The Four Leaders CIOs Should Collaborate with on AI-Search Experiences

Take a quick survey of how many search interfaces you have running in the organization. Count every content management system, all the customer-facing applications, and the portfolio of important SaaS tools with built-in search capabilities.

CIO, CMO, CDO, CX collaboration AI Search

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10 CXOs Share Their Powerful Leadership Lessons for Digital Trailblazers

I leave fifty transformation leadership lessons for Digital Trailblazers, my name of aspiring transformation leaders, in my new book with that title. It has ten chapters of in-the-moment stories to see how I handled blow-up moments, responded to innovation detractors, and formed diverse leadership teams. Each chapter ends with five summarized lessons, such as, “Ask for more than executive support; seek their endorsements and commitments.”

In one chapter, I asked several leaders to contribute their leadership lessons. I won’t spill the beans and tell you what chapter they’re in, but it’s one of the most important chapters in the book.

So in this post, I went back to two of these leaders and captured their insights from their recent real stories from Digital Trailblazer episodes on the Driving Digital Standup. I also have eight more from CXOs and industry leaders for you to digest.

1. Ask smarter thought-provoking questions by slowing down

“Slow down, and I mean, slow down in your head because I think we are used to running really fast, especially in technology. Fast is good. Fast can be really good. Fast is not so good when you’re using a sharp knife, and bad things can happen. So, I think we need to learn how to slow down mentally as well as in other things. And when you slow down mentally, and you have some reflection, and you don’t feel like you have to hear yourself talk, you get think time, and you’re able to ask better questions.” – Jonathan Feldman, CIO City of Asheville

2. Drive customer-driven transformations by making their lives easier

“Always focus on the customer first. How can you add value? How can you make the customer’s life easier? And that then translates into how you do things differently in your business. Our customer wants your high-quality products. They want them in a timely manner.” – Martin Davis, CIO at Mevotech

Watch Martin’s episode on the Driving Digital Standup

3. Transition to spiritual problem solving and mature past technology religion

“I think people in tech are very religious about their stacks; Zachman or they do ITIL to the nth degree. In the real world, people who are more educated, they’re less religious, and they’re more spiritual. I think the best technologists are not religious, but they’re spiritual in a tech sense. It’s more like an awakening, and you are not tied to a vendor or a stack.” – Sarbjeet Johal, Cloud Advisor to CIO and Industry Analyst/Influencer.

4. Extend your leadership skills by volunteering at nonprofit organizations

"If you’re an IT leader, a CIO, or CSO, you can get involved at the board level or as an advisory. But if you’re not, you can bring your expertise to help how they actually execute. Roll up the sleeves and show them how to use a particular technology or get involved in solutioning around technologies. There are just so many different opportunities and also an incredible opportunity to learn.” – Helen Wetherley Knight, Nonprofit CIO and Strategic Advisor.

Watch Helen’s episode on the Driving Digital Standup.

5. Encourage creativity dialogs to foster innovation

“Create an environment that fosters creativity by encouraging everyone, at any level of your organization, to bring forward new ideas. Identifying innovative ways to use technologies both internally and externally can take companies to new heights, and it’s important that employees know their value and the role they play in making that possible.” – Ciro Donalek, CTO and cofounder at Virtualitics

6. Reimagine business processes, then implement with low-code

“Market Leaders deliver superior customer experience by thinking end-to-end, reimagining their business processes, and making it simple for customers to do business with them across products, channels, journeys, systems, and brands. Market leaders are winning by investing in low-code platforms that enable them to roll out new products and services faster, adapt to the changing market needs quickly, and innovate faster.” – Anand Raman, EVP and COO at Newgen Software.

