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CW 128: Anthony Ormsbee-Hale

You and your mentee have met, started to get acquainted, and talked in general terms about what you’ll both accomplish during your mentoring partnership. Now what? Where do you go from here and how will you accomplish your goals with the mentee?  

Anthony Ormsbee-Hale shares activities that are designed to help establish goals, build trust and develop skills. These best practices are a great way to maximize your mentorship program through an effective learning and development approach. 

Hello and welcome back to Contributor Wednesday on the Bridge the Gap podcast for senior living. I’m your host, Anthony Ormsbee-Hale, Senior Vice President of Strategic Operations at Civitas Senior Living, and I’m thrilled to be a guest contributor with you all talking about the benefits of mentorship.

You and your mentee have met, started to get acquainted, and talked in general terms about what you’ll both accomplish during your mentoring partnership. Now what? Where do you go from here and how will you accomplish your goals with the mentee?

Mentoring activities are pre-planned engagement strategies you use with your mentee.  The type of mentoring activity you choose is typically designed to help respond to one of many mentoring program goals. For example, if you’re just getting to know your mentee for the first time, you may use an icebreaker activity that helps you and your mentee learn more about each other beyond the surface level and spur conversation. Whichever activity you choose to do, however, it’s important to follow the general policy of any learning engagement: plan with the end in mind.

A great way to begin your relationship with a mentee is to take them out for coffee. Simple, I know but an effective practice. The focus of your first mentor meeting should be to establish a baseline for your relationship. Getting to know each other in a casual setting will help your mentee release some tension. It’s not uncommon for mentees to enter the relationship feeling stressed, especially if you’re at more of a senior level within the organization.

So why coffee or tea? Ample research shows that caffeine does more than just give us energy, it can actually help relieve stress. Combined with a less formal environment like a local coffeehouse or tea shop, and your mentee will feel far more comfortable with you and with your mentoring relationship from the start.

While I suggest you do some goal planning during your first mentoring session, it may be a good idea to spend some time just getting to know each other. Keeping on the theme of casual, try focusing on informal discussion topics focused on building trust. Depending on your history with the mentee, you can decide the best course of action.

Once you have established rapport and built trust with each other, you can move into goal planning activities. In previous episodes, I’ve shared about strategic planning such as using Objectives and Key Results and documenting your plan on a professional development plan template.

Every good mentoring relationship should have measurable goals. That doesn’t necessarily mean you need to pull up a spreadsheet and start gathering hard data. Qualitatively-measured goals are often just as good as those can be measured with numbers. But you and your mentee will have a hard time tracking any kind of growth if you don’t begin the mentoring relationship with a clear set of goals.

There are multiple ways to establish goals, but we recommend you try REAL goals.

These are goals that are:





Try to let your mentee lead the way in developing these goals. It may help if you give them some thinking questions if they’re struggling to create adequate goals. You may even suggest some yourself. Importantly, work together to create a timeline for each of the goals you create. Just make sure you and your mentee are realistic regarding what is achievable within the timeframe of your mentoring relationship.

As you move through your relationship with the mentee, you may discover that time management becomes an issue. While many mentors prefer to assign homework tasks such as reading a book or completing a course, these are time consuming tasks that may conflict with the mentees current job duties. It is important for mentees to understand that a mentorship programs requires commitment and organizations should allow for time within the mentee’s workflow but we all know that day to day tasks often push out long term, aspirational tasks. Many mentees are looking for faster results and one study reports that mentees often believe their one on one meetings with mentors are not very productive. As you go through your meetings, you may find that you need to help your mentee prepare for a high stakes presentation or to have a challenging conversation with a direct report or supervisor. One effective practice to use in the moment is role playing.

You’ll find roleplay is a great way to help your mentee practice skills they want to learn through the mentoring relationship.  Roleplaying is a long-established and well-researched  practice that helps the learner step outside of themselves and helps the teacher get a better view of how the learner has progressed or where improvements may be needed. The biggest hurdle to roleplaying can be the comfort level of the individual being asked to roleplay. Try to keep the scenario simple, and as best you can, work within the comfort level of the individual. Ultimately, though, the goal of roleplaying is to get someone out of their comfort zone.

Role-play training is a social activity. Participants interact within the situations given, which can encourage them to work together to find solutions. Individuals can also analyze their own performances and provide tips or feedback for other participants. Here are some other benefits of role-play training:

It prepares participants for real-life situations. This activity allows employees to be in situations they may encounter at work and get feedback on their performances.

It indicates current skill levels. The facilitator of the session can analyze each employee’s current skill level and highlight their strengths and weaknesses to help them improve their skills.

It helps create empathy. Employees can act in customer roles during role-play training, which may allow them to understand the customer’s point of view and develop empathy.

