IT Buyers Say “We are OK.” Are you Sure? Part 1

IT challenges – After 15 years of running a consultancy for the world’s most powerful firms, there is one thing that still irks me. Every day we propose ways to make the lives of people we work with better and give them the tools data and methodology to make their companies more efficient. But whether it’s reduced cost, improved performance, or more flexibility, someone in the peanut gallery says:

“No, thanks. I’m okay. We’ve already got that covered. All good.” Bleh!

How good were you when half your staff was laid off because the VC didn’t deliver your next tranche? How good were you when your CFO had to explain that you missed earnings targets because of IT challenges and cost overruns? How good were you when you missed your kid’s recital or were pulled out of bed in the middle of the night because your provider fell over… again. Is it possible that, as good as you are at negotiating IT services deals every three years, there might be someone who’s better or has an edge because they do it 50 to 100 times every year with the wind at their back and data from the last 200 deals?

This first part of a 3-part series is about needing help, and not wanting to get help. It’s a weird blind spot for many IT and sourcing executives; a self-defeating and problematic approach — and so easy to fix. But you have to be open to change before you get the help you need. This is the funny type of article we don’t expect to get any “likes” from. We are just nudging change.

IT problems are hidden time bombs – excess cost, insufficient resiliency, scale limitations. But even when they’re glaringly obvious – outages, budget overruns, lagging performance, vendors that act like they’re the boss – IT managers will often say they’re okay. Why?

· · ·I always say in response, “I’m so glad you’re okay. How do you measure okay? Are you great? Could you do better faster or cheaper?” Do you all the offerings in the market?· · ·

Being okay doesn’t mean you’re in the best possible place.

“I’ve got it covered” often means “I screwed up and don’t want my mistakes uncovered.” Or it could mean “I’m here to build something of scale and don’t care what it costs the company, I just need to scale fast.” Or just “I’m too proud to ask for help.” Number 2 is quite perfect with me. Many of our fast growing clients like eBay, Riot Games, Blizzard, and Gap exploded in growth and did not know when it would level off. In many cases, they cared more about performance, scale and agility. Not cost, regardless they knew they needed help.

In business school, they call the source of many of these responses “the agency problem”. That means that deep-seated personal feelings and instincts take priority over doing what you were hired to do – get your employer the best return on each dollar it entrusts you with. When we look at others, we describe agency problems negatively – fear of change, risk aversion, empire-building. But flip the description around, and we all could admit to, say, wanting to protect our team, or ensure that the job gets done right, or prevent a pointy haired boss from interfering with technology he doesn’t understand.

But the further we go down the path of making sure our lives are free of headaches, the more we need to ask ourselves “am I working for the company or for me?” When I say “don’t fix what isn’t broken” am I really doing what’s best? Or am I just afraid to be exposed, to lose my budget, or to not be in full control?

What if moving past those fears opens up the possibility that you can be a hero for the company, the person who found ways to save money and more efficiently apply resources exactly where they’re needed?

The messenger doesn’t get shot when his message includes not just the problem but the solution.

And with all of that in mind, I’ll ask again. Are you ok?

In the next installment: So now that we admit we have a problem, how do we avoid making things worse with the solution?

Read: So now that we admit we have a problem Part 2

IT Buyers Say “We are OK.” Are you Sure?

The world we built is groaning under the strain of its own complexity, and nowhere is the tremor more keenly felt than in the digital cathedrals where our commerce and culture now reside. We are living through the great unraveling, a moment between worlds where the old maps are useless, and the new territory is being drawn in real-time by forces we barely comprehend. In this gap, in this vertigo of accelerating change, we are confronted with a choice: to face the brutal truth of our inadequacy or to retreat into the comfortable lie. And from the engine rooms of our civilization, from the IT departments and sourcing executives holding the digital world together, we hear a quiet, insistent, and terrifying refrain: “No, thanks. We’re okay.”

I’ve seen the cost of “okay.” I’ve felt it in the dead-of-night phone call, the cold floorboards under bare feet, the metallic tang of adrenaline as you realize a system—and a promise—has shattered. I’ve seen it in the forced, bright smile of a manager sliding a disastrous quarterly report across a polished boardroom table, the heavy, expensive paper a testament to a failure too big to name. I’ve heard it in the low, constant hum of server racks in a chilled data center, a sound like a million trapped insects, a sound that mimics the thrum of anxiety in the chest of the person who knows, who knows, they are one cascading failure away from catastrophe, yet still whispers, “We’ve got it covered.”

The agency problem, they called it in business school. A quaint term for a deep spiritual sickness. This isn’t just about individual pride or the fear of having one’s mistakes laid bare. It is a systemic rot. We have built economic and corporate structures that reward the appearance of stability over the messy, often painful, reality of growth and adaptation. Capital flows toward predictable, linear projections, punishing the honest admission that the ground is shifting under our feet. An executive’s compensation is tied to a narrative of control, not to the courage of admitting vulnerability. To say “I need help” is to risk your budget, your team, your status. In this system, the lie of “I’m okay” is not a personal failing; it is a rational, if ultimately suicidal, survival strategy.

I speak from participation, not judgment. I remember a deal, early in my career, built on a tower of assumptions I refused to question. I had it all covered. I was the smartest guy in the room, moving faster than anyone else. My own certainty was a fortress, until it became a prison. The collapse was quiet at first, then total. In the wreckage, I was forced to confront the man who wanted to be seen as infallible, the man who valued being right more than getting it right. I had to admit that my need for control was not a strength, but a profound fear of the unknown. It was a bitter, humbling, and necessary initiation.

What if the path to becoming a hero is not to slay the dragon, but to admit the dragon is there? What if the most powerful move is to confess you don’t have the map, and then to assemble the fellowship that can draw a new one with you? The messenger doesn’t get shot when the message is not just “we are lost,” but “I have found a guide.” The choice is not between control and chaos. It is between the illusion of control and the possibility of co-creation.

· · ·Are you okay? Or are you ready to be great?· · ·

The truth arrives whether you invite it or not.