The New Leader’s Guide to Success: 60 Mistakes Not to Make When Starting Out (and How to Avoid Them) – Part 1

The New Leaders Guide to Success - 60 Mistakes Not to Make when Starting out

Do you wake up every day wanting to be a colossal failure?

So why is it that so many new leaders fail (up to 50% of them, according to some studies)?

What it boils down to is that for you, as a new leader, to be effective, you must get up to speed quickly. This means learning the ropes fast, building your credibility quickly, and delivering results from the get go.

It also means avoiding “rookie mistakes” that put you behind the power curve or take you off course from your new responsibilities. Read on to discover how to avoid making mistakes on key leadership fundamentals and leading yourself so that you stay on top of your game.

Rookie Mistakes on Fundamentals

The fundamentals are the basic habits you must master in order to have any modicum of success as a new supervisor. This is the time when you need to up your game and seek to professionalize your approach to leadership—the fundamentals help you do just that.

  1. Not keeping a schedule and calendar. There’s no quicker way to lose your way as a new leader than to run your day by the seat of your pants. Your disorganization will permeate your entire span of control as a leader and induce chaos for you and your team that will make your job unnecessarily difficult.

ONE APPROACH: Use a system to get and stay organized whether that’s a day planner, Outlook calendar, Evernote, or something similar. If you’re lucky enough to have a secretary, work together to come up with a process to keep you on track.

  1. Losing track of due dates. This mistake is related to #1—if you stay organized, you’ll minimize the chances of missing deadlines. But more than that, it’s your responsibility to make sure things get done. Dropping the ball in this way is a sure way for you to fail to perform at the expected level and lose credibility.

    ONE APPROACH: In addition to a system to stay organized, conduct a regular review (e.g. daily, weekly) of your tasks and when they are due. That way, you’ll stay on top of the game as opposed to falling short.

  1. Getting bogged down with email. We live in the middle of an oversaturated, 24/7, information age. How many of us can go more than five minutes without checking our smartphones? From a leadership standpoint, you can ill afford to succumb to the addictive temptation of the digital realm. This includes thinking that you can lead from your email inbox. Doing so is a sure way to distort your view of what’s actually occurring around you and where you place your focus.

    ONE APPROACH: First, realize that not all emails, texts, and messages are equally important. Second, you don’t have to answer every email or respond to every text. Prioritize your incoming messages based on 1) who sent it and 2) the content. For instance, if you receive a hot email from your boss, deal with it sooner rather than later. The bottom line here is to control your email inbox and not let it control you and compromise your ability to lead.

  1. Not clearing your voice mail. Yes, voicemail still exists, and it’s important that you attend to it properly. Letting your voice mails stack up tells people 1) that you don’t care about them, 2) that you’re not organized, and 3) that you’re not responsive. When I was in the Air Force, I made a point of answering voice mail regularly, especially as I rose in rank and I would get calls from Generals and senior civilians. Trust me, those folks didn’t want to be kept waiting… and neither do those people who take the time to call you.

    ONE APPROACH: Make a point to clear your voice mail at least once a day whether that’s when you first arrive in the morning, over lunch, or at the end of the day. If your call volume is high, clear it more than once a day. When you leave for the day, your voice mail box should be empty.

  1. Not returning phone calls. This one is closely related to #4.

    ONE APPROACH: Nothing cosmic here. Quite simply, if someone calls you, call them back. And sooner rather than later. Be responsive and responsible. If someone calls you, either call them back right away or if you’re unable to get back to them at the moment, take a note and call them later in the day.

  1. Arriving late for meetings. It’s really bad form for you as a leader to be tardy to meetings whether you’re in charge of it or not. Look at it this way, everyone in the meeting is setting aside a part of their day to assist you with your agenda. In a sense, they’re there for you. So it’s a sign of disrespect to them when you’re late. The same applies if you’re late for someone else’s meeting.

    ONE APPROACH: First and foremost, keep track of your meetings through your calendar scheduling process. If you don’t have a process, here’s your cue to put one in place. Second, if events conspire and you end up being late, make sure that you apologize verbally upon taking your seat and offer a short explanation—even that reason is that you forgot about the meeting.

