By Mike Holley
First Assistant District Attorney in Montgomery County
Leadership is the art of influencing others to accomplish an objective. Traditionally, we think of leading those we directly supervise, but this is only one aspect of leadership. We also seek to influence our co-workers and those outside our organizations. One very significant class of “others” we influence are those who supervise us. This is what “leading up” means.
You may ask, why should I try to lead up? Why is this important? There are several reasons, and here are three:
First, if you can help your boss to more skillfully supervise you, you will enhance your own effectiveness. From a different angle, if you lead up well, you can mitigate a bad or struggling boss’s negative effects on your work. Additionally, you will improve your own supervisory proficiency as a byproduct of your efforts. You will have made yourself better.
Second, if you help your boss improve as a supervisor, you aid others in the office. Enhancing your boss’s skills benefits everyone your boss supervises now or will ever supervise in the future, not just you. The value you provide to your fellow employees multiplies over time and across your organization. You will have made the entire office better.
Third, if you can demonstrate how to follow well, other people in non-supervisory positions will emulate your example. Good leaders are good followers, and good followers tend to support one another. An office of good followers creates a powerful and effective team—and a happier one. Once again, you will have made the entire office better.
So, for at least those three reasons, leading up well is something to be pursued. And, unless you happen to be the county attorney or the district attorney, leading up is something you will have to do, whether you want to or not.
How to lead up
The starting point is the “grand unified theory” of leading up. This principle is not perfect (we will touch on its limitations at the end), but it will guide you in a thousand decisions. Here it is: “Be the kind of follower you want to lead.”
Simple, right? Yes, but deceptively so. This principle requires us to act with professionalism and dignity even when we are being mistreated. Which is hard. The principle calls on you to be your best self, even when others are not doing the same. Which is also hard. Still, as the Mandalorians say, “This is the way.”
But what does leading up look like, practically? This article contains specific guidance to that end, but I have an important caveat before we go further. Some of you are struggling with your work so much on a daily basis that the thought of trying to lead your boss seems overwhelming. Please do not be overwhelmed. Seize what helps you now, and save the rest for later. “Leave the gun; take the cannoli,” if you will.
Clear and effective communication
Your boss wants you to keep him “informed.” An immediate tension arises. He does not want to know everything, just what is “important.” And “important” is often a moving target, even and especially to your boss. (Here’s a quick set of definitions. Important: What you did not tell your boss but should have. Unimportant: What you did tell your boss but should not have.)
Here are three suggestions to help strike the right balance:
Press information consistently upward. This may mean daily or weekly updates on your work, or it may mean periodic briefings on major projects or developing problems. Update with intention, but do not flood your boss with too many details. How many details are too many? This depends entirely on your boss. Some bosses require a level of detail that bleeds into micromanagement, something we will discuss below. Too few details, however, and your boss will be unprepared to answer to his or her own boss when information is sought, or to give you good counsel when needed. If you are concerned the level of detail you provide is too much or too little—ask your boss. Adjust. Periodically ask again. If little to no information is flowing upwards, you are doing it wrong. Trust me on this—keeping your boss well informed is a powerful tool in leading up, and good communication covers a multitude of sins.
“Set apart” things of significance. Your boss is busy and overwhelmed, although he may not appear to be. (The same is often true for you.) When something is important, you must find a way to set the information apart so he sees the significance and can act in a timely manner. You may do this in writing, in person, or both. As advocates, you know how to communicate the urgent and the important. (There is a difference between “we are doing routine inspections on the dam next Thursday” and “the dam is collapsing right now!”) In extreme cases, it may mean grabbing your boss by both shoulders and saying, “Seriously, listen to what I’m telling you right now!” It may mean scheduling a formal meeting and making a PowerPoint presentation. It may mean a memo with the critical idea in red font at the top. It may mean repeating a message again and again, just as we do in trial. Figure out what works with your boss and do that thing. Be creative and adaptive, as leaders are required to be.
