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After establishing 100 mentor-mentee relationships in the firms that venture capitalist First Round Capital funds, Whitnie Low Narcisse set out to find out what the secret was that made some pairings special.

She found it starts with finding the right match. “Asking someone to mentor you is nerve-racking enough. You want to make sure you’re asking the right person,” an article on the firm’s website notes.

Ms. Narcisse found eight questions particularly helpful. If you’re being asked to mentor, try these four:

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  • Can I clearly be helpful to this potential mentee?: You want to be sure they have reached out with clear reasons or intentions for your help – specific needs you can address.
  • Can this person be completely open and honest?: It won’t work well unless they can open up about their problems and vulnerabilities.
  • Is this person prepared?: Do they tend to be proactive about setting up time to talk and an agenda before the meeting? Do they direct conversations and ask specific questions? “Be wary of people who want more general help or to touch base without a topic in mind,” the article warns.
  • Does this person give me energy?: Ideally, you want to gain from the encounters as well, learning things and being prodded through the conversation to reflect differently on your own situation. Talking to them should be a good use of your time.

For mentees, here are the four questions to ask (mentors should think about them as well, to be sure they are up to the task):

  • Does this potential mentor remember key details about me?: It’s not a good sign if in each session, you have to remind them about facts previously shared.
  • Will it be hard to explain the concepts or context of my job?: “You should choose someone who is close enough to your industry and functional area so that very quick, even shorthand explanations will do, and they can immediately dive in and understand your primary challenges and goals,” the article stresses.
  • Can this person give actionable advice?: You want a good teacher with specific ideas and tactics you can use. Be careful they aren’t too senior and removed from the day-to-day work.
  • Does this person seem present and focused?: Everyone is busy these days but in your sessions they should be giving you their undivided attention.

Kick off relationships around distinct problems or challenges. “One of the best ways to get a lot of value out of a mentor is to present something specific for them to help you solve,” the article advises. “You can be detailed in the help you need, and your mentor will know they provided concrete and measurable help. This is far better than asking someone for general or ongoing career advice.”

Build in off ramps. A mentor is more likely to work with you if he or she knows it’s not a perpetual commitment. Often mentees believe a mentor will stick by them for the rest of their career. That can happen but is the exception, given the commitment required but also the fact your own needs will likely change.

Create a schedule for connecting with the mentor but keep it loose. You’ll want to reach out urgently at times, when issues arise, but also have scheduled sessions.

“The key, however, is to not impose a rigid or unrealistic cadence. Everyone is busy, particularly very accomplished people. Things come up, fires break out. If you’re too dead set on a schedule, one cancellation can throw the whole thing off track. Instead, set a loose guideline − like every other week for a quarter, or twice a month for six months − not ‘every other Sunday’ or ‘every first Tuesday at 6 p.m.’ This will sound more reasonable on both sides, and minor rescheduling here and there won’t derail you,” the article notes.

Measure progress every meeting and share immediate goals for the relationship as well each meeting. And – this may be a big surprise – don’t call the other person a “mentor.” Nearly all of the mentors consulted identified use of the word as the No. 1 reason they were dissuaded or disinclined to talk to someone. That’s because it signals a “time suck.” So instead of asking, “will you mentor me?” try something like “Hey, I’m trying to get through XYZ specific situation or challenge, and I’ve heard from several people, including [name a mutual connection here] that you might be able to provide some insight or direction in this area. Might you have time to meet for coffee?”

It could be one of the most important “asks” of your career.

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Rifts and other riffs on mentoring

As academic physicians, Vineet Chopra and Sanjay Saint of the University of Michigan do a lot of mentoring. That has led them to highlight the importance of heading off rifts in the mentoring relationship or resolving them before they occur.

“It’s not uncommon for mentors and mentees to have a falling-out. What seemed like a perfect pairing on the surface may wind up being a total mismatch,” they write in Harvard Business Review.

Sometimes, the rift become obvious suddenly. Other times, the mentor may be completely unaware of the problem, as the mentor provides the wrong response on an issue. Usually the breech can be repaired.

“Mentors must recognize that disagreements and misunderstandings are almost inevitable in these relationships and that the mentor, not the mentee, is responsible for avoiding or repairing rifts. Smart mentors do not allow sores to fester or spats to escalate. They intervene early to keep the relationship on track,” they say.

The physicians also warn against “mentorship malpractice.” Mentors are dominant in the relationship and have to be sure they don’t wield power unfairly. Guard against:

  • Taking credit for your mentees’ ideas or using your power to take the lead position on their projects.
  • Insisting that your mentees advance your projects rather than developing their own.
  • Tying your mentee to your timeline, notably slowing their progress by being slow to get back to them.
  • Discouraging your mentees from seeking other mentors. That may comfort your ego but hurt them by preventing broader learning and recognition.
  • Allowing mentees to repeat common self-destructive mistakes without reining in such behavior.

Avoid these email openers

Here are 11 first sentences that Inc. columnist Jeff Haden guarantees will prevent your e-mail from being read because they waste the recipient’s time rather than getting to the point and often ignore the fact the person has decided not to connect with you:

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  • “I thought I would circle back ...”
  • “In case you missed this ...”
  • “I’m just following up ...”
  • “I hope this finds you well.”
  • “I hope you had a great weekend.”
  • “You might be surprised to learn ...”
  • “Did you know ...?”
  • “My name is ...”
  • “I would like to introduce myself ...”
  • “I know you’re really busy ... but…”
  • “I want to ask a quick favor.”

Quick hits

  • Research shows alcohol consumption before negotiations invokes aggressive tactics, makes a negotiator more prone to mistakes and leads to deals that are worth less value. But INSEAD Professor Horacio Falcao and financial services professional Alena Komaromi say that, if your overall tolerance level is high and the meeting is mainly for relationship-building purposes or if your goal is to find out as much information about your counterparty as possible, drinking could be appropriate and even helpful.
  • Sitting at your desk all day can be unhealthy but standing desks can lead to lower back pain, University of Waterloo PhD student Daniel Viggiani found in a study.
  • Mississauga Ont.-based presentations specialist Dave Paradi has seen a trend to participants at workshops not using paper handouts, preferring the information electronically. With screen sizes getting smaller, he recommends two slides per page as that makes the text and visuals big enough to see and use a PDF so it appears as you intended.
  • Forty-two per cent of Canadian workers have admitted to crying at work.
  • Don’t leave the person sitting beside you at a meal trapped in a cone of silence, as people to the right and left of that individual are engaged in intense conversation. Make an effort to bring that ignored individual into your conversation, advise the consultants at Shepa Learning Company.
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