Reading List for Managers and Future Leaders

I was never a big reader when I was younger, but I find that turning to the knowledge of experienced professionals and research analysts who have evaluated dozens or hundreds of scenarios or metastudies has greatly benefited my professional growth as my career has progressed. Many books deliver little nuggets of wisdom, but some key books have given me philosophies, frameworks and vocabulary that has helped me organize my thoughts, understand my specific situation and make sense of how to best move forward. As a result, I have found recurring instances of recommending the same set of books to various people in various situations. I thought I'd compile this list here and share why these are such powerful game-changers and must-reads. 

If you're in charge of a large or small part of an organization, or have influence over it, and are trying to effect a large cultural change, many of these books work great in office "book clubs" to get everyone speaking the same language and aligning to the vision of the future world. I've participated and organized these office "book clubs" multiple times, and have seen them effectively aide in the cohesion and crucial dialog the teams needed to have. 

In addition, I cannot stress enough that if you struggle to find time to read, listening to audiobooks on your commute, while you're working out or walking the dog, or traveling are all great ways to consume the material without taking time away from your family or other personal and professional pursuits. Most of these books have audiobook versions, and some will have accompanying PDFs to provide the benefit of the visuals even when you purchase the audiobook.

Extreme Ownership: How U.S. Navy SEALs Lead and Win

by Jocko Willink and Leif Babin 

This is a must-read for anyone in business, really, but especially for managers and wanna-be managers and leaders. There are some hard truths in this book that force self-reflection. Each concept is crisp and applicable to just about every organizational environment, and exemplified by the book's structure of military example and business application in each chapter. The war stories are heart-wrenching and exciting, and the takeaways are evident and challenging. Much of my professional philosphy aligns with and comes from this text. It is one of those books you can enjoy re-reading and get something new out of it with every read.

Multipliers: How the Best Leaders Make Everyone Smarter 

by Liz Wiseman and Greg McKeown 

I only recently picked this book up for the first time, but have gone back and read (or listened to) many of the chapters three or more times, and taken abundant notes which I've continually referred back to. This is a book with its own vocabulary, and it gave me the words to express and understand some of the techniques I was instinctively deploying and the behaviors I was seeing but not understanding. The intro felt a little too good to be true, but the content in the following chapters is really thorough and immediately useful. I've leveraged my learning from this book several times over in multiple contexts and have received immediate recognition and seen great success. Yes, it is that good. Whether you're looking to be a better manager, become a manager in the near future, or you find yourself in the unfortunate circumstance of working for a less-than-awesome manager, you can probably find multiple strategies and techniques to improve your work life and your effectiveness.

Why Do So Many Incompetent Men Become Leaders? (And How to Fix It)

by Tomas Chamorro-Premuzic

If you feel personally attacked by the title of this book, it might be worth a read to challenge your assumptions about your abilities. If the title resonates with you, it is also worth a read to make sure you're not unintentionally perpetuating the cycle. But don't let the title mislead you - this is far more than a case for diversity or a girl-power pick-me-up. This book has given me the framework I use to evaluate management potential and effectiveness. It does shed light on the multitudes of challenges women tend to face and why men generally don't have those same barriers, but it strikes more to the core of what good leadership really looks like, regardless of gender or any other demographic. 

 

Work Rules!: Insights from Inside Google That Will Transform How You Live and Lead

by Laszlo Bock

While I rarely get little more than an interesting read out of most books talking about the Big Tech or FAANG companies (and not everyone can work at facebook or google), this book cuts to the heart of onboarding, among other topics, and I think the power of a successful onboarding program is highly underrated. So for any hiring managers or people about to embark on a journey with a new company or radically new position, the advice here may be worth your while.

The Loudest Duck: Moving Beyond Diversity While Embracing Differences to Achieve Success at Work

by Laura A. Liswood

Diversity and inclusion are very dynamic topics, and the thinking has shifted so rapidly that there's just not a lot of good literature, in my opinion, that really deal with the right ideas and actions. This is an exception, the best work I've come across dealing with the issues in abstract terms and concrete examples. So many companies still relegate diversity to lipservice, but this is a really important topic to at least increase self-awareness for anyone in a leadership role.