There are 5 steps to facilitating a role playing session:

  1. Identify an issue
    1. Make sure participants clearly understand the problem you’re trying to address and what you want to accomplish during the activity.
  2. Describe a specific scenario
    1. Consider using scenarios that participants might experience in their work, such as collaborating on a team with other employees or marketing a new product.
  3. Assign roles
    1. Consider using scenarios that participants might experience in their work, such as collaborating on a team with other employees or marketing a new product.
  4. Have participants act out the scenario
    1. Consider using scenarios that participants might experience in their work, such as collaborating on a team with other employees or marketing a new product.
  5. Provide feedback
    1. Consider using scenarios that participants might experience in their work, such as collaborating on a team with other employees or marketing a new product.

For individuals that perform better when they can recall past actions in similar situations, this is a great exercise to complete.

Learning and development is an important component of any mentorship relationship. Two of my favorite methods of development activities for mentees include stretch assignments and job shadowing.

Stretch assignments proactively provide and effectively manage the future (and career expectations) of high-potential employees. They are unique and challenging experiences that optimize on-the-job development. Over the last few years, this tactic has clearly been on the rise because stretch assignments provide the opportunity for individuals to be tested for creativity, innovation, judgment and drive.

Leaders may sometimes feel like they can’t afford to provide stretch assignments to high-performing employees and forget that they can’t afford to lose these valuable employees either. Using stretch goals effectively can lead to a number of gains and desired outcomes when they are right for both the company and the individual.  Working with talent on stretch goals requires commitment, support, leadership and flexibility.

Two guidelines to consider when using short-term stretch goals

Ensure that the immediate goals are part of a larger, more ambitious effort so that whatever is achieved and learned is a building block, not an end-in-itself.

Intentionally design the short-term stretch goals in ways that force innovation, collaboration, and learning — so it’s not just a matter of working harder for a short period of time.

Stretch assignments are intended to develop specific and agreed to skills by providing the appropriate experiences. Devising the right strategy to gain experience and build skills can be done using a variety of assignments such as managing an intern, developing content for social media campaigns and reporting on ROI or assign the employee to an inter organizational task force such as a risk management team. When the global executive search firm, Egon Zehnder, asked 823 international executives to look back at their careers and identify what had helped them unleash their potential, the most popular answer, cited by 71%, was stretch assignments. By training, developing, monitoring, and witnessing the success of high performers, these people each become individually better and more valuable to the organization. The business will exhibit  higher levels of success, a more engaged workforce and the foundation for succession planning.

When it comes to mentoring, the conventional view is that it is a top-down process in which the mentor is the expert and the mentee is the novice. The fact remains that the mentor-mentee relationship is a mutually beneficial situation. Instead of focusing on what the mentor offers, reverse mentoring concentrates on what the mentee can teach the mentor. For instance, the mentee may be more technologically adept, have more recent formal training, and have a unique viewpoint as a young professional or a member of a certain generation. One activity to consider is reverse job shadowing and have the mentor shadow the mentee.

For the person who is being shadowed (the more junior party), they would get to demonstrate their hard-earned knowledge of processes, raising their own profile and make a good impression. It would teach them how to communicate succinctly, how to influence and allow them to take pride in their work.

For the person shadowing (the senior party): they get a chance to view part of their business that they likely don’t see in such detail and it offers the senior leader an opportunity to learn emerging practices and new technologies.

Last but not least, in a previous episode, I highlighted a role that some mentors play which is called a sponsor. In this role, the mentor or senior leader creates opportunities for advancement or growth for the mentee. While not all mentors may be in a position to provide job opportunities for their mentee, they can help the individual expand their network.

Helping your mentee expand their network is probably one of the most valuable things you can do as a mentor. That’s especially true for younger employees. Around 35% of Millennial and Gen Z workers who quit shortly after getting hired did so because their company didn’t give them a clear pathway for career advancement. Part of that comes down to having access to a larger network and career pathing.

Creating a networking event can is a good way to send off your mentor in the best way possible. Introducing them to your network:

  • Puts them on the radar of other executives and managers
  • Establishes relationships between them and potential future mentors
  • Allows them to put some of their newly-acquired skills into practice
  • Boosts their confidence
  • Helps them visualize a clearer pathway for their own career

There are some generational differences when it comes to networking that may be important to understand, as well. The whole concept of networking can feel dirty or sleazy to younger workers, leading many to avoid it altogether. By creating a networking event on their behalf, or making the networking more subtle and casual, you can help them overcome many of these challenges.

My hope is that these activities will prove helpful as those of you working  with emerging leaders in your organizations. While these activities may seem time consuming for all involved, they offer incredible benefits for the organization, mentor and mentee.

Thanks so much for taking the time to tune in today! I’m your host, Anthony Ormsbee-Hale, and I encourage you to connect with me on LinkedIn, continue the conversation around developing emerging talent. Until next time, stay well my friends!

CW 128: Anthony Ormsbee-Hale