April 06, 2021 Feature

How to Coach Your Employees—for Keeps

Eleanor Southers and Jill Meshekow
In order to keep your newly hired and trained talent, you need to work on continuous improvement.

In order to keep your newly hired and trained talent, you need to work on continuous improvement.

Drazen Zigic/iStock via Getty Images Plus

Do you ever feel that running your practice is like a marathon with no end in sight? Being a solo is hard work that keeps coming—sometimes at a relentless pace. While it may seem like an overwhelming task to jump off the track, even for a moment, the time and energy that you invest in those you entrust to help run your business will pay out in the long run. The bottom line? Coaching your employees for long-term success is worth it.

With the best support in place, who knows? You might even be able to let others take on a leg of the race, giving you the free time to concentrate on the strategic work needed to grow.

We share with you these simple tips to help you find and retain high-level talent through smart hiring, training, and coaching.

Hiring: Pick the Right Person

“People are not your most important asset. The right people are.”

—Jim Collins

The best coaching relationships always start with that first step—finding the right person for your team.

  • Challenge: As a solo, you typically don’t have anyone within the firm (i.e., a human resources department) to do the hiring. You must become good at looking for the “right fit” yourself.
  • Solution: You will need to be able to match the applicant’s skills, experience, and aptitude with the core needs for any position, and that means starting with a job description.

Here’s an example of why a job description is so important:

Erika is the first candidate that Alison meets for a receptionist position at her firm. Erika appears to be customer-service oriented, bright, and personable, so Alison hires her on the spot and cancels the rest of the interviews scheduled for the day so that she can get some work done. What Alison failed to make clear during the interview process was the fact that the most important elements of this job are punctuality and attendance. Erika would be in charge of opening the office and greeting early clients. Imagine Alison’s surprise when Erika shows up late every day for her first week on the job. Erika has no idea about Alison’s expectations and so is unconcerned about her start time and continues to be late.

Believe it or not, this is something that we’ve seen on more than one occasion.

If Alison had clearly outlined her expectations by formulating a job description and highlighting the most important aspects of the job, she could have saved herself the aggravation of Erika’s behavior and the time it will take to fire her and find a replacement. Erika would have known what she was expected to do up front and could have told Alison that she was not interested in the position.

This is an extreme example, but a better outcome would be hiring a receptionist who understands the core necessities or essential functions of a position (being on time and dependable) but might not be familiar with the nuances of Alison’s practice. In this case, good coaching is what could bring someone who has the basic skill set to the next level of success.

Finally, we recommend having a written employment agreement for every employee you hire. This can be as simple as an offer letter, but make sure that both you and the employee sign it. Include all benefits, working hours, vacation time, and holidays. Also include a probationary period of at least 90 days, and don’t forget the “at-will” clause if you are in California. This starts the foundation of understanding for both sides.


  • Have a complete job description ready for candidates to read before they interview, or, better yet, include this information in any ads you place while recruiting.
  • Emphasize the most essential aspects of the job.
  • Allow sufficient time to thoroughly interview the candidate.
  • Decide if the candidate fits your firm’s culture (if you don’t know about the importance of culture in an organization, Google it).
  • Extend a thorough offer letter or employment agreement.

Once you have the right person for the job, you’ll need to make it easy for the individual to contribute.

Training: Onboard Your New Hire

“The goal of education is understanding; the goal of training is performance.”

—Frank Bell

The first three to six months in the employment relationship can be considered a “honeymoon period.” This is the window of opportunity for you to flex your coaching muscles and clearly spell out your expectations while bringing your new hire into the fold.

  • Challenge: Solo practitioners do not usually have a robust, formal training program to rely on when onboarding new hires.
  • Solution: Determine the knowledge gaps that your new hire has and find or provide inexpensive resources to fill them. This can be a custom job.

We know, we know. The word “training” can bring on the negative connotation of dusty classrooms and boring chalkboard presentations—but it doesn’t have to be that way. In today’s world, basic online courses can be purchased individually for everything from customer service to Excel.

Just realize that providing the online tools does not get you off the hook personally for the development of your new hire. If you have a clear culture (see above), you will need to convey this to the individual and follow that up with solid coaching.

Let’s go back to our receptionist example. Depending on your clientele, your firm may have a distinct greeting when answering the phone or responding to an e-mail. Rather than assuming that incoming administrators understand how your particular business handles communication, make sure to have this information or script ready so that they can use it as a guide. Explaining why this is your preference is just as important. This will go a long way toward getting buy-in and keeping your front line maintaining your brand.

Knowing where to go for answers is just as important as having them. Take the time to connect your new addition with individuals or online information that can lead them to self-sufficiency. Ask for feedback for any additional resources that they may need.

Be sure to follow up with your new hire on a consistent basis to check for understanding and to help guide the individual in those areas where they may need help. This means a 30-60-90-day meeting for two-way communication on how everything is going. By having these touch points, any negative performance issues can be corrected quickly, and positive attributes can be emphasized.


  • Decide early on the areas in which you will need to “train” your new hire.
  • Provide resources for new hires to find their way.
  • Schedule frequent check-in meetings with your new hire to test for understanding. These are your coaching “moments.”
  • Be available to answer questions.

