How to Manage Any Problem–in 5 Easy Steps!

So, you’ve just been appointed manager of a high-performing tech team. Congratulations! You are on the fast track to career success.

One of the most important skills you’ll learn as a manager is what to do when your team discovers a major issue that threatens to miss deadlines, lose customers, or Leave Money on the Table. You may be tempted into thinking, “wow, we are in a real pickle now, but I don’t understand the system or have any special skills, so I’d better hope my team can come up with a solution!” Of course, you and I both know better than that. It is completely WRONG for reasons that probably exist!

Fortunately, this is actually a very easy situation to deal with, using a scientifically proven 5-step process that is 100% guaranteed. It is actually an iterative process based loosely on the “OODA loop” popular in military strategy, which stands for: Obscure, Oversimplify, Distract, Aggravate. Here is the patented process adapted for business managers.

Step 1: Ignore the Problem

Let’s be honest, you spend 7.2 hours a day in meetings, and must use those precious breaks in between meetings to refill your coffee mug and not listen to Status Updates that you request. You don’t have time to actually read your email. All but the most incompetent managers can perform this step naturally and without effort.

But wait. You aren’t just any manager. You are a high-powered, high-efficiency, Hands-On Manager. You want to Demonstrate Value. It is not enough to simply passively ignore your email. You might see a stray subject line and become curious enough to click on it. So it is very important that you actively, militantly ignore any and all emails relating to the problem, to avoid accidentally becoming informed of any of the technical details.

While you are doing this, your team has likely already found the root cause, identified possible solutions, and estimated how long they will take to implement. Do not allow this to divert you from your primary goal of remaining completely and totally oblivious to the problem.

Step 2: Wait for an External Complaint

Sometimes you will be lucky enough to have a real, actual Customer Complaint from a real customer who, despite your crack Customer Care team’s best efforts, somehow navigated successfully through the Choose-Your-Own-Adventure Voice Navigation telephone game and was able to speak to your one on-duty Human Representative. But this is not very likely. A much more reliable source of complaints is Higher-Ups, such as your Boss and your Boss’s Boss and so on, all the way up to the CEO.

If all of these people hate your product, which is often the case, you can entice them into trying it out again with the prospect of an Exciting New Feature. Yes, you’ll say, I know you hated it before, but we added a new feature! You must try it! Keep at it and eventually they will complain to you about the broken thing that your team has now been working on for 7 weeks.

Now you are in a New Situation. The problem is the same, the solutions are the same, the estimates are the same, but now you have the special sauce called Visibility, which you can transmute into Urgency using the power of Concern. As in: “I am Concerned that the CEO has started to notice that you are being productive without me, and therefore it is Urgent that I provide evidence of me doing Actual Work.”

Step 3: Call a Meeting

Both your Higher-Ups and your Minions understand intuitively that Meetings Solve Every Problem. Need to track progress? Have a Status Meeting. Need to communicate with the person who sits 2 feet away? Hold a Sync Meeting. Need to remind everyone that you are an Effective Can-Do Manager? Have a Review Meeting. Meetings are the ketchup of office work. There is nothing that they don’t make better, not even double chocolate donuts.

After several weeks of working on this exact problem, some of your subordinates may have gotten the crazy idea into their heads that they might be able to solve the problem on their own. Ha HA! Those jokers. What you need is a Discussion, so send out that invitation. For optimal results, send it out on the same day as the meeting itself, preferably no more than 2 hours in advance, and mark it as “important”.

DO NOT, under any circumstances, include an agenda or any summary of what you plan to discuss! This might allow some participants to prepare in advance, which might result in the mythical “Short Meeting” or “Early Ending”, which would leave you confused and unable to function between the end of the Discussion Meeting and your next meeting. Keep the subject line short and simple: “Discuss <PROBLEM>”

Step 4: Demand Easy Answers

Start the meeting by reviewing the short and incomprehensible report provided by the Customer, Higher-Ups, or other External Complaint. Ask your most senior members for an Explanation of the issue. At this point, some managers like to reject the Explanation and provide their own Alternate Explanation based on Clogged Pipes, Cosmic Rays, or Demonic Possession. You can adjust this to your preferences. Your version will be proven wrong, but the objective here is not to demonstrate knowledge, only to extend the duration of the meeting.

Once your team reaffirms the root cause and explains the solutions they are looking into, begin to make subtle suggestions that their solutions are ineffective, too complicated, or too time-consuming. For example: “I am worried that by the time this solution is implemented, everyone will have forgotten my contribution in the form of Taking Sixty Minutes out of your Day by having this meeting.”

Be creative with your criticism. Make sure to say prioritize and urgency a lot. Also try using synonyms like Triage and Stack Rank. If the meeting is progressing too quickly, ask the team to “deprioritize” some tasks that all of the other tasks obviously depend on, then watch as hilarity ensues. But most importantly, you’ll want to express deep concern that the solution could Take Too Long. Continue hammering the point, until the meeting is over, that there must surely be a Faster Way or an Easier Way and that if only Someone Other Than You could be a little more creative or clever, it could be done in 1/10th of the estimated time.

