Context, Metrics, and Motivations: 3 Tech Leadership Insights from Expedia

Joining Expedia after more than a decade in consulting jolted me into an entire new world.  While consulting generally hired recent university graduates who were molded in the ways of the firms, Expedia exposed me to colleagues with a broad range of expertise, motivations, and experiences in life and work.

I learned valuable lessons in working and leading at Expedia from transforming the internal audit team to leading the global consumer payments function.

Provide context

I was chatting with three early career software engineers in the break room - mostly small talk on what we’re working on.  I mentioned that I just left a meeting with the Expedia CFO to provide a status update on the consumer payments product roadmap and performance metrics.  ‘He cares about what we’re working on?!’ exclaimed a surprised engineer.  ‘Well, of course.  The company doesn’t make money if you don’t do your jobs.’  I responded.

At that moment, I realized that our engineers - and likely others on the business and technical teams - did not have the context for how their work fit into the Expedia ecosystem.  I believed that it was important for everyone - from the most junior team member to the executive - to have business and technical context for their work so they can make well informed decisions and flag concerns.

I started brown bag sessions for our consumer payments team providing an overview of how Expedia made money across our main products, how the payments ecosystem worked, and how their work fit into both of those contexts.  It was optional but highly encouraged - about half of the team attended.  I provided home baked cookies - that helped with attendance.

Not everyone wants to be promoted

In consulting, the career ladder was well defined and most consultants aimed to move up the career ladder.  We were ambitious, thrived on challenge, and adept at delivering in high pressure situations.

When I left consulting and joined Expedia, one of my direct reports told me that ‘not everyone wants to be promoted.’  I responded with ‘Ok.  I understand that.  But I still want you to learn, be challenged and grow in your role here.’  I reflected on his statement over time and challenged myself to provide learning opportunities while respecting their preference to stay where they are.

I still struggle with this one…while being extremely jealous of people who live very full lives outside of work.  I once worked with a woman who was a beekeeper, bellydancer, cosplay costume maker, and handloom weaver. She firmly set her boundaries to work 4 - 10 hour days so she had time for her hobbies.  I was enthralled by her!

Performance metrics may not align

‘Why is fraud bad?’ asked a product executive after I showed high fraud activity on one of our recently launched lodging products.  Fraudsters were booking hundreds of hotel rooms, and cancelling them within the 24 hour cancellation window to avoid the cancellation penalty.  Our lodging partners were screaming because they now have rooms that they are unable to sell in the limited amount of time.

I realized that performance metrics may be conflicting across the company.  This product executive was measured on gross bookings - how many hotel rooms do customers book.  So he wasn’t concerned with the negative impact on the lodging partners - hotels, bed and breakfasts, etc - that supply the rooms.  I realized that some employees - even executives - may only be focused on their individual metrics to the detriment of company objectives.

It is important to note that this product executive was a particularly challenging character.  In general, my Expedia colleagues focused on doing the right thing to achieve company objectives.

Moving from consulting to Expedia exposed me to a broader variety of people - motivations, aspirations, and past experiences - and taught me lessons that I applied in the next stage of my career.

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