There comes a time in every business leader’s career where they convince themselves that time-tested rules of effective leadership ‘don’t apply’ to them. Business Reporter’s resident U.S. ‘blogger shares an embarrassing example of why this mistake often ends in failure and frustration.
Have you ever heard the aphorism ‘A boss and her workers must be friendly, but they can never be friends’? I have; that phrase was drilled into us officer cadets back in the nineties. I heard from my sergeants-major that the phrase was also routinely taught to aspiring corporals and sergeants. It was a crucial ‘leadership lesson’ that every aspiring leader had to master before they were allowed to move into ‘management.’ If you haven’t ever heard it, now’s a good time to discuss why it’s important.
Disclaimer up front: I’m not arguing that bosses have to keep a frosty, emotionless distance between themselves and the people in their charge. That’s counterproductive. I’m also not arguing that a boss can’t have genuine affection for his or her people. Compassion is not only allowed, it’s necessary for growing trust. Bosses should care about their people and want to see them succeed.  A healthy and positive working relationship is key to developing high-performance teams. Note that I said ‘working’ relationship. That’s the key word, and the key concept for this argument.
A strong professional relationship allows bosses and workers alike to empathize with one another. It facilitates more effective communication and builds camaraderie. These are things that leaders need. Inexperienced supervisors often make the logical leap that leaders can be even more effective if they also become close, personal friends with their subordinates outside of work. Surely (the logic goes) that next step would simply improve on a known-good thing, right? And … no. It doesn’t.
The reason that we teach junior leaders to keep their professional relationships strictly professional (that is, not personal) is to ensure that a leader’s authority and credibility are never compromised by personal ties. No matter how well you get along, there comes a time in every working relationship where a boss has to enforce company standards. If she fails to do so, she lets the entire company down. Further: once a boss can be accurately accused of favouritism, her institutional credibility is shot. She can’t function. She’s not a fair and impartial ‘boss’ anymore … she’s ‘so-and-so’s pal.’
Workers recognize when one of their own is singled out by the boss for special treatment … and they rightly despise the lack of fairness.
What’s crazy is that every new supervisor believes that his or her situation is somehow different. They’re not like the millions of other supervisors who preceded them. They can ‘handle it.’ They’re too professional to trip up. They won’t make the obvious mistakes and jeopardize both a job and a friendship. Playing ‘by the rules’ is for suckers.
Think that you’re different? We all do at some point. I made this mistake once and have regretted it ever since. I knew the rule. I spent years practicing the rule. Then I broke the rule using that exact same ‘this-time-is-different’ rationalisation. It’s an embarrassing story … which means it’s a story worth sharing.
For context: I stood up my private consulting practice getting laid off in the early days of the Dot Com crash. I ran my business as a full-time endeavour up until 9/11 when a quirk of fate and timing caused me to get recalled to full-time military service for the airport security mission. By the time I got off military orders, the US tech sector had imploded. Tech spending was severely curtailed in the niche I’d chosen to specialise in, and most of my competitors were driven out of business. There was no way that I could keep the business afloat on the business plan I’d started with. I had to spool it down to a part-time activity for … well … forever. That’s how I’ve had to run it since mid-2002.
I didn’t want to give up on it, though. I was keen to try out new services and revenue models in order to keep the outfit financially self-sufficient, and hoped that someday I could find a service model that would let me run it full-time again. I shifted into mac OS tech support, then mac OS Server installations. I dabbled in the ‘official’ reseller market, too, but never sold so much as a single USB cable.
That’s another embarrassing story: I spent years playing by Apple’s rules, taking their classes, and getting their certifications in order to be a valued partner. Turned out that none of it mattered. Apple wanted their new Retail Stores to be successful and ran us independent consultants in circle until we gave up from exhaustion.
One Christmas, my best mate from university – let’s call him ‘Bob’ for tradition’s sake – flew into town. Over lunch, we hatched a plan to take his new hobby – developing quirky games for mobile phones – and use my business as a means to get his games out of his lab and on to the iOS App store. We sketched a basic business plan, agreed to split the after-tax profits, and said our goodbyes. Our plan was to have his apps posted for sale the month after we got registered as official developers. We’d meet up around the same time the following year and see if we’d made enough to post a profit.
A week after we shook hands on our plan, I registered the DBA certificate  that made ‘Barbacoa Softworks’ a legal thing.  I registered us in Apple’s developer program and secured all of the instructions for uploading new apps to the store. I paid all of the required fees, filed out all of the forms, set up the marketing, constructed the logo, and was ready to go. All I needed from Bob was his software – software that he’d already completed, mind you – so that I could upload his files to the app store for review.
