Skilling up your dev team - 8 things to consider when skilling-up your dev team
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Slides of my DevOps Pro Europe 2025 presentation Vilnius: Most IT organizations face challenges of being underskilled or understaffed, making it difficult to find skilled developers and manage workload efficiently. This leads to risks, dependencies, and delays, particularly when critical tasks depend on a few key developers. Investing in employee development is crucial for improving performance and attracting talent, but it requires strategic planning and collaboration. Companies are aware of this, so why do they keep failing? Successful upskilling involves team autonomy, leadership buy-in, and dedicated focus. This presentation outlines eight key considerations for effective upskilling: defining clear roles, identifying needed skills, conducting gap analyses, planning for future needs, exploring diverse training methods, securing leadership support, actively monitoring progress, and embedding upskilling into HR processes. By addressing these aspects, organizations can foster technical excellence and continuous improvement.
Skilling up your dev team - 8 things to consider when skilling-up your dev team
- 1. Skilling-up your dev-team(s) Derk-Jan de Grood – May 2025
- 2. Skilling up your dev team - 8 things to consider when skilling-up your dev team Most IT organizations face challenges of being underskilled or understaffed, making it difficult to find skilled developers and manage workload efficiently. This leads to risks, dependencies, and delays, particularly when critical tasks depend on a few key developers. Investing in employee development is crucial for improving performance and attracting talent, but it requires strategic planning and collaboration. Companies are aware of this, so why do they keep failing? Successful upskilling involves team autonomy, leadership buy-in, and dedicated focus. This presentation outlines eight key considerations for effective upskilling: defining clear roles, identifying needed skills, conducting gap analyses, planning for future needs, exploring diverse training methods, securing leadership support, actively monitoring progress, and embedding upskilling into HR processes. By addressing these aspects, organizations can foster technical excellence and continuous improvement.
- 3. Derk-Jan de Grood 1971 M The Netherlands Likes Coffee Music Cinema P<NLDDE<DERKJAN<<GROOD<<<<<<<<<<<<<<<<<<<<<<<<<<<<<< NB87HGNLD<<<SCANAGILE<<<2025<<<<<<<<<<<<<<<<<<<<<<<07
- 4. Key take aways Skilling up is both important and challenging 01 Embracing development practises help to skill-up 02 Top-down and bottum-up approach is needed 03 8 key items to consider 04 Give examples of pitfalls and risk in the approach 05
- 5. Challenge One common challenge across most IT organizations is that they are either underskilled or understaffed. Finding highly skilled developers is difficult. I've worked in organizations where this issue became critical, especially when a team member left and finding a replacement took an extensive amount of time. Understaffed Under skilled New talent hard to find
- 6. Consequence for development Risks Dependencies Delays Stress
- 7. Organizations should invest in their employees to enhance their skills and make them feel challenged, thereby becoming more attractive to both new hires and current personnel.
- 8. Skilling up! The way to go?
- 9. Clear Roles
- 10. Example I am the lead developer? I thought that was you! Am I? I thought I was the chapter lead
- 11. Skills Needed and Practices to Embrace What is needed and why !
