From Keynotes to Confident Aha Moments: Three Questions to Discover Your Agile Principles

This story follows the style and writing from my book, Digital Trailblazer. If you enjoyed reading this post, you’ll love the book.

I am close to completing my keynote at ETx Canada, a conference for Canadian CIOs, CISOs, and DigitalTrailblazers, and developed in partnership with the CIO Association of Canada. We’re in Kelowna, British Columbia, about a five-hour drive from Vancouver, but only a short distance to wineries, lakefront views, dozens of hiking trails, and challenging ski slopes. My kind of place.

Digital Trailblazers at nGage ETx Canada

The attendees prefer to keep their distance and sit at the back tables away from the stage. It’s a safe play because, should I bore them, they can shift their attention to their phones without guilt. So I speak from the floor, with lights blinding my vision, but with some more room to maneuver. Making eye contact and seeing the attendees’ reactions is hard, and I can’t glance at my slides to keep track of my storyline.

I feel like I am floating in the clouds without a compass and think to myself, “Are they having aha moments to my key message on why organizations need Digital Trailblazers?”

I finish the talk, there are no questions, and I wonder how well the audience absorbed my stories and lessons.

How I connect with audiences and silence my inner voice

Higher Gear CIOs
Higher Gear CIOs

It is my third presentation in three weeks. Two weeks ago, I was in Alpharetta, Georgia, at a dinner sponsored by PrivOps, speaking to Higher Gear CIOs – a great group of super-smart leaders asking me questions about becoming a data-driven organization. And last week, I spoke, and Vinny interviewed me at the Fairfield Westchester SIM chapter’s monthly dinner meeting. Thanks to Michael Voellinger of Yates Ltd for sponsoring copies of Digital Trailblazer for SIM members, and I was thrilled when Joe came up to me after my talk saying, "You killed it." I only got to eat after my talk, sitting across from Juanita, a brave marketing trailblazer in the company of mostly men technologist executives. Earlier that day, she asked me a key question about CTOs and CIO responsibilities, so I was totally prepared when one of the highly experienced leaders in the group asked me the same question at the end of my presentation.

I felt great at both events and believe my audiences totally got my message on how Digital Trailblazers grab leadership roles, drive proactive data governance, deliver impacting innovations, and empower people on agile ways of working.

Isaac at FWSIM

But this time, I’m not sure if the messages stuck. Still jetlagged, tired from a long day, and feeling like my timing was off. Cursing myself inside for only having a single espresso and not a double before the keynote. I should have killed one more slide and told longer versions of fewer stories. I can see Ginny Holden, who advised me on the keynote, nodding her head and saying to me, “I told you so.”

I only have a few moments for this quick retrospective. Those feelings are looming in my mind, but I have to get my shit together because I go straight from leading the keynote to moderating a panel of Allstars. Kevin Magee, Microsoft’s Canadian CISO, and Denis Gaudreault, Intel’s Canadian country manager, lead their own keynotes and are on my panel. Everyone wants to hear what these executives have to say, and I want to draw out a meaty conversation.

Innovation and security – how can CIOs deliver on both prime directives? What should CISOs say to their boards who don’t know the right questions to ask? How is Intel changing the culture from “Intel Inside” – expanding from one primary product Pentium line to competing with AI chips, delivering massive-scale IoT capabilities, and addressing supply chain challenges?

My panelists don’t disappoint, and Phil, the CEO of nGage Events, gives me a thumbs up as we leave the stage.

Define principles by debating questions that expose tradeoffs

And now I’m looking for feedback, but there isn’t time. We’re going to round table discussions, and I’m leading the one on agile innovation. I have a full table of leaders from big banks, consulting powerhouses, small manufacturers, and others. They’re here to vent, learn from their peers, and ask me the tough questions.

We cover some real zingers.

1.      How do we incorporate security into agile?

Innovation vs Security and Compliance

The question bothers one security and risk leader because his organization is spending time and money standardizing agile practices across many DevOps teams, but he’s not seeing a security “shift-left” mindset. Yes, there are standards, but they are facilitated by an expert who must be consulted before the dev team starts their implementation.

