Listen, I get it. Good help IS hard to find. I’ve been through a few bad apples myself. I’ve also coached many attorneys through the process of firing bad-fit employees, and hiring, on-boarding and training shiny, new employees.

However, if you find yourself going through this process over and over and over again, you might want to consider there could be an issue with your:

A) Hiring process;

B) Training process; and/or

C) Leadership (and/or management) skills.

In fact, there’s no way around it.

While we can’t get into all of that in just one blog post, I’m going to share with you two questions I think will make a big difference for you. The first is:

Am I setting clear expectations?

And the second is:

Have a created a system so my employee or employees, once they understand the expectations, can routinely report back to me their progress?

Do not underestimate the power of asking yourself these two questions in any situation where you feel an employee is underperforming. Oftentimes, we think we are communicating clearly when we are not. What may be so crystal clear in our own minds may not be clearly articulated to others. There may be steps missing. We forget all those soft skills we developed along the way as we invested years and years in our education, internships and those first jobs—and then we hire people with expectations that they will just know those things, too, by virtue of being in our presence.

As the Geico commercial famously says: “That’s not how any of this works.”

Many of my women clients, in particular, find their directives getting lost in translation because, as bosses, they often sugar-coat their expectations with niceties. They are so fearful their employees—whom they call “family,”—won’t like them, they wind up frustrated, upset and resentful.

What they fail to realize until it is too late, is that their employees are equally frustrated. And they are confused, too! Most employees WANT to do a good job when they are hired. They are hopeful this is a place where they will be happy, fulfilled and respected. Quite frankly, they’d rather come in, do good work, get paid well for it, and then go home and spend time with their actual families. They don’t need to you love them like a family member. Good boundaries serve everyone well.

Here’s a little secret I wish I had learned much earlier in my career: One can be direct and still be kind. We don’t need to be loved by our employees, we need to be respected by them.

On the flip side, we don’t need to be feared either. Have you ever had one of those bosses who take being a boss to the extreme? Like their credentials and title are anointings from God? Yeah, no one wants to work for that guy or gal. Just because you are “direct” does not mean you are being “clear.”


Setting clear expectations is about thinking about what it is you want before you ask for it, preparing for the ask, and then clearly communicating what you want to the person from whom you want it.

Do not underestimate the thinking and preparation part, particularly if you are new in making the transition from solo to CEO. It may take a little longer at first to train yourself to get the information out of your head and down on paper or documented in a computer file, but, oh will it be worth it in the long run! AND, it will help your communication so much, because now you have a document both of you can reference.


The most illuminating tools for understanding whether (or not) the other person is picking up what you are throwing down are questions:

“Do you need clarification?”

“Do you have any questions?”

“Is there anything else you need from me to get started?”

“The deadline is X. Do you have that on your calendar? Are you good with that? Is there any reason whatsoever you will not be able to complete it by that date? Any conflicts?”

“What am I missing? Is there any information you think I need to know on this file that I don’t have?”

You get the idea…


After you have clearly communicated your expectations, you need a system by which your employee can routinely report back to you their progress by the prescribed progress dates and deadlines. This needs to be an agreed-upon systems, one you have chosen for the firm for all the employees to use and for you to use. This could be a weekly firm meeting, it could be a daily email, it could be weekly notations in the case management systems, it could be reports prepared, printed out and on your desk by a certain date and time—you decide what you need and desire and communicate that to the employee.

When we leave this part open-ended, we wind up chasing the employee or employees for answers about issues we thought we had handed off to someone else. That turns us into nags and micromanagers. It makes us unhappy, dissatisfied, and confused about why our “system” isn’t working. We think it’s the employee’s fault, when it really is a failure to create an effective management system. Do not overlook this critical step.

If you liked this lesson, I’d love to hear from you! Please reply to this email with your feedback and let me know what you think.

If you need help growing a team based on your core values, click here to schedule an appointment with me and let’s talk about how I may be able to help you.