The IT Admins Playbook for Strategic Conversations with Executives

Summary

Host Landon Miles discusses the critical challenge of effectively collaborating with executive leadership teams in IT. He emphasizes the importance of understanding executive perspectives, communicating IT needs in business terms, and presenting well-thought-out options. The episode provides a checklist for IT professionals to engage executives successfully, highlighting the need for clear communication, metrics, and a solutions-oriented mindset.

Transcript

Hello and welcome back to the Hands-On IT podcast! I’m your host, Landon Miles. Whether you’re knee-deep in endpoint management or strategizing your next major IT initiative, we’re here to help you tackle the practical challenges of IT, one episode at a time. 

This podcast is part of Automox’s Autonomous IT podcast network—new episodes drop every Tuesday and Thursday. Don’t forget to subscribe so you never miss critical insights and actionable advice. 

Alright, team, today we’re talking about an age-old challenge for IT professionals—working effectively with executive leadership - also known as ... asking to buy things.

It's a critical part of being in IT, but not one that a lot of people enjoy. IT is the intersection of technology and people. Most of us are in IT because technology comes very easily to us. So this podcast will be a quick guide of how to work with your company's leadership.

Now, execs and IT teams often want the same thing—a secure, streamlined, and highly productive operation that drives the business forward. But here’s the thing. We approach problems from completely different perspectives. 

It’s not enough to just know you’re right or that your project is necessary. If you want buy-in, you’ve got to speak their language, relay your points clearly, and make your asks specific, and well thought out. But, before you even start the process, you'll need to speak their language.

Speak Their Language 

Think of this as translating IT into the language of strategy. Most C-suite executives aren’t focused on the fine details of system updates or patch schedules; they’re thinking of the big picture—growth, risk, costs, and outcomes. 

Here’s how you can adjust your approach to land your message effectively while staying true to the technical realities of the job. 

You know how when you're talking to your finance department, or sales, or any other department, and they start using their terminology, and you're brain hops into a bit of a different place for a few seconds? Well, the same thing happens to those departments when we, as IT professionals, go deeply into technical details.

1. Be Outcome OrientedInstead of focusing on the technical details, frame your projects in terms of how they support and drive the business forward. Use metrics and data to demonstrate the impact your solutions will have on operations, productivity, and growth.

2. Highlight Risks and Implications:Executives are ultimately responsible for mitigating risks and ensuring compliance. Speak to them in their language by clearly outlining potential risks associated with not implementing certain IT solutions or updates. Help them understand that IT goes beyond just technology; it's about protecting the company's assets.

3. Connect IT Investments to Business Outcomes:Rather than simply asking for a budget to implement new tools or systems, Quantify Everything You Can. Executives deal in numbers. Speak to them with clear metrics that tie back to risk or opportunity. 

Step One – Clearly Relay the Problem   

When presenting a new IT project or solution, it’s important to clearly communicate the problem you’re trying to solve. Use data and real-life examples to paint a picture of the current state and why it needs improvement. This will not only help executives understand the need for action but also build credibility for your expertise.

Here’s a tip—precede every key point with the thought, Why is this important

• Understand the impact to the business at large. If we don't do anything, what happens? If we implement it, what are the benefits? What’s the downtime and costs associated?

• Don’t Bury the Lead Hit the big point first. Jump back to your helpdesk days. If you're solving someone's problem, the more info they give you up front, the better. This is about relaying the “why” first, not just a rundown of everything you know, or how the technical implementation would work. 

Step Two – Prepare Some Options 

Present multiple well-thought-out options that allow leaders to feel they have some control over the decision-making process. Rather than pushing a single solution, three options, outlining the pros, cons, and associated costs of each. I always recommend the following format: minimum viable solution, full solution, and the do-nothing option. 

Break Down Each Option Clearly 

For example, if it’s about upgrading a critical system, you could present options such as: 

1. Minimal Upgrade“We could perform a partial upgrade on our existing system to address the most immediate risks. This has a lower upfront cost of $X but is a temporary fix, and we would likely need a full replacement within the next year.”

2. Full Solution - “A full system replacement would cost $X but would eliminate these risks entirely and future-proof our operations for the next X number of years. This can be rolled out over a period of X months to spread the cost.”

3. Do Nothing (For Now) - Doing nothing is always an option, even if it's a really bad one. Addressing this lets them know you've thought through the solution. “We could continue without action. There’s no cost today, but the risks of downtime, security incidents, or increased maintenance costs grow exponentially over time. This option carries the greatest level of risk to operational continuity.” 

Make It Easy for Them to Compare 

Use clear, visual formats like tables or infographics when presenting options. Highlight critical factors such as cost, risk, downtime, ROI, and operational impact. Executives are often juggling multiple priorities—help them see the decision clearly and concisely. 

Step Three – Be Solution Driven 

No matter the complexity or severity of the problem, frame the conversation around solutions.Always try to present problems with viable paths forward. Even if the solution is resource-intensive, show that you’ve done the legwork to make implementation as smooth as possible. 

This means being ready to address questions like:

• How long will it take to see results? 

• What internal resources are required to support this? 

• Who needs to be involved to ensure success? 

A solutions-oriented mindset positions you as a problem-solver rather than just the bearer of bad news, earning leadership’s trust and confidence. Be transparent about limitations or challenges, and avoid overpromising. Be open to feedback and other ideas. It’s the executive team's job to make informed decisions, so don’t be offended if they ask for more information. 

Final Steps – Anticipate Objections 

It’s not just about what you say—it’s about what they’ll ask back. The goal is to bring a well-researched, well thought out ask along with a mitigation strategy for identifiable risks. 

Common questions you're always going to get are, “Can we wait until X date for budget reasons?” or “What happens if we don’t do anything?” "Are there alternatives?" "Can it be done cheaper?" “Why is this important now?” 

These are common questions that you should definitely be prepared for.If there are questions that come up that you genuinely don't know the answer to, "I don't have that data readily available - but I can get you an answer shortly" is a perfectly good answer. 

Wrapping Up 

Alright, here’s your checklist for working with executive leadership effectively. 

• Speak their language. Use metrics, business outcomes, and plain language. 

• Relay the problem clearly. Define the stakes and use analogies or real-world examples if necessary. 

• Make your ask specific. Lay out exactly what you need, why it matters, and how you’ll deliver. 

• Prepare for follow-up. Anticipate those tough-but-fair questions—the stronger your prep, the smoother the pitch. 

Pro tip - if you find yourself struggling with putting this together, go make a friend in the sales department, and ask for some feedback/help. This is what they do all day, every day. 

IT isn’t just about the tech—it’s about communication, too. Executives are just people. You've got this. And when you master this, you’re not just an IT pro—you’re a business ally, deeply embedded in the success of your organization. 

If you’ve found today’s episode helpful, I’d love to hear from you! Find me on LinkedIn or drop into the Automox Community and tell me about the challenges you’ve faced when working with leadership—and how you’re solving them. 

Until next time, keep innovating, stay strategic, and practice those conversations. I’m Landon Miles, this is Hands-On IT. Thanks for listening, and we’ll see you next time.