You can guess what happened. I asked Bob for the app upload files and got nothing but a questionable excuse. ‘I’m busy,’ he said. ‘I’ll get them to you next week.’ A week later, Bob said ‘I’m traveling. I’ll get them to you when I get back.’ A month later, Bob said ‘There are a few bugs that I want to work out, and then we’ll be fine.’ Over and over, month after month. There was always a delay, always a plausible excuse. Six months into our ‘project,’ Bob told me ‘Oh, you can upload the files yourself any time you’re ready.’ When I reminded Bob that he’d never given me so much as a single byte of code, he feigned confusion … then ‘ghosted’ me.
The situation went on like this for the rest of the year. When Christmas came ‘round again, I asked Bob (as civilly as I could manage) if he was still serious about our project. I reminded him that we’d need to sell 400+ copies of at least one app (as Bob’s preferred $1 price point) just to recoup the fees that we’d already incurred. Also, I said, Barbacoa’s developer license was up for renewal. If he’d gotten cold feet and wanted to pull out, then I needed to know that ASAP. Bob swore that he was serious, and that this time he’d do his part and turn the game files over to me for upload. Seriously.
I renewed our developer fee. Bob didn’t come through. Go *#&$ figure.
Totally shocking and unexpected, right? Riiiiiight …
To this day, I have no clue what Bob had been thinking. I talked with him a few more times in the years since (when he needed a ride to or from the airport). He’s consistently refused to discuss what happened. It’s a mystery. I suspect that his apps weren’t as polished as he’d wanted them to be; since he couldn’t afford to invest the time required over nights and weekends to get them up to his usual standards, he must have preferred to not expose them to criticism on the app store. That hypothesis fit his personality. Still, he’d told me in our first meeting that his games were 99% ready to ship. Hell, he demo’d them for me on his personal smart phone All they needed, he said, was a publisher’s name and maybe a flashy logo. That was it.
In the end, I ate all of the costs of ‘our’ venture. I shut down the Barbacoa Softworks DBA a year later. We produced nothing, save for a valuable leadership lesson: never go into business with your friends.
I know that this isn’t a major drama. Netflix isn’t going to option my story as new original IP. It doesn’t even warrant a footnote in the Grand Book of Trivial Business Failures. It was, however, a decent lesson-learned and a good illustration of the principle.
What doomed our project wasn’t Bob’s inexplicable refusal to come through on his end of an agreement. We were doomed because I failed. Specifically, I wasn’t willing to trash decades of friendship in order to force Bob to live up to his commitments. I compromised my position as the senior partner and couldn’t hold him accountable. Or wouldn’t, if you prefer. Either way, it came to the same result.
I so look forward to reading the deluge of scornful and snarky ‘AH HA!’ e-mails about this from every leadership student that I’ve ever taught. Totally deserved. Fire when ready, everyone.
The most embarrassing part of the whole experience was that I was actively teaching leadership theory at the time in my full-time job. I lectured my students on maintaining a dispassionate, professional distance so that they didn’t compromise themselves. I broke my own rules because I couldn’t see how Bob would ever let me down. He’s always been a reliable mate. Surely this time was different …
Be friendly with your workers, your peer leaders, and your superiors. Seriously. It’s important to be a decent person as well as a responsible leader. Just don’t ever forget who’s running the operation. The boss has to remain the boss; friendship can’t be allowed to undermine the boss’s authority. In a similar vein, equal partnerships demand some sort of structural or contractual mechanism for ensuring that all partners perform their respective parts. Friendship can’t be allowed to undermine the operation. Friends are important, but business is unforgiving; every player has to do his or her part or else the venture fails. So, be friendly … But run your business as a business.
 Another popular lesson that my platoon sergeant taught me before I pinned on corporal stripes was ‘You don’t have to like your soldiers, but you must love them.’
 In Texas, a company can do business under a different brand name by filing a … wait for it … ‘Doing Business As’ form. It’s a way for the state to ensure that the correct taxable business entity gets taxed and audited correctly.
 We wanted a brand name that evoked Texas culture. The two of us had also traditionally breakfasted on Mexican-style barbacoa before heading off to weekend field manoeuvres with the ROTC battalion during our university days. Seemed like a logical fit.
Title Allusions: Eric Lavaine and Héctor Cabello Reyes, Barbecue (2014 film); released in Spain as Barbacoa de Amigos.
POC is Keil Hubert, email@example.com
Follow him on Twitter at @keilhubert.
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. ‘bloggersince 2012. His books on applied leadership, business culture, and talent management are available on Amazon.com. Keil is based out of Dallas, Texas.