The CEO’s Dilemma:

“Why, When & How To Develop Technology Fluency”

What board leaders can do to navigate the board leadership challenges and strengthen the effectiveness of the board

“A leader is best when people barely know he exists, when his work is done, his aim fulfilled, they will say, we did it ourselves” - Lao Tzu

Should the CEO play a significant role in the technology strategy of his/her organization? CEOs have enormous demands on their time. Complexity and ambiguity and uncertainty is increasing. Technology most likely plays a role in most organizations’ operations and perhaps in the strategy. The view of technology strategy for most CEOs is that it belongs to the CIO/CTO or some outsourced service provider. They (the CIOs) can present the technology strategy and the CEO will ask some questions or give them what they need but the CEO generally stays out of their way with the exception of regular updates. This is definitely one way to view the role of the CEO in crafting a technology strategy and it may work well in the short term and for a while depending on the maturity of the organization. However, in the long run, given the vital and significant role digital technology will continue to play in business strategy going forward, this view will yield poor outcomes. Why?

We believe, however, that there are relatively few (if any) organizations and businesses where technology doesn’t have a significant/material role in the long term. In our experience, most organizations rely heavily on technology as a business enabler or in some cases a business driver. However, their CEO’s experience the following dilemma/ challenges when it comes to technology fluency and its strategic benefits

the most significant challenges of board leadership fall into three main categories

Three fundamental reasons:

Reason 1: The less a CEO understands about the business implications of technology, the less he/she will keep understanding in the future. If you don’t use it, you’ll lose it; if you don’t use those neurons/muscles to gain an applied understanding of value creation using technology capabilities, you’ll lose them. Some will argue that they do use these muscles when they review the technology strategy. But we believe this is a passive vs active role and those mental muscles aren’t getting a real work out. You can watch an online workout and review how good it’ll be but without actively doing the exercises, your muscles will atrophy over time. In the long run, this weak understanding of technology will cause the CEO to view technology only as a cost-center and not a strategic value driver and the organizations results and performance will reflect this cost-center mindset. Over time, this mindset typically shows up as technical debt within the organization and trust us, that’s not where you want to be in this age of AI.

Reason 2: Culture- The less engaged the CEO is with the technology strategy, the less they’re able to galvanize the organization in support of enterprise wide culture transformations. Technology and the transformations that derive from them aren’t just about the technology themselves but they’re about a new way of thinking, being and doing in the workplace. It’s a culture shift that prioritizes agility, flexibilty and change. If the CEO is not high on technology strategy, then most likely the rest of the C-suite won’t be high on it either and this filters down to the organization and ultimately affects the culture. In our experience, if a CEO is all about how to avoid any technological change, it’ll be difficult for other C-suite execs to advocate for such changes. People debt like technical debt will result over time.

So what to do now, how does a CEO avoid change these outcomes or better still avoid them altogether.

There are three distinct practices (outlined below) that CEOs should prioritize to help them navigate these challenges. The key to maximizing the benefits from these practices is consistency (i.e. habitual process), otherwise they’ll only bear limited fruit.


Side Bar - Board Leadership Book Recommendations

Below is a list of excellent books new CEO, Phoenix Project - vigating board leadership challenges of both public and private boards. They offer practical actionable insights for board leaders and will benefit CEOs as well as aspiring board directors. 


The following three distinct principles combine to form a process that helps CEOs

board effectiveness. The central idea here is to master the process and not the outcome. If board leaders can master this process then the outcome will follow.

  1. Technology Fluent, Not Technology Expert: Most/Some CEOs may assume that they need to be technology experts to be actively involved with the development of the technology strategy. But that should not be the goal; the goal is to improving CEOs’ technology fluency. The goal is to have a good understanding of the technology capabilities and their implications for business value. The goal should not be how to deploy the technology capabilities and features. We can understand the benefits a car (or autonomous features in the car) without knowing how to build the cars or features themselves. Ironically, some “experts” can know how to build the cars (i.e. technology/features) and not know how the technology will impact the business and strategic drivers. In fact, that’s a very common complaint about most technology geeks.

  2. Strengthen CIO Relationship: The CEO-CIO relationship in many cases is not as strong as other CEO-C-suite relationships like that of the CFO or COO. Sometimes, this is because the “wrong” person (order taker, poor communication) is in the CIO role and other times it’s because the CEO does not value IT as a strategic vlaue driver. If you have the right CIO and CEO then there’s a pollination of the strategic ideas that happens when the CEO makes an intentional effort to strengthen this relationship. And it’s magic, when you get it right. The ultimate result is that the CEO can begin to appreciate IT as a strategic value driver.

  3. Culture of Technology Innovation: Galvanize the organization around the technology strategy and its benefits. A good example is the CEO as the champion of digital transformation and being very deliberate about communicating the importance of the transformation. In other cases, it’s equally crucial for the CEO to signal to other C-suite executives that technology is valued more than just a cost center and to energize the C-suite to become more tech savvy. When the CEO shy’s away from technology that can filter down to the rest of the organization.