Invisible Women: Data Bias in a World Designed for Men

by Caroline Criado Pérez

You don't have to be a feminist or even a liberal to be completely outraged by findings discussed in this book. I'll warn you now: the premise is that males are seen as the default, and females are simply deviations, anomalies or complications. This may seem overly judgemental/reactionary/conspiracy-theory-oriented, until you read some of the findings, like how women are being killed by oversights in a smorgasbord of ways. This book should be required reading for anyone in the medical, legal, political or academic professions, as well as anyone in any kind of design field, or anyone in any kind of business, or anyone who wants kids, has kids or knows kids. In short, it is recommended for all of mankind, which is, of course, male-default language in and of itself.

Traffic: Why We Drive the Way We Do and What It Says About Us

by Tom Vanderbilt

This is a bit more light reading, because let's face it, most of us are still (or back to) commuting to work and dealing with traffic congestion, accident-induced delays and just generally stupid drivers, right? There is a bit more to it, though; I've often compared good business planning to making smart decisions in traffic jams, and the human element is what makes both traffic and business so dynamic and complex. If you're a synthesizer (you draw inspiration or insights from seemingly unrelated contexts), you may really get a lot out of this book to help you in your management at work. And regardless, it gives you some interesting perspectives you can share when the topic of traffic comes up in conversation. 

 

Influence: The Psychology of Persuasion

by Robert B. Cialdini

A professor at my alma mater, Arizona State University, Dr. Cialdini is considered the world's leading expert on influence. Most managers and leaders have to inspire and influence to get work done and be effective, so this talent is absolutely critical to hone. While many are familiar with Dale Carnegie's school of thought, Cialdini seems to be far less well-known while delivering much more actionable and widely applicable concepts, in my opinion. I've referenced this book for creating strategies to improve cross-functional communication between warring teams, to creating profitable social media content and selling Girl Scout cookies. "Influence" is my Bible for how to get people on your side and supporting you, regardless of their relationship to you in the org structure. The examples in the book are a bit dated, but the principles haven't changed.

"Uptalk": The Power of a "Reputation that Proceeds You"

I've been assisted at least twice in my career by having a reputation that precedes me, and I am convinced it's a powerful tool and utilize it to arm my employees and peers to prepare for challenging undertakings involving convincing and influencing others. Before I get too far into the details, let me first clarify that having someone talk you up does not guarantee success - you still have to do the work and prove you were worthy of such high praise, admiration, and most importantly, respect. 

That being said, I'm convinced having someone credible give you credit sets you up for success in two ways: it gets people in the receiving mode to give you a chance and hear what you can teach them, and it gets you in the mindset that you can, and now must, deliver on that promise. I'll talk about each of these effects separately and then how they combine, but first, some examples and stories.

The shortest and most positively jarring interview I've ever had was with the Director of Finance at Henkel when I had applied to a Demand Manager job, a natural promotion from my Supply Planner role at the time. I didn't know him well, yet, so not only did I have no idea what to expect from him as a person, I wasn't sure what a finance guy would ask a supply chain person anyways. When I walked in, he said very abruptly, "I just have one question. Do you want the job?" His directness puzzled me momentarily, I thought I was being set up. I replied in the affirmative, and then stumbled through answering a slightly more "normal" question of why I wanted the job. He cut me off, saying, "Honestly, I just want to know that this is the job you want. If it is, you're a shoe-in. I've read your resume and heard about all of your accomplishments, you'll knock the socks off this position. And if, for some reason, he doesn't hire you, he'd be crazy to do so, but I would snatch you up." I reaffirmed that I wanted the job and thanked him for the words of confidence. "Don't thank me," he said, "thank yourself! You did the work. I'm just observing." The interview ended after that, and I walked out with my head spinning. 

