Planning Team Personalities

Colonel Daniel Sukman – Chief of Strategy, Joint Staff (Pentagon).

Dan is a recent graduate of LBL’s Mastering Strategy bootcamp hosted by the Army Strategist Association.

 

Ultimately, the team has to come first even though we all have individual goals and preferences.” –Bill Belichick

Some of the greatest coaches in professional sports include the likes of Joe Torre, Scotty Bowman, Phil Jackson, and Bill Belichick. What made each of these coaches great was not their ability to draw Xs and Os on a clipboard. Rather, each had a unique ability to manage teams with multiple superstars and role players to multiple championships.

For example, Joe Torre managed the 1990’s New York Yankees to multiple championships with a team composed of superstars such as Derek Jeter, Roger Clemens, and Mariano Rivera. Of Scotty Bowman’s multiple Stanley Cup teams, the 2002 Red Wings. Red Wings were composed of a stable of future hall of famers to include Steve Yzerman, Luc Robitaille, Sergei Fedorov, Nicklas Lidstrom, and Dominik Hasek. Phil Jackson’s Bulls had arguably the greatest basketball player of all time in Michael Jordan playing alongside hall of famer Scotty Pippen. Later in his coaching career, Jackson managed the personalities of Kobe Bryant and Shaquille O’Neal to three consecutive NBA titles.

Each coach understood that the key to winning was the ability to maximize the talent on his respective team. Talent includes the superstars who make tens of millions of dollars each year just as it includes players at the bottom of the roster earning the league minimum. The demand of professional sports coaches and managers to lead an assembled team of unique personalities is similar to what we demand of operational planning team leaders.

Often, planning teams contain members of the staff across each J-code directorate, and members of various divisions and branches within each directorate. Each of these members brings with them a unique personality and contribution to the dynamics of the team. Leaders in the staff must understand the various types of personalities they will encounter to effectively run an OPT, enhance the quality of discussions, and to provide a commander the best course of action. I offer a litany of archetypes that OPT leaders may encounter.

          The Strategic Philosopher: The philosopher talks a big game and can cite Clausewitz, Sun Tzu, Jomini, and other historical strategists at will. However, philosophers do not see themselves as action officers. Never ask a philosopher to create a power point slide, information paper, or any other actual product. However, you may find they will be glad to tell you what is wrong with your products at nausem.  To deal with a philosopher, the key is to channel their energy into a productive direction by capturing their thoughts on a white board or slide and move on.

          The Debater: Nothing escapes this planner. The debater is happy to spend an hour discussing a single line or word in your facts and assumptions. Often, the debater forms an emotional attachment to their respective point of view. The OPT will concede their point repeatedly again just to stop the debater from talking. After hours of vigorous debate, when it comes time to brief the commander, the point of contention and rigorous discussion is passed over in half a second with a head nod. The debater likes to think of himself as a red-teamer or devil’s advocate rather than the obstacle to planning that they are. It can be very difficult when someone decides to pull a filibuster in your group. There comes a point when healthy debate is no longer productive or becomes outright unprofessional.  If an issue is too thorny or the debate too passionate, the group lead should acknowledge the issue and then put it in the “parking lot” to be addressed later. One other thing that can work well is to spin off a sub-working group and put the debater in charge of resolving the issue.

The “parking lot” comes into play when the OPT has discussed an issue at great length but is unable to decide on an outcome. At a set time, the OPT leader should halt the conversation, write down the issue on a whiteboard (the parking lot), and move on to the next topic. After lunch, at the end of the day, or the next morning following a good night’s rest, the OPT looks at the “parking lot” and returns to the unresolved topics. Often, having additional time to think and reflect on a problem can lead to a better and more amicable resolution.

          The Tactical Genius: OPTs occur at the strategic and operational levels of command, but this guy wants to brief the risk of a single soldier dehydrating in the heat. Loss of basing rights and strategic access is of no concern to the tactician. The tactician is comfortable with troop leading procedures, but afraid to jump into the elements of operational design. Tacticians are useful in reminding the members of the OPT why prudent planning is important, in that the outcome will affect Soldiers, Sailors, Airmen, and Marines on the ground. The tactician hates staff work and will constantly remind others of that fact. The tactician is in a way the evil twin of the strategic philosopher. In dealing with the tactical genius, keep in mind that people are most comfortable with what they know well. The leap from tactical thinking, to an operational or strategic thinker is a difficult leap that many officers cannot make. The best way to get the tactician to think broader is to translate the problem at hand into terms that they understand. You can also try to draw deeper strategic lessons out of the tactical vignettes that they share with the group.

         The Grammar Nazi: No one is better at spotting a missing Oxford Comma within an order. The grammar nazi is useful to the OPT for proofreading products but will often side with the debater in making the point that passive voice is unacceptable. Don’t expect much creativity but retain him on the team for his proofreading and writing skills.  The best way to deal with a grammar nazi is to ask them what the document or product should say. That way their thinking is on display and they become part of the solution instead of part of the problem.