Step 5: Hover Over Team Members

You may have time to do this in-between meetings. However, in this one and only instance, you may have to cancel an existing meeting in order to perform this task.

Your mission is to Help the various people on your team until they give you a clear sign that they Understand and Appreciate Your Help, such as by saying “thank you” or killing themselves by jumping out a window or, for first-floor offices, drowning themselves in a restroom stall.

There are many techniques for doing this and it all comes down to your personal style. However, my personal favorite is the Helicopter Technique, wherein you pop up out of nowhere, run around from person to person looking very Concerned and Sympathetic, and eventually decide to sit next to the one who appears to be concentrating the hardest. I like to follow the Helicopter Technique with the Furious Tapping Technique, wherein I move the mouse and click things at an estimated rate of 28 times for second, periodically remarking on things I see on the screen, such as: “Hmm, is that thing over there supposed to do that?” or: “Does it bother you that I was picking my nose before I took hold of your pointing device?”

Eventually, after a few days of hovering, your team will start to become unproductive and stressed. Your work is now done, and you can resume your normal regimen of meetings or better yet, take a vacation.


You have successfully Demonstrated Value in a time of Crisis while under Extreme Pressure. Top executives will have noted your Proactive Approach and Leading By Example. Keep it up, and you might soon be Director or even Vice President!

I hope this guide helps jumpstart your career in management. Good luck, and remember: Your team needs you!


Why Oligopolies are Evil: The United Airlines Beatdown

United Airlines is in the news again, and as any reasonable person would predict, it’s not because of their extensive humanitarian efforts. For those who haven’t already heard the whole story or don’t want to slog through the New York Times article (or just don’t want to give them the clicks), here is the sequence of events in a nutshell:

  • UA overbooks a flight. Standard practice, usually no problem because passengers don’t show up.
  • The flight ends up being completely full. At this point, all passengers have already boarded.
  • Some low-level UA employees decide they belong on the plane, and some passengers who have already boarded will need to get off.
  • They offer a $400 pittance for people to give up their seats. No takers.
  • They offer an $800 voucher (negotiating lesson: always reject the first offer). Still no takers. Apparently – and this may surprise you – people traveling on business or who booked their vacations months in advance, spent 2+ hours at the airport and followed all of United’s draconian rules, are not too keen on giving up their professional and social lives in order to help some needy guitar exterminators.
  • They then announce that they will randomly boot 4 passengers off the plane.
  • The first 3 comply. The 4th, an Asian man, says he is a doctor who needs to get back to his patients and refuses to leave.
  • United staff decide that it is not worth the trouble and leave the man to enjoy a peaceful flight.
  • Hahahaha, of course they don’t do that. Instead, the doctor is dragged literally kicking and screaming out of his seat, and his face is smashed and bloodied on an armrest on the way out.
  • United makes a public statement indicating that they give zero fucks because the man was being “uncooperative” with their attempt to kick him off the flight for no reason at all.
  • United’s CEO, who just a few weeks earlier had been named Communicator of the Year, weighed in with another non-apology for “re-accommodating” the man whom they beat up.

This was all quite hilarious to watch play out, or infuriating if you’re wired that way. But here is the really depressing part:


This is the kind of PR disaster that should, in a just world, sink a company, or at least give them a good spanking in the stock market. What actually happened was: crickets, because every single trader out there worth his salt knows that all US air travel is owned by just 4 companies. You basically can’t lose with these guys, and any sudden dip is just an opportunity to increase your holdings. Unlike Starbucks, you can’t really hurt United’s brand, because their brand is already worthless; expectations of shareholder returns are based on sheer necessity, not brand perception.

It was, of course, not always like this. You may remember when there were 10 airline companies. But I was curious to see just how deep the rabbit hole goes, so I looked this up. It turns out that there have been dozens of smaller to medium-sized airline companies since air travel became popular:


It’s astounding. Delta alone seems to have congealed from over 15 distinct airlines at various times.

Oligopolies are to monopolies what oligarchies are to monarchies. Having more than one player on the field doesn’t mean they’re on different teams, and certainly doesn’t mean they’re playing to win. Oligopolies stifle innovation, and while some kooks blame “deregulation” for what happened to the airline industry, the truth is that air travel is massively regulated, including for example pages upon pages dedicated to how non-pilots need to be certified. If detailed requirements for carry-on tubas are “deregulation”, you don’t want to know what the “regulated” version looks like.

It’s interesting how the people fretting about cost disease always seem to leave out air travel; airfares haven’t actually gone up that much relative to inflation since the golden age, but the quality of service fell off a cliff, hidden costs such as baggage fees are everywhere, and if the market was working properly then average airfare costs should have gone way down. How did an industry that provides an essential service for so many people manage to stagnate so badly and kill off any flickers of genuine innovation or entrepreneurship? (And no, shoving a smudge-covered TV screen with a credit card slot into the back of each seat is not “innovation” in an era when most passengers already have video-capable personal electronics.)