I have a solution for that challenge. He wants some support answering, “How can security experts create guidelines, fewer guardrails, and very rare speed bumps so that DevOps teams build security using design principles and not by expert-in-the-middle directives?”

And this isn’t just a security challenge. Anytime subject matter experts must influence developers on best practices, there are questions on how to help agile teams become more self-sufficient by knowing, creating, and following the applicable non-functional acceptance criteria. UX specialists, data governance, architects, and IT operators all face the same challenge.

But before I can provide guidance, we veer to another question.

2.      How can a small team of about twenty experience the benefits of agile without the rigor?

That’s a softball question the size of a beachball, and I’m ready to pound it. It’s an interesting contrast to the first question. Our first question is from teams who need standards but not doctrines, and this smaller team needs agile principles, not rigorous practices. I hope neither of them is trying to be safe and attempt “scaling agile” because those agile release train tracks are too rigid for their goals.

“We call it iterative, not agile. No need for us to use jargon that requires explanation.”

I’m applauding in my mind. Fireworks and happy dances. I respond, “Yes, that’s the right idea. Use the best practices to develop an approach that works in your organization. Someone needs to prioritize the work based on business value, but maybe you don’t want to call them product owners. Some organizations have scrum masters, others will use a modernized name for these responsibilities, like ‘scrum facilitator,’ and others will find ways to operate without this role by assigning the responsibilities to others. Is that agile?”

Yes, it is. If it’s delivering results and impacts. If the team improves through retrospectives and when teams demo results to enable faster feedback cycles.

3.      How do we become agile organizations when everyone has a different vision of what it means to be agile and how to practice it?

I love this question, but I have to be careful not to go on the soapbox and try to deliver a long monologue. It’s the end of the day, everyone’s tired, and some of my colleagues have beers in front of them. WTF, where’s mine?

StarCIO Agile Way of Working

You see, fifteen years ago, bringing agile from startups to enterprises was challenging but not complex. We had technologists who came from waterfall project plans or dev shops with no practices. Scrum was empowering, and having a collaborative discussion using stickies, notecards, and whiteboards as the primary tools were far better than bogus Gantt charts without the magic wands to make things happen on time, on budget, and on scope.

Today, it’s complex because everyone coming to an org has seen and practiced some form of agile. It’s a SAFe, Spotify, LeSS cocktail of agile driven by the loudest voices. Now I am all for fusion cuisines when a master chef is leading the innovation, but I’m less of a fan of throwing several ingredients in a pot to see what works. Not when my business is counting on impacting outcomes, and agile is a means to deliver them, not the primary objective.

I let my colleagues discuss this challenge and end the roundtable with a simple comment. “Your organizations are all different. You should learn from experts, but you’ll want to empower your guides, your Digital Trailblazers, to figure out your agile way of working.”

Oh, I did get the feedback I was seeking, and people loved the keynote.

Not to leave you hanging – so in Episode 58 of the Driving Digital Standup, I provide more and more answers to these three questions and formulate your organization’s agile principles. You can watch it below, and I hope you’ll subscribe to the channel


  1. Isaac, my friend, 'you killed it" again. I love your writing style and always enjoy reading (and re-reading) your columns. Never doubt your ability to read the audience, field their questions and always leave them with valuable lessons and insights drawn from your writings -- even the timid ones way in the back of the room.

  2. Great Blog - enjoyed it! Thank you Isaac for being our featured speaker at the FWSIM event. Joe is correct - YOU NAILED IT!


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About Isaac Sacolick

Isaac Sacolick is President of StarCIO, a technology leadership company that guides organizations on building digital transformation core competencies. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld,, his blog Social, Agile, and Transformation, and other sites. You can find him sharing new insights @NYIke on Twitter, his Driving Digital Standup YouTube channel, or during the Coffee with Digital Trailblazers.