How to be a better mentor: 6 conversation starters

How to be a better mentor: 6 conversation starters

CIOs and IT career experts say mentoring is key to developing your talent pipeline and retaining stars. Here’s how to make the most of mentoring time

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August 15, 2018

Good mentoring relationships can be invaluable for developing the next generation of IT leaders, but they require shaping. “Like any relationship, the mentor-mentee relationship needs to be cultivated and will take time, energy, and focus,” says Craig Williams, vice president and CIO for telecom networking provider Ciena.

“Building trust and confidence is the bedrock of this kind of relationship, and while it’s important that the mentee take ownership of the outcome of the relationship, there are several ways mentors can help engage the mentee.” 

[ Want more advice from your peers? Read also: 7 habits of highly effective IT mentors. ]

The most effective mentors ask thoughtful questions to help understand their mentees – who they are, what they need, how they want to grow, and what they expect from the relationship. “Early-in-career professionals sometimes feel hesitant to engage with their mentors for fear they are inconveniencing them,” Williams says. “Asking questions and setting up a reoccurring check-in is a good way to help them feel that you are committed to being their mentor. Simply taking the time to ask and listen to understand will go a long way.”

A “how’s it going?” every few weeks won’t do the trick. Instead, IT leaders can consider incorporating some of the following conversation starters into their next mentor-mentee meeting. If you’re just beginning a mentoring relationship, use these tactics to start smart.

Get down to business

While the best mentors develop personal relationships over time, it’s best to start things off with a professional focus. “For the first conversation, stick to work goals and ideas around professional development,” advises Katie Ross, a recruiting partner with Heller Search Associates. “It’s a mistake to probe for similar hobbies or weekend activities because if there’s nothing in common, it can get awkward quickly and actually create a disconnect. Let your personal connection evolve more naturally through conversations over time.”

Ask about their preferred input style

“Ask your mentee what kind of guidance and direction they feel will help them most,” says Carol Lynn Thistle, managing director with Heller Search Associates. “This establishes a sense of trust and reduces the chance of defensiveness.”

Likewise, IT leaders can ask their protégés how they’ve felt about the guidance given to date and whether it’s been helpful to them. “Then use the feedback to validate or tailor your approach as their mentor,” Thistle says.

Set goals for the relationship

“We’ve all been there – when you’re early in your career, you might not know where to start.”

“A mentee should have an idea of what they would like to gain from the relationship, but we’ve all been there – when you’re early in your career, you might not know where to start,” notes Ciena’s Williams. “Asking questions centered around what the mentee wants to gain from the relationship is a good place to start.”

Consider talking about expectations (for each of you), time commitments, and frequency of interactions. “Mentees should have a reason and purpose for wanting to have a mentor,” Williams says. “It’s a tool and a resource to learn something, gain exposure, and create experiences they might not have direct access to experience. Everyone’s time is valuable, so setting clear expectations is an important component to agree on for a successful engagement.”

Bring up your mentee’s recent wins

Leading with a discussion of your mentee’s recent accomplishments can be a good place to start, says Thistle. It shows that you’ve been paying attention – and can open the door to a discussion of not only the IT professional’s strengths but also what he or she may have struggled with, in a way that’s comfortable.

Share a personal story

If there’s a particular topic or issue that’s important to address with the mentee but that may come off as negative or critical, consider using a different approach. “To avoid the risk of preaching, use stories from your past and real-world examples to make your point,” Thistle advises.

Provide reassurance

There may be periods in the relationship when there are no clear points of entry to a new discussion. Or you may both get too busy to meet. This can be the perfect time to simply remind your mentee that you care.

“A mentee’s biggest insecurity is that the mentor isn’t genuinely interested or invested in the meeting,” says Ross. “Use reassurance as your conversation starter. Tell them you are here for them and that you’ll be accessible.”

[ Why is adaptability the new power skill? Read our new report from HBR Analytic Services: Transformation Masters: The New Rules of CIO Leadership. ]

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Stephanie Overby is an award-winning reporter and editor with more than twenty years of professional journalism experience. For the last decade, her work has focused on the intersection of business and technology. She lives in Boston, Mass.

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