Give your boss bad news before you share it with others. Put another way: Never communicate bad news to your boss’s boss first. Never. You would not welcome this behavior from someone you supervise; do not do it now. Good news? Praise? Compliments? You may be able to share any of those with your boss’s boss first. But bad news, never. Tell your boss first. If you take away one thing from this article, make it this. And when you tell your boss about bad news, have a proposed solution at hand or have the problem already fixed. But—and this is significant “but”—take care not to delay too long to do either. Most good bosses would rather know about bad news sooner rather than later, and there is a direct correlation between how easily your boss can fix a problem and how quickly you tell him about it. Telling your boss bad news first is generally an act of loyalty, a topic we will cover next.
The duty of loyalty
Loyalty is a much-maligned and much-misunderstood concept. Often loyalty is used in a one-way manner: I am loyal to my boss, but my boss is not loyal to me. Or loyalty is described as blind allegiance irrespective of the truth. Neither of those descriptions is true loyalty.
Loyalty is a principled commitment to a cause or a person. In your case, it is both. You are committed to your office’s mission, and you are also committed to the person you work for—in that order. At a minimum, loyalty includes the following three concepts:
1. As a loyal follower, honor your boss with candor. Candor means telling him what you honestly think about an important matter. Do so in an acceptable way that your boss will receive—the right time, the right tone, and the right attitude. You express your opinion clearly to your boss. You do not withhold your views from him only to share with others. You offer your opinion—often asking for permission to do so first—at any time you believe your opinion may be needed by your boss to accomplish the mission. The acid test of loyalty comes after you express your opinion. If your boss chooses another option—assuming the choice is ethical—you adopt your boss’s decision with the same passion and resolve you would as if the decision were your own. As you implement your boss’s decision, no one—especially those you supervise—should know you initially thought otherwise. Further, you should not borrow your boss’s authority when telling others about the decision. Do not say, “Well, the chief wants X done.” This approach is not leadership; it is an abdication of leadership. Nor is it loyal. Say, “I want X done” or, if necessary, “The chief and I want X done.”
2. As a loyal follower, prioritize your boss’s success over your own. Work harder to make your boss look good than you do making yourself look good. Will this sometimes result in unfairness? Absolutely. In fact, I guarantee it will. Still, the truth will eventually become apparent to all. If you do good work, people will ultimately see it. If you are mostly concerned about accumulating personal glory, people will see that, too. On the other hand, if you are more intentional about making your boss succeed and making him seen as a success, then sooner or later, things will work out for both of you. Or at least for you. In any case, this is what loyalty requires.
3. As a loyal follower, complain about your boss the right way. We can all agree government employees have an absolute entitlement—nay, a duty—to complain. The right of a public servant to complain is in the U.S. Constitution. Complaining can be healthy, right up until your complaining undermines your boss’s ability to lead your team in accomplishing the mission. There is, then, a right way to complain and a wrong way to complain. Let us be honest with one another: You know the difference between the two. You do. Do the one, not the other. If you genuinely do not know the difference, there is some guidance in this endnote.
One other point about loyalty: I said you have two objects of your loyalty—your boss and the office’s mission. Your ultimate loyalty lies with the mission of the office. We should note together that the mission of every public office in the state of Texas requires ethical behavior in all situations and at all times. A boss who asks you to do something unethical is breaking loyalty with you and with the mission. Fortunately, this is not a common occurrence, so you should normally be free to serve your boss with confidence and to the best of your abilities. One of the ways you can serve your boss best is by helping him improve his own performance, which is our next topic.