Theories on the sector’s slow decline no doubt abound, as they do with health care, college, and so on. From a macroeconomic point of view, however, it looks like just another casualty of neoliberal corporatism. For example, the airline industry received a massive bailout in 2001 – around the same time that the final wave of consolidation began and new players stopped appearing. But that’s small potatoes compared to the $155 billion in subsidies that carriers received prior to the bailout. Just as TARP gutted the small banks and credit unions by giving the Wall Street cartel an unfair advantage, the massive airline subsidies very likely gave airlines like United, Pan-Am and TWA unfair advantages over the smaller upstarts, which they then used to crush and subsequently buy out those upstarts. Those that they couldn’t buy, they regulated (via the feds) into oblivion. I am speculating, of course, but industry transparency is so pathetically low that I don’t think we can ever know for certain.

Correlation is not causation, but it’s hard not to notice the clear historical correlation between regulation, subsidies, and monopolization. Now let’s all sit back and enjoy the quality services of United Airlines, United Health, Comcast, Viacom, and Verizon.

The Weakest Link: Transitive Trust

Raise your hand if you remember going through this sequence of events at least once in your life:

  1. You have a favorite doctor, hairdresser, babysitter, or some other professional whom you trust.
  2. One day, that person isn’t available. Maybe they are sick, vacationing, retiring, or moving away.
  3. “But don’t worry!” they say. “I have a friend/colleague who will take great care of you. Here, I’ll introduce you.”
  4. You follow their advice… and immediately regret it. Their replacement is awful. Incompetent. Maybe even rude.
  5. It takes several days or weeks to clean up the mess, and then you have to start from scratch on finding a new replacement.

If this story sounds familiar, then you’ve experienced firsthand the problem of transitive trust: You trust person X, exclusively. Person X trusts people Y and Z and chooses to delegate your trust to them. Depending on what they are delegating, the consequences can range from minor nuisance to life-threatening disaster.

During my Infosec days, I was introduced to this problem when my small employer was bought by a larger corporation. We had our network, and they had theirs. Our employees needed access to their network, and vice versa, but one of us had a much stricter security policy. That meant several months of periodic outages, lockouts, general confusion, and painful arguments about the policy itself.

Another example in the tech world is ads; even if the folks who run your favorite news site are squeaky-clean, they may choose an ad network that does not properly vet its advertisers, thus exposing readers to malware. Ad blockers are becoming a security feature.

Later on, I learned that this problem doesn’t only apply to systems; it also applies to people, as in the first example above. The difference is, in meatspace, we usually see it as an isolated incident and fail to identify the earliest point when our decision-making process started to go wrong. Many if not most of us will even continue to make this mistake over and over again, assuming that trustworthy or competent people can reliably deliver us other trustworthy or competent people, even though events rarely play out that way.

The human version of the problem is simple: Doing is not the same as delegating. They are different skill sets, but for some bizarre reason, our brains seem hardwired to believe that they are the same. It’s true that those with a certain skill are better at recognizing that skill in others via the quality of their work or technique; for example, I can easily identify a great coder by looking at their code, but can’t evaluate a football quarterback very well by watching them play. However, even if my skill assessment were perfect, trust in a person depends on much more than their ability to perform a task. There are social factors involved; work ethic; general intelligence; verbal/language skills; etc. I might, for example, have a high tolerance for tardiness in my colleagues, but if I’m not tardy myself, then a client of mine might be angry if I referred them to colleagues who were.

Smart companies who depend on highly-specialized skill sets recognize that this problem also applies to hiring. We hire people, who will eventually hire other people, who hire more people, and so on. The success and reputation of the company depends heavily on employee competence, so by necessity, we have a very difficult and complex hiring process that requires significant training and vetting for interviewers, involves several non-interviewers, and is extremely biased toward no hire. The consequences of taking on even a single unqualified hire are potentially catastrophic, if they manage to hire others who are worse than themselves. Despite all of these safeguards, bad hires have started to creep in, due mainly to constant pressure to “streamline” the process (AKA: lower the bar).

On the flip side, companies that don’t understand the Do vs. Delegate distinction can get into a lot of trouble, which is why many startups fail during the initial growth phase. At one startup where I worked, the founders were sales guys. They were phenomenal at sales, racking up huge contracts every few weeks. Eventually, however, they needed to dial down their sales activity to actually run the business; that meant hiring other salespeople. Surprise: those people were mostly awful. One simply underperformed; another was a blowhard who annoyed everyone else in the office. Then they took on a sales manager, who hired three other salesbots who were all fired on the same day for some serious ethical violation that we weren’t allowed to know the details of. Growth stalled out, because the customer trust that the founders had built up was subsequently broken by the founders’ delegates.

In systems and in life, it’s best to avoid second- or third-degree trust. Be suspicious when a person or institution you trust is telling you that you can trust a third party whom you’ve never met nor heard of. They may have good intentions, and there’s nothing wrong with following up on a referral, but treat that referral as you would any other unknown, starting with zero trust and plenty of skepticism, and keeping your options wide open. This applies to everything from your professional contacts to family friends to the news you read.

If you ever need to inflict this situation on someone else, be transparent about your actual level of trust and familiarity with the third party, and expect a rough transition. Like it or not, your own credibility will take a hit if your surrogate causes a trainwreck.

Bonus round: Consider how the transitive trust problem might affect larger institutions, including governments and entire nations.