  1. Using profanity. This one may seem like a no-brainer, but you’d be surprised at how many so-called leaders let themselves fall into this trap, “Oh, that’s just the way I talk.” That may be, but you’re not in the trenches anymore mixing it up with the team. You’re in a role where people expect you to set a good example, and speaking in a manner that is courteous and professional is part of it. Not only is cussing distracting, it is offensive to the majority of people you work with—even though most won’t call you out on it. I get it, sometimes it just feels good to let fly with a string of colorful curse words. But let those times be few and far between, and in private if you can help it. Best is not at all.

    ONE APPROACH: Cursing is a hard habit to break, especially if it’s embedded in the way you express yourself. Start by surrounding yourself with accountability buddies who will keep you straight and who will support you in your task. Next, learn to pause when you feel that exquisite profanity rising up from the depths. Silence is truly golden in this regard. Then replace the bad word with a good word. It will be awkward at first, but over time you’ll become more articulate and credible to boot. For those times when you slip, express your regret to those who heard it and move on, striving to do better next time.

  1. Dressing badly or inappropriately. Unfortunately, sloppy, thoughtless casual dressing seems to be the norm nowadays. This is unfortunate because 1) part of being a successful leader is looking the like one, 2) there’s a good chance you’ll leave money on the table over a the course of career because you don’t look the part, and 3) there’s a certain dignity that comes along with being a leader, and dressing like a bag of donuts is an affront to that dignity (your dignity!) Not only that, part of your job is to set a good example for those whom you supervise as well as to represent the company well.

    ONE APPROACH: Step up your game and dress well. This doesn’t mean you need to order up a bunch of custom suits (although if your environment calls for that, then do so), but it does mean that you assemble a well-fitted, business-appropriate wardrobe that marks you as a leader who cares. On the other hand, it doesn’t mean every day is casual Friday and you go with polo shirts and khakis every day. The whole idea of dressing well is to communicate an authentic presence that says 1) you are confident and 2) you mean business. Start with the basics. Make sure you that what you get actually fits. This is where going to a good menswear store (not a chain or department store) can help tremendously. Budget a little each month until you’re set.

    Suits and Sport Coat:

    • Navy blue
    • Medium grey
    • Navy sport coat (NOT a blazer with metal buttons). Recommend not using the jacket from your Navy suit so that the jacket and pants get the same amount of wear time.

    Pants to Pair with the Sport Coat (in year-round wool NOT cotton, chinos, khakis, corduroy, etc.):

    • Medium grey
    • Tan

    Dress shirts:

    • 4 white
    • 2 light blue

    Polos (for dress down days, e.g. casual Friday):

    • 2-4 in basic colors


    • 4-6 silk ties that coordinate with your suits and shirts (ask a men’s sales associate to help you if needed)

    Pocket Square:

    • White cotton or linen

    Shoes/Belts (buy the best shoes you can afford… NO athletic shoes, outdoor/hiking shoes, Doc Martin’s, etc.):

    • Black dress shoes/belt
    • Brown dress shoes/belt

    Socks (NOT athletic socks):

    • 3-4 pairs of navy dress socks
    • 3-4 pairs of medium grey dress socks
  1. Poor grooming. Closely related to dressing badly is poor hygiene. Falling short here is not only distracting to your ability to lead, but it can be crippling to your career as well, especially when interacting with your superiors or clients. Again, this may seem like common sense, but I’ll never forget the time when I was a young officer in the Air Force and I had to counsel one of my sergeants on hygiene. He used to change out of his boots before he left for the day. This wasn’t so bad. What was truly horrific was the awful stench of foot odor that permeated the entire office when we arrived the next morning.

    ONE APPROACH: Good grooming includes things like:

    • Taking a shower regularly
    • Using deodorant
    • Brushing your teeth
    • Attending to your hair (cutting, washing, and combing)
    • Keeping your ears and nose clean
    • Shaving facial hair if you’re a man, or at least keeping it trimmed. I know beards are in fashion at the moment, but the fact of the matter is, in the Western world, a man who is clean shaven is taken more seriously.
    • Cleaning and trimming your fingernails
    • Wearing clean clothes
  1. Forgetting to say thank you. What we’re really talking about here is extending basic courtesy to those you encounter in your daily walk as a leader. The power of a thank you, especially from a leader to a subordinate is a morale-booster and a motivator. It also shows that you value them and the work they do which is hugely important for an employee’s commitment to their work.

    ONE APPROACH: Make a point to say “thank you” on a regular and frequent basis to your subordinates (and clients). Even for seemingly trivial or routine things that are in their normal “job description.” Especially for those times when they go above and beyond or do an exceptional job.