Years later that conversation still makes me wonder if I'd be any good at finance, and if I'd like it, because it was something I had never even remotely considered, but he seemed to think I'd be an asset to his team. What's more, when I got the Demand job, I got the opportunity to see him in action and work with him, and he worked in a way that made me think finance was way sexier and more interesting than I had thought. Far from being nerdy number crunching and moving dollars around on a spreadsheet to make the corporate checkbook balance, he used his dollar-tinted glasses to lead us through challenging and productive debates to better understand risk, opportunity and how to improve on both.

The point of the story, though, was the fact that someone else, probably the hiring manager, had already talked me up so much that the finance guy saw no need to grill me or put me through the usual line of questioning for an interview. What's more, he expressed so much confidence in me, I contemplated what it might be like to work for him. I mean, if he had that much impact on me in 5 minutes, what could I do with his guidance for a year or more of 40+ hour work weeks? And honestly, the manager I did go to work for in that position, Brian, turned out to be the best manager I'd ever had, and to this day I still consider him the best manager I've ever had. Sadly, our time was cut short by the relocation, and I truly see it as a tragedy, because I think I had a ton more to learn from him, too. I could have grown and found my stride under Brian's leadership.

I loved my job at Henkel, until I didn't. Having come from the worst job in my career and worst workplace, Honeywell, I saw Henkel as a place where the grass was really greener, and that impression lasted for three years and two jobs. When Henkel moved it's headquarters and about 30% of it's employees from sunny Arizona to miserable Connecticut, myself included, much more changed than just geography and weather. I was done, and it was terribly sad because I previously had thought I might spend the rest of my career with Henkel.

We set our sights on Florida and Dallas as our #1 and #2 preferred locations, and I started job hunting. In an only-loosely-related message exchange on LinkedIn, I learned of an opportunity in Panama City, Florida in my former industry of aerospace. The person referring me, Mike, was a former Honeyweller (one of the few good ones) whom I had impressed early in my career, and was now the VP of Supply Chain for one of Honeywell's biggest suppliers, GKN, a company I knew well. If I got the job, I would be dotted-line reporting into him. Since I liked Mike, I was cautiously optimistic, the caution coming from my experience of aerospace as being an "old boys club" and a bit "dog eat dog."

Mike being a VP likely fast-tracked my resume through the process, based on how quickly I was getting calls and interview invitations. I joked with Jaiman about how, when your VP says, "This is the right person," HR busts a move to get that person. And in this case, I was that person. I suspect Mike also talked me up to the hiring manager.

My direct boss in the role was also a former Honeyweller. He, however, was not "one of the good ones" in my book. To be fair, I had never directly worked with Preston at Honeywell, but his reputation for being a monster was enough for me to know I wouldn't want to. I took the interview request and flew down to Panama City to meet with Mike and Preston and others. I won't bore you with all the details here, but relevant here is that Preston proactively admitted he had been a jerk and shared that he had changed his ways, which was quite encouraging. In the end, I had two great job offers, a very safe one in Dallas, and a terrifying one in Florida, and I took the job in Florida, consistent with my pattern of never choosing the easy route in anything.

What happened next is the point of this story. Preston presented me to the small leadership team at the time as if I was a diamond in the rough, they were all lucky to have me, and I'd be the informal head of the site. He even gave me the nickname of "Goddess Athena, Queen of All She Surveys." The nickname became a running joke, and when we made slides with our pictures on the top right to indicate who was presenting, my picture was replaced by an artist's rendering of Athena, and the leadership team all knew what that meant. Each time we hired subsequent members of the leadership team, Preston would have me interview the candidates and would tell them why my opinion was so important. So the existing leadership team, and everyone brought on board, was under the impression I ruled the proverbial kingdom.

