Don’t believe the client

We all have days like that. When you begin to feel that way about all your work, it may be time for a change.

It was a typical call from a fairly typical small/mid sized client. He wanted me to look into the option of using a “new system” to store all his files. Of course, it wasn’t really a system in any real sense. Just a cloud-based storage and document management application. And he wasn’t really clear on how he would use it except that he wants “everywhere access” to all his files, all the time. He also wondered if his existing file-management overlay software could work with it, after all, it’s just a mapping tool so can’t it map to this cloud thing the same way it maps to Windows folders and files? (Quick answer, no.)

I asked the question that I have asked this client dozens of times before. “What is the goal of doing this?” Then, “what do you think you’ll get rid of by buying this?”

I got a rambling answer about access anywhere, existing VPN access too slow. He may be moving to a virtual office. He may have remote employees. His lease may be up and he’s not sure he’ll renew. He wants to have flexibility. He wants cloud backups. A dozen jumbled justifications for doing something that — in all likelihood — a smart software salesperson has been nudging him to do.

But beyond this is the greater reality: he has no idea where his business is going, no plan for getting it there, and his technology purchases — as they have always been — are driven by impulsive reaction to an immediate point of pain with absolutely not thought as to how he really wants to run the business. In fact, it’s mostly an accidental business in the first place. No planning has ever been necessary.

He’s a very successful lawyer, and he’s built a successful business, but one of the things they don’t teach you in business school is that the vast bulk of businesses out there are mostly accidents, mostly don’t have anything resembling a business plan, and mostly exist because the founder or owner got lucky and has been able to ride that initial luck for years or decades.


They don’t teach you this stuff in business schools or in project management courses for a number of reasons. The first is pretty simple: the expectation is that you’re likely to work for a larger, better organized company. One that’s been around for years and is probably riding a lot more than just a lucky streak. It may have been founded by somebody who got lucky, but it’s moved beyond that stage. In those companies, expertise is widespread and there’s an expectation that things like strategy and plans will exist and be somewhat adhered to.

The second is more troublesome, and reflects the issues common in smaller businesses. Top business schools and other institutions are loathe to admit how much our successes or failures are the result of plain simple luck. Because really, if luck is the big thing, why pay for that expensive MBA? (When I got mine, in-state tuition at UCLA was still a bargain.)

Nick Taleb skewered the common institutional arguments in his first book, Fooled By Randomness, in which he demonstrated that in many fields (he’s a Wall Street trader by profession and focused his efforts there), luck is not only a contributor to results, but may be the primary one. Nobody likes to be told that the reason they are where they are is just plain chance. Fooled by Randomness was welcomed on Wall Street and in the halls of the world’s top business schools with about the same appreciation as a hand grenade rolling in with the pin out. You still don’t want to bring it up in any big-name business school or economics department.

Outside the world of the top business schools and the large firms they feed, you’re likely to find a world defined by exactly the kind of random success Taleb pointed out. The client I conversed with earlier was not a guy who got there with a plan. He had been a solo lawyer who arrived from overseas. He could have picked any number of specialties in the US, but picked the one he did. He had no way of knowing where it would lead him. He could have chosen to live in any number of neighborhoods, but he chose the one he’s in, for reasons unrelated to work. In that neighborhood he chose one of several available houses of worship, and by pure luck selected one where he would meet somebody from a large corporation who were able to use his services. But even then, he had no way of knowing and no plan for taking advantage of the fact that a unique set of geopolitical circumstances would later make his particular specialty extraordinarily valuable to that particular company. He definitely had no plan to build an entire practice with multiple attorneys, paralegals and other staff around a set of circumstances that could not have possibly been foreseen. And he sure wasn’t thinking about IT planning.

Most businesses aren’t so lucky. They may start with just as much talent and ability, but don’t have those lucky encounters. Nine out of ten will fail in the first year, unless they’re restaurants in which case it’s more like 19 out of 20. But this client hit the lucky streak and after several years of struggling with it himself, eventually needed to build out his IT systems.