          The Doctrine Nazi: Like the grammar nazi, no order or CONOP will escape the jackboot of doctrine. Heaven forbid there is a word or phrase that does not match what is written in a joint publication or service field manual. The doctrine nazi is difficult to argue with because they are using a classic appeal to authority to make their point.  It is important that doctrine does not become dogma, and it is rare that doctrine will provide the exact answer you need. To deal with the nazi, ask leading questions about the nuances of the context and situation that make the problem you are dealing with novel in some way.

          The Chaff: Does the font on slide 7 not match the font on slide 22? No worries, the Chaff will point out this glaring error that will more than likely invalidate the entire concept of the operation. The chaff provides no actual content or intellectual rigor in planning but is essential to formatting and uniformity in the brief. The chaff can be dangerous, especially when it is a senior leader. The best way to handle the chaff’s concerns is to note their comment and move on. Further, it may be useful to place the Chaff on night shift as a way to edit PowerPoint presentations before a briefing to a senior leader.

          The Costanza: This person has one line they must get into the brief at all costs. It may be a single fact or assumption in the mission analysis, or a nuance in the command relationships chart. Normally, a two-star told the Costanza to get that piece of information into the brief at all costs. You get this from the Costanza once a day, but as soon as it happens the Costanza is walking out of the OPT planning room on his high note, not to be seen until the next planning session. Keep in mind that some officers are not empowered by their superiors. To get the Costanza working for you instead of against you, ask them to approach their boss and get feedback that you can use for group work

          The Professor: One of your foremost experts on anything the OPT is tasked to do. The professor is happy to take the OPT through the crawl, walk, and run phases of mission analysis. Unfortunately, you only have two hours to get the final product in front of the commander. Professors often fail to understand the consequences of this timeline. The professor believes they learned from the best and will usually identify themselves as a graduate of the program that makes them the authority.  To address the professor’s concerns, develop a detailed time schedule up front and keep the group to it.  If you are the leader of the working group, lead it. If you do not, the professor will gladly lead it for you.

          The Guy from Band Camp: Every point or discussion begins with “When I was in Iraq” or “This is how we did it when I was in Afghanistan,” followed by a eight minute soliloquy on why his way is the only way. Again, people are shaped by their experience, and this can be a good or a bad thing.  Hear them out but ask them leading question to get them to apply their experience to the context of the problem at hand.

          The Wordsmith: This individual will ensure the OPT works until the very last second. Every word on every slide has a synonym that conveys a better meaning, is more direct, or better conforms to doctrine. Much of this wordsmithing occurs after approval of the brief by a general officer. Word by word the plan does not change, but by 3 in the morning the plan is completely unrecognizable to the original product and you are left explaining to a flag officer why you completely changed the plan. Of course, words matter, but if the debate over words derails the working group and becomes counterproductive it is the responsibility of the lead planner to intervene.

          The Wallflower: The wallflower attends every OPT meeting and sits quietly through each planning session without saying one word. He may be good for getting coffee or a food court run, but don’t expect any production. In fact, the wallflower is mad when you ask him to make coffee for the group as he was changing his Facebook profile picture when you asked. Although he provided no content to any product, his “participation” and “valuable input” in the OPT is annotated on his OER and end of tour award.  Some people are naturally introverted, and that is o.k.  Try to get them involved by asking them leading questions and getting to know them better. You may also want to approach them after a group session and ask for their feedback one-on-one.

          The Escape Artist: First cousin to the wallflower. The escape artist shows up to each planning session to ensure his name is on the sign in roster…and that is the last time you will see him for the day, unless you bump into him at the gym, the PX, or the food court. The escape artist will do anything to avoid sitting in the OPT, to include crawling through 500 yards of human waste a-la Andy Dufresne escaping from Shawshank. He may return for key briefing, but only if his boss is expected to attend as well. If someone is determined not to be part of the team, there is little that the working group leader can do to bring them into the fold. Try circulating a sign-in roster at the start of every group session, that way at least they know that someone is noticing their absence.

          The Ghost: Second cousin to the wallflower. The ghost will show up the first day of the OPT, never to be seen again. The ghost may be a competent and hard worker, but your OPT does not rank high on his or her list of priorities. You email the ghost only to receive an out of office reply. The ghost may be on leave, receiving household goods, or working on his masters degree. The ghost is in many places, just not where you need him.  To deal with the ghost try to make them a member of the team. Instead of chastising them for their lack of participation, acknowledge those people that are contributing and then ask the ghost to add their two cents.

          Super Crazy Acronym Guy: Spouting out acronyms nobody understands at a cyclical rate is this person’s modus operandi. Acronyms provide a cover to conceal their respective ignorance and overall lack of awareness, yet somehow everyone just nods their collective heads when he speaks. When the acronym guy speaks, tell him that you do not know what he means and ask him to explain.

