Q1: Your company doesn’t do yearly evaluations but you’d like feedback on your work.
Yes you want to sing your own praises but you shouldn’t do it from a “me, me, me” place. You should bring up your specific accomplishments in terms of how it’s helped the company. In a review environment, self praise should come up not in a defensive way but posed in a way that you are looking for ways to improve, like, “My XYZ project just got picked up by the client,” is there anything I could have done differently or with future projects like these to learn and grow? When you’re looking for feedback, you don’t want general answers, you want basically an agenda for targeted areas your boss can comment on. And the 1-4 ranking is what some bosses offer if they have scheduled reviews. This way there is no neutral option like 3 would be in a 1-5 ranking. Often times bosses — I think the good ones — ask for feedback on their leadership style but don’t offer unless they ask.
Q2: You really need a raise to stay at your current company.
Asking for a raise is one of the most important conversations you will have so take it really seriously. Set a formal calendar appointment to show this is a big deal. Create documents like you would for any presentation with a copy for yourself and your boss. Practice a bunch of times in the mirror, with a friend, with your dog, whatever. And, look at your overall compensation package and not just your base salary. Sometimes getting more vacation time, transportation or cell phone bills covered or one day a week working from home can be more valuable than a pump in cash. So go in with a cash option, a perk option and a combo option. Remember, companies usually don’t open up the corporate coffers just because they feel like it. If you don’t ask the answer is always no.
Q3. You want to take a week’s vacation this summer for a family obligation, but you know your coworker is asking for the same week off.
You don’t have to be besties with your co-workers but they can be your biggest allies. People want to work for and with people they like. That’s just life. You want your co-workers to root for you. You don’t have to give them TMI but you should be real and human and tell them about your plans. If they are flexible, they will likely help you out. If they aren’t and you’re not able to change yours then you should go together to your boss and ask for the same time off and let her or him know that you can be reachable for urgent email and you’ve set it up so your tasks are fully covered. Your boss with appreciate the camaraderie because the last thing a boss wants to deal with is drama.
Q4. You’re traveling with work and everyone is going to a pricey restaurant that night. You’re not allowed to expense it for work and you can’t afford it.
If it’s a dinner with friends you might split the check evenly regardless of what everyone ordered but in a work environment, it’s commonplace to pay separately especially if some have an expense account and some don’t. You don’t want to lie and you don’t want to complain about not having one because no one likes a liar or Debbie Downer, it could get back to the wrong person and generally it’s not cool and bad karma.
Q5. You used to work for a laid back company that didn’t care what you posted on social media. Now you’ve moved to a stricter place.
As much as we talk about getting in trouble with social media time and time again. Some people just don’t learn and pay the consequences. Don’t be that person. Often times you can use social media to help share things that help the company at large. So do that for the possibility of praise because that often gets noticed. Use it as an asset not a liability.
Q6. You’re late to a meeting because you have a “lady problem.”
Women particular suffer from the “I’m sorry” syndrome. I used to say it all the time…until I started counting just how many times I say it during the day…it was crazy. I was apologizing when people bumped into me. Men apologize too but only when they actually do something wrong. Life happens. People are late to meetings…instead of offering more information than is necessary or putting yourself in a weak position off the bat, just turn it into a positive and say thank you for your patience and move on.
Q7. You need to reschedule a work meeting.
Again, this happens to all of us. No need to get into the details. C’mon. And watch the apologizing. Also, no one likes the game of “where do you want to go for dinner? No, where do you want to go?” cycle in your personal life. This ping pong match of “what time works for you? No, what time works for you?” is the professional equivalent. Make it efficient and offer specific times.
Q8. You are in the market for a mentor.
“Will you be my mentor” a weird thing to say. If you have one, it’s known. You don’t need a title to get the benefit. Also, a mentor doesn’t necessarily need to be in your field. You can get advice from someone who isn’t in the weeds with your specific industry, they might have a good outsider’s perspective. And, don’t forget not every mentor needs to be “above” you so-to-speak. You can and should learn for people on your professional level, too. You often want to see how they might and have handled something as they may have more practical insight and specific knowledge of the intricacies than someone way senior that might be out-of-touch with the issue you’re dealing with.
Q9. You haven’t been able to stop thinking about starting your own business.
Sometimes realizing you don’t want to do something is just as important as realizing you do want to do something. If you are obsessed, let’s say, with starting a cupcake shop. Try it on the side first. You might realize you loved baking but you hate sourcing ingredients and managing accounting and prefer to keep it as a hobby. Well, great, you got it out of your system and didn’t leave hastily for the dream rainbows and butterflies for a cupcake business.
Q10. You’ve tested your business idea on the side and you’re ready to make the leap to be the boss of your own business.
Starting a business is not all about passion and drive and dreams to make millions. You have to be prepared with logistics: money to live on if you don’t make money in your first year, which you likely won’t, and being OK with likely not having health insurance and other benefits. Keep it real: most businesses fail. Go into it knowing that you’ll fail at a lot of stuff. In business and life, it’s better to beat low expectations. If you have high expectations and you don’t reach them it’s more disappointing than if you were realistic and pleasantly surprised when you do soar.