Improving your boss’s performance
Not every boss is great. There, I’ve said it! And even the best of bosses is not always perfect because people are not perfect. Leaders strive to improve performance with everyone with whom they interact, and improving our boss’s performance is no different. Here are three considerations as you do so:
1. Work intentionally to make your boss better. Your boss likely takes actions (or fails to act) in ways that have negative consequences he does not fully appreciate. Gently, professionally, respectfully, but clearly explain those consequences to him at the right time. (You may want to ask for permission first.) Along those lines, you should encourage your boss, and do so regularly. Everyone needs encouragement, regardless of how strong he appears to be. Especially encourage good behavior or progress in problem areas. Does your boss have a propensity to yell? When he does not yell when correcting you or someone else, tell him how much you appreciate the professional manner he took in addressing the deficiencies at issue. Does your boss “bottleneck” decisions (meaning, hold on to things longer than he should so you cannot act)? Then be sure to recognize when he makes timely decisions, and tell him how much you appreciate his decisive action and how helpful his timely decision will be to the team. Does your boss struggle with leadership principles generally? Talk to him about leadership ideas when you can. Read leadership books yourself, and discuss those books and concepts with your boss. (Willink and Babin’s Extreme Ownership and Lencioni’s The Ideal Team Player are good examples to share.) In short, just as you help your subordinates develop, help your boss develop, too. We can all use help, and providing help is what leaders do.
2. Identify the different varieties of micromanagement and deal with them accordingly. Micromanagement is a perennial complaint about bosses, and micromanagement works directly against a boss’s effectiveness. But micromanagement comes in different flavors. Here are the main micromanagement categories and a response to each:
Boredom. Your boss is bored, so he begins taking your work as something to do. This type of micromanagement is the easiest to deal with—find something constructive for your boss to do. Direct his work in a way that meaningfully helps you or the greater mission: “If you have time, I’d appreciate it if you would look into this thorny jury charge issue for me.”
Trust. Your boss does not entirely trust you. Ask why. Find out if there is something you can do to repair a breach of trust and raise the level of trust. Take it head-on and ask him directly. Do not do anything to undercut this trust. Also, be patient. Trust usually comes with time.
Insecurity. Your boss is insecure. Insecurity is the most challenging type of micromanagement to deal with. A boss who is insecure will do the work himself as a guard against his fears. Fear is a challenging emotion which we all feel to varying degrees. To deal with this type of micromanagement, you may need to have a direct conversation with your boss, and likely more than one. Another option is to reassure the boss not only about your work but his. But, frankly, you may not be able to convince your boss to be more secure, especially if your office is a fear-based environment or your boss grew up in a fear-based culture. In that case—and I am sorry to say this—you may have to learn to stoically and professionally bear with the micromanagement. And then promise yourself not to perpetuate this behavior when given the opportunity to supervise others.
Standards. Your boss does not think you are meeting the standard, so he gets involved in your work because standards matter. Ouch. If your boss is right, then you have to up your game. If your boss is wrong, you have to talk things through with him if you can. These debates are common in our profession as the nature of our job lends itself to different judgments as to how best to do our work. Standards are often a subjective thing in this sense.
In determining whose standard is correct, there is something important to remember. Specifically, remember that “your” case is not your case. The case belongs to the county attorney or the district attorney. You are formally entrusted with its care, and yes, you will get all the blame for the miscalculations and errors you make in handling the case, but make no mistake—it is not ultimately your case. The county attorney or district attorney delegates his or her authority to a subordinate based on how s/he values that leader’s judgment. That leader—your boss—has received this authority and now exercises his professional judgment to the best of his ability. Your boss sets the standard. So, as difficult as it may be, remember this important point before you decide that your way is right and your boss’s way is wrong. Put another way: I suspect that when you are in charge, you will assume your standards, not your subordinates’, are the ones to be followed. Be humble enough to follow well.
As we mentioned earlier, one characteristic of micromanagement is the demand for information at an unreasonable level of detail. By unreasonable, I mean a level of detail that prevents you from getting work done or that creates excessive, unnecessary labor. In responding to this challenge, I am reminded how my friend Jud Waltman handles a similar situation. Mr. Waltman is an exceptional civil lawyer who deals with clients in serious cases. Some of these clients insist on constant updates. Jud will tell these clients something like, “Mr. Jones, I understand and appreciate you want to know what’s going on, but if I’m talking to you all the time on the phone, that means I’m not working on your case.” Jud’s statement captures the essence of the problem: “If I am spending so much time telling you everything I am doing, I cannot do anything substantive for you, and you want and need me to do substantive things for you.” See if this approach works with your boss. It may not. Micromanagement is an intractably annoying problem; the fire ants of boss behavior, if you will.
