Digital leadership and the search for critical hires 

This blog was originally published in March 2021 and has been updated for stats and relevancy.

Every year, new developments in the digital world emerge that prompt workplace transformation. The unparalleled urgency for technology advancement during the COVID-19 pandemic tested the ability of organizations to adapt faster than ever before. Even in a post-pandemic world, digital transformation is still equally as important. Companies that prioritize digital transformation will grow and thrive while those that don't, will struggle to survive. 

Now that remote and hybrid work has become the new normal, keeping up with technology is crucial. Over the last two years, big data leaders in the C-Suite have played critical roles in decision-making along with key tech hires. These positions, ranging from data scientists to cybersecurity leaders, drive innovation and are heavily relied upon to influence executive-level agenda items and roadmaps. This ensures that continued timely transformation occurs. As such, it is imperative that leaders hire the right talent to expand the executive team.

What makes a good digital leader? 

Digital leaders plan and implement new technology to advance an organization’s overall values and goals. This requires a great deal of business acumen and the ability to measure business impact – including the financials, operations and active work needed to implement long-term solutions. The mindset “on time, on budget” is critical for a digital leader to create positive ripples in their respective industry.  

How this translates across upper management varies greatly. As an example, for a chief data officer, translating data into business action is vital. Tech teams are often hyper-analytical and challenged to actively take steps with data that’s been accrued. For a chief information security officer, the ability to protect and then navigate and resolve data breaches effectively paints the picture of a good data leader.

While the definition of a digital leader may vary by industry or by organization, this statement still holds true: finding someone with a passion for innovation is key.

Prioritizing digital leadership in your executive search efforts will make a grand statement about your company's aspirations and inevitably help steer your company in a positive direction. 

Finding a great digital leader may feel elusive if you haven’t done your due diligence around readiness. Evaluate readiness around the current state of your tech stack and allocate timelines before rushing to hire someone to fill the role. If you’re not prepared for the future, rallying support and staying within budget will be difficult. This ensures a realistic progression around shifting market spend so your end-goal tech has long-term viability.  

How to find critical hires to support digital leadership 

Understand their motivations 

To truly understand what attracts senior leaders to an organization, it’s important to know what motivates them first. Identifying their pockets of appetite and current career goals will help you compare their interests against your company objectives. For example, if a tech leader has already migrated two organizations to Workday or Amazon Web Services (AWS), they may want to do something different now to diversify their repertoire. If that’s your major wishlist item but you’re not ready to deliver on a promise of different requests after migration, your digital leader might not stick around (or come onboard at all).  You can remedy this by providing clarity around what they’re being hired to tackle and how it's going to impact the organization over time. 

Consider asking your prospective digital leader questions like: 

• How have you measured business impact in the past?
• What active work do you do to implement initiatives? 
• If you could do a project again, what would you do differently and why?  
• What are you looking to accomplish during the first six to twelve months on the job? 

Guarantee internal support 

One person can rarely turn the tide in an organization. With tech positions in particular, the lack of a budget and companywide buy-in can hamper digital transformation efforts. Being sold a dream but inheriting a nightmare can be problematic. See promises through with action; that comes with support.  

Leadership support from other C-Suite executives shows the intention to align and contextualizes why hires and upgrades are happening within an organization. This includes budgets and any other necessary resources that will be needed during a digital transformation. A strategic leader simply articulates the business reason but additional support from other executives is critical if an organization wants to thrive.  

Consider temporary C-Suite positions 

The power of temporary positions has made itself known across all workforces in recent years, and leadership positions are no exception. The hyper-competitive talent market, new COVID-19 variants, the introduction of hybrid and remote workforces, and high inflation rates are creating new business challenges. Hiring a temporary or "interim" executive can help remedy some of these challenges which is why it has become one of the most popular hiring trends in 2022. Considering temporary leaders demonstrates adaptability in hiring markets and can be a launchpad for making change in your organization. Whether it’s leaders between positions or those considering a change, don’t discount the reward of a temporary leader to test the waters and see if cultural alignment is truly there. 

Not a desire, but a need: Every company must digitally transform 

A digital-first approach must be fostered by the entire C-Suite and manifested across all areas of the organization. This means that all the lessons learned about digital transformation during the COVID-19 pandemic should become hardwired into an organization's mission, business strategy and company culture. Leaders must be able come together to solve present challenges without forgetting that technology is constantly evolving and changing. Doing so requires leaders to be fully versed on how technology intersects with and advances their mission so that they can pivot from being reactive to proactive to predictive.

Many digital leadership positions are in high demand and low supply – with diversity top of mind. As a result, organizations need to ensure that their digital leadership is diverse and inclusive. Taking due time to thoughtfully approach digital leaders with the intention of benefiting their careers and your company simultaneously will prove beneficial to finding critical hires.