Strategies for Creating Successful Mentorships

Strategies for Creating Successful Mentorships: Spread Your Sunshine Keynote for the Martin County Bar Association ("MCBA") Solo & Small Firm Committee

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Spread Your Sunshine Founder Melanie S. Griffin, Esq. recently delivered a keynote address to the Martin County Bar Association (“MCBA”) Solo & Small Firm Committee. As further detailed in the recording, this presentation explores strategies for creating successful mentor pairings, including learning about various mentorship types, the critical start to a mentoring relationship, the importance of honesty, mentoring meeting preparation, matching successful formal mentor pairs, contacting potential mentors using the "Three-Contact Rule," and additional best practices for communicating with mentors, including thanking them. While this program was presented to MCBA members, almost the entire discussion is applicable to professionals across all industries. We therefore hope these ideas help fabulous YOU as you build meaningful mentoring relationships that help you shine your brightest.

Mentor Defined

The world is your oyster - mentors can be older or younger than you, the same sex or opposite, inside your industry or out. What is important is that the mentor is: (1) a trusted resource; (2) who can give you advice in the instant situation. Sometimes this may involve consulting someone younger, for example, if you are more established in your career and want social media tips. Other times, you may need advice from a more senior mentor, such as early in your career when you want advice about seeking a promotion.

Three Types of Mentoring Relationships

There are three different types of mentoring relationships:

(1) Coach

A coach assists you with learning a specific skill. Given a coach’s niche focus, a full-fledged mentor-mentee relationship may not develop. At the end of your time together, however, you will have mastered a new skill, such as how to improve your conversion rate, i.e., the number of prospective customers you convert into actual clients.

(2) Mentor

The most common mentoring relationship is that between a mentor and mentee. While such relationships can be longer or shorter, they typically last a year with the goal of helping you grow professionally.

(3) Sponsor

A sponsor is an influencer with the power and connections to advocate for you “in the room” when you are not there. Sponsors typically assist in elevating your career, such as when you are being considered for a promotion or assignment to a significant work project or client.

The Critical Start to a Mentoring Relationship

Frequently at the end of mentoring relationships, mentors and mentees lament that they did not hear from each other. Mentors can assert that mentees should bear the work and show deference, taking the lead on scheduling the pair's meetings. Likewise, mentees can argue that mentors should schedule the meetings, as they are busiest and know when it is most convenient to connect. Both are right and both are wrong – either could initiate contact. What is important is that at the beginning of the relationship, they determine who will shoulder the responsibility by setting boundaries and expectations for the mentorship. For example, at the outset, mentors and mentees should discuss:

- Who will initiate contact?

- How will you meet (e.g., via e-mail or phone conference, electronically, in-person, through networking events, a combination of the forgoing, etc.)?

- How frequently will you meet?

- Will your conversations be confidential?

- For how long will the relationship last?

- Will you be social media friends/followers? On which platforms?

- What is the mentor's expectation for the relationship? The mentee’s? For example, is it reasonable for the mentee to assume that they will accompany the mentor to networking events? Or that the mentor will assist with the mentee’s job search?

Determining the parameters of the mentorship from the beginning helps to ensure that both the mentor and mentee receive the maximum benefits from the pairing and feel comfortable in the relationship.

The Importance of Honesty

Honesty is a key ingredient for building a strong mentorship, as it is only effective if the mentor and mentee are honest with each other. To illustrate, assume the mentor and mentee are based in Chicago, the mentee wants to transition to San Francisco within the next year, and the mentee does not share this goal with the mentor, leaving the mentor under the impression that the mentee will be professionally based in Chicago for the immediate future. The advice given by the mentor may be inapplicable, as the mentor is unaware of the mentee's true professional goals. The mentor may also be hurt and feel like they wasted their time when they learn of the mentee's plans, potentially, and unnecessarily, burning a professional bridge. Additionally, by not sharing their plans to move with the mentor, the mentee is missing the opportunity to learn what connections the mentor may have in San Francisco that could help the mentee or what advice the mentor may have about corporate transitions.