3. Set reasonable and healthy boundaries. Setting boundaries is as difficult as it is important. Yes, you owe good communication and consistent loyalty to your boss, but you also owe yourself, friends, and family something else: a resolute commitment to your well-being. Ironically, setting healthy and necessary boundaries helps your boss as much as it helps you, partly because an unwell follower will eventually be an ineffective follower.
As we consider where to place boundaries, we have to make a distinction between playing hurt and playing injured. Playing hurt is something we all must do from time to time. It involves dealing with the daily challenges and the hardships of the work. Our job is tough, and tough people are needed to do this job.
Playing injured is different. Playing injured is a situation where you can no longer work effectively, where you have significantly harmed your physical or mental health, where addictive behaviors seriously compromise your effectiveness or where your relationships fracture in a serious way. Being injured is not shameful, but it is something we should be honest about and we should all seek to avoid, individually and together.
To avoid injury, you have to set appropriate boundaries. Once set, you have to respect these boundaries yourself and then train your boss to respect them. This process looks different for everyone, but I want to emphasize (after having failed at this personally and profoundly) that you will ultimately create the boundaries that exist, not your boss.
For example, electing to take non-emergency calls or respond to non-urgent emails during your family vacation? You have set the standard. Choose not to ask for more help when needed, and instead work such long hours your health and your relationships start to suffer? You have set the standard. The kid cases you are working beginning to get to you in such a way that real mental health problems are developing, but you are too proud or private to say so? You have set the standard. Allowing your boss to push your ethical boundaries so far you do not recognize yourself anymore? You have set the standard. Ultimately, these standards become the boundaries between you and your boss. If these boundaries are in the wrong position, everyone suffers, including your boss. You can understandably rail at your boss when this occurs, but, as a leader, you can only rightfully blame yourself.
Ultimately, your efforts to set boundaries may not be completely effective. What you may have to do to serve your boss, your office, and your own wellbeing best is to simply say, “No more of X behavior.” How hard is that? Well, it does not get any harder. But it is the thing to do before you walk away, burn out, or blow up. It is what leaders do.
A few other suggestions
Spend time understanding what is important to your boss, and make those things important to you, too.
Defend your boss and your office against all others, even if you do not particularly feel like it.
Do not put your own professional development solely on the shoulders of your boss. His shoulders cannot bear that weight, and you will be unnecessarily and constantly frustrated.
Look for ways to make your boss’s job easier.
Recognize your boss’s strengths and weaknesses. Promote the former and shore up the latter.
Consider that your boss may see things from a different vantage point than you do and may have challenges you do not fully appreciate. Remember that being a boss—any boss—is not as easy as it looks.
When you have a significant dust-up with your boss, and you will, begin the next day with a fresh start, like a professional. Grudges are for amateurs.
Make the decisions you were hired to make so that your boss does not have to. If you need your boss’s input for a decision, one technique is to say, “I intend to take course of action A.” Then give your boss enough time to say, “This is the wrong course of action. Take course of action B.” This method works very well until it does not.
The worthwhile is rarely easy
We started by saying that the grand unified theory of leading up is to “be the kind of follower you want to lead,” and we said this principle would guide you in many of your decisions. We also said this principle has some limitations. For one, you may not yet appreciate what is required to be a boss at the next level, so your judgment on a particular issue may not be fully formed. For another, you may find that your boss has a different leadership style than you do. What you would expect in a situation is not necessarily what your boss would choose. Make this allowance for your boss. Communicate well and adapt accordingly.
Make one other allowance for yourself: Remember that leadership is tough. Nothing you do to influence your boss—or anyone else—happens easily or quickly. There is no “one and done” technique that will bring automatic results, and there never has been. Leading is the long game. You may have to fight the micromanagement problem during your entire time with your boss, making only incremental headway. You may make progress with your boss in one area, only to see a setback in another. Such is the nature of leadership. Nevertheless, keep at it. Keep the faith. Keep working. Keep leading up. This is the way.