You are now ready for the next step in your journey as an employer.

Coaching: Lead Your Team to Success

“You don’t build a business—you build people—and then people build the business.”

—Zig Ziglar

In order to keep your newly hired and trained talent, you will need to work on continuous improvement. This is another tedious-sounding activity, but if you invest the time up front, it could save you countless hours of grief in the long run.

  • Challenge: Most solos concentrate on the work in front of them. After all, you are the main provider of cash flow for the business. Perhaps you need some ideas on how to break away from the grind and focus a bit more on others?
  • Solution: See below for best practices when coaching your team.

Some of these may seem simple and intuitive, but, again, as we get busy, we sometimes forget to use what we know works. So, here it goes. . . .

  • Set up regular one-on-one meetings with your employee on a consistent basis. This is the time when you can go over all that is right and wrong in the world and can be a feedback loop that works both ways. They make for those perfect coaching moments.
  • Never criticize your staff in public because, well, nobody likes to hear those things aired around others. Use that one-on-one time that we talked about to go over areas of improvement. It will give you time to formulate your delivery to be most effective, as well as time to cool down if you need it.
  • If you do have to give an immediate correction, make sure that it’s productive and specific so that the employee can meet your expectations. Here are some examples in order of, um, increasing effectiveness, and this time we use an attorney as the employee:
    • Criticism that is just plain bad sounds something like this, “Didn’t you learn anything in law school?” And, yes, this is a real example.
    • There is another type of criticism that is specific but has an element of shaming and may not be accurate. It goes, “I told you the motion was due on Wednesday, and I haven’t seen it.” Motivating, right? Especially not if the attorney/employee was told that it was due on Thursday—in writing.
    • Next, we have the criticism that is specific but incomplete, such as, “The brief you did on the Jones file lacks enough good cites.” This seems to indicate that the partner wants the attorney to go back and find more cites. The problem here is that it is too general, and the attorney doesn’t really know which part needs bolstering. The attorney will waste time trying to guess what is lacking.
    • The most useful criticism is specific, true, and complete. It goes something like, “The brief you did on the Jones file lacks enough good cites. I want you to find more cites, especially in the area of the deregulation issue that will explain our position more clearly. I need it by tomorrow at noon.” (You can see that this is the most productive feedback).
  • Follow up with touch points on any negative feedback. If your employee improves after a conversation, make sure that you mention this the next time you meet. On the other hand, if the improvement is not happening, you can test for understanding.
  • Put it in writing. After you have a coaching session with your employee, it’s best to send an e-mail with an outline of what was discussed. Whether it’s a positive new task or a performance issue, it’s nice to have a record. Be sure to include a due date if there is something specific that you are asking for.
  • Invest in your employee’s continued growth and development. Nobody works harder for a leader than someone who feels valued. Invite your employee to join you in a meeting to discuss their goals and how you can help or use one of your one-on-ones as a personal goal-setting session. You can offer to provide some of the tools that your employee may need to achieve those goals.
  • Recognize that employees appreciate valid praise sometimes more than a bonus. We’re sure, like most of us, that they would be happy with both, but surveys have shown that recognition is valued highly in the workplace.
  • Set up a review process. The best coaches give continuous feedback so that their employees know exactly where they stand at any time and there are no surprises—either negative or positive—but it’s still important to set a formal time to document and discuss development past the 90-day time frame. Whether you decide to do so quarterly, semi-annually, or annually, a consistent review process will go a long way in keeping your employment relationship on track.
  • Don’t let things “fester.” What do we mean by that? If there are areas of performance that are not improving with continued coaching, learn to document and discontinue. Sometimes you may feel as if you have been doing everything “right,” but the individual just isn’t “getting it.” In those cases, it may be best to terminate employment and move on. Don’t allow time constraints or workload to cloud your vision.


  • Make sure to deliver continuous feedback to your employees. In this case, nobody likes surprises.
  • Set up consistent times when coaching can come first.
  • Be mindful of the messages that you use when you do coach, along with the way that you deliver them.
  • Encourage your team to be their best selves and grow as individuals.
  • Most importantly? Take the time to coach.

Your support team can either make, break, or considerably slow down your solo practice. Continue “coaching them for keeps” for the continued success of your business.

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Owner of Professional Legal Coaching, Eleanor Southers (southerslegalcoach.com, 831/466-9132) coaches attorneys across the United States at all stages of their development who want greater success and fulfillment in their careers. She does this on a one-to-one basis in person, by phone, or via Skype, assisting the lawyer to identify issues and create pathways to overcome problems. She is the author of Be a Better Lawyer: A Short Guide to a Long Career (ABA, 2014).

 Jill Meshekow, SPHR, SHRM-SCP, is a skilled human resources director with multi-faceted experience in both the nonprofit and for-profit space. With more than 20 years of HR experience working through the complete employee life cycle, her favorite area of focus is individual and team development. Jill is passionate about creating corporate cultures that create win-win situations and feels that coaching your team is at the top of the list to achieve that goal.