Career Advice from Best Boss & Worst Boss

My family and I frame dinner conversations around “best and worst” – as in “What was the best part of your day? What was the worst part of your day?” This helps us 1) have something to talk about other than homework or driving/activity schedules, and 2) get to know each of us handle daily challenges.

I have worked for some great leaders, and some not-so-great leaders, and have learned something from each one of them.

Below are some of the career advice leaders have given me over the years. Can you tell which advice came from the best bosses and which from the not-so-great bosses?

  1. When sending emails to a group of senior leaders, always put the distribution list in alphabetical order by last name. This makes it easier for recipients to see who else received the memo and removes any semblance of hierarchy or favoritism.
  2. Spend time at the beginning of calls and meetings getting to know your colleagues. They will remember that you asked about their family, their weekend, or their job.
  3. Use email subject lines to communicate what you are asking the recipient to do, and by when. For example:
    1. Review Requested by MM/DD: <subject>
    2. Input Requested by MM/DD: <subject>
    3. Approval Requested by MM/DD: <subject>
    4. Reply Requested by MM/DD: <subject>
  4. Apply an “Optics” lens periodically. What are the possible perceptions someone might have about what you are doing/saying, and how much does that matter to the overall success of the program/initiative/meeting?
  5. Always get away from your desk for lunch. Even if you just go for a walk or grab Taco Bell across the street, leave the building and don’t eat lunch at your desk. (Everybody touts this advice… and then schedules conference calls over lunch!)
  6. Don’t share information about your personal life such as your hobbies or your family. It sounds unprofessional.
  7. At work functions where alcohol is served, always order sparkling water with lime, but ask the bartender to serve it to look like a gin and tonic. That way people will think you are having a drink.
  8. Never use the bathroom on airplanes. (OK, so stories about unsanitary conditions on airplanes back this up.)
  9. Volunteering for extra-curricular activities like organizing the company picnic make it look like you don’t have enough work to keep you busy.
  10. Summarize your accomplishments more than one time a year. Keep a running list of your objectives and your accomplishments against them, and note where you contribute in ways beyond your annual objectives. Send the list to me periodically if I forget to ask for it.

The Tally

Best bosses career advice includes numbers: 2, 3, 4, 5, 10

Worst bosses career advice includes numbers: 1, 6, 7, 8, 9 (although I regularly practice #1 and swear by it as a way to reduce communication drama).

The common theme across Best Boss advice? It expressed concerns about me, my performance, my satisfaction at work, and ways I could make a difference or impact.

The common theme across the Worst Boss advice? The need to manage perceptions of me, and even potential perceptions of me. And, it all sounded a little paranoid.

Except #1. As OCD as it sounds, and as little it matters, I can’t stop alphabetizing email recipient lists …

Heather Nelson is a partner with PeopleResults. You can reach her at or on Twitter at @HeatherGNelson1. Sign up to receive the PeopleResults blog at Current.