The rest of the article provides additional details and context for each of the practices as well as advisory guides/resources (board agenda and board leadership succession) that will help board leaders get a jump start on the process.

1. Become Technology Fluent

Becoming technology fluent means more than being a user of technology products but it does not mean becoming a technology expert as noted previously. The key question is how does a CEO becoming technology fluent and it starts by first addressing the obstacles to technology fluency from the CEO’s standpoint. This is then followed by proactively adopting the practices that will sustain this tech fluency as it’s not a won and done deal but an on-going effort for as long as he or she is in the CEO role.

Obstacles: There are three main obstacles and these include:

Not-my-job Mindset: The belief that becoming more tech savvy is not the CEO’s role and should be completely delegated to the technology chief (CIO/CTO, etc.)

Time: I don’t have the time, experience or background to learn and become fluent in technology. I’ve already got too much on my plate and can’t prioritize this also. I need to focus on what only the CEO can do. Well, only the CEO can truly galvanize an organization around a digital transformation effort and/or a culture of valuing technology benefits and that requires that the CEO is fluent in technology so he/she can lead by example and walk the talk.

Not Needed / Required: I don’t need to be tech fluent or savvy to be effective. Does the CIO need to be business savvy to be effective? Maybe not but his or her effectiveness will diminish in the long run without an intentional effort to become business savvy. In a similar way, the CEO’s long term effectiveness will diminish over time if he or she does not become technology savvy especially in this digital era.

CEOs can employ a combination of practices to become more fluent in technology. These will be practiced on an on-going basis and they include:

Get access to a good internal or external resource, coach, mentor and perhaps the CIO or technology chief if the right person is in that role. By good resources we mean someone who has operating experience in the technology function; someone who understands technology and the business implications and who can communicate business value of technology using relevant analogies, stories, illustrations.

Start with 1hr a month and adjust as needed and your job is to ask questions and listen intently. If you don’t understand it, then they didn’t explain it well enough should be your guiding principle.

Before

  • Set director expectations

  • Design and build an effective agenda

  • Integrate informal events and learning - dinner before meeting day and education sessions, outside speakers, etc.

  • Board materials and board pack / pre-reads - guidelines

  • CEO / Chair sync up calls/metings

During

  • Maintain focused discussions

  • Skilled facilitation - see section on facilitate meaningful discussion

  • Executive session

  • Board dynamics and board culture - virtual/hybrid, etc.

After

  • Debrief with CEO and preserve confidentiality of executive session

  • Post meeting surveys

  • Activate follow up on actions from board meetings

CEO Role in Digital Transformation

A board meeting agenda is the flight plan for board directors. It defines the destination route, altitude and timing of decisions by prioritizing the focus areas and topics directors spend their limited time on. Effective agendas strike a delicate balance of strategic and critical operational topics. This can be a challenging task, even for seasoned board leaders. The guide below offers practical advice on creating effective board agendas

2. Strengthen CIO Relationship

The best way to strengthen that relationship is to spend “quality” time with the CIO. This action presumes that the right person is in the CIO role. This approach won’t work if the wrong person is in that role (see modern CIO qualities side bar for the definition of “right”). Ideally this time can be coupled with the time used for tech fluency to maximize the time and get leverage. However, be careful to keep this time focused on strengthening the relationship and improving tech fluency. In other words, resist the temptation to focus on putting out operational fires in technology and or CIO coaching. Your primary job is to be curious, listen, ask questions, learn and test your understanding

Bring a business strategy problem to the table (in advance) and work with the CIO to solve it together. Offer something of value to the CIO such as business strategy or industry context. And yes, seek to understand the CIO as a whole person and not just as a resource to help the organization advance its mission.

g relationships.

You can’t just say trust me and voila, you’ve inspired trust and you should expect it to be instantaneous either. Trust take time as well as effort. There are a few vital actions that board leaders can take to inspire trust:

Model the right trusting behaviors - These are behaviors that are derived from strong genuine character and competencies. The principal trusting behavior is genuine care for others (i.e. the CEO, peer directors, management liaison). Caring about them as people instead of just employees that have been hired to do a “job”. Intent matters, not just how do I get the most of out them but how do I help them become the best that they want to be or could be. It’s a mindset that values the interests of others above ourselves and it is by far the most effective way to inspire trust. Other values that drive trusting behaviors include integrity, consistency and humility. Board leaders have to create the opportunity to model these values and behaviors in interactions with the CEO, peer directors and select management liaisons.

CEO-Board Chair Relationship

This may seem obvious to some but we have found that there are several instances when this relationship is neglected or ignored and where it’s barely cordial or even tense/dysfunctional for several reasons. For example, lead independent director and CEO have a negative history, activist-elected lead independent director, CEO perceptions about adequate understanding of the business. The point here is if intentional steps aren’t taken to build, re-build and sustain mutual trust and respect, the CEO-Chair relationship will become tenuous and will make board meeting very ineffective and not definitely not positive.

