The Real Reason Business Execs Hate Their IT Department
If you've ever walked out of a meeting with your IT or security team more confused than when you walked in, this one is for you. I break down five specific ways your technology team is losing you in the boardroom, the budget meeting, and every conversation in between. This isn't about hating technology. It's about demanding the communication, accountability, and strategy you're actually paying for.
- The 3 things you should get back every time you ask "are we protected?"
- Why your team's shopping list habit is costing you money you don't need to spend
- The difference between risk management and fear management
- What accountability actually looks like on a technical project
- Why the jargon isn't a sign of expertise, and what clarity actually signals
If you're a business executive looking for an independent strategy advisor, apply for a 30-minute call at https://titanof.tech.
Watch the video version: https://youtu.be/QcgZ2c3KFYw
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Independent fractional CIO for owners of $5M to $50M businesses. Technology and cybersecurity strategy, with no tools to sell, no commissions, and no conflict.
Work with me: https://titanof.tech
Transcript
If you don't hate technology, you hate being made to feel stupid by
Speaker:the people you hired to protect you.
Speaker:And if you've ever walked out of a meeting with your IT or security team,
Speaker:more confused than when you walked in, uh, that's kind of not on you.
Speaker:That's a system failure and is costing you money, time, and real
Speaker:risk exposure while everyone stands around pointing at dashboards.
Speaker:I want to show you exactly what's happening and what
Speaker:to start demanding instead.
Speaker:I saw this play out in real time on Reddit of all places.
Speaker:At the time of this recording, like a week ago, a business owner, non-technical,
Speaker:they run a company doing the Department of Defense contracting with federal
Speaker:government contracting, and they posted a simple question in an industry form.
Speaker:They used a managed service provider to handle all of their technology
Speaker:needs, and the company themselves needed a cybersecurity certification.
Speaker:It was a 40 word question.
Speaker:Does their MSP need to get certified too?
Speaker:I gave them a straight answer.
Speaker:Uh, simple.
Speaker:If the MSP isn't storing or processing any of the controlled data that the
Speaker:government has or that they have, they don't need the accreditation themselves.
Speaker:I gave them a link to the scoping guide that the government has so they could
Speaker:understand the requirements and told them they, they probably don't need to
Speaker:switch providers if they didn't want to.
Speaker:It's done.
Speaker:It's clean.
Speaker:It was useful comment, at least I thought it was.
Speaker:Anyway, then the other comments started piling on, well, actually, if the MSP has
Speaker:direct access to this and if they're doing that, then blah, blah, blah, blah, blah.
Speaker:I have no doubt that that business owner closed their laptop more
Speaker:confused than when they opened it.
Speaker:I almost guarantee it.
Speaker:Here's the thing.
Speaker:That's not one bad Reddit comment.
Speaker:That is it.
Speaker:And cybersecurity industry in a single thread, just a single reminder to me.
Speaker:And that's what happens in your executive meetings, your boardrooms.
Speaker:So what happens in your budget meetings?
Speaker:So here are five specific ways your technology team is losing you.
Speaker:And what you should be getting instead,
Speaker:number one, they go straight into the weeds and they leave you there
Speaker:when you ask, are we protected?
Speaker:You should get three things back.
Speaker:Typically speaking.
Speaker:You know, what's the risk?
Speaker:What does it cost to fix and what happens if we don't?
Speaker:That's it.
Speaker:Three things.
Speaker:Instead, you may get a 12 layer breakdown of a network segmentation
Speaker:strategy that requires a computer science degree to follow, and when
Speaker:you stop asking questions, not because you got the answer, but because you
Speaker:gave up, they take that as a win.
Speaker:If your team can give you a plain language risk summary in under a few minutes,
Speaker:that's a communication failure on their end, not a comprehension failure on yours.
Speaker:Number two, they bring you a shopping list when you need a strategy.
Speaker:You've seen this.
Speaker:They walk into a budget meeting with 12 new platforms, subscriptions and licenses.
Speaker:Each one can be technically justified.
