My little brother just started his first real job a few weeks ago. I am about 9 years ahead of him in my own career at this point, so for Christmas this year I thought I would pass along my stash of career development and leadership books along with the following letter containing my own personal advice. These are books like Jack Welch's Winning and things like that. Anyway, I figured I could also post this (first post through Steeve!) for posterity and for you wonderful people. Let me know what you think!

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Congratulations on joining the rat race! We’re happy you’re here. As they say, misery loves company.

I’ve been here for a few years already, so I thought I would take the opportunity to give you some totally unsolicited pointers and advice. I’m also gifting you my stash of management, leadership, and career development books, because I have long since given up trying. There’s one more that I’d recommend that I don’t have in print, and that is Good to Great: Why Some Companies Make the Leap...and Others Don't, by James C. Collins. I listened to this as an audiobook and I’d say it’s right up there with The 5 Patterns of Extraordinary Careers as the best of the bunch. The others you can feel free to browse, but they probably won’t be super helpful until you find yourself in a leadership position.

So I figured in addition to those books, I’d also write up a little letter to you sharing some of the lessons I’ve learned along the way, as well as some anecdotes about things I am proud of and things I am not so proud of.

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General Advice

Digital is permanent and not private. Never write anything in an e-mail you would not be OK with your boss and HR reading. You should probably extend that to include your family and the media. This also goes for instant messages, text messages, and web sites.

Also, people are exceedingly lazy and will sometimes add people onto a thread without reading the entire thing and realizing something embarrassing is farther down. Don’t be that guy, but also don’t put something out there that would possibly be a disaster if this were to happen to you. Have those really nasty or tough conversations over the phone or face to face. Send a sanitized summary via e-mail afterwards. “Regarding what we discussed over the phone, I agree that we should proceed with the plan to charge the client...” sounds so much better than “those cheap jerks stiffed us on the last contract, so double the fee and send out the invoice.”

Always send grammatically correct e-mails, unless it is a 1 on 1 e-mail with a peer you’re close to. Nothing looks worse than an e-mail full of typos and shorthand. Acronyms for proper nouns and/or abbreviations are OK, but skip the “per mondays req. PFA.”

You can never be too polite over e-mail. Conversely, people can interpret a curtly worded e-mail as aggressive or even attacking. Sprinkle in lots of “please, unfortunately, at your earliest opportunity, unable to” and try to steer clear of anything that could be construed to sound snarky, bossy, or sarcastic.

The “notes” field on a PowerPoint slide should always be scrubbed for inside information before sending it on to anybody. You have to check each slide. Even if you don’t use notes, someone who authored the document before you might have.

Respect the chain of command. Never go over your bosses head to one of his peers or to his own boss. If you need to talk to them, just give him a courtesy heads up first. Going to HR is tricky but I would say you can do this without telling your boss. But if it’s for something he could fix, give him the opportunity to fix it before going to HR.

Whistleblowing: you have to follow your own moral compass on this one, but the way I see it, you should only report something to HR or to your management if you think you would get in trouble if it ever came out that you knew about something and didn’t report it.

If something is important to your boss, it needs to be important to you. If it’s an event, be there.

Assimilate into company culture. Wear just a smidge nicer clothes than most of your peers, but only slightly so. Use the same terms for things as everyone else. Embrace the slang. Fit in. Go to any and all company events where more than 10% of your co-workers will be there. Participate in the internal events/initiatives that have 33% or more of the office involved. My first year at my job, I joined the golf league. Even a few years later, I still say hi to people I only ever met on the course.

Don’t be afraid to ask to be included in things. One of my favorite tricks is if I have a meeting with my boss and we wrap up and he’s headed elsewhere, to ask where he’s going. If the answer is that he’s meeting with a superior, I’ll ask if he minds if I come along to listen and learn. It’s a win all around for you regardless of what he says.

If everything is a priority, nothing is a priority. Don’t be afraid to triage things. One of my favorite tricks with my clients is to make them rank their wish list in priority order. Tell me what is your most important thing, then your second, etc.

One of the best pieces of advice I’ve ever gotten is to think of your day as you juggling a bunch of balls. You have glass balls and rubber balls. If you’re going to drop a ball, make sure it’s a rubber ball. Most days I will pause before I go home and think “do I have any outstanding items that must be done today?” About once every month or two this exercise has saved my bacon as I suddenly remembered a thing from noon that day that I needed to get out but something else had come up and I forgot about it. So I stay the extra 10 minutes and voila, I keep the glass ball in the air.