Actions To Consider - Board Chair

  • Schedule one-on-one time with the CEO on a regular basis and preferably in person. This is a high-leverage action

  • Humbly acknowledge the CEO’s role and magnitude of the weight on his/her shoulders

  • Find common ground and interests in and out of the boardroom

  • Engage in regular touch points between board meetings. The CEO should also take the initiate in scheduling these touch points

  • Ask for feedback

  • Lift them up

  • Seek ways to provide meaningful value to the CEO in and out of the boardroom

  • Genuinely care about the well being of the CEO and not just as the leader of the organization

Now rinse and repeat the same principles and approach for cultivating board peer and select management relationships. There are a few important nuances that you should keep in mind though; especially for the management relationships. Keep CEO apprised of touch points with his executive team.

3. Cultivate A Tech Savvy Culture

The other prvious two practices serve as a good foundation for this one. Once the CEO is tech fluent and has strong CIO relationship, then it’s time to galvanize the organization around technology and it’s benefits. Two practical ways to accomplish this are:

Share your efforts and commitment in becoming more tech fluent and why. Encourage other C-suite leaders to do the same

Business Technology Retreat: Host a tech retreat for the business functions and leaders that will benefit from enhanced technology understanding and business implications. The focus is not on users that are technologically challenged but business leaders that will benefit from integrating technology capabilities in their business functions if they had a better understanding

Appreciate, recognize and reinforce the tech savvy culture behaviors as often as you can

Serve As A Mentor: There are two ways board leaders can serve as mentors; first is to invest time/effort in the CEO’s personal and professional growth. This signals a commitment to see the continued success of the CEO and the organization. Board leaders should still leverage questions (not directives) mostly in this role, although there may be cases where explicit guidance yields a better outcome. The second is to mentor potential board leaders either through formal programs or informal arrangements. Board leaders should nurture and mentor new board leadership talent and develop a board leadership succession plan and pipeline that’s reviewed on a regular basis.

The end goal is to bring out the best in the CEO, management and peer directors. An effective chair will seek to continue to elevate the capabilities of these individuals in very tangible and specific ways. He or she will model the character traits and behaviors they’re trying develop in the boardroom in service of elevating the effectiveness of the board. They will not try to run the organization or be the CEO but instead provide proactive and wise counsel as needed. Other times they will be a listening ear and listen deeply to what is and what is not being said. Great care must be taken by the board chair or LID to preserve their independence and objectivity because the more time they spend with the CEO and other peer directors, the greater the chances their independence/objectivity becomes influenced


CEO Advisory Guide: Modern CIO Success Attributes

When defining CIO role expectations, CEOs tend to prioritize technology competency over other critical success attributes such as change leadership and strategic agility

The typical outcome when this happens is that IT strategy projects either stall or fail to achieve the desired objectives. This advisory guide helps CEOs with the prioritization effort of the modern CIO role


Advisory Note For CIOs

It bears repeating, excellent executive communication is a critical skill worth developing because it significantly influences your effectiveness. We have seen poor communication skills limit and derail the careers of otherwise talented CIOs. This applies to most technology executives that have engineering backgrounds. Please invest the time/resources required to work your communication muscle on a regular basis, it’ll have a high payoff for you.

There are two habits that will enhance your executive communication skills, especially when you have to present to the board or business leaders.

  1. Ask how you want the audience to feel? Not what you want them to know or what you think they want to hear but how you want them to feel. For example, do you want them to walk away feeling excited, like wow! or informed. Do you want them to enthusiastic about what your technology strategy will deliver? This will help you focus on the business benefits instead of technology features and will greatly enhance your effectiveness.

  2. Practice the narrative that’ll create the intended feeling/outcome. This typically involves using a simple analogy or story that is relatable and relevant to the topic. The key here is to keep practicing this skill of translating your topics using simple tools like these. It takes practice but it is absolutely doable and we encourage you to continue working at it.

CEO Leadership Moment

In our experience, there are many CEOs who believe that their role in the technology function is limited and therefore do not make the effort to become fluent in the language of technology. Some even proudly proclaim that they don’t need to be fluent in technology because they have a great CIO and a great technology team. It may be true in the past and in some current/existing cases that CEOs may not need to have some sort of basic fluency in technology. However, from now and into the foreseeable future, CEOs will need to raise their game and become fluent (not expert) in technology. Otherwise they’ll risk missing new value-creation opportunities and possibilities that the CIO may miss given his/her limited view of the entire enterprise. Digital technology is one of the most important growth engines for organizations. Don’t miss your leadership moment to galvanize the organization around this growth engine to create value for your stakeholders

Let’s Create Value Together

As iron sharpens iron, so one person sharpens another Proverbs 27:17