EP003: Tech Communication Culture: Hits & Misses

Today’s episode attempts to decrypt the ins and outs of good communication. Tony and Ron are joined by industry veteran Jose Caballer whose knowledge and skill in both team leadership as well as interpersonal one-on-one communication have given him a pretty good perspective on how communication tools and practices have evolved in the tech industry.

 

Tune in for serious insight on how Agile can streamline and improve remote team management, how to address difficult conversations, and what the future of communication looks like.

 

Key Takeaways

 

[:09] Tony introduces today’s guest, Jose Caballer, a 20-year veteran in the tech space who took a front-row seat in the .com boom. In 2012, he started The Skool, an online education startup that helped teach designers, developers, and marketers how to align their vision and goals to collaborate with less friction, and in 2017, he licensed the Skool to The Futur and left to continue his journey.

 

Clashing communication styles [2:52] Jose shares the story of a boss who yelled. They’re still friends today: it’s a communication thing.

 

Changing times [6:16] Jose explains what he does today as a software designer teacher, coach, and consultant (from UI to UX to Creative Director to strategy and facilitation) and touches on how communication has changed in the past 20 years.

 

The tools, practices, and methods available to analyze and enhance communication have evolved. Jose talks about the multidisciplinary nature of teams in tech, which has made them progressively more complex. As such, communication issues have evolved and we need to be careful to take all sorts of narratives into account.

 

From verbal to remote [11:12] Jose speaks to his own experience training a remote software team that has issues with a lack of cohesion and clarity. Weaving Agile into their process enabled proper documentation as well as a higher level of detail and fidelity, which in turn interrupted their missing deadlines and misunderstood requirements issues.

 

Dear leader [16:08] Ron gives an overview of the transition from Waterfall to Agile which occurred from the mid-’90s to early 2000s — he dives into culture-driven differences in leadership styles that can go as granular as city to city (San-Francisco vs. L.A. vs. NYC).

 

Succeeding and failing together [20:00] Communication gets easier when the scope of what is being explained is made smaller through Agile. This, in conjunction with smaller groups in a team-based setting, reduces conflict over time. Jose explains how cultural differences and the type of industry may affect how easily Agile is adopted.

 

You have a meeting from 9 to 5 [24:20] Plannings, done properly, and with the right facilitator can be brilliant. Ron and Tony touch on one-on-ones which are a relatively recent standard practice addition.

 

If there’s a downside to Agile it may be the tendency to creep towards a meetings-focused culture; Tony shares a recent conversation he had with a client on the resulting 9-to-5 meetings with a bit of work sprinkled in at the very end.

 

Jose gives his thoughts on what he calls meeting hell!

 

Online collaboration [33:04] Ron shares how business apps can actually change informative communication if the right habits are put in place and if they are adopted company-wide — we’re looking at you finance people…

 

Jose talks about the impact age and gender can have on how well people take to different types of synchronous and asynchronous communication tools; he shares some professional examples of this as well as how Agile helps mitigate some of these issues.

 

High fidelity [39:25] Ron talks about the importance of network and tool fidelity in being able to receive and read social cues, as well as his hope that emojis lose their