Rookie Mistakes When Leading Yourself

  1. Forgetting your roots. It’s all too easy to let your leadership position go to your head, no matter if you are a new leader or an experienced one. Leaders have power. Power over resources, power over decision, and power over people. This is an intoxicating mix that can sidetrack you from your true purpose as a leader, and that is to serve. Besides, no matter how good you are or how important you think you are, you can always be replaced.

    ONE APPROACH: It’s vital to keep yourself grounded in your new position. Never forget where you came from and how you were raised. The surest antidote to arrogance is humility. Make a point to reflect regularly on your core values. Surround yourself with people who will be straight with you rather than tell you how great you think you are.

  1. Compromising your core values. The pressures that come with leadership such as delivering results, making your numbers, and meeting performance expectations can challenge your ability to stay on the right track ethically. You’ll also face situations that involve questionable activities and deal with people who have no compunction about crossing the line. Add to that your own ambitions and goals and you have a recipe that could lead to moral failure. Is this really the end you seek?

    ONE APPROACH: Take the time to ponder what you’re all about. Reflect deeply on those principles that underpin the way you live your life and without which you’d lose your way. Then write them down. If you want a jumpstart, search online for a core values exercise, or better yet work with a coach who can guide you through the process. When you encounter a situation or a person that challenges your core values, consider your options for moving forward in a way that keeps your values intact.

  1. Thinking your way is best. When I was in the Air Force, we used the phrase “my way or the highway” to describe those in charge who were domineering, dictatorial, and close-minded. They were very difficult people to work for. I am not proud to say that early on in my career those words described me pretty well. What I learned was that it’s good to be confident in your abilities, but not so much that you shut off the opinions, insight, and advice of others who in fact might know more or have more experience than you. By acting in this way, you shut people down and demotivate them, which in turn results in substandard performance and unnecessary difficulty in getting things done.

    ONE APPROACH: Step back out of yourself, and make a point to consider the opinions of your team. Be willing to change your mind, modify your thinking, or adjust your decisions if better ideas come along. Sometimes, your way just might be the best. If so, be prepared to state the reasons why. If it is, your folks will recognize it. But whatever you do, make sure you don’t let yourself be so dominated by overconfidence and a desire for control that you shut down discussion and dialogue.

  1. Not accepting guidance and feedback. There will be times in your leadership walk when you just don’t get it right. You might actually make a mistake, a wrong decision, or a bad call…or be on the road to doing so. These situations are not the time to shut down and act as if nothing happened or even worse pass the blame.

    ONE APPROACH: Provided you are following the advice above and have your ears open to hear, you’ll find that people will attempt to help you stay on track. Always be open to correction and receptive to advice. This may require that you eat a little humble pie from time to time, but it’s a crucial step for you to take if you want to learn and grow as a leader.

  1. Ceasing to develop your expertise. We live in a world that changes at rapid pace. Knowledge, technology, and processes all advance. Part of your job is to stay abreast of those changes so that you can help your organization and your team stay competitive. In addition, if you fall behind or otherwise don’t work to understand new, ongoing developments in your field, your team will perceive you as less able to lead effectively. In turn, being less credible will make it more difficult to do your job.

    ONE APPROACH: Formulate a yearly plan to keep pace: take refresher classes, attend conferences, participate in seminars or webinars, earn a certificate, or enroll in a degree program. Most importantly, read: books, web and magazine articles, trade magazines, and journals.

  1. Allowing your emotions to get the better of you. When you’re in charge, people key off of your emotions. Whether you come into work happy, sad, or angry, your temperament has a ripple effect on those around you. I experienced this in a particularly impactful way when I first became the commander of a small communications squadron in the Air Force. Often, I would come into work in “deep thought” about the challenges of the day. Apparently, my expression was less than friendly because word would spread that “the boss wasn’t in a good mood.” I quickly learned to adjust my demeanor, not so much for my benefit, but for theirs: I didn’t want my mood to impact their ability to approach me or otherwise focus on getting the job done. If you have a habit of flying off the handle or regularly going overboard emotionally, know that your behavior will have a negative impact on the morale and performance of your organization. If you’ve ever worked for a boss who raged, screamed, cried, or otherwise created emotional drama, you know what I mean. Don’t be “that boss” because you won’t engender the trust of your team or—crucially—your superiors who count on you to make solid, level-headed decisions for the company.

