5 tech questions a CEO should ask on their first day in office

CEOs shouldn't leave all the technology decisions to the CTO or CIO. Here are five questions CEOs should consider on day one.

Image: iStockphoto/dolgachov

As CEO, your role is chief vision-caster within the organization. And, increasingly, part of a CEO's vision for his or her company will have to take into account the technology that empowers and enables employees to get work done.

Even if the company you are leading is not a "tech" company, per se, it is nearly impossible to avoid making decisions based on the impact technology will have in your workplace. When you take the reins at a company it is critical that you develop a plan on how you will approach technology.

When you first land in the office of CEO, here are five tech questions you can ask to help determine the path of your company.

How well is the current strategy working?

Any time you step into something new, you have to establish the lay of the land. This is especially true for company leaders. As you're beginning to see how things work, pay special attention to the existing tech strategy.

"On day one, it's important to take a pulse of the business you're inheriting," said MongoDB President and CEO Dev Ittycheria. "Set up meetings with leadership to understand the technology investments the company is making to drive the company's overall strategy."

In addition to meeting with leaders, meet with department employees to determine what seems to be working and what challenges exist, Ittycheria said. As you have these conversations, take note of points that are made that seem contradictory to the tech goals you have for the company and react accordingly.

Are we enabling efficiency?

Technology, by definition, helps users to more easily get work done. Whether that's through automation or an increase in power, a good technology strategy should be enabling your employees and leaders to be as efficient as possible in their daily work.

In determining operational efficiency, Carbonite CEO Mohamad Ali recommends asking questions such as:

  • Are we selling in the most efficient way?
  • Are our data centers the most efficient?
  • Are our support centers the most efficient?
  • Are our IT systems enabling efficiency?

"Running an efficient company creates profits that allow investment back into the core of the business - products, and ultimately allows one to win in the marketplace delivering greater value to investors, employees, partners and most of all, customers," Ali said.

Do our customers have the tools they need?

Customers drive business, so it makes sense that one of the key decisions you need to make early on is whether or not you are providing the proper tools and services to your customers.

Take a look at some of your relevant customer data to determine if your website, for example, meets the needs of your customers. If you can, create a survey that asks customers how they feel about your company's technology. For example, do they like your email customer service form, or do they prefer a chat system?

Christy Wyatt, CEO of Good Technology, said another important question to ask is whether or not customers can interact with you as the CEO and the brand? Whether you are consumer or enterprise focused, she said, technology should assist that interaction, not hinder it.

"Too often user experience projects get prioritized behind other business systems," Wyatt said. "Very few investments could be worth more than building a great customer experience."

How should we approach new projects?

A big decision that needs to be addressed with your CTO and CIO is how you will approach technology projects in your tenure.

Enterprise IT, especially, used to be an all-custom affair. Now, there are a plethora of off the shelf and out of the box solutions that perform just as well in certain situations. So, you must decide what aspects of your technology need to be custom-coded, and what can be taken care of with an existing market solution.

"You need to think pretty hard about this, because a lot of capital can be consumed in specialized projects, and you may not even fully know what outcome you need to achieve until after you have completed the project," said Steve Sadler, CEO of Allegiancy.

This decision also affects what software model you will go after for your organization, Sadler said. SaaS and local solutions both offer their benefits, but you have to make the final say.

What parameters should I set?

Possibly the biggest part of being a good leader is knowing how to trust and delegate to the people around you. If your organization has a CTO and a CIO, you must be able to trust those people to take the helm on the business's technology.

That trust must go beyond your executive team. On your first day, Ali said, you must begin analyzing your senior team to determine if they can polish and execute on the company's vision with technology.

"This is probably the most important decision during those first days: Who stays, who goes, who is on the watch-list, and what new skills need to join the team?," Ali said.

Once you know the proper team is in place, you must make the decision of how you'll set boundaries and parameters in place. Wyatt said this starts with understanding your organization's risk profile, and making sure that is communicated properly to the right people.

Set hard parameters around IP and assets that pose high risk first so you and your executive team have strong lines that you know cannot be crossed. Then, set the expectations and parameters for the less vulnerable aspects of your IT, because if your team knows how much room they have to move and experiment, they will be encouraged to make decisions independently of your input.

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