Another great piece of advice is that you can afford to be wrong as long as you’re fast. If you notice your mistake before anyone else does and you proactively fix it, it’s almost just as good as if you never made the mistake at all. I have gotten very fast at what I do, and this speed allows me to mess up from time to time with minimal negative consequences. On the other hand, I’ve had coworkers who took days to complete what I could do in 2 hours, and so when their end product was messed up, it was a way bigger deal for them than for me.

Don’t sit on bad news. Just pass it on as soon as you can. Nothing has ever gotten better for me the longer I sat on it.

Your job will be so much easier if people like you and if they trust you. Trust is most important, but if you can get someone to like you too, that’s ideal. Easiest trick I’ve found is just to ask the person about themselves. Over and over. Every time you see them. Whatever they gravitate towards conversationally, whether it’s a project at work, their family, or their hobby, stick to that topic the majority of the times you speak with them. Manipulative? I guess. But I am well liked at work so I really don’t care. My boss won’t shut up about his dog, so I just embrace it and ask even more questions about the thing. With another guy, I just talk about his motorcycle. Another guy, I ask him what he’s working on and how it’s going, because that’s what he loves talking about. That’s the easiest way to get people to like you: don’t talk about yourself unless they specifically ask, and stick to their favorite conversational topics. I hate sports but a one guy who loves the Patriots. So if I know I’m going into a meeting with him, I make sure I look up the score from last weekend so I can at least lead off with “heck of a win we pulled off against Atlanta, eh?” Even though I didn’t even see the game, he’ll go on and on without any further participation from me besides the occasional nod.

People love a problem solver, not a problem creator. Try to only offer solutions, and not be the guy to announce why something won’t work. If you have to make an objection, immediately follow it up with a better idea. The worst thing you can do is to shoot something down without a better idea. Don’t criticize something without offering a better alternative.

Find a time-management/to-do list solution that works for you. I have experimented with OneNote, with Outlook flags, color coded categories, e-mail folders, a spreadsheet, sticky notes, a dry erase board… nothing stuck. Currently, I like using Outlook calendar events to myself. While I’m on a call, if an action item comes out for me, I’ll make myself an appointment for later that afternoon to follow up on the action item. Sometimes I will also open a blank e-mail and draft a couple words if the action item is just to send someone an e-mail. Anyway, just find something you like and which works and doesn’t require a lot of overhead and maintenance to be successful and try to be consistent about it.

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Lessons from my own career

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Solve the Boss’s Problem

One of the best things you can do as an employee is to figure out a problem that is plaguing your boss (or client, or even co-worker) and then go solve it. The best case scenario is if you unilaterally identify it and come up with a solution, but it’s also great if you can get in on the project if one is already underway. My biggest win in my career was probably when I was working as the communications officer for a field hospital. The personnel department maintained all kinds of information about soldiers using multiple Excel spreadsheets. Things like who was on a medical profile, who had PTO coming up, who had an expired annual training, stuff like that. The spreadsheets lived on Sharepoint, so only one person could edit it at a time, and if they left it checked out, no one else could edit it until that person checked the file back in. Every week, the commander had the personnel staff brief him a summary of all the various statistics. It took someone nearly an entire day to compile all the information into a neat and tidy PowerPoint presentation, and by the time the meeting actually happened, the data was 2 days old. I noticed this and did two things. First, I converted the Excel spreadsheets into Sharepoint Lists, which could be edited by multiple people at the same time and never needed to be checked in or out. Second, I build an interface in Microsoft Access that could connect to those lists and dynamically populate the graphs summarizing the data at the click of a button. The commander could run that weekly meeting and get real time data any time he wanted from his desk with just a couple mouse clicks. He loved it, and I got a glowing annual review from him. The personnel shop loved it too. It was a huge win for everyone.

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Know The Background Information Before a Meeting

I’ve had to deliver a few presentations to C-Suite level people at my clients over the years, and the times when I get attaboy’s from my boss have been the times that I knew what I was talking about better than anyone else in the room. I was able to speak confidently and inspire confidence in the audience with my command of the subject matter. If you can go into a meeting knowing all the background information behind what you choose to put on your slides, it gives you this feeling like you can’t be surprised by any question. If you also take the time to think “OK, what are the questions that I really hope no one asks” and come up with good answers ahead of time, you’ll have that in your head in case it comes up. I spent a few meetings early on in my career just dreading a question I didn’t have a good answer for. It really undermines your entire presentation if that’s stuck in your head. So, know all your background info. Best reply ever to keep handy: “I don’t have the answer to that with me, but I will get back to you later today with an answer.” 100% success rate for me so far, but it only works if you use it judiciously.

