A couple of weeks ago, I celebrated my
1,000th blog post, an achievement I am just as proud of as publishing my two books,
Driving Digital and
Digital Trailblazer.
In the post, I shared three time-tested lessons for digital trailblazers and
thanked many contributors to my weekly
Coffee with Digital Trailblazers.
“Look at your company as if it were your first day on the job. What would your first impressions be of how your business is operating?”
That’s my opening statement to Chapter 1 of Driving Digital, which is just as relevant to CIOs and IT leaders when considering a technology department’s performance. I read this statement to kick off a recent Coffee with Digital Trailblazers, where we discussed IT turnarounds, telltale signs of underperforming departments, and the tactics Digital Trailblazers take to turn them around.
I love this time of year in the United States when we have a brief pause from our complex lives and get the chance to break bread with family and friends. Thanksgiving means a lot more for me this year, but I will have to leave the story on why for another time.
Long-time fans of my blog will remember some of my other Thanksgiving posts
– two of the 1,000 articles I just celebrated. (See the
1000’th post here).
Today’s post, my 1,000th published article, marks an achievement I am tremendously proud of and excited to share.
Here’s the funny story of how I started writing. My journey into blogging
and speaking began 18 years ago when someone told me, “Isaac, great social
networking site, but it needs to plug into the blogosphere.” All I heard was
“blog,” so I wrote my first post on
application logging.
When you meet Joe Puglisi, see him moderating a panel on stage, or participate in his SIM members in transition calls, you instantly know he’s someone you can learn a lot from.
Joe was one of several key contributors to a recent
Coffee with Digital Trailblazers, where we discussed who the right people are to lead digital
transformation initiatives. Several of us collaborated after the episode and
identified 50 attributes of Digital Trailblazers (publishing soon) that we
organized into five competency areas. You can read more about the
Digital Trailblazer Competency Areas
and watch the video where I share
my top five Digital Trailblazer Attributes.
How should CIOs and IT leaders prepare their organizations to pursue
generative AI opportunities while mitigating risks and navigating cultural
and workforce impacts?
It’s a top-of-mind question for every CIO, especially as Boards ask about
company AI strategy, while 51% of CEOs expect their CIOs to lead the company’s AI efforts.
When interviewing for an entry-level role, would you know if you had a future Digital Trailblazer sitting before you? That was the topic at a recent Coffee with Digital Trailblazers, where we discussed how to evaluate, hire, and train entry-level employees in product management, DevOps, data science, marketing, information security, and other roles with high potential to become Digital Trailblazers.
When I was CIO at a construction industry data, analytics, and media
company, I was deeply interested in how technology and sustainability would
drive the industry’s future. Could a new smart building technology or a
green innovation lead to funding new construction that improves people’s
experiences and enables a more sustainable future?
Many agile and scrum teams want to be left alone so that they can do their work. The last thing they want is leaders looking over their shoulders and overseeing their to-do lists, even when they struggle to complete their sprint commitments. Whatever the blocks impeding their progress are, they’ll work through them, though maybe not at the pace, schedule, or quality leadership expects.
Digital transformation is hard work, from developing a strategy to leading a culture change. CIOs, CMOs, and CDOs quickly realize that executing digital transformations requires prioritizing strategic initiatives, assigning team leaders, and establishing the right balance between self-organization and developing standards.
I can’t imagine guiding large-scale digital transformations without knowledgeable and influential architects. Architects guide solutions, seek standard practices, and target building extendable and reusable platforms and services. Without architects, organizations add risk to their implementations that can delay releasing capabilities, create integration gaps, increase costs, and generate operational complexities.
I’m a strong proponent of hybrid working.
Requiring a strict in-office presence can be hard on many employees with
long commutes, family caretakers, or people with physical disabilities. The
collaboration needed by
Digital Trailblazers, especially ones leading DevOps and agile teams, is rarely achieved by
jumping from meeting room to meeting room or expecting people to develop
meaningful relationships at the water cooler.
During the pandemic years, DevOps and agile team leaders had to adjust their
collaboration practices to support remote work. I’ve previously written
about how to conduct
remote sprint reviews and retrospectives
and other tips for
hybrid work for agile and DevOps teams.
Today,
Digital Trailblazers
must be more strategic about collaboration and decide why, when, and how to
organize in-person and hybrid meetings. Executives and leadership groups
often do this through workshops and offsite meetings to bring people outside
their day-to-day responsibilities and focus on collaboration,
problem-solving, and decision-making. Digital Trailblazers, especially
DevOps and agile team leaders, should consider workshops as a critical tool
to enable hybrid work while empowering team and cross-team
collaboration.