Honestly, I thought the Athena joke was funny, but I didn't give it much thought otherwise, and didn't let it go to my head. I thought I knew better than that. Surely when things get tough, supply chain would get the shaft, as it always had previously in my career, and the Supply Chain Manager (me) would be in the hot seat and blamed for everything. I knew the position was a stretch for me anyways, so I focused on the work. What I was also doing, perhaps semi-consciously, was trying to prove Preston right, to live up to the hype.

So while I was trying to get things in place and live up to my reputation, I was unaware of the respect I was commanding by my peers and even superiors. Then one day, it smacked me in the face (in a good way, but equally as astounding). We were in a leadership team meeting without Preston, and I don't even remember what the concern was that we were debating, but suddenly all heads turned my way without me even saying anything, and I realized the team was looking for me to guide us out of whatever jam we were in. And that wasn't the last time. After a number of similar occurrences, I mentioned it to Preston during one of our private conversations and he expressed that he wasn't surprised, I have the characteristics that make me a great leader, regardless of my place in the org structure. Even at this junture, where he could have pointed out his part in gaining respect for me, he made it all about me, boosting my confidence and giving me a higher bar to aim for.

It happened so regularly that I found I grew into it and flourished. I found my stride as a leader, not just of my own little function, but of the whole site. I think the phrase "fake it til you make it" sounds like something deceptive, but I felt like I did that genuinely. I didn't know what I was doing, but I knew the next steps I needed to take, I knew the principles I needed to guide me, and I worked through it until it came natural and I had "arrived."

Lessons

I'll again state here that having a positive reputation preceding you only goes so far. I actually have seen examples where this didn't work for other people because they couldn't back it up or live up to the praise. This happened in Florida multiple times, and I found myself in coaching mode with people, even going so far as coaching them on being effective in the areas in which they were supposed to be experts. So, I will caution against using this to justify or attempt to cover over a bad hiring decision, for example. If the person plainly doesn't have what it takes, you can't uptalk them into suddenly being high performers. In fact, doing so may reflect poorly on your judge of character and general decision making. To paraphrase Shakespeare, a weed by any other name is still a weed. If you ever find yourself in the awkward position of getting high praise that reaches so far beyond your competency level, here's what I would recommend. Don't call the leader out in front of everyone, and don't refute the praise or try to add qualifiers on it. Instead, have a private conversation with the leader as soon as possible, thank them for the high praise and explain that you lack the confidence they put in you. Next, be specific with what you feel you're lacking, and in the same breath, ask for advice on how to rapidly get up to speed on those areas. If you tell the leader that you're terrible at everything they just praised you for and you have no idea what you're doing, the conversation will likely not be a good one. But if you share very specific areas of concern, and ask how you can immediately repair the gap, they will see that you have their back, and will (hopefully) appreciate the honesty and willingness to learn how to execute whatever they just proclaimed about you publicly.

Alright, so let's presume now that you are a respected leader and have a high performer or potentially high performer that you're bringing into a group or a project, or asking them to initiate something. As a respected leader, you can help smooth the introductions and set up for success both the high performer and the team as a whole, by describing the strengths of the person which will be applicable and beneficial. For example, I've introduced an employee to a new consultant by saying, "He's the mastermind behind this tool, and is intimately familiar with the challenges and tactics needed to move the needle." I could have said, "He connected the files and added some features, and has worked with the team to troubleshoot." Both statements are true without leaving anything out, yet the former statement imbues confidence while the latter diminishes the accomplishments and competence of the individual. The consultant was in need of an expert, and he trusted me but wasn't sure if he could trust this individual whom he didn't yet know. I knew the individual would do a great job answering the consultant's questions, likely better than I could, so I needed to give the consultant confidence to seek him out.

We can also use this uptalk method to imbue confidence on the individual. I work with some absolutely brilliant people, keen observers and analytical, solution-oriented thinkers. I'd like to count myself among them, but I know as a leader, I can't be the expert in everything, and I can't be the only expert on anything, otherwise everything will be on my plate and we'll only move as fast as I can move. Instead, I need to encourage my team members and peers to be the expert and the leader that we need. 

