Middle management has a bad rap. I enjoy the role. You get the freedom and authority of being a boss while retaining the safety net of having a boss. It’s the best of both worlds! That is, of course, assuming you have a good boss. And, naturally, you also want to be the best possible boss you can be.
Some say it’s actually the worst of both worlds. Being a boss is hard, and having a crappy boss just sucks. That is, unfortunately, also true.
In my career, I’ve worked hard at being a good boss. I’ve also had good bosses, great bosses, incompetent bosses, and bosses who were genuinely terrible human beings. That’s a lot of boss experience to draw on.
Here I share the best advice I’ve received from the best and worst bosses, and my career experiences that have taught me most about what a great boss does.
The Best Advice
As a middle manager, you often get advice about being a boss from your boss. Sometimes the advice is good even when the boss is not. But the best tips come from the best bosses.
Here are 10 valuable and memorable tips I’ve been given on bossing from bosses.
1. Don’t stroll
One of the best bits of advice I’ve received was from a boss I had only briefly but truly adored. He said, “Never walk past a group of hard-working employees with your hands in your pockets.” Don’t meander or stroll holding a cup of coffee. People who work for you are working hard and that’s the last thing they should see.
He advised I always walk swiftly, with purpose, carrying a notepad, with my head up. It’s not just that you want to look like you’re working, but you should look like you’re working.
2. Vent up
This is a great piece of advice that I received from a terrible boss. She definitely didn’t follow it. The fact that this boss was so bad about her own advice drove home for me the value of this rule, making it even more memorable.
Never complain to your employees. Not about your bosses, your peers, the company, and certainly not about other employees. Your employees might feel a temporary camaraderie with you, but they will lose respect for you as an authority figure. They also might wonder what you say about them when they aren’t there.
When you have complaints or issues about your job, those concerns belong in a discussion with higher-ups only. It makes more sense to vent your problems to someone with the authority to do something about it anyway.
Do you worry about coming across as a complainer to your boss when you vent up? That brings me to my next bit of advice.
3. Don’t bring up a problem without a solution
Have you ever had a boss you liked, but who wasn’t a great boss? I have, and he imparted to me this gem. It’s more advice for an employee than a boss, but I share it as a middle manager who is both. It’s great advice.
There is a fine line between informing your boss of a concern and being a complainer, and that line is whether or not you also bring a possible solution to the table. It doesn’t have to be a great solution, maybe it’s not even plausible, but you will find that bringing up at least one suggestion changes the tone of the discussion.
Generating a possible solution also improves your view of the problem. It’s just a good exercise in general.
Consider the difference in these scenarios:
“Hey boss, there aren’t enough parking spaces and it’s really annoying in the morning when I can’t find one and have to park down the street.”
versus
“Hey boss, we don’t have enough parking spaces for all the cars and some of us have to park down the street. Is expanding the parking lot a possibility? Maybe we can look at incentivizing carpooling for employees. What do you think?”
The second version will have a good boss making a note and saying they will look into some options and get back to you.
The first version is probably going to render something like, “Get here earlier then.”
4. The second best decision is the wrong one
This advice is a variation on a famous quote from Teddy Roosevelt. He said, “In any moment of decision, the best thing you can do is the right thing, the next best thing is the wrong thing, and the worst thing you can do is nothing.”
The point of this advice is that it is imperative for a boss to make decisions. Make them quickly and decisively. Obviously, you hope to make good choices and that comes with experience, but the worst thing is to be paralyzed by indecision. When others are looking to you to decide, do it.
5. Praise publicly, admonish privately
It is inspiring and motivating to see a coworker who deserves recognition receive it. It is even more so when it’s you receiving the praise! Individuals and teams require their hard work be noticed, and it’s valuable to let everyone know that good work is appreciated.
I’ve had the benefit of a boss who really lived this advice, and I loved to pass on notable praises to him so my employees would receive public recognition from the higher echelons of the company, making it more meaningful and memorable.
On the flip side, you should never embarrass, shame, or call out an underperforming employee in front of others. This action diminishes trust, not only with that employee but also with others who fear they might receive similar treatment. Besides that obvious advice, you should always give employees a chance to privately respond to performance issues. There may be something you don’t know.
Speaking of something you don’t know, there is nothing more frustrating than a manipulative coworker getting away with slacking or getting credit where it isn’t due. How do you avoid making this fatal mistake? See the next tip…
6. Know what’s going on
One of my favorite bosses was hated by all the slacking employees in the company for this reason. This was his advice to me and he lived and breathed it.
