Help me be a good boss

I’m a tutor. I go house to house in some of the suburbs of NYC, visiting students where they live.

Business has been good, so I’ve hired someone to help me with (and, at some point, hopefully, take over) my scheduling.

My new scheduler is a virtual assistant who lives in Colorado. She has a lot of experience in many different types of customer service and calendar maintenance. Her communication skills are terrific, and her husband is a truck driver, so she understands planning routes in order to maximize results and minimize transit. On top of all of that, she’s a mom, with a busy household calendar, so she’ll understand the parents’ concerns when they’re trying to work out a tutoring schedule.

I’m really excited to have her, and I think this could work out beautifully. While I’m waiting for my lawyer to draw up a non-disclosure agreement (everything about my families is confidential), I’ve been thinking about how to be a good boss.

So far, I’ve come up with:

  1. Be clear about what my scheduler’s job is, and what I want and don’t want her to do. Ultimately, she’s helping me build relationships with these families. I’m OK paying for extra time she spends on the phone chit-chatting and building rapport with parents, or if it takes a few email or text exchanges to make a family really happy with the scheduling they get. Customer satisfaction is more important than expedience to me, even though I’m paying by the hour.

  2. Suggest ways for her to do things, but don’t insist that she do things exactly my way. If she can think of a better way to do something, I’d love to hear it. (I’m hiring her for customer service skills that I might not have. If she knows of a way to handle scheduling that would make this a zillion times better, I’d be happy to adopt it. But I have to know what it is she wants to do, so that both she and I know exactly what the schedule looks like at any given time.)

  3. Make sure that she doesn’t feel penalized for doing a good job. For example, as she learns more about what I need from her, she might people scheduled faster. Less time working = less money, but maybe I could give her more responsibility, or ask her to do other stuff, so that she’s working as much as she did before. (And maybe I could give her a raise, because a great scheduler would be worth it.)

Any other suggestions for things I should or shouldn’t do? I’d love to hear them.

Give her frequent feedback, which is good to make a point of doing especially when you work remotely from each other. This should include both positive things (passing along compliments from clients is especially nice), and course corrections where things could go better. Consider scheduling a periodic meeting (I’ve always called them 1:1’s) for this specific purpose - I think they are particularly important for remote employees.

This is more philosophic than specific but when I’ve managed people/projects, I’ve always tried to live up to this: Boss vs. Leader.

This doesn’t really apply in your case but one principle I used was that I always represented my supervisors when I was talking to my subordinates and represented my subordinates when I was talking to my supervisors. Don’t just agree with whoever’s in the room with you.

And remember that when you do a favor for one person, you’re usually going to be making somebody else do more work. Don’t try to be a nice guy who grants every favor because you’ll just end up putting a lot more work on other people. Grant favors when appropriate but have a justification for doing it.

Don’t overthink it. It’s just one employee.

Make sure she knows how to do the job. This also means you setting attainable standards and making sure they are upheld. “I need my schedule by 8:00 PM Sunday” or whatever

Make sure she has everything she needs to actually do the job. Software, or whatever.

Make sure she has time to do the job.

Schedule a review after 6 months to see if everything is on track or if there are any issues that need addressed.

After a year, if you are satisfied, maybe a bonus or raise.

Immediately pass along any praise from customers directed toward her.

Be open-minded when it comes to new ideas. Don’t immediately say yes or no without thinking about anything new first.

Remember, you are not her friend. You are the boss.

You’re probably already overthinking this. That said, explaining why you need/want something, or why you want it a certain way tends to get better performance and morale.
Sharing how their efforts are contributing to your success is always good, once this is happening. Do not link this to their compensation etc.: most people by nature want to do a good job, or be helpful. Once you attach a certain reward to specific actions, you remove it from the social sphere to the transactional, and this is often counterproductive.
This does not mean to not reward them if things go well, but that’s what raises are for.

Read the book “One minute manager”.

Take a post graduate class on supervision - Hopefully one which has mostly other supervisors in it as students. Those students are out in the real world and you learn more from them than you do from the teacher (who hopefully is also a supervisor teaching part-time).

Other than that, be positive with your comments. And you work for her! Your job is to see she has all the tools necessary so she can do her job. If she needs something (like scissors to cut paper), get it for her.

Thanks, everyone! I’ll let you all know how it goes.

Listen. And remember: if the person screws up, and you’re not ready to fire that person, then it’s your fault. Figure out what you need to do to make sure they don’t screw up again.

A lot of people are afraid to be “the boss” or overcompensate and act like tyrants. Mostly employees just want clear direction on what you want them to do (or not do). Just be direct without getting all emotional