Five Things You Should Ask Your Next Generation IT Leader


Demands on IT leaders have changed rapidly as consumers seek more of a one-to-one customized relationship that can be managed at the point-of-sale or on a smart phone. The challenge for every industry is that consumers are getting spoiled by companies like Amazon, Apple and Uber who provide a frictionless, easy-to-use and reliable experience. It’s no longer how your company compares with your competitors, but how your services compare with these excellent companies.

In hospitality, there is almost always a physical delivery of a service. Matching the quality of the on-line experience with the on-location experience becomes a critical and challenging objective. Great tech leaders tend to come out of two camps: an engineer who has committed themselves to learning the business side and can drive a product launch and therefore the business road map, or a business person who has made it their goal to be able to understand technology issues and has learned to drive complex technical projects. These “bilingual” technology leaders are worth their weight in gold.

Interviewing the executive who will lead your IT group and interface with marketing, sales, and product teams is difficult. Here are five questions you should ask this critical technology leader:

  1. At what scale have you been operating? How many people report directly to you? How big is your annual budget? How many outside vendors do you manage? How many transactions are you processing weekly? Have you made many management/board presentations? It is very important your new leader have had experience operating at the scale you will need them to manage. Someone who manages a large budget and a team of 60 at a large company may not adapt well to an early stage growth company. Someone who was managing a system for selling large ticket items (like BMWs) is going to be out of their element selling $12 quick service meals.
  2. How technical are you? Some managers can push a lagging team member aside and take over programming code. Other managers are not coders, but are very good at managing technology projects, listening carefully and challenging a team of engineers if they are padding the budget or sandbagging the time line. Someone in your organization must get under the hood on their technical skills and decide which version is best for your challenges.
  3. Are you willing to ship a solution that is close to being correct or does everything need to be perfect before going live? The software industry is good at getting an excellent product out the door and then upgrading as demands require overtime. Perfection is a worthy objective but can slow progress dramatically. Skunk works projects and beta trials can be very effective development tools, and some agility and willingness to experiment is highly desirable. You may have a region or a franchisee that would make a good beta site for new ideas.
  4. What is your experience with e-commerce, mobile ordering, apps, kiosks, CRM systems and loyalty programs and what do you see as appropriate for our business? These are critical functions and an IT leader who is not used to supporting these is probably too deep in enterprise infrastructure, supply chain, financial reporting or security. Success with some of these tools may be critical to your success. To be strategically helpful to revenue growth, IT leaders need to have experience and a point-of-view on these functions. Building a seamless integrated customer experience is the holy grail, but it is not “one-size-fits-all” and you need a leader who can bring experience to the table and modify it to fit specific business and customer needs.
  5. What are your personal passions? More so than other executives, it is interesting to learn what IT leaders do in their spare time. A candidate who plays the cello in a local orchestra or renovates turntables or refurbishes British sportscars has diverse interests and passions. IT leaders need to be passionate about their job, and an outside hobby which takes a lot of passion, time, skill and detailed knowledge can be indicators of business performance.

We always look for someone who has a track record of sticking things out for 3-10 years rather than bouncing through a series of 12-18 month engagements, which is common with engineers. We always ask our clients to make a clear list of the “key attributes” of the ideal candidate at the front end of the process and then score candidates as they come in. In a full employment market, you may have to compromise on one of your criteria and it is good to have articulated and circulated the ‘wish list’ up front with the hiring team.

Finally, when a candidate raises their hand, it is critical to roll out the red carpet, make the candidate feel welcome and move quickly to interview and make a hiring decision briskly. Good people are in demand, and if the hiring process is slow, or fails to show off the organization in the best light, it is likely the in-demand, competent people will go elsewhere.


Ted Pryor is managing director of Greenwich Harbor Partners, a Connecticut-based executive recruiting firm that specializes in recruiting senior executives and independent board members in media, hospitality, technology, and business services.

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