It’s easy to think someone is doing a good job because you like them. Maybe you see them often and they relay to you all the work they’ve accomplished. If something in their purview is falling behind, maybe they seem to have a good reason. Perhaps it’s someone else’s fault, according to them.
It is incumbent on the boss to know what is true and what is false. If someone says they met their quota, you should know if that’s true. If they didn’t because they claim the parts aren’t available, you should know that, too.
I’ve heard the advice “trust but verify” thrown around but I hate that phrase. It doesn’t make sense – if you trust you don’t have to verify. In my experience, “verifying” has been used to spy and try to catch someone in a lie. Frankly, I’ve only heard the phrase used by bosses who gossip and scapegoat.
The advice “know what’s going on” is similar to “trust but verify” but it’s not checking up on the veracity of what someone says. It is being aware enough of the status of work for which you are responsible that you simply know whether a statement is accurate and to what degree it might be a mischaracterization. This knowledge comes from a lot of communication and involvement. It’s difficult but critical.
7. Keep employee notes, good and bad
This advice may seem obvious to an experienced boss, but it’s something bosses need to be consistently reminded to do. When performing an annual review, an employee should not get what most of us get – an assessment reflecting the last six weeks. Give your employees the respect they deserve by commenting on ways they’ve met and exceeded expectations all year. Also, have enough notes to recognize improvements over time, as well as degradations in performance.
The toughest part about following this advice is developing a system you can maintain. One boss’s advice to me was to send myself emails with my quickly jotted notes each week. Do what works for you and be consistent.
8. People will meet your expectations
This is a bit of advice I actually gleaned from a parenting book and used to my advantage when I taught university courses. It is good advice for bosses as well, and while no one has ever technically given me this advice, I’ve seen successful bosses using it.
The parenting advice goes like this: Your children will rise up to meet your expectations, but your real expectations, not just what you say.
See, if you say to your kids, “I expect you to be on your best behavior at the restaurant,” your kids know that you don’t actually expect this. If you did, you wouldn’t bother to say so. Instead, you are telling them that you hope they will behave but you believe you have to remind them.
The same is true for people in your employ. Communicate clearly what is expected, then expect it to be accomplished. If you ever catch yourself saying something to the effect of, “If you don’t…,” or, “If you can’t…,” just stop yourself right there.
“Let me know if you run into a problem,” is sufficient to leave communication lines open.
Someone once said to me, “People don’t come into work and say, ‘I’m gonna do a really crappy job today.’” People who work for you are there to do the best they are capable of on that given day. Know that and let them do it.
9. Have a brand
This is really interesting advice I got from a super unique, very fun management course and I’ve always held fast to this memorable tidbit.
As a boss, you should have a brand. Think of how you want your employees to see you. For me, it was this: As a boss, I am honest, authentic, reliable, and predictable. For you, it might be no-nonsense, compassionate, fair, or innovative.
When you have determined your brand, write it down where you, and only you, will see it periodically, like taped to the inside of a drawer. You will not tell anybody what your brand is, you will simply embody it. Ensure that every decision you make, and every action you take as a boss, reflects this branding.
This is one of the best ways to become the boss you’ve always wanted to be.
10. If you’re the smartest person on your team….
….you’ve done a terrible job of recruiting.
I’m not sure where this advice came from but it’s memorable and I consider it one of the most important reminders for a boss.
Bosses sometimes get to thinking that they are the boss because they are the smartest. You might be a boss for a very good reason. Perhaps you have a ton of experience and an enviable background. Maybe you’re certain you know what’s best in any given situation.
It’s important to have perspective. Other people do have good ideas. Not sometimes, but often. While you may know exactly how you want to handle a situation, there is value in trying something new. There is value in giving an employee the reins. There is value in developing an individual or your team by allowing them to try something new – even if it fails.
One thing to always remember is this: When you are a boss, you are not paid for what you do. You are paid for what your team does. This isn’t The YOU Show. Don’t forget to let go, and let your team shine. If you’re a great boss, they will.
What do you think of this advice? Do have something to add? I’d love to see it in the comments.
A few years ago, during the pandemic and at the start of The Great Resignation, I posted a rant on Medium.com about my “hardass” boss, and how he was so much better than “cool” bosses. If you’re interested, you can find that here.
If you’re curious about me and my career background, check out this short post here.
Find other career-related posts on this Generation X, midlife, lifestyle blog, here.
Thanks for reading!