    ONE APPROACH: When you find yourself getting overly emotional, especially angry, take your mother’s advice and count to ten. Stepping back from the situation and breathing a few deep breaths actually works to calm the emotional part of your brain. Check yourself to make you’re getting enough sleep, you’re not overly caffeinated, and you have a support network with whom you can vent and get advice. Finally, if you’ve got a real anger management issue, get help so that you have the tools to deal with it and overcome it.

  1. Failing to build a support system. There is a good deal of truth in the saying that “it’s lonely at the top.” Pressure, doubts, struggle, and stress come with the territory. Your burden is heavy enough without having to carry it all by yourself. That’s why having people you can trust, talk to, and confide in is so critically important for a leader. Early on in my career, I thought I could do it all myself. It took me a while to recognize that I needed the support of people outside of the organization to help me deal with the challenges of leading. Those people really helped keep me balanced.

    ONE APPROACH: Start early to build a support network of people outside of your work environment. Although a close family member can be a good choice, look to include mentors, professional colleagues who share a similar career path, and certified leadership coaches.

  1. Becoming a workaholic. It’s a heady experience to get promoted into a leadership position. It’s your first chance to make a bigger impact, and the boost you get from the increase in authority, prestige, and (for most) pay is exciting. In today’s go-go world, the temptation will be there to work harder and longer; and your company will happily absorb every bit of that and more. Sure, you’ll very likely reap rewards from your commitment, but as the old adage says, “All work and no play makes Jill a dull girl.” Eventually, you will pay the price in terms of a healthy, balanced, meaningful life. Keep at it, and you’ll look back after 10, 20 years and wonder if that workaholism really made you happy. Think of it this way: Do you really want your epitaph to say, “Here lies a hard worker who spent mega-hours at the office”?

    ONE APPROACH: To set the stage to avoid the workaholism trap, sit down and list the important priorities in your life. Yes, work is a priority—you have to put a roof over your head, eat, and take care of your family—but what else is there that makes your life fulfilling? It could be family, your social life, hobbies, fitness, your faith and a myriad of others. The key is to gain perspective and understand that work (contra Karl Marx) is not all there is in life. Then, put in place habits that ensure you incorporate those priorities as an integral part of your daily existence.

  1. Neglecting your family. As exciting as it is to be moving up the career ladder, you won’t be doing it alone. Your family will be climbing it with you, that is if you look after it. There was a friend of mine who recalled a very senior 3-star General telling a group of young officers, “If you’re not divorced in this business you’re not working hard enough.” He practiced what he preached too. I don’t know about you, but that’s pretty sad. Now, there will likely be times when you are called away on business, and you’ll miss a special event or a big day, even your anniversary! But neglecting your family is a direct result of working too much and forgetting your priorities.

    ONE APPROACH: It’s all about how you handle those absences. Use technology to assist you: phone calls, Skype, and video calls for example. When you’re home, make family time quality time. As much as you can, orchestrate your schedule so you can be there for those special events and big days. In short, invest in your family because they’ll be with you long after your career has ended.

  1. Assuming everyone is like you. A common individual misperception is that everyone thinks, believes, and acts the same as you do. We are mystified when people disagree with us, become impatient with us, or are turned off by us. Of course, the reality is that NO ONE is exactly like us. There may be people who are similar to us in certain ways, but to expect that people are automatically going to understand you is a wrong assumption. The consequences of holding this false belief result in unintentional interpersonal conflict. Although conflict is normal when a group of human beings gets together, chronic conflict due to a lack of really understanding each other is detrimental to the organization and the team. We can plainly see these consequences play out on a daily basis in our government and in the media.

    ONE APPROACH: “Seek first to understand” your employees, your peers, and your colleagues. Put yourself in their shoes and attempt to view the world through their eyes. Even better, talk to them and get to know them. What are their likes and dislikes? Their hot buttons? What motivates them? What’s their background? Listen to how they talk, act, and react in various situations. Instead of imposing your intellectual framework and belief structure on them, take into account their point of view and account for it in your dealings with them. If you want to really take it to the next level, hire a coach to conduct personality assessments on you and your team and then outbrief the results to everyone. This is an excellent way to improve your understanding and increase your tolerance of those who differ the most from you.

  1. Piling the stress on yourself. Stress comes with the territory when you’re a leader. It’s a tough enough job without you adding any more to it. This can happen when your ambition exceeds your personal and organizational resources. In your zeal to “make it happen” you press too hard and tax your spiritual, psychological, and physical reserves. It’s one thing to have high expectations imposed upon you, it’s quite another to impose them on yourself.