Speaker:All of them adding up to a number that makes your CFO
Speaker:probably wanna flip the table.
Speaker:Here's what you should be asking before any of that.
Speaker:What can we cut?
Speaker:What are we already paying for that we're not fully using?
Speaker:Uh.
Speaker:Where can we shrink our exposure without spending another dollar
Speaker:optimization before addition?
Speaker:Every single time.
Speaker:If your team's first move is always buy something new, they're thinking like
Speaker:technologists not like business operators, and you're funding that difference.
Speaker:Number three, they treat every risk like the building is on fire.
Speaker:So eventually you stop believing any of it.
Speaker:When everything is critical, nothing is, and your team knows this, even
Speaker:if they won't say it out loud.
Speaker:Real risk management is not eliminate all risks.
Speaker:That's impossible and should never ever be the goal.
Speaker:The conversation you should be having with your security team
Speaker:is, which risk do we reduce?
Speaker:Which do we transfer, like using cyber insurance to transfer some
Speaker:risk, and which ones do we accept because the cost of fixing them.
Speaker:Outweighs the realistic probability and the impact so you have high impact, low
Speaker:priority, accept, transfer, and reduce.
Speaker:If you're not having that conversation, you're not doing risk management,
Speaker:you're doing fear management.
Speaker:And fear management is designed to make you feel like you're always one bad day
Speaker:away from disaster, which conveniently justifies more budget requests.
Speaker:Demand a risk, register with clear priority tiers and
Speaker:then hold everybody to it.
Speaker:Number four, they won't commit to a timeline and then act surprise
Speaker:when you lose confidence in them.
Speaker:Technical projects, just by their nature, are unpredictable.
Speaker:I know that I've been doing this for a long time.
Speaker:They know it as well, but the answer to unpredictability is
Speaker:not refusing to set a deadline.
Speaker:The answer is doing proper testing and proper validation before anything
Speaker:touches your live environment.
Speaker:So that when something goes wrong and something almost always does go wrong,
Speaker:it's a one or two person inconvenience.
Speaker:Instead of this a, a large company wide outage, you don't
Speaker:need your team to be perfect.
Speaker:You need them to be accountable.
Speaker:Those are very different things, and if they can't tell you what's happening by
Speaker:when and what changes, if the timeline shifts, that's not a technology problem.
Speaker:That's a project management problem, and it's yours to fix if you don't address it.
Speaker:Number five, the jargon isn't accidental.
Speaker:I want you to really hear this one.
Speaker:When you can't follow what your IT or security team is saying,
Speaker:your instinct might be to assume you're not tactical enough.
Speaker:Flip that.
Speaker:In every other discipline, whether it's legal or finance or medicine,
Speaker:professionals are expected to explain complex things in plain language
Speaker:to the people that they serve.
Speaker:Cybersecurity or technology is the only field that somehow
Speaker:convinced the business world.
Speaker:That confusion is a sign of depth.
Speaker:It isn't.
Speaker:Clarity is competence.
Speaker:If your team can explain a risk, a recommendation, or a project status and
Speaker:language that you can act on, that's a skill gap on their side of the table, and
Speaker:it means you're making decisions without the information that you're entitled to.
Speaker:Alright, so here's what to take with you in a short little quick format.
Speaker:Five signs your IT and security team is failing you.
Speaker:One, they bury you in detail before you've asked for it.
Speaker:Two, they bring a shopping list when they should be bringing a strategy.
Speaker:Three, they manufacture urgency on everything so you stop trusting any of it.
Speaker:Four, they won't commit to a timeline, which means you
Speaker:can't hold them accountable.
Speaker:Five.
Speaker:They hide behind jargon and they let you believe that's your problem.
Speaker:Now, I've been on the other side of this table.
Speaker:I've worked with executives who've been burned so many
Speaker:times by their technology teams.
Speaker:They stopped asking questions almost entirely, and that
Speaker:silence is an acceptance.
Speaker:This a resignation.
Speaker:You deserve better than that, and frankly, your business depends on it.
