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 unprofessional image since their function is to quickly and easily lend context to otherwise emotionless text.

 

Difficult conversations [44:20] Tony offers that the multitude of communication tools, practical as they may be, can facilitate the avoidance of difficult discussions.

 

Ron shares the ideas behind his belief that nothing can replace a face-to-face when it comes to difficult conversations, from clarity to liability.

 

Jose opens up about his own challenges with tackling difficult conversations and the feedback he gathers in order to improve. He also touches on the importance of driving communication and touching base with your people if you feel a lack of clarity.

 

Put your rational hat on [50:00] “At work — as hard as a conversation may seem — the stakes probably aren’t as high as you think they are.” Ron explains how he grew into the man that runs towards the difficult conversations — and is assigned more of them lately.

 

He also opens up about the fear still present when it comes to hard conversations in his personal life — for him, the emotional stakes are much higher and the outcome more difficult to predict.

 

Jose shares the tips and tricks that have helped him be braver about difficult personal conversations: “Who am I being if I don’t have this conversation?”

 

Tony shares his own take on hard personal conversations being less challenging for him than professional ones “It seems highly unlikely that I will *eff up 20 years of relationship with one conversation.”

 

The future and the speed of communication [1:00:44] The compression from complex abstract thought to language is currently only as fast as each person’s processing power and available vocabulary library, and that is currently the speed limit of communication in general.

 

Speaking, reading, and writing also force a speed synchronization, which the future, with its promise of unfiltered thought should seriously explode (see Neuralink).

 

Clear and efficient communication is difficult in its own right. It can and should be trained like any other skill and it begins with your own mind; Agile can help.

 

Thanks for tuning in.

 

Mentioned in this episode

Hipchat

Slack

Discord

Zoom

Google Apps Suite

 

More about our guest

 

Twitter: Twitter.com/josecaballer

Facebook: Facebook.com/josecaballer

Website: Josecaballer.co/about

 

More about your hosts

Podcast: tonywongpodcast.com

Agile Coaching: Agiletony.com

Executive Coaching: Agiletony.com/mental-and-emotional-agility

Twitter: Twitter.com/agile_tony

LinkedIn: Linkedin.com/in/tonywongdigitalonion

Youtube: Youtube.com/channel/UCJyT0C_nrzAZ9GhmOXaSRRw

 

Co-host Ron Williams on LinkedIn: Linkedin.com/in/ronwilliams