However, while many of them have the competence, some of them lack the confidence. So I'll attempt to get some of my confidence to rub off on them. I'll set them up with expectations, such as, "I expect you are going to learn so much more about this topic than I could ever learn, and you'll become our site's go-to expert." Or, "You have the buy-in from senior leadership on this, so the people you'll be working with have been assigned by their managers. We need you to now wrangle them in, set expectations, and get them all moving in the right direction." In either case, I will likely actually keep my finger on the pulse of the project and make sure it continues running smoothly, or help remove barriers as they start to crop up, but I want the employee to feel compelled and capable of doing it without me. 

I will also allow for minor failure to let the employee learn and adjust to the failure. Counterintuitively, letting small failures occur also helps boost confidence because great people who are anxious about a role or project need to know they will be safe even if they fail, as long as they take corrective measures. Obviously, if the project is clearly headed for catastrophic failure, I'll step in and provide additional guidance or resources, or redirect if needed. But minor failures are great ways for future leaders to learn, build respect and trustworthiness, and shows to me as their leader how they handle issues. I learned of a specific way to uptalk in a book I read, and I've used it successfully in encouraging a team member to make a decision using their best judgement. The phrase is, "I give you 51% of the vote." Meaning, I can weigh in with my point of view when asked, but the employee gets to make the final call.

My Magic Power: Action-Oriented Emails

Activator. Communication. Individualization. Responsibility. Achiever.

Those are my top five strengths according to Clifton Strengths Assessment. If you've never taken a strength finders quiz or haven't done it in a while, I personally recommend it. It's a tool, just like anything else, not a magical horoscope or personality quiz like those found on facebook. But if you put your earnestness into it, you can get some insights out of it.

I helped get traction towards resolution on a problem one of my team members had this past week. The problem had been lingering on with no progress for weeks, and my team member wasn't even sure of the status or whose court the ball was in, per se. Ultimately, more information was needed, and my team member was able to obtain the information needed, and so volunteered to do so in order to get one step closer to resolution. And then, he thanked me for my help; and in his appreciation, I saw relief. Relief that someone heard him, and actually did something. Relief that he wasn't alone. Relief that he had support. I'm a new manager in this organization, and there are a world of problems for me to solve, which is exciting, but also, daunting. Yet, all I can do is tackle them one at a time, the most important first, and do my best to, well, do my best.
So when my team member thanked me, it made me reflect on what it was I actually had done. Truthfully, it wasn't much. Not to me, anyways. My team member thought the issue was pending a decision or direction from the director of quality. Since the director of quality happens to sit a few doors down from my office, I popped into his office a couple times that day to see if I could chat with him, but I kept missing him. I always prefer face-to-face communications over emails, but in this case, I didn't want the issue to sit while I kept missing him. So I took my team member's email and forwarded it to the director of quality with a short, concise intro, request for action and offer to provide additional info as needed.

To be honest, while my team member had provided some info to me over the phone, I didn't fully understand the problem, just that it was something he had attempted to address and it had not been resolved yet. So about an hour later, when a quality engineer stopped by my office to ask for more info, I didn't have much to provide. He said the director had forward  the email to him and asked him to work on it. I was able to get my employee on the phone to answer the questions that I couldn't, and the three of us talked through next steps in order to resolve the issue.

What had I done? Well, to start off, I had seen no evidence from the email chain that the director of quality had even known about the issue, let alone anyone in quality; it had been assumed that he or someone from his team were involved. So in some ways, all I did was connect the dots. But I suspect there's more to it than that. The whole organization seems to be email-happy, meaning they will shoot off emails to 15 or 20 people, and the emails will circulate and go back and forth, and to their credit, some problems do get resolved in this manner. But when we're bombarded with emails, we tend to look for shortcuts, and seeing long or vague emails likely means we'll pass over those messages with the intention of coming back to them later, and later never comes. Or worse, maybe we see so many people on copy and assume someone else will address it, or they'll let you know if they need your help, meanwhile they're assuming you're working on it simply because you're on the email chain. So the difference between those lengthy emails to 20 people and mine, was that mine was directed at one person, and was concise, with a call to action.

