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Surviving (& Thriving) a Retail Peak Season

Updated: Jul 24, 2019




Are there any Black Friday or Cyber Monday shoppers out there?  I don't know about you, but the first released BF ad immediately increases my heart rate just thinking about all of the deals and excitement that the time of year brings. 


At Target, we spend all year preparing to ensure that this season is delightful for our guests.


And it's even more exciting from a technology perspective.  Behind the scenes, for about 72 hours straight 24/7 (rotating on call, of course), our command centers are packed with team members with a shared focus: to provide the best peak season ever!


We have these command centers across our corporate offices in Minneapolis (MN), Brooklyn Park (MN), and Bangalore (IN).  Folks from 40+ teams that all power target.com are huddled around monitors and dashboards to ensure that guests have a pain free and delightful shopping experience.


One of my teams was feeling especially proud during this time - we were the ones that built many of the 'Observability' offerings for cloud-based Target.com applications.   We coined the term 'Observability' to describe the metrics, logging, and alerting products.


Teams were able to confidently monitor their applications' performance, gather sales metrics, and even make real time decisions and watch how our guests react such as introducing new promotions.   This was all possible because teams had the tools to enable full confidence in the health of their applications.


This led to an awesome peak season.


We could walk away from this experience as a great success and start planning for next year.  But, I'm always one to overanalyze and live in the past.  I want to ensure that I am looking back at my experiences, successes, and failure and see what I can learn from them.


I enjoy reflecting on the story of how my team transitioned from overworked and drained to an accomplished team without any remorse or regret.  What were the qualities of these individuals that made us so successful?  I'll walk through each of these, including tactical learnings that you can take away as leaders starting today.



Around June, we always start taking a serious look at our .com ecosystem - this includes overnight performance tests that require live monitoring, proactive alerting, and logging to enable reactive analysis on our guests' experiences.


Pretty quickly, we started to realize that our existing 'observability' offerings weren't cutting it, and we needed more visibility to confidently monitor and analyze our environments.


Imagine driving a sports car with a broken odometer or check engine light.  It would be very unsafe to continue using the vehicle without full visibility to how it is performing.


Similarly, we did not want to go into our most important season without full confidence in how our site was performing.


We quickly formed a team [hodge podge of people] to build out new Observability offerings for cloud-based applications that power target.com.


When the team initially formed, life wasn't so rosy.  We felt like chickens running around with our heads cut off due to our lack of a cohesive vision.  It also didn't help that we had 3 different product owners rotate in and out within a couple months.


Work life balance was also sacrificed for every member of the team during this time.  We only had 4 full time Engineers covering US time zones and no offshore coverage.  As I previously mentioned, performance tests were run almost daily as we approached November.  This required team members to rotate on call which often included working all day and actively monitoring our platform during the performance runs overnight. 


Additionally, our platforms were very unstable for several weeks at a time as we powered through upgrades and enhancements feverishly to prepare for the peak season.


Lesson #1:

This leads right into my first lesson.  Fortunately, I was able to quickly articulate that the team lacked a solid vision and realized that we needed to focus some energy on defining our problem statement and vision.  Once we had this, and all team members were able to the problem statement articulate, in English, we all felt a lot more centered and focused.


Tactical takeaways from this lesson that I learned:


  • End meetings ASAP that are not making progress towards solving the problem

  • Use a binary voting system to make decisions faster.

  • Make the problem visible to all team members and partners.

  • Ask team members to articulate the problem in their own words, and how their tasks enable the solution.

  • Decrease barriers between the team, your customers, and your leaders.


Lesson #2:

It is very important that leadership comes from everywhere in an organization, regardless of titles.  From Associate Engineer to Principal Engineer - everyone has valuable, unique ideas and that is why we hired them.


As a boss, practicing techniques of servant leadership has helped me decrease the amount of hierarchy on my teams.   In my opinion, some of the best ways we can empower our team members is honestly by completing of the tasks they don't have time to, or don't enable them to grow as individuals.   


Summarizing, Servant Leadership is flipping traditional leadership upside down - instead of direct reports 'working for you', you are working for them.  This should not go as far as submitting their weekly time sheets, or scheduling their doctor appointments, but it does mean taking on tasks that will allow the Engineers to do what they love - building stuff.


I have also found it especially valuable to customize incentives based on each unique team member.  There is a great book that discusses the various forms of motivation and how to best adhere to the intrinsic and extrinsic motivators of each unique individual.


Lastly, ensure that the team is exposed to frequent commitment from leaders who care about the problem.


Tactical takeaways:

  • Watch out for hierarchy that does not serve your team - Ask your team members to watch out too.

  • Dedicate at least 50% of your time to tasks that will serve your direct reports to make their lives easier.

  • Set personal daily goals of where you want to spend your time. 

  • Take action if reality doesn’t align with your goals.

  • Use 5 minutes of your weekly 1:1s with team members to understand what drives them individually.

  • Gather everyone who cares about the outcome of your project 1x per week to express commitment, re-articulate value, and celebrate wins.

Lesson #3:

This should go without saying, but Engineers are humans.  They have their own motivations, needs, and lives outside of work.  As leaders, it is important  that we are paying attention (and taking advantage of) all of these characteristics that make them human. 


It will immensely benefit your relationship and the trust that you build with that team member.  Be respectful, listen to their perspectives, always assume positive intent, and never, ever pressure them to put work before their personal lives.  It has been proven across hundreds of studies that happy people = successful employees.


Prioritizing work over personal lives will never be sustainable.  Do not allow any of your team members to attempt this.


Tactical takeaways:

  • Spend time talking about, or (ideally) experiencing, non-work activities together as a team.

  • Measure success based on how human customers will benefit from your work

  • As a leader, listen more than you talk.

  • Encourage vacation time, personal days, etc.


If I could leave you with one message from my learnings from this experience, it would be:


Your focus as a leader is to serve your team members.  If you do that well, everything will fall into place.

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