Am I alone in this belief that in-person meetings and workshops can help
Digital Trailblazers accelerate transformation and improve collaboration
with DevOps and agile teams? I’m not!
“As with many engineering teams, in particular, many of our engineers are
hybrid or fully remote and, with that, comes a separate set of demands, so
it’s important to get the balance right on in-person meetings,” says Naggi
Asmar, chief engineering officer at
Matillion. “Ultimately, hybrid and
remote team leaders must be agile and willing to adjust their leadership
style to best fit their employees’ needs. Whether developing better
communication, improving collaboration, or being more intentional with
face-to-face time, businesses must be open to adjusting their approach to
accommodate today’s global workforce.”
Here are several reasons to schedule workshops:
“In the realm of hybrid work, mere office presence is not the same as
meaningful collaboration,” says Marko Anastasov, co-founder of
Semaphore CI/CD. “Do gatherings
reignite passion, synergy, and innovation?”
In other words, workshops can help teams raise their
emotional intelligence (EQ)
and drive creativity – two key elements needed to drive innovation, and
that’s often less effective when done on Zoom, Microsoft Teams, or through
the drudgery of in-office meetings.
There are good reasons why sales organizations schedule at least a once-a-year gathering. Digital Trailblazers should also consider yearly offsites, full-team get-togethers, and workshops aiming to align on yearly objectives.
“To build a great engineering culture, the entire team should get
together once a year for at least three days,” says Jim Gochee, CEO at
Blameless. Use this time to align
on shared goals, to educate and train, and to build connections. I’ve
successfully used this approach for over a decade.”
For medium and large enterprises, CIOs, CTOs, and CDOs should consider
gathering the entire DevOps and agile team organization to
create meaningful self-organizing standards, discuss
learning objectives, and review vision statements of
digital transformation objectives.
Grant Fritchey, product advocate at
Redgate Software, shared several
reasons you might want to schedule workshops and offsites to address common
challenges facing DevOps organizations and agile teams.
At a recent
Coffee with Digital Trailblazers, a LinkedIn audio event I host on Fridays at 11am ET, we discussed several
best practices for organizing offsites and workshops. Executing a meaningful
workshop where people walk away with deeper relationships and the group
solves key problems requires planning.
Digital Trailblazers! Join us Fridays at 11am ET for a live audio discussion on digital
transformation topics: innovation, product management, agile, DevOps,
data governance, and more!
The best well-laid plans should be open to real-time adjustments and pivots.
Below are twelve considerations:
Here’s where workshops miss the mark:
Bottom line: Big offsites and workshops are expensive and are
outliers to standard meetings. Significant good can come from them, but the
value is in the follow-ups. The to-do lists and decisions need to be folded
into the appropriate tools to ensure that short and longer-term actions
aren’t lost in emails and documents.
If you need help organizing your offsite or workshop,
let me know, and please review our
Driving Digital Workshops.
At a recent Coffee with Digital Trailblazers, a LinkedIn audio event I host on Fridays at 11am ET, we discussed the topic of driving creativity and lifelong learning. I wrote in Digital Trailblazer, “How you encourage innovation, experimentation, learning, and smart risk-taking is critical in transforming organizations,” and I was eager to learn how other transformation leaders respond to this challenge. Thanks for sharing your insights, Joanne Friedman, Emily Ricketts, John Patrick Luethe, and Ashish Parulekar.
At some point in your career, you’ll be handed the microphone and asked to deliver a presentation for a big investment. You may be a product manager looking to develop a new product offering, a data scientist seeking additional funding to experiment with large language models (LLMs), or a DevOps engineer seeking buy-in for a new AIOps platform. Whether it’s your first big pitch or you’re a veteran presenter, you know that successful investment presentations require preparation.
I am writing today’s blog post from Tucson, where I wrote the epilogue to Digital Trailblazer.
“I’m taking a different type of walk today, a hike actually, on one of the
trails winding through Saguaro National Park in Tucson, Arizona,” is how I
opened the chapter where I reflect on my journey writing the book. I took a
similar but much longer hike yesterday through Sabino Canyon.
We had an active conversation at last week’s Coffee with Digital Trailblazers on navigating the risks when experimenting with generative AIs and large language models (LLMS). My panel included Joanne Friedman, Joe Puglisi, Heather May, Tyler James Johnson, Ashish Parulekar, Roman Dumiak, and Gary Berman. They shared where gen AI provides value and what risks Digital Trailblazers must address when experimenting with them in their organizations.
