Upskilling Staff Into Team Leadership Roles • Financially Simple


Upskilling is a valuable asset in the business world. Good coaching is beneficial for both the mentor and the mentee. The employee is benefitting from your experience. On the other hand, the trainer gets to sharpen their skills and increase their network. Perhaps you’ve identified a promising young talent in your company, and want to help them grow. But, where do you begin? What’s the most effective path to accelerate their growth? How do you measure progress? And, just as important, how do you know when to end the coaching relationship? Today’s entry is going to look at some of the ins and outs of upskilling staff.

Follow Along With The Financially Simple Podcast!

This week on The Financially Simple Podcast:

  • The Benefits of Mentorship (1:03)
  • How to Effectively Mentor an Employee (6:32)
  • Set Clear Goals (10:37)
  • When to Stop Mentoring an Employee (11:05)
  • Unfettered Access, Assigning Blame, and Being Non-Committal (12:05)
  • How to End the Mentorship (12:45)
  • Conclusion (14:40)

Benefits of Upskilling Staff

Whether we realize it or not, counsel is an important part of our personal and professional lives. As you’re growing up, you likely had several people pour into your life. Think about it. Did you ever have a teacher or a coach that really invested in you? Perhaps it was a family member. Regardless of who it was, someone took the time to instruct you and guide you as you matured.

As an entrepreneur, you might have had someone train you in how to run a business. Through networking, you could have found a handful of business owners with whom you’re able to discuss ideas for your own business. These are the people who can give you valuable insights into what works and what doesn’t based on their own experiences. They can open doors for you through their connections. Although you may not be receiving formal priming from them, they are acting as mentors in your life.

Similarly, you might be nurturing employees in your organization. That’s a good thing. It’s how you grow. Likewise, it’s how you develop talent in your business and help your team achieve their professional goals. Training up an employee has many benefits. While it’s commonly known that trainees benefit from this relationship, it can also have positive implications for you, and your business. But how does each party benefit?

Personal and Professional Growth for the Teacher

Developing an employee is an investment. It requires your time and, in some settings, money. If you’re shepherding team members, you’re probably not doing so for personal gain. At least, not directly. However, the mentoring relationship can provide personal and professional benefits to you. So, what do you get out of upskilling an employee?

First, nurturing employees helps you realize your own potential, providing you with opportunities to explore and learn the intricacies of a subject. As you dig deep into a subject with your trainee, you enrich your own knowledge and sharpen your skills. Teaching others is a great way to identify key points in any process. Even if you’ve performed a task or proficiency a thousand times, helping someone else develop that skill can provide a fresh perspective. In turn, this could help you identify more effective performance methods.

Similarly, the skills related to teaching are valuable in your own career development. Nurturing people is a great way to develop your ability to focus your attention on another person. Meanwhile, careful and non-judgmental listening is critical for effective communication, building trust, and leading others. Additionally, mentorship could help you to feel more fulfilled in your job. A study published in the Journal of Vocational Behavior shows that leaders who help develop others have greater job satisfaction and are committed to their organizations.

How Your Team Benefits from Professional Coaching

Taking an employee under your wing enables them to gain insight into an organization’s culture and systems, preparing them for the professional world. However, there’s a dual benefit at work, here. On one hand, your team member is receiving a form of advanced on-the-job training, potentially fast-tracking them to achieve their professional goals. On the other hand, they benefit by learning from your hard-fought experience. This could give them a leg up in their own development.

Employees who are actively participating in a team leadership development program often benefit from their leader’s networks. You have valuable connections in the business world. Networking is vital for climbing the corporate ladder, so having a close relationship with a successful mentor can be essential.

Friends, professional development is important to many employees. Therefore, it comes as no surprise that MentorcliQ reports that 90% of workers who have a mentor report being happy in their job. Additionally, 93% of workers believe their professional development relationship was useful. It’s clear to see that employees who receive mentoring are happier in their roles, but how does this benefit the business?

Business Benefits

Many companies have struggled to maintain their labor force since the start of the pandemic. In fact, 51MM American workers have quit their jobs in the past year. That is a staggering number of workers that businesses will need to replace. The same MentorcliQ report states that US businesses lose close to 1 trillion dollars annually due to employee turnover as the cost to replace an employee can be up to 2x the employees’ salary. However, employees who are involved in professional development programs have a 50% higher retention rate than those who aren’t.

These numbers are supported by the 2022 LinkedIn Workplace Learning Report. In it, they found that 94% of workers would stay longer if their employer offered more learning and career development opportunities. But how do you know when to conclude the relationship?

Effectively Nurturing Potential Leaders

Camille Detouillon, a Client Experience Consultant at Élo Mentoring, says “a mentoring relationship should be voluntary, sincere, and structured.” Both parties should want to have a teaching relationship and must clearly establish what they want from it. Proper professional advisement involves regular communication to proactively address problems and track progress. One-on-One meetings are a great tool for this, but coaching goes beyond having regularly scheduled “check-ins.”

No two relationships are the same and there are many ways to train someone. However, you should stick to a few common guidelines to ensure that you and your team member are getting the greatest benefit from the relationship. So, what are these guidelines? I’m glad you asked!

  1. Remember that your employee is their own person. They will have their own way of working and communicating. Likewise, their version of the ideal career path may be different from your own. 
  2. Allow them to fail. Many of the greatest lessons are learned through failure.
  3. Encourage them to take risks. Taking calculated risks can enable your employee to grow and learn to trust themselves.
  4. Ask questions that allow them to come to correct conclusions on their own. This can help them to realize they’ve known what to do all along.
  5. Have them explain things to you. This is a great way to ensure they understand why things are done a certain way. Additionally, this can give you valuable insight into how they think and learn. You might even learn a few new tricks from them.
  6. Actively seek opportunities to teach your employee. They will appreciate your investment in their growth and development.