This is my super power, I concluded. It's the Activator that calls someone to action. It's the strength of Communication that enables me to deliver the right message. It's Individualization - knowing how to reach the right person. And it's accepting my share of the Responsibility and Achievement. My team member had been sending emails, but they weren't reaching the right people or stirring them to action.

However, all is not lost if you don't happen to be an Activator-Communicator-Individualizer-Responsible-Achiever. You don't have to have that exact combination of strengths to develop this super power. In fact, it's not a super power at all - it's a skill. And like most skills, you can practice them and get better at them.
If an issue isn't getting the right level of attention on it, ask yourself why. Has the importance not been clearly articulated or understood? Are the right people aware of the issue? Are you SURE the right people are aware of the issue? As I mentioned before, I usually prefer face-to-face discussions, and I think I would have gotten similar or better results had I been able to catch the director of quality for a quick chat - I may have learned then that he actually had not been aware of the issue at all, or perhaps he had breezed by the email because he didn't realize it was needing an action from quality. If you're not getting results from repetitive emails, stop the emails and go have a conversation, or set up a meeting if you have to. At most, allow yourself only two unanswered emails before you try a different tactic.
There are other reasons the issue isn't getting addressed. Maybe the email communications are too long and confusing; if someone reads it and isn't clear what the problem is or how he/she can help, then the email may be ignored, or put on hold for "later" and eventually forgotten. 

The absolute best advice I can give you when your emails or requests are seemingly ignored is to just ask yourself how you could do better. You can't control others, but you can control your approach, and so that is always where there is opportunity. Beyond that, here are some specific things to keep in mind to make the most of your requests. 

Tips for Action-Oriented Emails:

• Address the email only to the person or people who really need to do something. When you start copying a person's boss, or your boss, or a ton of other people, sometimes recipients feel like they're being trapped, or that they have to respond quickly rather than helpfully because everyone will see the response.
• Provide context. Especially if you are writing to someone you don't know well or at all, make sure you provide a some information about how you decided he/she would be the  best person to help. Briefly explain the situation so that the recipient doesn't have to dig through the email to find out what you're talking about.
• Be specific in your request, preferably writing the name of the person from whom you are requesting help, and as much as you can about what action you'd like to see completed. If I say, "Go figure out why this isn't working," that's pretty vague and could be quite daunting. But if I say, "Can you help me understand why I'm seeing this number on this screen?" that's much more specific and provides a clear expectation of what you want help with.
• Be concise. Attach supporting documents or forward emails with additional information, and reference the additional information, but keep the body of your message short. If there are more than one request or a number of steps involved, use bullets or numbering to avoid long paragraphs and help break up the requests.
• Be humble. If you're asking for help, it's okay to lean into your lack of expertise. You don't necessarily need to flatter the recipient, but reference why he or she is the right person to take the next step. You could say, "I'm looking for quality's expertise here on what the next step is to resolve."
• Be helpful. Offer to provide more information or make yourself available for a discussion. There is nothing worse than feeling like someone is "throwing it over the wall" and dumping something on you, so don't do that to other people. Most problems require some sort of cross-functional collaboration, otherwise they wouldn't be problems and we would just fix them, right?

Absolute Don't's for Action-Oriented Emails:

• Forward an email without providing a (useful) reason.
• Insult or attack. Not just in emails, just don't do it.
• Complain or whine. If you feel you have a valid concern, it's definitely better to address verbally if you can. If you just want to let off steam, do it with someone you trust and let them know you are just need to vent for a minute.
• Convolute the issue with past problems or off-topic issues, like this: "It's just like Fred to go off and ignore his work queue, just like he did last week when I needed him to approve my request."
• Assert you know the answer, make commands or USE ALL CAPS AND BOLD AND UNDERLINE AND COLORS ALL TOGETHER.

