Keil Hubert: Raison d’Eatery

What can you learn from an idle discussion about where to go for lunch? Business Technology’s resident U.S. blogger Keil Hubert argues that small interactions like this are critical tools for building credibility and strengthening employee morale.

I tell a lot of stories about terrible bosses in my columns; heck, my third book is exclusively about terrible bosses. Terrible boss stories are some of the best vehicles I know of for exploring poor decision making processes and counterproductive leadership techniques. If I’m honest, I also enjoy telling the tales… they were all painful to live through, but a little distance helps to make them funny. I’ve learned, though, that I need to remember to break up the horror stories with some examples of leadership successes so that my columns don’t get overwhelmingly dark. That said, let’s talk today about lunch – specifically, about a group of people trying to decide where to go for lunch.

That topic came up for discussion at the office last week on a perfectly normal Wednesday. We’d all reached a good stopping point between meetings and conference calls. Our department head [1][2] made a public announcement to the cubicle farm that we should all go out as an group and have a working lunch somewhere comfortably away from the campus. All of our team members prairie-dogged up over the cubicle walls to pledge their fealty to the boss (in the form of a lunch agreement). As we assembled, someone asked where were going, and the boss suggested that we choose his favourite burrito place. Heads nodded. People started sorting out optimal carloads.

As we all made our way to the car park, I asked the boss to explain why he always preferred to drive out of his way to the burrito place just over five miles north of our office when there’s another identical store from the same chain only four miles west of the office. It’s only a couple of minutes’ difference in travel time at motorway speeds, but it wasn’t obvious why he consistently chose the further location over the nearer one. Everyone in the crew went silent for a second, as if I’d called the boss out.

‘There are two reasons,’ the boss said, without any hesitation. ‘First, there’s nowhere near enough parking at the western store so I always have to waste time hunting for a spot. Second, that place is always packed, and there’s never a line at the northern store.’

There isn’t much room to queue in this particular chain, so if the line gets held up, you can wind up waiting your turn outside — no matter the weather.
There isn’t much room to queue in this particular chain, so if the line gets held up, you can wind up waiting your turn outside — no matter the weather.

I nodded my agreement and opened the fire door to the car park. The boss asked if I’d prefer that we go to the western store instead. I laughed and shook my head. We all went to the northern store as originally pitched.

This may seem like a trivial exchange, but it really isn’t when you drill into it. I submit that it’s one of the marks of a superior leader. Let’s break it down and analyse the individual behaviours in play:

First, the boss was positively receptive to being questioned in public about his rationale behind a decision that he’d made. Being willing to be questioned in front of witnesses takes a significant measure of self-confidence. One of the common, underlying attributes of most of the Evil Bobs that appear in my stories is that they couldn’t stand being questioned. Bad leaders treat any such questioning of their orders as a challenge to their rightful authority, and they often overreact. I’ve been yelled at, sneered at, condescended to, and publicly abused by terrible bosses for having the temerity to challenge the boss. In most cases, their violent overreaction came about from a core of fear – fear that their position wasn’t truly secure, that they’d be found out as inadequate, or fear of having to face aggression from a minion if their reasoning was rejected. Not so, our boss; our department head knows that he’s respected and valued by his team, so he rightfully treats questions as questions – nothing more.

Second, our boss actually had logical, plausible reasons for his decision, and wasn’t self-conscious about sharing them with us. That shows both an ordered mind, and a willingness to embrace transparency. Most people have difficulty understanding why they do what they do; they’ve never been challenged to rationalize their decisions. Further, a great many leaders eschew introspection as if it were a debilitating disease. They can’t explain why they choose one tack over another (because they haven’t the foggiest idea what their logic might have been), and therefore couldn’t articulate a plausible argument if their life depended on it. I’ve seen 50 year-old executives turn scarlet and venomous when asked to break down the logic behind a given decision. Many Evil Bobs that I’ve worked with would have rather yanked out one of their teeth than have to justify their unexamined, logic-bereft, and juvenile thought processes. As before, our current team lead doesn’t suffer from that sort of impediment; his personal preferences are based on sound reasoning, and he’s able to explain his position on pretty much any given issue without apprehension.

I’ve never understood people who were terrified at revealing their reasoning behind a decision. It makes me wonder just how bizarre their inner universe must me.
I’ve never understood people who were terrified at revealing their reasoning behind a decision. It makes me wonder just how bizarre their inner universe must me.

Third, our boss was open and receptive to a potential counterargument. He recognized that other people might not agree with him, and he invited us all to either challenge his assertions or to lobby in favour of some other store attribute. He appreciated that he might be wrong. That’s a staggeringly rare trait in a leader, and it’s precious beyond measure. It means that the boss can be reasoned with, and is willing to consider another person’s input without letting his personal biases interfere overmuch with making a sound decision. The overwhelming majority of managers, directors, executives, commanders, and other assorted personages that I’ve dealt with usually let their title and their power over others go to their heads – they began to mistake their career success as some sort of evidence of possession of superior judgment. Most of the Evil Bobs that I’ve written about were renown throughout their respective agencies for being criminally resistant to other people’s opinions. They treated the perspectives of ‘lesser creatures’ as loathsome; things to be avoided like soiled bandages. A rational and mature leader, on the other hand, both respects and actively seeks out his or her people’s perspectives because they might learn something. That characteristic requires healthy measures of humility and respect.