7. Build a culture of experimentation, learning, and engagement

“Digital trailblazers know that technology is rarely the barrier and that the ability to build a culture of experimentation and be curious about problems, solutions and the user experience is instrumental in bringing new products to market. These trailblazers seek to understand perspectives versus waiting to respond. Finally, they know how to involve and engage others in the ideation and decision-making process without losing control of the business decision.” – Chris Williams, Chief Operating Officer, Interaction Associates

8.Change and transformation management is a day one priority

“Start thinking about change management on day one – even before you build your data or digital products. It’s a crucial step for adoption.” – Nir Kaldero, Chief Data, Analytics, & AI Officer at Neoris

9. Align infrastructure objectives with business goals

"While executives know that digitizing their IT infrastructure can improve scalability and profitability, their attempts sometimes fall short. Why? Leadership teams often overlook crucial steps needed to ensure their digital transformation efforts add value to their business goals." – Arthur Lozinski, Co-Founder and CEO of Oomnitza

10. Understand who and how people are impacted when driving change and transformation

"If you are tasked with leading a change effort, big or small, think about the potential impacts on the people that will be affected. Machines don’t care (yet). Humans do. Make sure you are thinking about the people." – Walt Carter, Chief Digital Officer at Homestar

10+ Plan, deliver, and transform as a Digital Trailblazer

And here's one more that Walt shared after reading Digital Trailblazer.

"Isaac’s thinking on transformation, change, and leadership comes from practicing in the arena: you’ll find practical wisdom and great tools and techniques in each story he shares from the trails he blazed! He has earned my highest recommendation!" – Walt Carter

Thanks Walt!

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How SMBs Win with Agile and DevOps: Differently than Large Enterprises and Tech Companies

Tech companies often have the people and skills to fully operationalize DevOps practices (CI/CD, IaC, AIOps, etc.). They generate revenue from technology services, so there’s a strong cultural motivation for dev and ops to collaborate, while automation often has direct financial benefits. They are also less likely to struggle with legacy systems, tech debt, and outdated data centers.

Large enterprises with thousands of developers and applications are more likely to focus on scaling agile – getting multiple agile teams to follow scrum processes consistently, develop rigorous KPIs, and prioritize practices that lower team interdependencies.

But small and medium-sized businesses (SMBs) often have different agile and devops challenges and opportunities. With fewer people, they are less likely to have all the DevOps skills than a tech company or need to address the prescriptive processes associated with scaling agile. They focus more on defining agile cultures and ways of working across the org – not just in tech – and must prioritize which DevOps practices yield benefits.

What SMB problems and opportunities shape their agile and DevOps?

Dan Waddell, Chief Growth Officer of XOR Security, shares a perspective on agile in SMBs. “As a small business, we have to run our internal operations and system development with an agile mindset,” he says. “With limited resources, we have no choice but to be really smart in how we operate within our engineering lifecycle.”

And what does being really smart entail? Dan continues, “Waterfall and its linear processes just don’t work for us – we need to be able to collaborate in near real-time and make very quick decisions. We truly practice what we preach and share that ethos with our customers as we help introduce a more DevSecOps-focused approach to application development.”

Collaborating in real-time, quick decision-making, and shifting-left security practices are all key to nimble SMBs that must work efficiently and deliver frequent customer benefits.

And what about managing cloud infrastructure, especially in medium-sized businesses that might be in hybrid clouds with mission-critical apps running?

Lior Koriat, CEO of Quali, says, “It’s important that SMBs plan for scale early to better manage their infrastructure and processes. Think about the control and scalability of your DevOps processes and teams and invest in tools that will simplify developers’ access to infrastructure while helping infrastructure and operations teams manage costs, enforce governance, and establish predictability to scale their DevOps efforts intelligently.”

Enabling developers to spend more time working on customer opportunities and managing costs are two attributes I pick from Lior’s comments that should be important to most SMBs.

How can SMBs succeed with agile and DevOps

I work with many SMBs that want the culture, customer experience, employee innovation, and operational benefits of agile without the overhead of SAFe and other agile scaling frameworks. They want easy-to-implement DevOps, even if it means that some processes aren’t fully automated.