- 12. Practices? A small container of skills, knowledge and mindset needed to perform a certain task well
- 13. BIQ workshop
- 16. Practices
- 17. Trust in the business case Stakeholder involvement while setting up the roadmap Collective planning process which involves business stakeholders Confidence votes on the planning Clearness of the release success criteria Roadmap takes criteria into account: deadlines, parallel work, inter- team dependencies Mapping the release on customer journey Define business validation tests Check alignment with the strategic business plan Release aims to provide intelligence and insights Organization of tests that do not fit in a sprint Define how feedback on product quality and progress is gathered Testing as a cross- team responsibility Test strategy on epic level (high level test plan) Inter-team dependencies in the portfolio management DoR on epic level (technical) DoR on epic level (business case) Design sprints Business readiness in the planning Include capacity planning on operational level Test automation strategy How to demo and how to test? Definition of Ready (DoR) Test plan on user story level Backlog of two sprints ahead Proper refinement in the team Three-amigo peer review TDD and BDD to drive planning and user requirements Architects, security & usability experts, and users involved during refinement Risk assessment included business risks Estimate busines value and use techniques like WSJF Peer review on code and test results (registration) DoD describes the quality measures Version control is in place Focus on automation Pair work Cross team agreement on coding standard Collective ownership of the code Organise review with stakeholders Automate regression test Assess and resize test set Have version control in order Regression test strategy Making quality a cross-team responsibility The pipeline includes automated regression testing Compliancy regulations Align approach and planning Have a collective review session Automated smoke test Interface testing Service virtualization Testing is a cross- team responsibility Scrum-of-scrums to align test activities and dependencies Automate integration tests Test management Incident handling with cross-team triage Coordination of the end-to-end tests Include end-to-end test in the CI/CD pipeline Involvement of right users and stakeholders Test management with end-to-end focus Testing in production Monitor behavior in production Pilots Quality focus in the program/ interorganisational appoach Organisational readiness testing Busines validation test Testing the operational model Linking to the performance indicators Root cause analysis Error log testing Monitoring in production Automatic updating or restoring the system Monitoring user feedback (e.g. online and social media) Analyzing user behavior Prediction models (using AI for instance) 75
- 18. Trust in the business case Stakeholder involvement while setting up the roadmap Collective planning process which involves business stakeholders Confidence votes on the planning Clearness of the release success criteria Roadmap takes criteria into account: deadlines, parallel work, inter- team dependencies Mapping the release on customer journey Define business validation tests Check alignment with the strategic business plan Release aims to provide intelligence and insights Organization of tests that do not fit in a sprint Define how feedback on product quality and progress is gathered Testing as a cross- team responsibility Test strategy on epic level (high level test plan) Inter-team dependencies in the portfolio management DoR on epic level (technical) DoR on epic level (business case) Design sprints Business readiness in the planning Include capacity planning on operational level Test automation strategy How to demo and how to test? Definition of Ready (DoR) Test plan on user story level Backlog of two sprints ahead Proper refinement in the team Three-amigo peer review TDD and BDD to drive planning and user requirements Architects, security & usability experts, and users involved during refinement Risk assessment included business risks Estimate busines value and use techniques like WSJF Peer review on code and test results (registration) DoD describes the quality measures Version control is in place Focus on automation Pair work Cross team agreement on coding standard Collective ownership of the code Organise review with stakeholders Automate regression test Assess and resize test set Have version control in order Regression test strategy Making quality a cross-team responsibility The pipeline includes automated regression testing Compliancy regulations Align approach and planning Have a collective review session Automated smoke test Interface testing Service virtualization Testing is a cross- team responsibility Scrum-of-scrums to align test activities and dependencies Automate integration tests Test management Incident handling with cross-team triage Coordination of the end-to-end tests Include end-to-end test in the CI/CD pipeline Involvement of right users and stakeholders Test management with end-to-end focus Testing in production Monitor behavior in production Pilots Quality focus in the program/ interorganisational appoach Organisational readiness testing Busines validation test Testing the operational model Linking to the performance indicators Root cause analysis Error log testing Monitoring in production Automatic updating or restoring the system Monitoring user feedback (e.g. online and social media) Analyzing user behavior Prediction models (using AI for instance) 75
- 19. Boost your DevOps teams
- 20. More….PMP game
- 21. Link practices to issues
- 22. Let’s zoom in a bit…
- 23. Purpose… We no longer care for big transformations and agile humbug. No, we need better quality… many customers are complaining And we need to seriously reduce development costs.
- 25. Todays and Future Needs
- 26. Todays situation / Gap Analysis
- 27. Example
- 30. Where do you spent your time on?
- 32. The new Value framework 33 • Financial Impact • Customer Opportinutiy • Compliance • Enabler (epic) • Enabler (team/time)
- 34. Tomorrows system / Product vision
- 35. Future world / Technology trends
- 36. Insurance claim
- 38. Trends and innovation • Top down or Bottum up • Definition of innovation • How innovative do you want to be? • What if the teams like it? And of course….
- 40. What skills do we need for this?