          The PowerPoint Ranger: Present in every OPT. The PowerPoint ranger has the intellectual capacity to match anyone on the OPT. However, due to his or her youth and competence with modern technology the OPT lead will put them in front of the computer to nug on slides. Fortunately, the PowerPoint ranger has leverage and knows it. Ultimately, the person creating the slides is the gatekeeper for anything the commander will see. Like the freshman in college with a car, making friends with this guy is essential for success. The PowerPoint ranger is drawn to the keyboard like a moth to a flame.  To ensure the knowledge and wisdom of the PowerPoint rangers in the OPT are applied to the problem set, occasionally, rotate them out and make them sit back and think.

The Anchor: Occasionally, a staff directorate will send their newest planner to participate in the OPT. Often, the new planner has no actual planner experience, having spent the better part of their career at the tactical level, driving ships, or flying airplanes. The Anchor does not understand the planning process, nor does the anchor understand how to fulfill his or her expectations. Indeed, a fresh planner with little to no experience requires more direct oversight and detailed explanations of each product the OPT develops. And much like the anchor of a ship, this OPT member can bring the planning group to grinding halt. To effectively manage an anchor in the OPT, consider assigning a seasoned planner as a guide or mentor. With a little enthusiasm, leadership and investment, the right OPT leader can transform the anchor into a member of the OPT core.

The Seagull: This planner floats above the OPT. Rarely seen until the rehearsal brief when he or she will then shit all over the product. The seagull will offer no solutions to all the problems with the plan, and frankly does not understand why nobody likes them.  It is best to not let the seagull derail things. The best way to deal with the seagull is to acknowledge his point and move on to the work. It is all right to say, “thank you for your input, we will account for that accordingly.”

The Senior Leader: Often, a senior ranking person will be a part of an operational planning team. Rarely a general officer and most commonly a colonel or navy captain. These OPT members are intelligent but can often think of themselves as the de-facto OPT lead, when in fact they are merely a member. This can lead to the senior member waiting to speak last in all conversations, with the self-understanding that his or her word is final on the subject at hand. To overcome this obstacle, OPT leaders should try to engage the high-ranking individual in the OPT in the middle of the discussion, or continue the discussion after the colonel / captain speaks. Moreover, there are a variety of Red Teaming techniques detailed in this handbook that are useful to ensure no voice is silenced from an over burdening officer.

The Bad Apples: In his book The Power of Bad, John Tierney describes three types of bad apples.[1] Further, he describes how each type can undermine positive dynamics within a group. The first bad apple is the slacker. The slacker will always show up, although he will show up late. The slacker will spend half of his time working on a product, and the other half scrolling through and updating his social media pages. Products will be riddled with grammar and spelling errors and will require time from the rest of the OPT to fix them.

The second bad apple is the downer. No matter how anyone else in the OPT is feeling on a particular morning, the downer will take the time to tell a sad story. The downer is a pessimist, who will continually advise the OPT that their products do not really matter, and that the OPT will probably miss its deadlines.

The third bad apple is the asshole. It is a harsh, but completely appropriate word to describe some of the toxic personalities that can infect the OPT. The asshole will talk behind people’s backs. He will mock members of the OPT, openly criticize products that he spent no time working on, and less time understanding.

The best method to deal with a bad apple in the OPT is to get rid of them. Disinvite them from the OPT, remove them from the access roster, bluntly tell them their services are no longer required. Sometimes this requires asking the boss to speak to the bad apple’s boss to have them assigned to another project, and hopefully one that they can work on alone.

          The Core: This is a group of individuals. Where they work on the staff is irrelevant to the products they produce, and the intellectual capacity they bring to the team. Out of a group of 20, there may be only six or seven core members. They arrive early, work late, and put together the briefings and orders over the course of multiple 16-hour days. Often, you may catch them together in the dining facility taking a 15-minute break to eat their one meal of the day. At the end of the day, all the core members want to do is see their family for a couple of minutes after their workday and before they fall asleep. The core is happy to leave the building, and often let others get drunk and take the credit for their work.

To get the most of any group, it is important to establish the accepted norms of behavior up front.  A group leader can of course dictate norms but is much more effective if everyone in the group has a vote. This way everyone can understand what is expected and what is not.  When you take the time to establish norms there are no surprises. Try printing out the norms and post them in the OPT room.  When someone is talking to excess or derailing the work remind everyone what the rules are and bring the group work back on track.

Leadership at the operational and strategic level is about the ability to manage personalities. Like the task of professional sports coaches, the better one can meld the disparate group of individuals into a team, the greater the success of the organization. Legends such as Phil Jackson and Joe Torre understood this aspect of group dynamics. Their ability to manage and get the most out of everyone on the team from superstars and third stringers is the genius behind their success. OPT leads would be wise to study their methods to manage everyone on the team from the PowerPoint ranger to the elusive ghost.

 

[1] John Tierney. 2019. The Power of Bad: How the Negativity Effect Rules US and How We Can Rule It. Penguin Press.

A smaller and edited version of this chapter originally appeared on Task and Purpose: https://taskandpurpose.com/16-people-make-every-operational-planning-team

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Colonel Daniel Sukman