 

Level-Up - Tips for Honing this Skill Even More:

Practice Individualization. 

This is all about learning how people work. You have to learn about the specific person. If you're unsure, you can ask colleagues whom you trust what advice they might have about working with this specific person. You could go out of your way to ask them how they're doing and try to develop a relationship with them (again, this is much easier and more natural face-to-face). If one tactic doesn't work, it's usually not because they're a big jerk. Try another tactic.

Provide a reasonable due date (and a reason for it). 

This is about setting expectations, and actually gives you a chance to emphasize the importance of the request. Many people respond well to due dates, because it allows them to plan out what they can do in order to support their response. It also allows them to prioritize if they have a lot of requests. It is important, though, that your due date isn't unreasonable. Saying "ASAP" is useless, so scrub that from your vocabulary. Sending a request at 5 pm on Wednesday and requesting an answer by 8 am Thursday is also a little tough in most cases, because you don't know that the individual will even receive it in time to respond, let alone have sufficient time to process it along with their other regular tasks, etc.  You could say something like, "Please let me know next steps by COB Tuesday, since I have to report out on the numbers to corporate first thing Wednesday morning." It can also be helpful to put the due date in the Subject line, like, "Chemical imbalance issue - need action by COB Tue" so that it is clear in the emails heading what the expectation is.

Propose possible solutions. 

I challenge my teams to come to me with proposals instead of problems. This is a good practice in any scenario. It could be that really have no idea, but often, if you think about it enough, you could at least come up with a proposal, even if it turns out being wrong (and that's okay, remember the "humble" thing, you're admitting you're not the expert and that's why you're seeking help). Often, when an expert receives a proposed solution, they can have an immediate feel for whether or not it will work. When given a proposal, an expert could choose to accept the proposal, modify it slightly, or provide a completely different proposal. In any case, you've done some of the heavy lifting for them, which allows them to see more clearly a path to move forward. Providing a propose solution also has the added benefit of showing the recipient that you've thought through this issue, and aren't just passing it on like a hot potato to get it out of your hands.

Use with Caution (Expert Level):

Ask stupid questions. 

Sometimes I take the "humble" thing to an extreme when my initial messaging doesn't work, and I'll ask "stupid questions" to elicit the kind of thinking I'm looking for. Some people like to tell you the 30-year history of why this widget needs that button, and they end up not answering the question or addressing the issue. When dealing with this kind of person, sometimes you have to really simplify the questions, and ask them one at a time, even. Asking something like, "What functional role is responsible for pushing that button?" is a lot more specific than, "What are the roles and responsibilities of all involved with this widget?" This is definitely a tactic you only want to use when you're getting nowhere with higher-level conversations and questions. You certainly don't want to ask stupid questions right out of the gate and all the time, because then people might actually start to believe that you're stupid.

Name drop. 

Let's face it, there are people out there who avoid work unless their feet are held to the fire. Rather than escalating the issue to their manager or putting the bosses on copy, sometimes it is simply enough to say the name of a person of importance. "Fred Wilkinson asked me to get with you on the best solution..." or, "I need to present this to Bob Chambers next week and I really don't want him to think we have a broken process here." Depending on who those made up names are in the situation, that could carry sufficient weight to scare a person into action. However, this should be  used as a last resort or in cases where you know this is the only way to get something done with this individual. Used too much, this could become a "boy who cried wolf" scenario and lose its effectivity.

Underline, bold, italicize or color specific words.

I rarely do this, but when I do, it's to highlight just one or two important things when I feel like there's a lot going on in the email and I can trim it down sufficiently. This can be to highlight a due date, a part of a question or action, or to help clear up a misunderstanding. I would recommend using only one, or at most, two, font alterations; so either you use bold and underline, or bold and red font, or just bold, for example. If responding to a lot of questions, sometimes I'll say, "See responses below in blue." and then actually answer the questions in blue in the forwarded email rather than repeating the email. This could include responding to a question with a clarifying question.