Here are some of the best practices I work with them on during my center of excellence programs:

On developing an agile way of working in SMBs:

Use scrum collaboration tools like Jira Software, follow basic scrum practices, and define responsibilities – but acknowledge that people on agile teams will likely wear several hats. For example., you might have a product owner also taking on business analyst responsibilities or have to split how a tech lead spends time across multiple teams. The scrum master is usually not a role in small organizations, and agile teammates often split those responsibilities.
Focus on agile continuous planning so that teams make better decisions around scope, sequencing, and addressing technical debt. Lightweight estimating practices are used for faster and better decision-making on MVP and priorities and less for micromanaging team velocity.
Aim for greater business leader and stakeholder participation by collaborating on vision statements, opening sprint reviews for everyone’s participation, and developing customer feedback loops to help drive priorities.

On establishing DevOps practices in SMBs:

Let the pain points dictate the priorities, and don’t follow a boilerplate best practice playbook. For example, orgs facing outages may implement observability, monitoring, or AIOps before CI/CD because they require improved reliability before increasing deployment frequency.
Automate highly repetitive tasks without committing to 100 percent automation. For example, if an app’s code changes frequently but the database structure doesn’t, it’s ok to focus CI/CD on code deployments and implement a manual and documented standard operating procedure to support database changes.
Define and prioritize your operational and cultural non-negotiables and choose specific language around the expectation and its importance. For example, a small B2C company might state, “We fix production defects first before working on new features because …” as a guiding principle connecting ops to dev priorities.

SMBs have more choices about why, what, how, and when they implement agile and devops best practices. Reach out to me with your questions.

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3 Ways Data-Driven Organizations Enable the Future of Work

Two disciplines, becoming a “data-driven organization” and enabling the “future of work” are related objectives, and excelling at one can accelerate the other.

We seek data-driven organizations where leaders use data and rely less on intuition when making decisions. We want to help all employees access data, analytics, and the tools to ask questions, discover data sources, and expose potential answers with data visualizations.

Essential digital transformation practices by Isaac Sacolick

All organizations must find ways to use data, analytics, and machine learning to strategic and competitive advantages. A report from DataStax shows that an organization-wide strategic focus on real-time data increases the likelihood of a “transformative impact” on revenue growth by 2.3 times.

The future of work means many things to different people. Improving the culture. Excelling at diversity, equity, and inclusion. Driving sustainability. Automating more repetitive tasks and accelerating innovation practices. Supporting hybrid working, collaboration, and globally dispersed teams. McKinsey shared 56 foundational skills in four categories: Cognitive, interpersonal, self-leadership, and digital, while MIT reports people in data-driven organizations are data literate and comfortable working with AI.

Enable the future of work with these five data-driven practices

In my new book, Digital Trailblazer, I share several of my stories about leading data-driven organizations, from marketing departments adopting citizen data science to nonprofit organizations investing in dataops.

So how does enabling a data-driven organization prepare them for the future of work? Here are three ways

Automate dataops, but encourage data prep

Many organizations still have departments and outsourced teams handling data operations with tasks to load data sets in manually. They run scripts, check for errors, and make manual data quality fixes.

Other organizations have automated some dataops, but the process and skills are siloed to a department, selected data sets, or embedded in one application.

And while many orgs have data prep tools, they are more often used by a select few analysts when exploring new data sets. There’s often a disconnect in operationalizing their work and taking their prep into a production process.

Creating standards and centralizing some dataops activities is a key responsibility of chief data officers, yet getting the organization onboard with their charters isn’t easy. Attack this challenge because it’s hard to be data-driven and seek data literacy when the data pipelines are a tangled mess of technical and data debt.

Centralize data catalogs, data dictionaries, and ML training data

When a waterfall fills a pristine lake three miles into the forest, is there a well-marked trail for people to find it? Once I’m at the lake, are there clearly identified steps to easily find the waterfall and climb it to its source safely?

You have lots of data sources, and maybe you’ve centralized them in a data lake, but that doesn’t mean employees know how to find usable data sets, have access to them, or understand the policies on how they can and cannot use them. That’s the role of data catalogs and why they are key platforms to enable transformation.

But data-driven organizations do more than cataloging their data sources.