 Consider your relationship with law enforcement as an example. We are continually seeking ways to positively influence our colleagues in the law enforcement community. This, too, is leadership.
 Mandalore is an Outer Planet marked by savage and unrelenting war. The Mandalorians are—ah, just forget it.
 Peter Clemenza, Corleone Family capo, The Godfather. Paramount Pictures, 1972 (Francis Ford Coppola, dir.).
 If you want to see an excellent example of this concept in the negative, go back and watch officials from the Department of Public Safety brief lawmakers on the new hemp law and THC testing. (Yes, I went there.)
 ADA Donna Berkey likens a boss to a firefighter. If you alert the firefighter to a fire early, he may be able to save the house and your property. If you wait to let the fire really get going, you may not be so fortunate. And for heaven’s sake, don’t try to cover up your mistake. As the Watergate scandal and every episode of every sitcom has taught us, covering a mistake only makes things worse.
 Candor involves your best judgment on matters of consequence, not merely your preference. Preference is reserved for those in charge, which you may lament now, but you will appreciate when you are in charge.
 Here’s some ancient wisdom about speaking out of school about your boss: “Even in your thoughts, do not curse the king, nor in your bedroom curse the rich, for a bird of the air will carry your voice, or some winged creature tell the matter.” Ecclesiastes 10:20. We might update “bird” for “social media platform.”
 Don’t bother trying to find the source. The language is found between the emoluments stuff and recess appointments. In that generalish area. Just trust me on this one.
 Please do not be offended, but I do not believe you. I think you do know. As Justice Oliver Wendell Holmes once famously said, “Even a dog distinguishes between being kicked and being stumbled over.” The same is true about complaining about your boss. But, OK. Imagine you are a British soldier in the trenches of World War I. Complaining about the High Command, the cold, the mud, the rats, the war, your allies the French, your enemies the Germans, the food, the equipment—all fine. Complaining about officers, generally, is fine. This type of complaining is good for your mental health and can bond you with your fellow privates in the trench. But when you start talking about how your particular officer—probably named Lieutenant Reginald Wadsworth Highsmith or something equally ridiculous—does not know what he’s doing, how you are sure he will get you all killed, how many mistakes he’s made, how unprepared he is to lead, and how poorly Lt. Highsmith has done in previous assignments, you are doing it wrong. Now you are now simply undermining your boss, sowing destructive doubt with your coworkers, and endangering the mission. And you are not exhibiting appropriate loyalty.
 “When you take my tasks from me, I am left with the impression you don’t trust me to do them. Is this the case? Do you not trust me with this work? Why not? What more can I do to gain your trust?”
 A great and terrible leadership opportunity is bearing with a bad boss as a professional. Your example in difficult circumstances will be instructive to others, and it will hone your character to a fine edge, an edge you can later use to stab the bad boss. I kid. No stabbing.
 One significant negative consequence of setting unhealthy and unwise standards with your boss is that it trains your boss how to treat others who follow after you.
 I have been instructed by TDCAA that if you get fired because you said “no” to your boss, TDCAA is not legally responsible for anything I have advised. Or ever will be. In fact, they don’t even know me, and they are not sure how this article made it into the journal. They also say they have a great job bank to check out if you do get fired.
 “Fredo, you’re my older brother, and I love you. But don’t ever take sides with anyone against the family again. Ever.” —Michael Corleone
 This guidance comes from the aforementioned Mr. Waltman. I would add that you should be careful about saying, “If you are going to make all the decisions, then why do you need me?” Sometimes the response is, “That’s a very good question. Why do I need you?” Then it’s back to the TDCAA job bank.
 Remember that your boss is deluged with information. If the decision is important and you did not “set it apart” so that your boss could react in time, and then later your boss disagrees with the decision, then, yes, you will have documentary proof that you asked for guidance beforehand, but you will also leave a very negative impression in your boss’s mind. You will have “won the battle, but lost the war.”