IT leadership: 6 questions mentors should ask mentees

Mentorships can be a powerful way to help individuals succeed in their professional journey. These questions can help both sides get the most from the relationship
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One of the most rewarding things I’ve done in my professional career is to serve as a mentor for others. Numerous people freely gave their time and expertise to help me get to where I am today, so I’m always happy to return the favor.

The benefits of mentoring are plentiful. According to a SurveyMonkey study, nine out of 10 employees who have a career mentor are happy in their jobs.

At Improving, we have an initiative that is part career coaching, part mentorship. The aim is to help our people reach their career goals, and the approach is customized to each person’s needs.

[ Also read 3 IT hiring myths about generational differences. ]

I’m currently working with three individuals through this program. Each has a unique set of aspirations and struggles. While their paths may be different, I find myself leaning on a common set of questions in many of these interactions.

Let’s explore six questions you can ask mentees to help them further their career.

1. What challenges are you currently facing?

This is a great question to lead off with. We all have relationships that are rocky or problems we can’t seem to resolve. These issues challenge our focus and sap our productivity.

We need to shine a spotlight on these issues and really discuss them. Most won’t be resolved in four meetings – much less one – but it’s helpful to talk through them and devise a game plan. If your mentee can walk away with something actionable, it provides direction and helps them feel like they are making progress.

There is also a companion question that may be more relevant in a follow-up meeting: “I know you were really stuck on that challenge last time we spoke. Have you made progress? If you’ve resolved it, what did you learn from that experience?”

2. Where do you want to focus in the coming weeks?

Most of the people I work with are actively working toward ambitious, long-term goals. While it’s great to have goals, they can often seem overwhelming and inaccessible when viewed from a distance.

It can be helpful to break these long-term goals into smaller, more manageable tasks. We like our people to focus on SMART goals: Specific, Measurable, Achievable, Relevant, and Time-bound.

Suppose, for example, one of your mentees wants to become better at public speaking. That’s a fantastic professional skill to develop, but it’s rather abstract. How can you develop a plan to get there? How will you know if they’ve achieved success?

If you utilize the SMART goal approach, you might establish speaking at a local user group in two months as a valuable first step in that journey. If you then line up a series of these SMART goals (such as presenting a conference talk or a client presentation), the mentee will slowly build up their experience and confidence in public speaking until they become highly proficient at it.

3. How are you engaging professionally?

No one is an island, but some technology professionals construct their professional life to be just that. Being isolated and not growing your circle of influence can greatly impair your career development.

Being isolated and not growing your circle of influence can greatly impair your career development.

This question focuses on how your mentee is putting themselves out there. How are they fostering connections that will be critical to their long-term success? This might be attending an upcoming corporate social event or something as simple as getting into the office once or twice a week. The key is to push them slightly outside of their comfort zone to help them establish confidence in these professional interactions.

[ Read next: What's the difference between a manager and a coach? ]

4. How do we make it actionable?

When I’m mentoring other leaders within the organization, pain points often surface. Things either aren’t working or could be running much more effectively. Be aware that these conversations can easily turn into gripe sessions in which the mentee airs their grievances but nothing actually changes.

It’s always valuable to bring awareness to things that aren’t working, and it can certainly be cathartic. But don’t stop there – lead the conversation toward how things could be improved. What does it look like to get from dysfunction to excellence?

If you consistently focus on how to make things actionable, your mentee can become a positive force for organizational change. Over time, their mental process should unconsciously go from identifying a problem to mapping out a solution to improve it.

If you consistently focus on how to make things actionable, your mentee can become a positive force for organizational change.

5. Are you getting everything you want out of this relationship?

Mentorship should be a collaborative experience where both parties bring something to the table. For example, I bring motivation, expertise, honesty, and direction. My mentee sets the agenda, is open with their ideas, and ultimately does the work. If either one of us fails to uphold our side of the bargain, the value disappears and the relationship will likely go with it.

When starting a new mentoring relationship, set expectations. Clarify what you think you are trying to accomplish – and what you aren’t – and ask your mentee to do the same. Letting the mentee drive should help them take the relationship to where they want it to go, but it’s helpful to step back occasionally and ask “Is this still working for you? Is there something we could do to make this relationship more valuable to you?”

As a mentor, you are here to help. If you’re missing the mark, you need to recalibrate before things get too far off track.

6. How can I help?

This is by far the most powerful question in my arsenal, and I close every session by asking it. At its most basic, mentoring is about sharing experiences, helping people grow, and assisting them in finding their path. Help is the common thread that connects everything in this space.

I want this one question to resonate with my mentee long after we finish our conversation. I love it when my mentee reaches out when they hit a wall or just need another perspective. It doesn’t have to wait until your next scheduled talk. That person should know that you’re invested in the relationship and want to see them succeed. These four words perfectly encapsulate the core of mentorship.

Powerful questions are critical to maximizing the time you have with your mentee. The key is to make your mentees stop and think about their answer. Your questions should serve as a launching pad for additional exploration and trigger a deeper conversation around that topic.

And remember that hearing the answers is just as important as asking the right questions. If you’re not practicing active listening, the questions you ask are irrelevant. Each represents a bookend in communicating effectively.

[ Learn how CIOs are speeding toward goals while preventing employee burnout in this report from Harvard Business Review Analytic Services: Maintaining Momentum on Digital Transformation ]

Mark Runyon works as a director of consulting for Improving. For the past 20 years, he has designed and implemented innovative technology solutions for companies in the finance, logistics, and pharmaceutical space. He is a frequent speaker at technology conferences and is a contributing writer at InformationWeek.