Survey your CRM and count how many date, currency, category, and attribute fields people must understand before using them in their analysis. Proactive data governance practices, including creating data dictionaries and profiling data sets, help people understand data’s meaning before they apply it to their analysis and decision-making.

Lastly, organizations with many data scientists working independently in different departments recognize the cost and complexity of creating ML training data. They’ll take steps to centralize this data and make it easier for more people to link and load it into their own machine learning and analytical models.

Ban presenting data in PowerPoint, Spreadsheets, and Tools Disconnected from Data Sources

Data driven organization by StarCIO and Isaac Sacolick

In my first book, Driving Digital, I share one of my data center of excellence frameworks for getting executives on board with data-driven practices. It requires taking the PowerPoints and spreadsheets away and presenting real-time data directly from workflow tools (CRMs, ERPs) or analytics solutions (Tableau, PowerBI) at meetings. I tell the stories behind the framework in Digital Trailblazer.

The “past of work” had only a few people that could wrangle their way to meaningful data analysis, presentation, and storytelling. Today, these responsibilities must be democratized, but a Digital Trailblazer’s efforts will fall short if the executives in the room still want their insights presented as 5-course meals with creative plating that masks what goes on behind the scenes to prep and cleanse ingredients.

Several additional practices of evolving data-driven cultures help enable the future of work, and I’ll share two more ways in an upcoming episode of the Driving Digital Standup. Sign up for the monthly Driving Digital Newsletter and get an alert when it’s up.

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From Bug Fixing to Board Meetings: Easy Learnings for the Digital Trailblazer

As we're winding down till the end of summer, the beginning of the school year, and the start of the very busy Q4/budgeting season, I thought to take a break from writing.

But not learning! I hope you'll spend time this week catching up on some reading and viewing, including my latest video and my top 2022 posts (so far) that I share below.

Introducing the Digital Trailblazer Author Interview Series

For those of you reading my new book, Digital Trailblazer, find the URLs at the end of each chapter to get access to the Digital Trailblazer Community. Once you access it, you'll see checklists, templates, chapter-specific content, and access to my special events where you can continue your learning experiences.

Below is the first of a 10+ part video series of interviews conducted by StarCIO's Chief Feedback Officer and Digital Trailblazer's editor, Ginny Hamilton. You can get access to more of these videos in the Digital Trailblazer Community, and I'll slowly be releasing a subset of them on the Driving Digital Standup channel.

Each video is about 10 minutes long, and Ginny asks me some tough questions about the chapter. In chapter 1, I bring readers on the journey from bug fixing to board meetings. Here's Ginny asking me about why I started the chapter with an f-bomb, and how to prepare for your first presentation to the Board of Directors.

What’s in the Budget? 7 Investments for CIOs to Prioritize

I am getting ahead of the curve and sharing with CIO and IT leaders several priority investments they should consider for 2023.

My perspective: Many SMBs and large enterprises have invested in digital transformation for several years. Whether we’re heading for a recession or a correction, leaders must sense the shift in financial winds and refocus their digital transformation visions and roadmaps to reflect how the economy impacts their businesses and industry.

CIO Digital Transformation Budget Priorities by Isaac Sacolick

Identify your business’s digital transformation force multipliers

Digital Trailblazers will seek force multipliers in their digital transformation priorities. Investments in force multipliers have some of the following attributes:

Have the potential to impact revenue and cost savings
Improve both customer and employee experiences
Enable IT and DevOps teams to operate both smarter and faster
Deliver innovation but also enable companies to transform the culture by operating safely and more securely
Accelerate transformation by developing leaders and maturing digital practices

With these attributes in mind, I asked several technology partners to provide insights on 2023 investment priorities. I share their perspective and follow-up with why I believe the investment is a digital transformation force multiplier.