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Keep Business Relationships Professional

Don’t share your salary with anyone. I did this a few times with co-workers and peers, and without fail, the relationship gets weird after you do it. Just keep it to yourself.

Keep your opinions to yourself about anything even remotely controversial. I really messed up at a job once when I was just standing around shooting the breeze about what everyone did that weekend. I had mentioned that we went out to meet up with one of my wife’s gay friends and a few of his buddies. At the end of the night, they asked if we wanted to stay with them at their place because it was close by, we had been drinking, and I had a long drive home. I told the story with a kind of “oh heck no, that would never happen” attitude, and the Director of Operations picked up on it. I’ll never forget her words… she turns to me and says scornfully “oh you’re not a homophobe, are you?” I immediately tried to walk it back, explain that I had never met these people before and it wouldn’t matter if they were gay or straight, I didn’t want to sleep at a stranger’s house, but it was too late. In her mind I was from then on a hateful bigot. Could have avoided that animosity if I had just kept my mouth shut and not gotten too comfortable. So watch the stories you tell too, because they can really say a lot about you as a person. And you can’t control how people interpret what you say, either.

Tailor your profanity usage to the lowest common denominator within earshot. If you’ve never heard someone swear before, don’t swear in front of them. This goes double with people outside your organization. Even if they are dropping F bombs, at max only let some milder words out around them. Never ever use a racial slur or other epithet around anybody you are even tangentially connected to professionally. Don’t mock people’s accents behind their back. You will spend the next two weeks wondering if the other Indian person who happened to be behind you at the time complained to HR.

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Don’t Fight Electronically

I have a long-standing adversary at work. She hates me. I don’t really care for her, either. But she hates me, I really truly think she does. I told someone once, “I’m not saying that if there were a button she could press that would kill me she would press it…. But if there were a button she could press that would save my life, I don’t think she would do that either.” She takes every opportunity she can find to make me look bad in front of other people, or to point out when I make a mistake. I have learned to handle her by catering to her sense of “you must always follow the rules rigidly at all times” and things have gotten a little better. That’s when she was the one to drop the ball on something her team owed me. I got so angry that she had not only broken a commitment, but had given away the resources I would need to recommit delivery in the next two weeks. This was after I specifically asked her to reserve those resources just in case we missed the first commit. She said she was so sure we would make it, that she wouldn’t hold them back. Well, when I discovered that we were going to be not 2 but 4 weeks late because of her gaming the resourcing plan to make her team look better, I put in my new request for resources into our web application with a very snarky note about how I was disgusted at the multiple broken commitments and how I don’t appreciate the games being played. Once I hit save, it was etched into a web program that could be viewed freely by anyone in the company. She wasted no time in telling her boss, a VP. I got a pretty stern talking to for that one. So bottom line, if you gotta beef with someone, beef face to face. Never do it electronically. And never ever do it electronically in a public forum that doesn’t have a delete button for when you realize what a stupid impulsive thing you did 5 minutes after you saved the comment.

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Guard Your Reputation

In my first unit in the Army, I got pretty good at my job, and I was pretty friendly with my peers as well. Our weekly meetings with the senior staff started to become times when we would make little inside jokes and just generally not take things seriously. This worked OK at first since the old commander knew I was competent and he didn’t really care. But then we got a new commander, and soon after he started, I really dropped the ball on something. I think my buddy and I made a joke about it during the meeting or something like that, and it all kind of escalated to the point where we looked terrible and it became kind of a big deal. Anyway, hearing about this whole situation from his senior staff was the first time the new commander had heard my name. So from then on, guess what he thought about me? A guy who didn’t take his job seriously and was bad at it on top of that. Luckily I had already made arrangements to move on to another assignment, so I didn’t have to work for him long, but he gave me a pretty mediocre review when I left. If I had stayed it would have been rough. So you can spend a year building a solid reputation only to throw it all away with a few jokes and a mistake.