Finally, by demonstrating that he possessed a rational thought process, our boss taught everyone within earshot that they could predict how he’d likely respond to a new situation. That, in turn, encouraged his people to use our initiative and good judgment when we found themselves having to engage customers without him – by asking ‘what would the boss do in this situation?’ and then reasonably interpreting the answer based on the context of the encounter. This is old-school empowerment: by encouraging his employees to act according to their understanding of his desires, he increased his team’s effectiveness and pre-emptively decreased the odds of a team member misstating the department’s position on something or other. I’ve suffered under far too many Bobs who were rabidly paranoid about letting any clues escape as to what they wanted of us; they often craved a state of persistent paralysis among their direct reports. When workers became utterly flummoxed about what they could and couldn’t do to further the boss’s aims, it meant that they constantly had to return to the boss and ask for direction – thereby inculcating a sense of learned helplessness.

I appreciate that the example I’m offering is a ridiculously little thing; as the adverts tell us ‘it’s just lunch.’ That, I submit, is exactly why this example is so important: a good boss takes advantage of every practical opportunity to train and mentor her people. She teaches her people how she wants them to succeed in the workplace. The selection of a lunch spot has effectively zero business impact. It does, however, have great potential for teaching her people just who the boss is (or who she wants to be), how she thinks, what she values, and how she prefers to interact with her people when the stakes (or steaks) are low. A hundred small interactions like this paint a much more comprehensive picture of a boss’s character than any bombastic, formal presentation ever could.

People are flawed creatures. We all – every one of us – make mistakes. We misinterpret what’s happening what’s right in front of us. We fail to notice critical clues. We let cognitive biases and flawed logic poison our decisions. We fail. That’s an essential element of the human condition. Every boss occasionally succeeds through sheer dumb luck, and fails despite the best of intentions – even the Evil Bobs. That’s why it’s critical to the smooth functioning of the workplace to treat people as they actually are, and not as some sort of idealized comic book hero or villain. Real people are complicated, messy, and difficult to work with. No one is either completely virtuous or totally vile (try as they might).

I’ve known people who equated generating some PowerPoint slides with thwarting a costumed supervillain. Thanks for ‘saving Gotham’ again, Chad.
I’ve known people who equated generating some PowerPoint slides with thwarting a costumed supervillain. Thanks for ‘saving Gotham’ again, Chad.

Every leader is, therefore, an imperfect amalgamation of experiences, perceptions, and deeply ingrained emotional reflexes. The key to ‘managing’ your boss is to understand how they think so that we can predict (with reasonable accuracy) how they’ll react to a potential future event. The smart employee works this equation out and changes his or her behaviour to optimize for the best possible boss response. The best leaders understand this process, and therefore make a concert effort to provide her subordinates, partners, and bosses with the critical data points that they all need in order to understand her. It’s a virtuous circle. The employees gain more confidence and less anxiety, and the boss engenders greater compliance and productivity. The entire team performs better because it experiences less disruptive drama.

Our team’s burrito lunch turned out fine, by the way. Nothing special. We went, we ate, and we discussed how to solve a thorny process flow problem. Then we all went back to the office to translate our arguments into solutions. There was no drama – exactly as lunch should be. Also, exactly as any part of any day at the office should be.


[1] Normally, everyone that I profile in a Business Reporter column gets rechristened ‘Bob’; I’m not giving the boss a name at all in this story since he’s my actual, current boss, and because we’re too close to a bunch of Evil Bob stories that I shared in March and April. I don’t want to inadvertently tar the fellow with my usual Bob brush, even by accident.

[2] In another departure from standard practice, I’m actually sharing a story about a place where I currently work. Normally, my policy is to avoid mentioning anything about a current employer or current client, as a matter of professional courtesy. I’m making an exception in this case because the story nailed exactly what I wanted to talk about this week, and because I asked the boss-man for his permission to share the story. He was gracious enough to agree, so here we are.


POC is Keil Hubert, keil.hubert@gmail.com
Follow him on twitter at @keilhubert.
You can buy his books on IT leadership and IT interviewing at the Amazon Kindle Store.

Keil-Hubert-featuredKeil Hubert is a retired U.S. Air Force ‘Cyberspace Operations’ officer, with over ten years of military command experience. He currently consults on business, security and technology issues in Texas. He’s built dot-com start-ups for KPMG Consulting, created an in-house consulting practice for Yahoo!, and helped to launch four small businesses (including his own).

Keil’s experience creating and leading IT teams in the defense, healthcare, media, government and non-profit sectors has afforded him an eclectic perspective on the integration of business needs, technical services and creative employee development… This serves him well as Business Technology’s resident U.S. blogger.

Keil Hubert

Keil Hubert

POC is Keil Hubert, keil.hubert@gmail.com Follow him on Twitter at @keilhubert. You can buy his books on IT leadership, IT interviewing, horrible bosses and understanding workplace culture at the Amazon Kindle Store. Keil Hubert is the head of Security Training and Awareness for OCC, the world’s largest equity derivatives clearing organization, headquartered in Chicago, Illinois. Prior to joining OCC, Keil has been a U.S. Army medical IT officer, a U.S.A.F. Cyberspace Operations officer, a small businessman, an author, and several different variations of commercial sector IT consultant. Keil deconstructed a cybersecurity breach in his presentation at TEISS 2014, and has served as Business Reporter’s resident U.S. ‘blogger since 2012. His books on applied leadership, business culture, and talent management are available on Amazon.com. Keil is based out of Dallas, Texas.

© Business Reporter 2021

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