    ONE APPROACH: When you find yourself suffering from self-imposed stress, the key question to ask yourself is why? Maybe your ego is in charge or how you feel about your self-concept is compromised. Ask yourself too if the brass ring you’re chasing is really worth the price you are paying in terms of the stress you are experiencing. Remember that you have a choice in the matter: after all it’s you that’s generating the stress, not someone else.

  1. Forgetting to exercise. Very often when you enter the leadership ranks, the hours you work per day goes up significantly. If you add in family commitments and other personal and professional obligations, the precious time you once had to exercise gets squeezed. Perhaps you’ve never created the habit of exercising. Soon enough, you find yourself weighing more (maybe a lot more). And once those pounds are on, they’re difficult to remove. Not to mention the deleterious health effects that come from inactivity.

    ONE APPROACH: The thing is, exercise becomes more—not less—important for your well-being as a leader. Working out is an excellent way to clear your head, gain energy, and relieve stress as well as keep the weight in check. If you find yourself fighting to find the time to exercise, first and foremost resolve that you will make the time. Then, analyze your work routine and your home commitments and bounce those against your ideal workout time. Clear your schedule to create an inviolable window for exercise. Next, think about your favorite exercise. What really motivates you? If you’ve never made a habit of working out, select something that interests you. In addition, it’s always better to have an accountability partner to help you at least get to the gym, the studio, the park, the pool, or on the road. Finally, set a goal or series of goals that are achievable. It’s a great feeling when you start ticking those goals off as you gain fitness. The goal could be as simple as starting a fitness class or as challenging as completing an Ironman triathlon.

  1. Not getting enough sleep. As a general rule, we are chronically sleep deprived in the United States. To make up for it, we consume massive amounts of caffeine which in and of itself is unhealthy. Poor sleep hygiene decreases cognitive functioning, slows normal healing and recovery processes, and contributes to chronic stress. With these negative consequences of sleep deprivation, why do we continue to abuse ourselves in this way? Especially leaders, who need to be at their best each and every day.

    ONE APPROACH: Ideally, kick caffeine to the curb or at least cut it back significantly. From a scientific standpoint, once you’re addicted to caffeine, much of the benefit from the stimulant is nil anyway. Naps are very effective for closing your sleep deficit, even ten minutes. In fact, a NASA study showed that 26 minutes is ideal to “reboot your brain” and give you performance boost. The best option of course is to tack on an additional hour (or even two) to your nightly sleep cycle. From a personal standpoint, when I was in the Air Force, I routinely used a combination of naps and at least 8 hours of sleep a night to keep me functioning at a high level. Sometimes the mission required that I had to run a sleep deficit, but the fact that I wasn’t already short in the rest department gave me a good cushion to rely on.

  1. Thinking you’ve arrived. Ah, yes. You’ve made it. You’re finally in charge. Everyone is going to listen to you and hang on your every word. All you need to do is show up, kick back, and relax because you’ve got the reins. If you’re thinking this way, I hate to dump of cold bucket of reality on you: don’t let your pride blind you to the necessities and responsibilities of leadership.

    ONE APPROACH: As much as you think you know, you’re just getting started, and a little humility goes a long way. Keep yourself grounded and keep things in perspective. Know that there are limits to your capabilities and that you’ll need the help of a lot of people—especially your team—to achieve any modicum of success.

  1. Criticizing others in public. It’s easy to get frustrated when you’re in charge. Your exasperation can be about a situation that’s not going well, but typically it ends up going in one of two directions: your boss or one of your direct reports. Listen, not only does “stuff” happen, but anytime you put of group of people together there will be friction, and friction results in disagreements, conflicts, and interpersonal strain. What you never want to do in these circumstances is criticize in public. Not only is it unprofessional, but your critiques rarely result in productive outcomes. People end up getting angry or even worse holding grudges and seeking some sort of revenge. Most crucially, productivity tends to drop. Not good if you’re the one accountable for results.

    ONE APPROACH: I got a piece of advice early on in my career that served me very well over the years, “Praise in public, criticize in private.” That one nugget saved me much frustration and heartache in my leadership walk. When I did criticize (in private), I did one of two things: 1) I vented to a trusted colleague or 2) I attempted to turn the criticism into counseling so that the individual walked out of my office with their dignity intact with a reason to improve their behavior.

Part 2

35 more tips await you!  Go to Part 2 of the New Leader’s Guide to Success »


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