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Verify What People Tell You

When possible and reasonable, check up on what people tell you to make sure it is factual, especially if that information is going higher up the food chain (our outside the organization). When I arrived in theater for my deployment, I had to sign for inventory on behalf of my boss who was out of the country. Part of that was ammunition, which was stored in tagged and sealed boxes in a locked shipping crate. There were two types of ammunition – one kind had 1000 rounds to a box, the other had 1200 rounds to a box. But the boxes themselves were the same size regardless. Oh and they were super heavy and cumbersome and just generally sat in one place since it was “for real this is war” ammo that has never and will probably never need to be used. So all this kind of made me drop my guard. I remember being shown a wall of boxes on one side of the container, and a wall of boxes on the other. I was told the 1000 round boxes were on the left, and 1200 round boxes were on the right. I verified every tag to make sure all the boxes were sealed. But some boxes had the labels facing the wall while others had the labels facing out where I could read them. I did the simple math to verify the count was what the paper said it should be, and signed for the ammo. Well when the time came to transfer the ammo to the next unit, the guy doing the inventory decided he wanted to see all the labels. So we hauled all the boxes out to show him, and lo and behold one of the boxes on the left hand side was actually supposed to be on the right hand side and vice versa. So the total count was still correct, but it was 200 off in either direction. Which meant that technically we had “lost” 200 rounds of ammunition, and it almost became a really huge deal and could have even ended some careers if people wanted to be jerks about the whole thing. Luckily I think there was some one star general that could just wave it away and when it got to his level he took mercy on us and no one was burned at the stake after all. But that was a very tense few days in between, and it was technically all my fault.

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Financial Advice

Always contribute enough to your 401(k) to get the company match. That is free money.

If your company offers multiple health insurance plans, and an HSA is one of them, I highly recommend going with that unless you run the numbers and can prove the alternative is better. If you do go with an HSA, max out the contribution limit each year. Money into a 401(k) is good, and you should still go for your match, but money in an HSA is even better. In addition to being taken out before state and federal income tax, it is also taken out before Social Security and Medicare taxes, netting you an extra 7.65% in savings for each dollar you put in there. Plus you can use it on all kinds of things besides doctors visit’s, like over the counter stuff from the pharmacy, dentist bills, or prescription glasses. And if you end up with a big pile of it, you’ll have no shortage of medical bills in retirement, so you can use it for that. And you can even pay insurance premiums with if if you ever find yourself uninsured or when you retire and want a supplemental Medicare plan. I can’t say enough good things about an HSA. Note that this is not the same thing as an FSA, which is a “use it or lose it” annual account, and one that requires a lot more foresight and planning to be useful.

Don’t jump ship without a lifeboat in the water unless you have no choice. The freedom to be choosy with job offers is a great place to be. You also don’t want to be stuck in an unemployment window. The longer that lasts, the harder it will be to get back into the workforce where you want to be. So always be “casually looking”, and when the day comes that you are ready for a switch, don’t give your notice at your current job until you have an actual offer letter.

When you get that offer letter, one of the most critical things you can do for yourself financially over the course of your entire life is negotiate for a higher salary. Even if you are impressed or happy with the offer, ask for more. 20% if you feel that wouldn’t be unreasonable, but even 10% even if you think the offer is already too high. No company is going to pull the original offer altogether if you do this. As they say, the worst they can say is no. So ask. The compound nature of raises (they will almost always be done as a percentage of your current salary – i.e. here is a 5% raise) means this will literally pay dividends over the course of your career. Other items are negotiable too. Once you have an offer in hand you can ask about things like the PTO policy. For example, if they only offer 10 days a year to start, ask for 15. Fight for yourself. They want to hire you, but they also have a bottom line to worry about and they will likely low-ball you with their first offer.

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Conclusion

Keep your guard up. Watch what you say, write, and do. Don’t let it down because someone makes you feel comfortable, or because you’re emotional. That is when you’ll make a mistake that could derail your career.

The only time I’ve ever truly felt good about something I was paid to do was when I made that data tracker for my boss in the Army. Otherwise, my career has brought me extremely small amounts of fulfillment, and virtually no satisfaction or sense of purpose. I am OK with this though. My job is a means to a greater end. If you enjoy your work, you are far more lucky than I. The best I think most people in America can reasonably hope for is fair compensation for a job you are good at alongside people you can tolerate for a boss you respect. If one of those four pillars is missing, you should start hunting for a better fit. But I personally don’t believe I will ever have a “dream job” that I actually wake up energized for and looking forward to each day. If you spend a few years chasing that, you’re going to get really jaded and disappointed. My advice is to just look for those basics and then let the dream job find you.

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