Similarly, mentors should honestly share constructive feedback with mentees. Although it can be uncomfortable to provide a mentee with such information, that is the commitment the mentor made to the mentee. By failing to do so, the mentor is not doing their best to help the mentee grow and shine. Additionally, the mentee is counting on the mentor for such feedback - they would much rather discuss an area in need of improvement with a trusted resource who has their best interests at heart than hear it from their superior who may take corrective action (or worse).

Mentoring Meeting Preparation

To maximize the value of the mentorship, the pair must understand that their relationship is not a friendship. Over time, you may become friends with your mentor or mentee. Unless and until that happens, however, you should prepare for each mentorship encounter as if most of the time together is a business meeting during which you will learn from each other and grow professionally.

To ensure each mentoring meeting is productive, consider having the mentee provide two to four discussion items a week in advance of the meeting. Such an “agenda” will set the tone for the meeting, keep the discussion on track, and allow the mentor to prepare their answers, including by utilizing additional resources when helpful. Likewise, the mentee's thoughts will be organized and focused on the information they must obtain to be professionally successful.

Alternatively, the pair could agree to pre-set meeting prompts or the organization that made the match could assign discussion topics. For example, the mentor and mentee may agree, or the organization may assign, that in January they will discuss networking strategies, February community involvement, March best social media practices, and so on.

Organic v. Formal Mentorships

The start of a mentoring relationship may happen organically, such as when a mentor and mentee are drawn to each other and voluntarily agree to work together, or formally, such as when a mentor and mentee are paired by their mutual employer or a civic organization. While organic mentorships are oftentimes the most successful given the natural connection between the mentor and mentee, formal mentorships are also effective, especially when a mentee desires feedback but is too shy to seek out a mentor or does not know anyone with knowledge of a certain topic.

Beyond origination of the relationship, key differences between organic and formal mentorships include the length of and requirements associated with the relationship. Because organic mentorships are voluntary relationships between two people who oftentimes feel a "spark," there is no defined end to the pairing - it may last a lifetime or fade away as the mentee's needs change or the mentor's abilities evolve. Similarly, an organic mentorship has no "requirements" beyond those voluntarily agreed to by the participants. If you are fortunate enough to connect with an awesome mentor who is willing to invest in you, however, maximize the opportunity by doing the hard work necessary to learn as much as possible from the mentor. Like most things in life, your commitment to the relationship will directly impact how much you benefit from it.

Different from organic mentorships, the terms of formal mentorships are usually defined and determined by the organization who created the pairing. At a minimum, the originating entity usually prescribes for how long and/or how many times the mentor and mentee must meet and the requirements that must be fulfilled to successfully complete the program (e.g., topics that must be discussed, activities to complete together, etc.).

Matching Successful Formal Mentor Pairs

To successfully match mentoring pairs on behalf of an organization, carefully consider the breadth of the pairing criteria. Oftentimes, mentees are given leeway to request a very specific mentor - for instance, a red-headed female, in Iceland, with two biological sons and one adopted daughter, who founded her company, with seven-figure annual revenues, by the age of twenty-five. This example is a bit extreme, yet not far beyond the desired mentor descriptions some organizations elicit from mentees. Doing so will likely cripple the success of your mentoring program. 

Firstly, more than likely, said Icelandic woman does not exist. Once that is realized, the organization likely has two options: (1) inform the mentee that no match will be made because no mentor matching the defined criteria exists; or (2) pair the mentee with a mentor who does not match the mentee's description. Either way, by overcomplicating the matching criteria, the organization did not properly manage the mentee’s expectations, causing the mentee to think they would be paired with the unrealistic Icelandic woman and be unhappy with the "subpar" mentor with whom they are ultimately paired. In the latter instance, more time than was necessary or valuable was likely spent on the matching process. These outcomes can be avoided by reducing the pairing criteria to that which is necessary to successfully match mentoring pairs.

