Map company cars, car fuel, vans, van fuel and employer-provided medical benefits.[5]
Next step: Ask your payroll provider how it is preparing.
🌐 Global Human skills still matter
In Korn Ferry's survey, 91% of respondents expect coaching and people skills to become more important.[1]
Next step: Give managers one practical coaching scenario to practise, not another slide deck to read.
📚 Featured Articles
Featured posts
🎙 Podcast of the Week
The HR Technology Trends 2026: AI is Expanding Jobs, Not Replacing Them
This week's episode looks at why AI adoption in HR is correlating with workforce growth rather than cuts, and what that means for how HR teams plan headcount and skills for 2026.
🎧 Listen on Spotify →📅 Events & Webinars
We have no events scheduled this week. Stay tuned — new webinars and meetups will be announced soon.
See all events & past webinars →💡 Founders Perspective
"When change arrives faster than the answers, people notice whether support is clear and usable. Our job is not to perform certainty; it is to make the next helpful choice easier."
— Emma Olie
💜 ABOUT SIDEUP
More choice, without harder administration.
SideUp helps employers offer more choice without harder administration. Flexible benefits, reimbursements, recognition, eNPS, pulse surveys, and HR and payroll integrations can make support easier to navigate and give teams useful insight for attraction and retention.[6]
Want to see SideUp for your team?
Book a SideUp demo →References
[4] IRS — Publication 509, Tax Calendars 2026 — Form 941 third-quarter filing dates
[5] HMRC — October 2026 Employer Bulletin — Mandatory payrolling of benefits in kind