Things to Consider When Mapping Out an Upskilling Program

Although mentoring is a relationship it needs to be structured with measurable action steps. These help your team member to achieve their goals while enabling you to track their progress and address any issues that might come up. Without this deliberate structure, you might as well just be friends discussing work over coffee. Therefore, to ensure you’re making the best use of your time, you must establish clear goals for it. Once you’ve determined goals, you can create actionable steps to achieve them.

Additionally, you’ll want to clearly state what the team member will get at the successful conclusion of the program. This could be anything from a new set of career skills to a promotion. Outlining these goals at the start of your relationship will give both parties a clear expectation for the duration of the program.

When to Stop Teaching an Employee

Now that we’ve looked at some of the many benefits of nurturing employees, we need to explore when to stop the shepherding relationship. Ultimately, there are two reasons for ending a professional development relationship. Either the outlined timeframe of the development plan has reached its conclusion or the relationship has soured. Eventually, your mentorship will come to an end. When it does, it’s important to recognize this and not drag out a coaching relationship that is no longer bearing fruit.

The Outlined Timeframe of the Relationship Has Reached Its End

The length of the program should ultimately be based on the team member’s professional development goals. For example, if they have the desire to become an industry thought leader, their development could take a little longer as you work with them to achieve the depth of knowledge, leadership skills, and notoriety required to reach their goal.

Formal professional development programs typically operate within a predetermined length of time. In these programs, development coaches and their understudies usually work through a scheduled series of actions and objectives according to the employee’s needs. These formal programs often have a 12 to 18-month lifespan. However, there are successful mentorships that span decades. Regardless, it should be easier to identify when it’s time to end the relationship in this scenario, as the timeframe has been clearly outlined.

When the Relationship Has Soured

Unfortunately, there are times when a mentorship must end because you’re dealing with a toxic or uncoachable employee. But what are the signs? How can you know when you’ve reached this point? There are several red flags to look for, but here are a few of the big ones.

  • The employee expects unfettered and on-demand access to you. This could be a side effect of attempting to control the relationship or a sign that your employee has grown too dependent. Either way, your time is valuable and has many demands. You can’t be perpetually bound to their needs.
  • They assign blame to you or to others rather than accepting fault for failures. Toxic understudies will often blame their instructors when the advice they receive doesn’t work out perfectly. Just because you’re the coach doesn’t mean you have all of the answers all of the time. Likewise, accountability is vital to personal and professional growth.
  • The team member is noncommittal to actions discussed in your development sessions. This could indicate that they are unwilling to put forth the effort to grow or improve. If this is the case, you’re wasting your time and resources by teaching them.

As I said, these are just a few of the red flags that could indicate the need to discontinue a professional development program. When you see signs like these you must act decisively. Right now, you’re probably thinking, “Ok, Justin. How do I end the relationship?” I’m glad you asked!

Ending the Developmental Relationship

If the relationship is ending on a positive note and all of the outlined goals have been achieved, ending the mentorship is relatively easy. In this scenario, it’s important to have a final meeting where you and your protegé review the progress made throughout the relationship. During this meeting, you should discuss:

  • How/whether the goals defined in the development plan have been achieved. Ultimately, this will paint a clear picture of the steps taken to develop certain skills/goals and can provide you with insights on what worked and what didn’t for future advisement.
  • What made the relationship a success? Was it personal compatibility? Effective communication and application of experience? Common goals? Mutual benefits? There are many things that can determine whether a professional development relationship is successful. Identifying what led to that success can help both parties in the future.
  • What obstacles did you encounter during the program? What tactics were applied to overcome them? In business, and in life, things rarely go exactly as they were planned. How each of you responds to adversity dictates outcomes and provides valuable experience.
  • What would you do differently if you could start over? This really gets into the value of nurturing leadership qualities in your team. As you work toward each objective in the development plan, there will be lessons learned. With each lesson, you should identify if there was a better way to handle the situation or execute the task.

However, If the relationship is ending because your employee is uncoachable or otherwise not a good fit for professional development, you must address these issues in your conclusion of the program.

Ending a Developmental Relationship that Has Soured

The best case scenario in this situation is a mutual agreement. If both parties agree that ending the relationship is the best possible outcome, it can leave things amicable. In this result, it’s possible that the team member remains in good standing as an employee, even if they aren’t a good candidate for mentorship.

In other cases, you may find that your employee becomes withdrawn or stops attending coaching sessions altogether. This could indicate that their goals have changed or that the relationship just isn’t working. If this is the case, it’s important for both parties to talk transparently about the reasons for ending the relationship. Speak directly and candidly to your employee if you feel that you need to end the relationship. While it can be awkward, it’s better to acknowledge a lack of chemistry or other issues than to leave loose ends.

Wrapping Up…

We all have something to learn. As you enter into a professional development relationship with your employee, perhaps you could also benefit from having someone pour into you. A business coach could provide that counsel to you. If you’re considering how mentoring a team member could help you further develop your skills as a business owner, reach out to us.

Look, I know life is hard. I get that. But life is good. Where people are involved, things can get messy. That’s why knowing when to end a professional coaching relationship, for better or for worse, can be frustrating. But it doesn’t have to be. By watching out for the red flags of a toxic employee and measuring the progress of your formal development plan, we can at least, make it financially simple. Let’s go out and make it a great day!

Is your company benefitting from a thriving career development program? Could you benefit from the counsel of a trusted business advisor? Either way, reach out to us to see how we could help you!

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