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Top insights from 150 engineering leaders: challenges, solutions, and learnings

Top insights from 150 engineering leaders: challenges, solutions, and learnings
Photo by Markus Spiske / Unsplash

Over the past year, I had the privilege of interviewing 150 engineering leaders from various tech companies. I then derived insights from their answers by using Kypso.

These are the top challenges and solutions that were surfaced:

Communicating is DIFFICULT

Language barriers, framing conversations, and multicultural communication are tough for almost everyone.


1. Creative communication: encouraging team members to repeat tasks or provide feedback in their own words.
2. Being aware: understanding that words can be interpreted differently by different people is crucial.
3. Using frameworks: implementing communication frameworks, such as the C4 model reported enhanced communication by encouraging clear and concise documentation of ideas and designs.

Cross-team collaboration

Coordinating projects, recognizing the work of other teams, and unblocking tasks pose significant challenges for engineering teams.


1. Meetings, meetings, meetings: regular sync meetings to allow team members to catch up on project updates, align efforts, and address any potential roadblocks or dependencies efficiently.
2. Task forces: establishing cross-functional task forces to tackle specific challenges or address critical issues.
3. Champions: empowering people within each team who act as advocates for specific ideas.

Lack of visibility

The leaders’ job is to optimize performance, and many of them struggle to gain knowledge on their teams’ work.


1. Manual work: enforcing teams to report status manually.
2. Meetings, again…: sync meetings and 1:1s to gain deeper understanding of the work that is done.
3. Tools: using tools that provide performance metrics, eg. PR metrics.

Knowledge management

Issues such as lack of clear processes, tracking decisions, organizing knowledge and finding the relevant information in all the different tools.


  1. Structuring: establishing effective search capabilities and organizing information in a structured manner.
  2. Tools: many leaders now are trying out new tools in this domain: chatbots for knowledge bases, AI enterprise search and more.

(A word on how I got these interviews: Some of the interviews were warm connections, but mostly I did cold reaches on LinkedIn. I then summarized each interview in Notion and ran Kypso)