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The Six Questions Sales Leaders Should Ask Their IT Department


I have been in IT for 25 years, and I'm often surprised by how infrequently IT teams are challenged by their business functional customers within the organization. Sure, there are often complaints about IT speed and cost, but there are ways to challenge your IT team in a positive way and encourage them to up-level their game.

Sales leaders, in particular, should feel free to ask IT the tough questions as a way to better align goals and objectives on both sides.

Here's the thing: Sales teams in medium- to large-size enterprise companies are heavily reliant on IT to enable key capabilities for them anyway — mobile, quoting, configuration, opportunity management, and so on. When they then proactively engage their IT teams, they can benefit in three ways:

  1. A better understanding of the IT projects
  2. The ability to influence IT priorities
  3. The chance to up-level the strategic thinking of IT

The challenge questions you should ask can be divided into two general categories: strategic and operational. As an IT insider, I recommend these questions in each category to better understand, influence, and up-level your IT team.

Keep in mind that in each of the cases below, if IT doesn't have this documented information readily available, that's a red flag.

Strategic IT Questions

1. What is IT's strategic planning process?

Is there an effective process to align IT with the business goals and objectives? Is the process documented and easy to understand? Is it actually followed? Are priorities and decisions actually made from that strategic planning process? Is sales influencing that strategic planning process?


2. What is IT's strategic roadmap for the next 12–24 months?

Does IT have a strategic roadmap that extends beyond a quarter? Does it have a view toward the future? If not, it could indicate a very reactive, order-taking IT team. If so, is the sales team aware of and in agreement with that roadmap? Is sales influencing that strategic plan?


3. What does the enterprise architecture (EA) future state look like?

Is there an EA team that is focusing on the longer term and taking a more strategic architectural view? Is that EA team focused on fixing fundamental issues, like retiring legacy systems, filling key business capability gaps (for example, omni-channel, social listening, B2B2C), and ensuring that emerging technologies are on the future state architecture (for example, AI, predictive analytics, IoT)?


Operational IT Questions

1. How is IT increasing speed, cost, and quality of delivery?

What to look for: Is IT moving to an Agile Scrum development model? Is it using Continuous Integration and Continuous Delivery processes? Is IT using hackathons to accelerate learning within IT? Is it using a Dev/Ops model to increase quality of deliverables? Is IT pushing to cloud and subscription-based models to reduce and avoid large CapEx expenditures?


2. How is IT building talent?

Does IT have a strategic and focused plan to build IT talent? Is there a formal mentoring plan? Is it using peer programming to accelerate learning? Is IT attending external conferences and training? For Salesforce learning, is it using Trailhead, and how many badges has it earned?


3. What are IT's key success metrics? KPIs?

Does IT have a dashboard of key success metrics that it tracks? If so, what are the trends of those metrics — flat, down, or up? Do those metrics ultimately help improve the customer, partner, and employee experience? Metrics should be focused on business capabilities, not primarily on system up-time, which does not easily translate to improving the overall experience of customers. Metrics should enforce teamwork through successful, quality delivery, adoption, and usage.

A good way to create a dialogue around these questions is to set up a meeting (allot a couple of hours) with sales, sales ops and IT. Send out the questions ahead of time. Use the meeting time to review the answers. Such dialogues can be invaluable in reinforcing the importance sales places on IT, as well as challenging the IT team to up-level its strategic approach. I recommend having this dialogue on a quarterly basis. You will help create a much more strategic IT team if you do.

Sure, there are often complaints about IT speed and cost, but there are ways to challenge your IT team in a positive way and encourage them to up-level their game.”

Brett Colbert | Solutions CTO & VP of Enterprise Architecture, Salesforce

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