To that end, many mentees need help with basic issues like what to wear, tips for polishing resumes and cover letters, navigating relationships with difficult managers, and so on. These issues do not require advice from the Icelandic woman; they can be addressed by a myriad of professionals inside or outside of the mentee's industry, as it is usually not until an advanced stage of a mentee's career that a specific, more sophisticated mentor is needed. Thus, when creating your mentoring program application, only seek the basic criteria necessary to find a mentor for the level mentee at issue, that is commensurate with the manpower and mentor pool available to you.

Adhere to the "Three-Contact Rule" When Initiating Contact with Potential Mentors

Turning to organic mentorships, when, as a potential mentee, you meet someone you want to mentor you, contact them. If you do not follow-up, the meeting value is diminished, and it is unlikely that such new contact will become a useful coach, mentor, or sponsor to you. The worst possible outcome is hearing "no," and that possibility, that will only be a brief, minimally negative experience in the grand scheme of life, is far outweighed by the possibility of hearing "yes" and the benefits of such a relationship. To maximize your chances of a “yes,” adhere to the “Three-Contact Rule” - contact the potential mentor three times, at least two different ways, always showing deference.

To explain, if you first contact the potential mentor through a LinkedIn message and do not hear back, do not assume that the person is uninterested in mentoring you. Even though the potential mentor has a LinkedIn account, they may not monitor it, or even if they review their feed, they may not check their messages. To determine if mentorship potential exists, consider emailing their work address that can be found for almost all professionals on their LinkedIn profile or via a diligent Google search. Alternatively, call their office, for which the number can usually be found online, and ask to speak to their assistant or leave a message on their voicemail. Each time provide the potential mentor with a short, pleasant message explaining why you believe they are the perfect mentor for you. Avoid referencing the prior communications (at least in any way that could be offensive) and do not use a generic message that is not tailored to the recipient.

If you follow this advice, oftentimes, the potential mentor will respond, and hopefully, agree to be your mentor. If not, however, and this person is truly a dream advisor, give them a break instead of giving up. Establishing relationships with successful professionals takes time for a myriad of reasons ranging from their busy schedules to your initial lack of credibility with them. You are also unaware of their circumstances, for example, if they are overwhelmed with a significant work project, aging parents, illness, divorce, or some other all-consuming issue. Your patience deferentially contacting them again later may pay off, as their situation may have changed such that it is then the right time to connect.

Best Practices for Following Up with Potential Mentors  

Turning to the substance of the communication to send in conjunction with the Three-Contact Rule, whether the initial communication is a hand-written note (recommended to stand out!), email, direct message, or otherwise, concisely tell the potential mentor why you are contacting them. For example,

Dear Elba,

For as long as I can remember, it has been my dream to become a news reporter upon graduation from college next year. When researching alumni who can help me best prepare to appear on air, your profile was reviewed. The types of stories you cover, meaningful way you engage your audience, and market size you serve dovetail my professional goals. Given these synergies, can we please connect for twenty minutes at the time and place or via the medium of your choosing to discuss your career journey?

Understanding the demands on your time, if, in two weeks, we have not connected to schedule a meeting, I will email your assistant to determine if this is an opportunity in which you are interested. In the meantime, please know that your consideration of this request is very much appreciated.


A short, tailored communication like this one tells the recipient that you want to speak specifically to them without being overwhelming.  

It also intentionally does not end with, “Looking forward to hearing from you soon.” Oftentimes, the recipient will not initiate contact upon receipt of the message, or at least not as quickly as you might like. You then feel awkward reaching out again, as you do not know why the potential mentor did not respond, for example, due to lack of interest, a busy schedule, or for some other reason. You will avoid such a predicament by ending the initial communication with something like that set forth above. If, within the referenced period, the potential mentor contacts you, awesome. However, if they do not, you can confidently initiate further contact at the specified time using the Three-Contact Rule.

