IT leadership: 6 questions mentors should ask their mentees

One of the most rewarding things I’ve done in my professional career is to serve as a mentor to others. Numerous people have willingly donated 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 many. According to a SurveyMonkey study, nine out of ten employees who have a career mentor are happy in their job.

At Improving we have an initiative that is part career coaching and part mentoring. The aim is to help our employees achieve their career goals and the approach is tailored to each person’s needs.

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

I am currently working with three people through this program. Each has a unique set of aspirations and struggles. While their paths may differ, I base many of these interactions on a set of common questions.

Let’s examine six questions you can ask mentees to help them advance their careers.

1. What challenges are you currently facing?

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

We need to put these issues in the spotlight and really discuss them. Most won’t be resolved in four meetings — let alone one — but it’s helpful to talk through them and develop a game plan. When your mentee can go home with something actionable, it provides direction and makes them feel like they are making progress.

There’s also an accompanying question that may be more relevant in a follow-up meeting: “I know you were really stuck on that challenge from the last conversation. have you made any progress If you solved it, what did you learn from that experience?”

2. What would you like to focus on in the coming weeks?

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

It can be helpful to break down these long-term goals into smaller, more manageable tasks. We want our people to focus on SMART goals: specific, measurable, achievable, relevant and time bound.

Suppose one of your mentees wants to get better at public speaking. It’s a fantastic professional skill to develop, but it’s pretty abstract. How can you develop a plan to get there? How will you know if they were successful?

Using the SMART goal approach, you can establish a presentation to a local user group in two months time as a valuable first step on this journey. Then, by setting a series of these SMART goals (e.g. presenting a conference paper or a client presentation), the mentee will slowly build their experience and confidence in public speaking until they are very proficient at it.

3. How do you get involved professionally?

No one is an island, but some technology professionals construct their professional lives that way. Being isolated and not expanding your sphere of influence can severely hamper your career development.

Being isolated and not expanding your sphere of influence can severely hamper your career development.

This question focuses on how your mentee presents themselves out there. How do they nurture connections critical to their long-term success? This could be attending an upcoming company social event or something as simple as coming into the office once or twice a week. The key is to slightly push them out of their comfort zone to help them build 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 mentor other leaders within the organization, pain points often come up. Things either don’t work or could run much more effectively. Be aware that these conversations can easily turn into bitch sessions where the mentee voices their grievances but nothing really changes.

Calling attention to things that aren’t working is always valuable, and it can certainly be cathartic. But don’t stop there – lead the conversation towards how things could be improved. What does it look like to go from dysfunction to excellence?

With a consistent focus on making things actionable, your mentee can become a positive force for organizational change. Over time, their mental process should subconsciously shift from identifying a problem to developing a solution to improve the problem.

With a consistent focus on making things actionable, your mentee can become a positive force for organizational change.

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

Mentoring should be a collaborative experience where both parties contribute. For example, I bring motivation, expertise, honesty and direction. My mentee sets the agenda, is open to his ideas and ultimately does the work. When either of us doesn’t keep our side of the bargain, the value disappears and the relationship is likely to go with it.

As you begin a new mentoring relationship, set expectations. Clarify what you think you are trying to achieve – and what you are not – and ask your mentee to do the same. Letting the mentee go should help them get the relationship where they want it to be, but it’s helpful to occasionally step back and ask, “Is this still working for you? Is there anything we could do to make this relationship more valuable to you?”

As a mentor, you are here to help. If you miss the target, you’ll need to recalibrate before things get too far off course.

6. How can I help?

This is by far the strongest question in my arsenal, and I close each session by asking it. At its core, mentoring is about sharing experiences, helping people grow, and helping them find their way. Help is the common thread that connects everything in this area.

I want that one question to resonate with my mentee long after we’ve ended our conversation. I love it when my mentee reaches out when they hit a wall or just need a different perspective. It doesn’t have to wait until your next scheduled conversation. This person should know that you are invested in the relationship and that they want to thrive. These four words perfectly sum up the essence of mentoring.

Meaningful questions are crucial to making the most of the time you have with your mentee. The key is to get your mentees to stop and think about their response. Your questions should serve as a starting point for further exploration and spark a deeper conversation on the topic.

And remember, hearing the answers is just as important as asking the right questions. If you don’t practice active listening, the questions you ask are irrelevant. Everyone is a bookend when it comes to 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 ]

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