- 43. Different Ways to Skill Up Hiring new people with new skills, knowledge or mindset
- 44. Securing Buy-In from Leadership
- 45. Yes, No or Don’t know
- 46. Embed Upskilling in the HR Cycle
- 47. How it all ties together
- 49. HR R o l e s a n d f u n c ti o n s S k i l l m a n a g e m e n t H i r e r i n g n e w p e o p l e O r g a n i s e c o m p a n y w i d e t r a i n i n g S u p p o r t o t h e r f o r m s o f k n o w l e d g e t r a n s f e r Team Set Team Goals Invest in exchange of knowledge Express team needs Brainstorm on different ways Product management T o d a y s n e e d s Tomorrow's product F u t u r e p o s s i b i l i ti e s Management & leadership Approve initiatives Skill up as management Support and facilitate Governance and reward Lead and set goals Translate trends to skill forecast
- 50. HR R o l e s a n d f u n c ti o n s S k i l l m a n a g e m e n t H i r e r i n g n e w p e o p l e P r o v i d e c o m p a n y w i d e t r a i n i n g S u p o r t o t h e r f o r m s o f k n o w l e d g e t r a n s f e r Team Set Team Goals Invest in exchange of knowledge Express needs Brainstorm on different ways Product management Todays needs Tomorrow's product Future possibilities Management & leadership Lead and set goals Approve initiatives Skill up as management Support and facilitate G o v e r n a n c e a n d r e w a r d Practices Bridge between problem and solution Make improvements smaller Track progress, prioritize and share successes
- 51. 8 Key Considerations for Upskilling Your Dev Team • Clear Roles - Defining precise roles and responsibilities. • Skills Needed and Practices to Embrace - Identifying essential skills and effective practices. • Inventory / Gap Analysis - Assessing current skills and identifying gaps. • Future Needs (Including Leadership Vision) - Planning for future requirements with insights from leadership. • Brainstorming Different Ways to Skill Up - Exploring various methods beyond traditional training. • Securing Buy-In from Leadership - Highlighting the importance of leadership support, as it requires time and financial investment. • Active Monitoring and Communication - Continuously tracking progress and communicating the urgency and successes. • Embedding Upskilling in the HR Cycle - Integrating skill development into the regular
- 52. Thank you! Derk-Jan de Grood Principal consultant and Innspirator tel: + 316 51807878 mail: derkjan.de.grood@innspire.nl web: www.innspire.nl podcast: innhetmidden.wordpress.com/ blog: djdegrood.wordpress.com linkedIn: linkedin.com/in/derkjandegrood/
- 53. Out Now (or anytime soon) ! Revised 2025 edition. Including new chapters on Value framework, clover model and a 4th wave! First 2021 edition
- 54. Further reading Built-In Quality: https://www.infoq.com/news/2021/02/agile-build-in-quality/ https://djdegrood.wordpress.com/books/the-waves-of-agile-value-delivery-in-medium-and- large-organizations/ Technnical Agile practices: https://www.agileconnection.com/article/agile-technical-practices-if-only-you-knew-them Practises make perfect game: https://djdegrood.wordpress.com/training-and-workshops/ Clover coaching model: https://djdegrood.wordpress.com/wp-content/uploads/2025/02/grood-level-up-coaching-s kills.pdf
Editor's Notes
- #5: One common challenge across most IT organizations is that they are either underskilled or understaffed. Finding highly skilled developers is difficult. I've worked in organizations where this issue became critical, especially when a team member left and finding a replacement took an extensive amount of time.
- #6: This situation introduces risks, dependencies, and delays. For instance, if all front-end development tasks pile up for a single front-end developer, or if unskilled developers take on tasks, or if the pressure to deliver overrides all efforts to improve the development process, the impact can be significant.
- #7: Organizations should invest in their employees to enhance their skills and make them feel challenged, thereby becoming more attractive to both new hires and current personnel
- #8: From my experience, successful upskilling requires autonomy within teams. Teams understand their needs best. However, buy-in and guidance from leadership are also crucial. Investing in skills requires dedicated focus and time. Simply announcing that 30% of development time can be used for improvement is not enough. More comprehensive measures are needed. This is a topic where collaboration is essential among teams, chapter leads, scrum masters, agile coaches, and transformation coaches.
- #11: Bij rtl senior dev In the team was also the chapter head of the dev-practices team.
- #44: Alternatives to Training 1. Peer Learning & Knowledge Sharing Brown bag sessions Show-and-tell Lightning talks 2. Collaborative Work Forms Pair/mob programming Mentoring or buddy systems Team rotation 3. External Inspiration Customer visits or field research Company safari (visiting other organizations) Meetups & (internal) conferences 4. Self-Study & Exploration Book clubs or reading circles Tool time or exploration days Hackathons or internal challenges 5. Reflection & Feedback Retrospectives focused on learning Postmortems / after action reviews Deliberate practice with feedback