That’s where I came in.


The challenge is that when a business comes together around a streak of good luck — and many of them do — it’s really challenging to attempt to impose any sort of planning or strategic thinking. It’s utterly alien. I’ve seen companies with over $100m in revenue that still operated without much of a plan. Sure, once you hit a certain size there is usually a CFO who puts together something resembling a budget, and maybe somebody who’s doing some marketing planning, but I can think of one $120m CEO I worked for who to the very end stated his strategy as “success is 1% inspiration and 99% last-minute changes.” He was proud of not planning. He made t-shirts and hats with the company logo and that slogan on them! He’d probably still be running that business today, if he hadn’t decided that as CEO he should be allowed to consider his own lavish lifestyle as a marketing expense, since he saw himself as a celebrity figurehead no different from other celebrity CEOs. (While he was in many ways the quite the embodiment of the image he was selling, he was virtually unknown outside the company and certainly not a celebrity spokeperson.) The private equity investors who paid his sizable IRS bill insisted on a very different way of running things and pretty much killed the company.

As a technology consultant to that kind of business, you have to realize that you’re not just implementing technology, you are probably providing the only outside impartial advice the client receives, and are the only check on impulsive responses to immediate problems. My current client has three different electronic address books because two of them were purchased as easy solutions to pressing problems, when doing it the “right” way would have required some thought, planning and expertise that did not exist prior to my arrival. Years later, I still can’t get this client to dump the two “satellite” address books that are perpetually out of sync. The same client runs no less than eight Outlook plug-ins because each addressed a single pain point quickly and with a minimum of fuss. But Outlook crashes all the time bringing his email productivity to a halt.

You have to disbelieve the client. When a mid-sized client tells you “I found this solution, it looks great, when can we do it?” it’s not the same as a large corporate client telling you that they’ve selected a software package and now need implementation advice. The latter have both the expertise and experience to have made a rational (though perhaps wrong) decision and you can feel safe moving forward. The former has probably fallen for somebody’s sales pitch, or is engaged in what one of my mentors called “management by magazine.” They’re not bad people and their hearts are in the right place, but they’re just not trained to look six, twelve or 24 months down the road, or to understand the implications of the latest silver bullet they think they’ve found.

As a big-firm implementation consultant, it’s often a mistake to ask “why?” I was asked to leave a big consulting firm early in my career for asking “why?” far too often. Big firms have their own logic and there is usually a rational reason for doing things, even if it’s not the reason one might hope for. My final project in that space involved a mid-cap public company spending over $4m on an SAP implementation. There was absolutely no good business reason for doing the project. The logic, as I later came to realize, was purely political: a single application environment drove the company towards a consolidated IT department. One of the two co-directors of IT was squeezed out and the remaining one — the guy who had pushed for SAP in the first place — got a C-level title. The company was no better off and in some ways it was worse off, but that was not the reason the project was being pushed and as far as my employer was concerned, that wasn’t any of our business.

My boss at the time had no problem with us being used as a weapon in an internal political squabble. I did. We stayed in touch over the years, and I’ve found that he’s just as uncomfortable being a truly independent, neutral adviser as I was being a highly-competent but obedient cog in somebody else’s machine. Not everybody is temperamentally suited to every position, and that makes the world interesting.

As a consultant to smaller firms, asking “why?” is essential. Personally I like the Japanese “5 whys” approach to figuring out what’s really on my client’s mind. The person who has asked you to do something may not have a good reason for making that specific request, let alone a strategy within which the request fits. There’s just an immediate point of pain that might be addressed in multiple ways and a single option that somebody presented. (Or, even worse, a Google search that yielded a well-paid-for “sponsored” link.) You have to be far more than an implementation or administration expert who will do what you’re told and leave when it’s done; you have to truly be a trusted consultant, who can nudge the clients towards a strategic view, even if it’s against their nature to think that way.

It’s one of the most rewarding, but also the most frustrating parts of the job.

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