Mentoring

Making the most of mentoring partnerships: Mentors share their thoughts

By Sophia WornickFebruary 6, 2018

As part of our “Ask me Anything” series that poses questions from our user community to our mentor community, we recently asked three Everwise Mentors to share their experiences about how to make the most of mentoring partnerships. Our community posed a variety of questions around starting out a mentoring relationship, making ongoing mentoring effective, and taking action. Thanks to the following mentors for sharing their successful practices:

Curt Kwak, Chief Information Officer at Proliance Surgeons

Kenneth Robb, Cyber Security & Risk Consultant at Citadel Cyber Solutions

Michael Lepore, Distinguished Engineer, Business Unit Lead Architect at Cisco

Starting a mentoring relationship: Identifying needs and building trust

Starting out a mentoring relationship right is critical to success. How do you define needs and determine what this specific mentoring relationship is all about?

Communication is key. Michael Lepore advises both sides should establish what goals to accomplish. “I have participated in several Everwise mentorship relationships, and each one is different.” Sometimes conversations help evolve goals into something quite different. “Work with your mentor to figure out where their strengths are, be honest with them about where your challenges are, and you should find a fit where you can both benefit.”

Curt Kwak adds that even random thoughts in these conversations can serve as building blocks. Writing thoughts down and grouping them into themes can help crystalize the essence of the partnership.

Since open communication is so important to mentoring, what’s the best way to ease into a partnership to develop trust?

Lepore suggests being honest with each other, sharing stories of challenges and opportunities, and being open about failures. Kenneth Robb shares that he tries to learn as much as possible about the protege early on so that he gets a full picture and develops a deeper understanding of the entire person. Kwak agrees, and adds, “It’s mutual. It’s not a mentor trusting the protege or the protege trusting the mentor. They both need to trust each other.”

Maintaining a successful mentoring partnership: Meetings, goals, feedback

Once mentoring is set up, what are some practices to get the most out of the relationship?

Regular and frequent meetings came to the forefront here. Our community had questions around the specifics of mentoring meetings–agenda, frequency, tracking goals and providing feedback, and how mentors get the most out of the relationship.

How do you structure mentoring meetings for success? Our mentors shared several approaches. Kwak prefers a dynamic agenda to promote spontaneity. “It’s ok to cut the meeting short if there’s nothing more to discuss!” Robb uses a standard format focusing on goals and progress. Lepore lets the protege define the agenda to ensure buy in and ownership. “It’s important for the protege to drive things, typically with a set of questions or problems that they have encountered recently that they could use a different perspective on.”

What is the right cadence for meetings? Too frequent and there is not enough time for substantial change; too infrequent and the newly-formed relationship might suffer. Robb finds every 4-6 weeks best. Lepore agrees, and adds “I also encourage my protege to talk asynchronously if anything comes up, and keep things flexible.” Kwak prefers more frequent meetings  – weekly or bi-weekly. “I think once a month is too long. […] If you are truly invested in this relationship, you will find a way around meetings and other obligations to make this work.” Mutual agreement is key here.

Once you have an agenda and established a cadence, what questions should proteges ask? Lepore sees struggling to find the right questions as a goal issue. “Having a goal that you don’t have an avenue to work on means that you don’t have a lot to talk about when it comes to challenges.” He suggests breaking longer term goals into short term, achievable, realistic goals that the protege can make daily or weekly progress on. Questions around the short term goals will naturally evolve. “As a protege, you need to have very specific needs/desires defined. You can’t rely on the mentor for this”, Kwak adds. The SMART goal framework is something to consider here (specific, measurable, actionable, relevant, time-bound).

Setting realistic, achievable goals helps drive the conversation–how do you track goals and progress? All our experts agree that the protege is accountable for this. “Writing goals down helps clarify and keep the protege focused on why they are doing this in the first place. Keep good notes and honestly track your progress”, suggests Robb. Kwak adds that the mentor is not a manager, and is there to support the protege, not monitor progress. Lepore says “The specific goals that we work on in a limited time mentorship might change from the start to the end as we clarify and drill deeper.”

One member asks about building an objective feedback mechanism to help improve return on time invested by both parties. Kwak says he looks for commitment from the protege to make the relationship work. Lepore agrees, and adds, “I look for commitment and honesty from my protege. Part of that honesty is letting me know if the relationship isn’t working, or if they feel that conversations aren’t valuable.”

What benefits do mentors see in the relationship and how do they ensure they accomplish them? Kwan indicates he learns something new from each protege, allowing him to improve as a mentor. Lepore agrees. “I set ground-rules up front to let the protege know what I’m looking for and what the expectations are from my side (usually very simple: the protege owns the agenda and making the conversation productive, and I expect honesty and feedback about how useful the interactions are for them). I have yet to find a relationship where we can’t make it work.”

Taking action – taking risks, career growth in a company and balancing work and life

Sometimes a protege sometime has to get out of their comfort zone, taking actions that seem risky or intimidating. How can mentors support them? Kwak and Robb like to assure proteges by sharing their own stories. Lepore agrees, and adds that the decision to try something risky has to come from the protege. Sharing both positive stories and those were the action resulted in failure, but not catastrophic results, helps boost confidence. “One other technique I have used is to talk about the worst-possible case. What could happen? How bad is it? And then talk about how to setup a safety net so that the worst case is protected. Sometimes facing that reality helps break the fear cycle”, he says.

When it comes to advancing within a company, when is the best time and how do you go about it? “I don’t think it’s based on years or time. It’s more about where your confidence and desire are at a certain point in your life”, says Kwak. “It comes down to having a strong and competent manager to help you navigate the waters. If that does not exist, I will often recommend an internal mentor”, adds Robb. Lepore draws from his 17-year career at Cisco and advises, “Stay focused on what your current role is, and being awesome in that role, while looking around to see the current climate and opportunities.” He adds that ongoing conversations with the manager and other influential people help identify those opportunities, and that often advancements are not official job changes but job enrichments.

How can mentors encourage work/life balance for themselves and proteges?

Kwak suggests following the example of Sir Richard Branson to not separate work from life, but focus on life balance in general. He describes six daily practices: 1) rise early, 2) limit screen time, 3) write lists, 4) make time for sport, 5) make time for loved ones, and 6) embrace something new every day. Robb likes to focus on spiritual texts to find meaning. “This, to me, requires constant mindfulness as our culture rewards us for ignoring our families and working non-stop.”


Lepore sets goals for all areas of his life–his family, his career and personal achievement (in his case, long distance running), and then prioritizes accordingly. “I have found it’s not a matter of having time to do things, but it’s a matter of making the time.”

Thanks again to Curt, Kenneth, and Michael for contributing their time and expertise. Visit our website for more information about the Everwise software platform, Everwise Mentoring program, and becoming an Everwise mentor.

Sophia Wornick

Sophia Wornick

About the Author

Sophia is the Marketing Events Manager at Everwise where she is responsible for creating engaging and meaningful experiences – both on and offline. She is passionate about the San Francisco Giants, wine, and listening to podcasts.

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