Regarding further communications, the forgoing message makes follow-up interaction as easy as possible for the potential mentor by offering to connect at the time and at the place or via the medium most convenient for them. Like many subjects, the contemplated discussion can effectively occur on a phone conference, via Zoom, or over coffee or a meal, whatever is easiest. By deferring to the mentor, you increase the probability that they agree to the meeting and it is quickly scheduled (as opposed to waiting to meet when it is most convenient for you).

Finally, reread the message above and consider that it may be the second or third communication from the mentee to the potential mentor. Read in such light, the communication pays deference to the recipient and is respectful. While it may be possible to gracefully inform the potential mentor of your previous communication attempts, it is unlikely a successful mentorship will be established if a sentence like the following is added at the beginning of the message, “You didn’t respond to my LinkedIn message, so you are now being sent this email.” Rather, the safest bet is to begin the conversation anew and not mention prior messages.

Best Communications Practices During the Mentorship

Once the mentor agrees to a relationship with you, you will maximize the relationship by periodically (e.g., bi-weekly, monthly, quarterly, etc.) contacting the mentor assuming they are agreeable to hearing from you with such frequency. To stay in touch, consider sending a short two-paragraph email wherein each of the paragraphs is a maximum of two to four sentences. In the first paragraph, connect with the mentor, and in the second, include your “call to action.” For example,

Dear Melanie,

Hopefully you are doing well and your week is off to a great start. It is exciting to share that last week, a new client was assigned to my portfolio. The strategies you recommended during our last meeting were implemented, and they sure paid off.

Given this additional client, at the end of the month, my manager will consider me for a promotion. Before then, can you please connect for thirty minutes at the time most convenient for you to conduct a mock interview? Your feedback regarding my proposed responses would significantly boost my confidence when meeting with my manager. Thank you for considering this request, your help is greatly appreciated.



Dear Qaree,

Hopefully you are doing well and your week is off to a great start. Attached hereto is a newspaper article published last week. The surprise ending is fascinating and made me think of our recent conversation about employee experiences in the workplace.

Speaking of the workplace, as you know, my goal this semester is to find a summer internship. Despite having gone on several interviews, I have yet to receive an offer. To assist in my continued search, this week, can you please connect me with a recruiter who may be aware of unpublished opportunities? Looking forward to your thoughts, the time you invest in our mentorship is valued and makes a positive difference in my life.


Note that these two examples accomplish at least two mentee goals in each paragraph. By sharing an accomplishment or piece of news in the first paragraph, the mentee fluidly connects with the mentor and explains how the investment made by the mentor is making a difference in the mentee’s career.

Similarly, in the second paragraph, the mentee identifies the issue with which help is needed and by when assistance should ideally be given. Mentors are not mind readers. To maximize their usefulness, such information must be provided in the email title and/or body.

Thanking Mentors  

Gratitude is expressed in the example messages above to emphasize that mentors value feedback letting them know that the investment they made in you positively impacted your life. It is likely unnecessary to give a monetary token of your appreciation, such as a gift card, meal, or other present. What is treasured is a hand-written note detailing the difference the mentor made in your career, whether on a 99¢ greeting card or luxurious customized stationery created using Copper Engraved Dies. Indeed, copper sheet-fed dies are used for flat foil stamping, single-level embossing, intaglio printing, and letterpress. During the process, the copper recuperates heat quickly, much faster than any other metal, making it an excellent choice for foil stamping applications. Click here to find out more about it.

And, to listen to this keynote address in its entirety, please click here or on the video above.

Now that you are a mentorship pro, is there additional information you want to receive from Spread Your Sunshine?! We’re sure there is, so please share your ideas by emailing or sending Spread Your Sunshine a message via FacebookInstagramLinkedIn or Twitter. We love hearing from you, as together we are strongest.

Referenced Resource

15 Invaluable Laws of Growth by John C. Maxwell

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