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Exit Interview by Patrick Donegan – Newsletter #101

By: Patrick Donegan

For some time, I’ve been looking for one “source” that curates modern takes on HR Tech, perspectives from the people who build it, and its impact on enterprise — something that’s tailor-made by professionals for decision-makers.

I never found it — so I decided to build it.

Every week, I’ll be sharing fresh insights on tech platforms, design, data, and the future of work — straight to your inbox.

My Thoughts

Well, I hope none of you flew Southwest this holiday season. 🫣

To recap: Winter Storm Elliot began disrupting air travel just before Christmas. 🎄 While other major airlines did experience travel interruptions, none came close to Southwest. Between December 25th and 26th, the single airline canceled more than 5,500 flights, with most passengers being notified less than 48 hours before their takeoff time. To put that in perspective, Delta Airlines, which had the second-highest number of cancellations, barely topped 300. 🤨

When Southwest continued dolling out delays and cancellations as other brands resumed regular flight schedules, it became evident that weather was not the only cause of the company’s travel woes. ⛈️ Several days into the chaos, the company finally acknowledged that problems with their scheduling system were partially to blame for the disruptions. Crew members soon began providing details (and apologies) on social media, saying that pilots who were ready to fly 🛫 could not get in touch with their own airline’s representatives. Employees said they had no way of locating stranded crew members — despite many being stuck at airports alongside passengers. 

The saga continues into the new year, and this piece from Dallas Morning News offers a very solid overview of everything that’s happened so far. 📜 But why things have unfolded the way they have — and what it means for Southwest — is what I want to focus on today.

The root cause of the issue comes down to one topic we know very well: digital transformation. ✨ Or, more accurately, a lack thereof. For over a decade, Southwest has been reluctant to adopt new technology. They were one of the last US airlines to switch from paper to digital reporting. 😳 In 2018, they faced a multi-million dollar fine from the FAA for unsatisfactory data management because they were still manually counting bags 🧳 (put simply, “guesstimating”). According to Southwest’s pilots union president, the company’s IT is a child of the 90s. And in an interview with one news outlet, another union representative for Southwest’s flight attendants actually said the following [very unnerving] phrase:

It almost became a running joke around the company that we aren’t able to make certain changes because it would involve technology.

Take it from Southwest: If you think you can get away with avoiding investing in your tech, you can’t. 🙅 And forgoing long-term digital investments to achieve short-term returns will cost you more than money. (Don’t get me wrong, though — it will cost you a lot of money 🔥 💸 🔥). You lose reputation, employee trust, potential partnerships, and ultimately, customers. We focus a lot on employees and internal elements of business, but, at the end of the day, businesses rely on customers. This is why their experience must be prioritized above costs and certainly above shareholders. Experience is the key to gaining loyal customers. So heed the moral of this unfortunate tale: Bite the bullet and invest in your tech, or Pete Buttigieg will be the least of your worries. 👹

As someone who flies quite a bit, few things have been able to pull my attention away from this story. ✈️ 👀 But let’s get back into the swing of it by covering some other, less vindicating topics.


Tech Innovation at Work

The 1:1 virtual coaching company TaskHuman 🧍has rolled out a mentorship program to complement its existing corporate coaching offerings. Just like the trends we’ve seen with in-person feedback, TaskHuman’s research has found that the infrequency of traditional coaching sessions, such as quarterly seminars, significantly reduces its impact. 📉 In combination with the agility 🐆 and accessibility of their mobile-first platform, TaskHuman lets employees connect with a team of specialized mentors, overcoming the challenges of traditional mentorships like aligning schedules and finding the right match.

In partnership with the DE&I platform Emtrain, Cisco announced its latest initiative to create better workplaces. 🧑‍⚕️👍 The company is in the early stages of rolling out a proprietary anti-discrimination and inclusive training program within their organization as well as to all global partners and suppliers. In a press release, Cisco EVP and Chief Policy & Purpose Officer Fran Katsoudas emphasized the growing role — and responsibility — of organizations both in and out of the office, saying, “We’ve seen time and time again how companies can influence behavior and society beyond just their own workplace. At Cisco, we have made a commitment to promoting and advancing social justice within and outside the company, and we know we can lean into our ecosystem of partners and suppliers to join us on this journey.” 🤝

The Changing Workplace

Many things are up in the air right now, but research from PTO solutions vendor Sorbet 🍦 is giving us very clear direction on how to support employee wellness in the new year. Amidst burnout, economic uncertainty, and the return-to-office standoff, unused PTO in the US has reached record heights. The 2022 report reveals that workers are leaving 55% of their total paid time off on the table, up from 28% since the last major survey in 2019. Though the pandemic made great strides in helping recognize and normalize the importance of work-life balance, the lingering fear of a recession and layoffs may be keeping employees at their desks. 😰 I think post-holiday is the perfect time to reinforce positive messaging about PTO. Take advantage of your team feeling recharged from holiday breaks to drive home how beneficial time away from work can be, and open the conversation up for questions about PTO policies. 🏖️ Check out Sorbet’s full survey here.


And finally, I invite you all to take a look at this article from ADP about the common causes of DE&I fatigue. 🥱 With the start of every new year comes inherent, renewed motivation, making it the perfect time to revitalize projects that may have lost steam. 🚂 Set aside time to review your DE&I program’s engagement and ensure all messaging and policies align with the best practices for long-term, healthy initiatives.

Editor’s Picks

Patrick Donegan Chief Strategy Officer

Patrick Donegan

Chief Strategy Officer

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