Mentorship

3 Questions Senior Professionals Should Ask A Mentor

Senior professional meeting with a mentor

Many senior professionals have had their career plans thrown for a loop because of the pandemic. This can lead to mixed emotions—a sense of loss on the one hand and the prospect of new opportunities on the other hand. A mentor can help to balance the two emotions and to clarify a path forward.

Losing a job or feeling like your trajectory is thrown off-track is upsetting, it may even unsettle your sense of identity in the corporate world. Perhaps a week ago you were recognized for your contributions to business growth, you were busy with staff management, executive meetings, and frequent contacts with other business entities. Shifting from this position to a job seeker position is naturally jarring and working with a mentor can offer an opportunity for new insights and perspectives on what to do next.

Senior professionals are not alone now

They should not assume that they stand alone in shouldering this burden. Mentors can be partners in the journey. At the senior level, special considerations must go into structuring the mentoring sessions to deliver the intended benefits. The mentor and mentee have to prioritize the process so that it isn’t sidetracked by other demands. Many senior professionals will find that their mentor is actually at a similar career point to them, or even the same experience level. This might feel strange at first, asking for advice from someone “at your level” but in fact it just means that the mentor may even more be able to relate to the mentee’s challenges, concerns and hurdles.

The right mentor can make a difference

A mentor, as an outside perspective, can offer context-specific just-in-time direction drawn from experience, wisdom, and a network of connections that are highly relevant to solving the mentee’s problems and achieving the desired goal. Four needs in a mentoring relationship are satisfied with this mentor profile: relevant experience, broad vision, connections and trust. This is why Ivy Exec always asks what your industry is, and what the main topic of discussion would be in order to make the best match possible. Beyond work compatibility, personality matching is important too and harder to guarantee. If a first mentor session doesn’t go as hoped, this shouldn’t impede future sessions with different mentors. It may take a couple of tries to find a solid fit but once a good one is found it’s worth the wait.

Focus on keeping your session productive

Mentorship, like many business relationships, is tougher than it looks. Limited meeting time, and often not knowing or understanding each other well can put a strain on interactions.

mentor meeting with menteeFor the mentee, in addition to the stress of losing the job and finding something comparable, it’s the anxiety of working effectively with a mentor and sharing highly personal information. Can a mentor guide them through the challenging times to get their career back on track?

For the mentor, it is no easier. They confront many risks and unknowns. Can I help the person? What if I fail? Do I have the time and needed resources to be effective?

Addressing these challenges and concerns head on can actually help you make sure you set a clear agenda and tackle your questions and issues as efficiently and effectively as possible. Acknowledge your concerns and your needs to get the most out of your session. It’s easy to get sidetracked with light-hearted small talk, but facing the hard issues directly is a much better use of both parties’ time.

Ask Your Mentor The Right Questions

When you first meet your mentor, it can be hard to know where to start. Ask the right questions to see if it is a fit, and if it is, map out a “plan for success” conducive for both parties. Remember, even if you have different experiences or backgrounds it’s these differences especially that can open your mind to new pathways forward.

Here are three questions senior professionals can ask the mentor in their first meeting, during this national crisis, to ensure that they get the most out of the session: 

QUESTION 1: Have you ever been in my situation—lost your job or been laid off during a national crisis or major restructuring in your company?

This question helps you gauge your mentor’s empathy with your situation and opens the dialogue for you to share your thoughts and emotions about your situation. If the mentor says yes, you feel a certain comfort that he has been there and done that. It also makes your situation less ominous.

If the mentor has been in a similar situation, your follow-up questions would be:

    • What was your initial reaction?
    • What actions did you take?
    • How did you recover from it?
    • Did you need help to get back on track?
    • What or who helped you the most?

QUESTION 2: If the mentor has not personally experienced such a situation, ask, “What would you do if you were in my shoes? How would you approach the situation?”

You cannot expect mentors to have an easy answer ready to this question, and in fact you actually don’t want a direct answer. Your question paves the way for an open and honest discussion about your situation. It also helps both of you understand how professional mentoring for exeutivesand if you can work with each other.

Follow-up to Question 2: Have you mentored a senior professional facing a similar situation to mine?

Being in a situation is different than helping someone in a similar situation. If the mentor has worked with someone in a similar situation, ask the following:

  • Were you able to make a difference?
  • What was the outcome?
  • How did you help them get back on track?
  • What roadblocks did you notice them putting in front of themselves?

Question 3: Finally, you want to know what you can expect from this mentoring session. What role can the mentor play in your job search? How much time would they be willing to dedicate to the mentoring. It is critical to define the role of the mentor, and set and manage expectations.

Keep an open mind to mentoring

Job searching is stressful enough without misunderstandings and disappointments compounding the issue. But a healthy mentoring relationship can ease tensions and relieve the burden of doing the search alone. A supportive and proactive mentor can help you develop coping skills, job seeking strategies, and get you primed to take the next step in your career even during these challenging times.


Schedule a session with a mentor!


About the Author

Mala Subramaniam is an Executive Coach, speaker and instructor of business courses with a passion for teaching. She is an adjunct faculty member at UCSD and an Ivy Exec Mentor with twenty years in influential marketing roles at companies such as IBM, GE Healthcare, and Dun & Bradstreet. She is also a best-selling author whose book, Beyond Wins, gives the principles for success in business negotiations.