7 Priorities for CIOs

1. Leverage observability data with AIOps

“The biggest trend in AIOps right now is the companies feel they have enough observability data. For the past 10-15 years, they have acquired more tools that give them visibility across their applications, clouds, containers, and legacy environments. Most companies are arriving at a tipping point where they have so much data and don’t look to generate more. They look for tools that allow them to turn that data into something that’s actually actionable and insightful. And we see that a lot of the center of gravity AIOps technologies is moving towards the kind of data analysis, data insight.” – Elik Eizenberg, co-founder and CTO of BigPanda

* Why AIOps is a force multiplier: AIOps enables IT Ops to support more apps running in hybrid clouds, more frequent deployments, and improve customer and employee experiences.

2. Establish and enrich customer data and analytics

“As companies face the reality of an economic downturn, team leaders will be tasked with doing more with less. While this will be challenging, economic circumstances like this can also provide clarity on which priorities CIOs should be focusing on. Improving operational efficiency is, of course, top of mind for many, but maximizing customer data should also be near the top of the list. In short, creating connected customer experiences should be a top priority for every organization. Having the tech framework in place to break down data silos and give teams a holistic customer 360 that will allow them to market with truly personalized messaging will be the difference between companies thriving or just surviving in today’s economic climate.” - Kazuki Ohta, co-founder & CEO of TreasureData

* Why a CDP is a force multiplier: CDPs establish a centralized view of a customer, their interests, and activities. Product management and DevOps teams use CDPs to improve customer experiences, and they also simplify work for marketers, customer support, and compliance functions.

3. Improve customer and employee collaboration with AI-enabled search

“Employees feel stifled and frustrated as they struggle to track down mission-critical information in today’s increasingly complex hybrid workplace. Intelligent search makes all company knowledge findable from anywhere and delivers a more empowering and rewarding experience by tailoring it to each person’s unique needs at any given moment.” - Nicolas Bordeleau, vice president of products at Coveo

* Why intelligent search is a force multiplier: Retail, ecommerce, and subscription-based media sites can see increased revenue from intelligent search capabilities, and all companies can improve customer support functions and employee productivity.

4. Enhance hybrid working capabilities

“CIOs should prioritize budgeting for tools that make their post-Covid workplace model work. If you choose a hybrid strategy, with different people coming into the office on different days and using different desks, they need the ability not only to book desks but also to have visibility into who’s meeting where and when, so they can connect with teammates. And they need advanced collaboration tools to tie in with remote staff. Periodic analysis of how workplaces are being used is also key for space optimization, real estate needs assessment, and overall post-covid strategy tracking and adjustment.” - Nadir Ali, CEO of Inpixon

* Why hybrid work is a force multiplier: Improving hybrid work is not a single technology or investment but represents a new way of working for many organizations. What worked through accelerated rollouts to support remote work during the pandemic now needs a more thought-out strategy for improving collaboration, including driving more departments to support multidisciplinary teams and agile ways of working.

5. Deliver and manage more ML in production

“Ensure you have enough budget to fully deploy and scale those models in production – including the budget for cloud consumption, MLOps capabilities, support and maintenance, and change management with the business (change in processes required for adoption).” - Nir Kaldero, chief data, analytics, & AI officer at Neoris

* Why MLOps and Modelops are force multipliers: Many organizations invest in ML but struggle to push models to production and realize the benefits. Organizations can support smarter and faster deployments by adopting MLOps (for data scientists) and ModelOps (for model governance) and establishing a full ML model lifecycle.

6. Increase data security, dataops, and data governance programs

“In 2023, network and data security will continue to be top budget priorities for every CIO, especially as the explosion of VPN usage opens new threat vectors. IP address intelligence data provides the context security teams need to mitigate risks, such as identifying whether inbound or outbound traffic is tied to a VPN, proxy, or a darknet, whether it’s residential or commercial traffic, as well as the VPN provider’s name and URL. CIOs will invest in and prioritize access to IP address insights so that they can gain context around a break in and set proactive rules as to who can access a network, who should be flagged for additional authentication, and who should be blocked automatically.” - Jonathan Tomek, VP of research and development, Digital Element

* Why data management tech and practices are force multipliers: While many CIOs, CDOs, and chief data scientists focus on delivering data visualizations, machine learning models, citizen data science, and other analytics, there’s been a lag in corresponding investments in data security, dataops, and proactive data governance.

