Diversified Search Group’s Tony Leng on Post-COVID Digital Leadership

Tony Leng, MD, Lead Practitioner, & OMP, at Diversified Search Group

Covid accelerated every organization’s digital transformation processes, and there is no going back. Technology and business have become inextricably linked, and the talent war for capable digital leaders has become more intense.

Tony Leng, a Managing Director and Leader of the Digital Transformation and CIO/IT Practice at Diversified Search Group (DSG), has witnessed firsthand how successfully—or not—companies have responded to these challenges. Frequently cited as the most well-networked CIO search executive in the country, Tony helps companies upgrade their digital capacity by conducting searches for transformational digital leaders. Working for Diversified Search Group, one of the fastest-growing executive search firms and the only Forbes top-ten firm founded by a woman, Tony has placed over 100 high-level IT executives. This search experience, combined with his leadership of the Bay Area CIO Forum (comprising top CIOs) for the last 15+ years, gives him a unique insight into the technology talent landscape.

Trends in CIO/IT Executive Search

Tony identifies several key trends currently taking place:

(1) COVID-19 was an existential threat to many businesses and brought digital preparedness into sharp focus. Organizations that pivoted effectively because of the groundwork previously laid had their digital strategies and budgets accelerated in 2020. Poorly prepared ones? They rapidly discovered that they needed to replace their technology leadership.

(2) Digital technologies allowing organizations to enhance their customer/user experience have forced organizations to address their technology stack and introduce modern architectures.

Simply put: compute/cloud, store/data, presentation/ engagement—these must all be thought through, which has given rise to roles overseeing strategic architecture.

(3) Particularly crucial to the points above are data, the fuel for digital. The ingestion, quality, privacy, security, availability, and use of analytics (AL/ML) are key to driving digital transformation—and this is making the chief data officer (CDO) position increasingly vital.

(4) The cloud, data, micro-services/APIs, work from home, etc. have also increased the focus on an organization’s cyber elements, making digital security and privacy issues key agenda items at every board meeting.

(5) Digital trend acceleration is being mediated by societal shifts related to the slaying of George Floyd, which has rightfully increased the urgency of creating a more representative workforce. The United States’ lack of success in systematically addressing this over the past few decades has been exposed, and most organizations are consequently seeking technical talent that is more illustrative of the country at large.

(6) The pandemic has exacerbated the imbalance of men and women in the tech workforce: while the ratio of men and women entering the workforce is 50/50, many women quickly leave, with but a few rising to senior technical ranks. As a result, myriad organizations are increasingly implementing new strategies to provide more effective support for women in their careers, including sponsorships, mentorships, and potential-based recruiting. Equally vital are STEM initiatives being adopted across the country, which are designed to lay the groundwork for future tech talent.

The Leadership Agenda

COVID-19 has also influenced the leadership agenda, bringing about in its wake widespread acknowledgement of the need for rapid change.

(1) It has become apparent that top-down leadership, with all the bottlenecks it creates, is simply unsustainable—it cannot provide the speed necessary to be competitive.

(2) The increased digitalization of the workplace is forcing leaders to find relevant ways to empower, challenge, and build trust with staff. The leaders best equipped to do so typically nurture the following attributes: empathy, vulnerability, authenticity, and openness. It is vital for leaders to demonstrate these attributes if they are to build any kind of meaningful trust with their teams, particularly in the digitalized world brought about by the pandemic.

(3) Culture-building in particular has become more difficult. Work-from-home (WFH) technologies enabled businesses to function during the pandemic, but social capital built up over years is being eroded, and new techniques must be adopted if cultures are to remain intact. There is a “Great Resignation/Reevaluation” taking place at present (see Tony’s blog: www.tonyleng.com), and in light of the unprecedented workforce turnover and quit rates, urgent innovation is necessary to build culture in our predominantly digitally mediated times.

(4) Relatedly, many entry-level staff members are understandably feeling disenfranchised, since mentorship by osmosis and the office-based connections typically formed early in one’s career are harder to recreate digitally.

(5) One counterpoint is that productivity has typically increased during Covid, sometimes as a function of reduced travel, but also because agile teams are often autonomous and self-governing. This is typical of a Product-based (rather than a Project-based) Agile team, because of its focus and frequent interaction, and CIOs are reorganizing their departments on this basis.

(6) Combined, despite the historic relevance and scope of responsibility currently experienced by senior tech executives, the above factors are causing IT executives great stress, because they are spending lots of time with peers, direct reports, and in skip-level meetings, to ensure that they maintain contact with all relevant constituents, build culture, and that there is broad motivation across the organization. Consequently, they are working longer hours, which is resulting in increased burnout among their ranks as well. This is one reason for the “Great Resignation” at senior levels.

A Limited Talent Pool

The skyrocketing demand for tech talent has inevitably strained the talent pool. Many traditional organizations are now competing for talent with the FAANG companies (Facebook, Apple, Amazon, Netflix, Google), and this competition has yielded a number of insights:

(1) Speed is—unsurprisingly—of the essence. Traditional companies must move quickly if they are to hire good tech talent. An inability to act quickly and decisively is a clear signal that either digital initiatives are not particularly important to a company, or that the culture/environment won’t allow prospective hires to be successful even if they do join.

(2) Traditional pay bands are accompanied by a slew of problems. Particularly:

  1. Historic marketplace data employed by an HR department are out of date within six months, and the current war for talent is hot.
  2. Traditional pay bands and internal equity prevent some traditional organizations from being competitive in hiring DEI talent.
  3. A vital strategic question organizations must address is: “How important is hiring seniorlevel DEI talent to us, and what are we willing to do to make it happen?”
  4. Many CIOs are adjusting pay to reflect the market, and it looks particularly bad if someone comes to poach your talent, and only after they receive an offer do you attempt to bring them up to the market rate. You need to know the market rate and pay accordingly; otherwise, your candidates will assume you are taking advantage of them.

(3) One technique organizations are employing to access tech talent is recruiting in secondary U.S. markets or offshore. It helps ameliorate some of the aforementioned challenges, but it does increase the pressure on leaders to manage remote workforces effectively.

(4) A degree is no longer considered vital. Many traditional organizations are still fixated on bachelor’s or master’s degrees in the tech arena, but they are not as relevant in the tech disciplines as they are in other fields. Technology is advancing so quickly that the material someone covers in college is out of date within five years. Degree-related requirements are often an artificial barrier. Most CIOs are looking for curious, continuous learners—candidates must possess IQ, EQ, a thirst for knowledge, and a healthy dose of humility (which typically grows over time as a specialist understands how much there is left to learn!).

Moving Forward

Working in the executive search industry allows Tony and his colleagues to be among the first to see marketplace trends. As a result, executive search professionals find themselves uniquely positioned to guide technology leaders as they lead their organizations on their digital journeys.

Looking at 2022 and beyond, the work being done by Tony and his colleagues to cultivate new leadership for changing world will result in exceptionally prepared CIOs and other digital transformation leaders who will empower organizations to navigate the societal transformations taking place now and in the future.

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