7. Invest in your people and talent development

“It’s less about the technologies but more on the talent and people side. It would help if you were ready to acquire or develop talents such as gaming engineers, VR/AR designers, and data engineers. These key profiles will help you create, power, and grow your metaverse presence for your company.” - Nir Kaldero, chief data, analytics, & AI officer at Neoris

* Why investing in talent development is a force multiplier: You don’t realize the benefits of digital transformation investments without a successful transformation to new business models, improved customer experiences, and leveraging data/analytics to strategic advantages. As I share in Chapter 10 of my book, Digital Trailblazer, getting early adopters onboard is relatively easy compared to middle-late adopters and detractors. Establishing a learning culture and developing centers of excellence are the keys to transforming the culture.

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3 Ways to Develop Meaningful Relationships with Business Stakeholders

You have a big idea - maybe for a customer-facing application that will drive revenue, an analytics dashboard to help operations reduce quality issues, or a marketing campaign that may attract new prospects. Right now, it's just an idea, but you want to invest a few hours per week researching and planning a business case. What should you do?

You have three options: (1) Do nothing - and maybe regret it later, (2) Plan the project on your own (i.e., a skunkworks project), or (3) find one or a few executives to partner with on the vision and planning.

I prefer and advise Digital Trailblazers to open door #3. I'd rather get a partner onboard, even though that often requires stepping out of your comfort zone. If you read or listen to my new book, Digital Trailblazer, you'll see that taking on this challenge is critical, even though you probably would rather jump right into planning and implementing.

No relationship with a key business stakeholder?

Many of us, including me, are introverts. The idea of approaching someone you don't know can be super intimidating. So, if you need to connect with an executive or key business stakeholder and don't have a preexisting relationship with them, that can feel like an insurmountable barrier.

Some will give up without trying and go to door #2, but this is often a mistake. You might invest a lot of time researching and planning a dead-end program. And if you believe you have a unicorn idea, well, then you're back to opening door #3 and needing stakeholders and sponsors. Why not get them involved from day one?

The real hurdle is approaching a business stakeholder, knowing that you don't have all the background knowledge, business context, and a solidified idea.

So let me help you fix this in two steps: first, developing a new relationship with a business stakeholder and then transitioning it into a meaningful relationship.

12 steps to create a new relationship with a business stakeholder

I recorded my very simple, 12-step plan in episode 52 of the Driving Digital Standup that you can watch in under ten minutes. Watch it below, and I hope you'll subscribe to the channel. Then, please scroll below it for three more steps on going from a new relationship to a meaningful one.

Transition from new to meaningful business relationship

In the video, I recommend going through the 12-step plan at least three times before conceptualizing the following ongoing practices. You'll develop a solid relationship if you do these three activities consistently.

1. Prepare to give a lot before asking for anything in return

The best salespeople I know give, give some more, and continue giving. They don't ask for much and often don't have to because they prioritize building relationships with buyers and decision-makers that will most likely ask them for assistance.

At your business, you're not selling in the same way as a vendor. You'll likely have to ask for sponsorship, investment, and partnership, but if you play your cards right, it won't feel like you're asking. It will feel more like a discussion and an agreement to work on something together as a partner.

So, give continuously. Provide feedback, data, and insights. Share opinions.

2. Break bread whenever possible - travel together if it's an option

Chapter 6 of Digital Trailblazer starts with my flight to India with Eleanor, an executive at my company. We were heading there to meet technology companies, but part of my objective was to forge a partnering relationship with her on several objectives. Today, Eleanor is a mentor and a good friend.

We started working together long before that trip to India, but our relationship truly developed through our regular breakfast meetings.

Breaking bread is a key step to developing a personal relationship.

3. Guide them on options and let them decide

Digital Trailblazers should consider themselves as innovation and transformation guides. Learn the customer value proposition and market needs. Understand opportunities and pain points. Recommend solutions.

But want a meaningful relationship with the business stakeholder or key decision maker? Give them options, and let them decide a course of action.

Are you ready for door #3? I would be glad to answer your questions.

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