40 Questions To Ask A Mentor

Imagine you approached someone you admired, and boldly asked that person to mentor you. And the answer was “Yes!” But a year into the relationship, those monthly mentoring sessions might not invigorate you like they used to, and aren’t quite as energizing for the mentor, either.

4 Types Of Questions To Ask A Mentor

1. Stories

To break the ice, have your mentor tell a story from his or her own career. Hey, everybody likes to talk about themselves! For example, you could inquire: “How did you get to where you are today?” or “How did you land your current role?” But you could also ask more specific questions that address your career objectives and concerns. Some questions to consider:

• Was there a time you messed up and felt like you’d failed? How did you bounce back?

• How did you learn to embrace risk-taking?

• Tell me about a recent business setback. How did you recover?

• Think back to five years ago. Did you envision your career as it is today?

• Was there ever a role you applied for and landed, but weren't 100% qualified to do? How did you proceed?

• What do you wish you had known before taking your first management role?

• Which leadership skills were the most difficult to develop?

• Can you tell me about a time when you had a difficult boss? How did you handle the situation?

• What’s the most important leadership lesson you’ve learned and how has it proven invaluable?

• How did you develop the skill of speaking so engagingly in front of groups?

2. Situations

Now that the conversation is flowing, get more granular in your requests and bring a specific situation to your mentor--one that you’d like help navigating. For example:

• I tried to delegate a task last week and it did not go well. Can we work through what to do differently next time?

• Who are the people I need to align with in this organization to achieve success?

• My boss said I need to be more strategic. What does that mean?

• How can I let my boss know that I don’t need to be micromanaged?

• How can I stay connected to key influencers who do not work in same office or geographical area?

• When trying to gain buy-in to implement a new program, what tactics have worked for you?

• My performance review is coming up. What type of preparation do you most appreciate seeing from your employees?

• I have two very different career path options available to me. Can you weigh in to help me make a final decision?

• I'm considering a career transition. What are some other areas of the business that might be a good fit for me?

• I’ve heard that taking a stretch assignment could help my career trajectory. What are the pros and cons?

3. Self-Awareness

One of the greatest gifts you can give yourself is the gift of self-awareness, meaning the ability to see yourself as others view you. That way, if you like how you’re perceived, you can embrace it and take steps to strengthen that positive perception. If you don’t like how you are currently perceived, you can take steps to shift that perception to a more positive one that supports, rather than undermines, your career and leadership goals.

After starting with the obvious question: “How do you think others perceive me?” become more specific, so your mentor can assist by “holding up the mirror” and providing detailed feedback on how your actions and communication are impacting the way others see you. Ask questions such as:

• How am I viewed? In other words, what's my personal brand in our organization?

• Where do you see my strengths?

• What do you see as some of my blind spots and how can I improve?

• How I am viewed by leadership?

• What do people say about me when I’m not in the room?

• Could you offer feedback on ways to improve my executive presence?

• Do I come across as strategic or tactical in my day-to-day communication?

• Am I viewed as high-maintenance when I send my boss weekly status updates?

• How could I have communicated my idea more clearly?

• When I presented at the last meeting, how did I do? Did my communication style support the message I intended to deliver?

4. Skill-Building

Is there a skill you’re currently working to enhance, such as project management, long-term strategic planning, delegating, or public speaking? Use questions like these to ask your mentor for advice and resources to help you polish that skill:

• How can I become a more assertive negotiator?

• Can we role-play asking for a raise and a promotion?

• How can I become better at managing people who do not report to me?

• Do you have any quick tips for re-energizing an overworked team?

• Can you recommend a book or resource for dealing with difficult conversations?

• What practices can you recommend for dealing with nervousness when speaking to groups?

• I have been asked to facilitate a team-building activity at a staff retreat. What are some keys to success?

• What’s a good methodology or tool for project management and tracking team commitments?

• Do you have a template that you use for long-range visioning and strategic planning?

• What new skills do I need to move ahead?

With these four types of questions and their accompanying examples, you’ll never sit through another mentoring conversation wondering if the other person is finding the discussion useful. And give this list to those whom you mentor, encouraging them to use it to maximize the value of the time you spend together.

10 Questions to Ask a Financial Advisor

Before you commit to a financial advisor, you want to make sure you’re hiring the best person for you and your situation. Start by asking yourself a key question, then check out the ten questions you should ask an advisor before hiring one.

First, what type of financial help are you looking for?

1. I just need to get started investing for my financial goals: A robo-advisor may be the best fit if you're just starting out or only need investment management. For a low fee, these computer-based services choose and manage an investment portfolio for you. Some also offer access to financial advisors if you have questions about your investments or your goals. Robo-advisors often have low or no account minimums, so it's easy to get started.

2. I want personalized financial advice but don't need to meet my advisor in person. There are many services that offer online financial planning for less than you'd pay a traditional in-personal financial advisor or financial consultant. These companies provide complete investment management and holistic financial planning; the major difference is that you'll meet your advisor virtually — by phone or video chat — rather than in a local office. Most services pair you with a dedicated advisor or certified financial planner; some less-expensive options offer access to a team of advisors.

3. I want a local advisor or a wider array of financial advice: On the other hand, if you want in-person financial planning or have a more complex situation, you may decide a traditional local financial advisor is right for you.

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10 questions to ask financial advisors

If you think exploring a relationship with a traditional financial advisor is the right move, be sure to ask these ten questions during the interview process.

1. Are you a fiduciary?

A fiduciary works in the best interest of the client and only recommends investments that are the best fit. Nonfiduciaries, such as broker-dealers, need only to recommend products that are “suitable” — even if they're not the lowest-cost or most ideal for you.

2. How do you get paid?

Advisors can use a variety of fee structures. To keep it simple and avoid conflicts of interest, focus on fee-only advisors. They don’t get commissions for selling products.

"Make sure it’s fee-only — those particular words," says Alice Finn, founder of PowerHouse Assets and author of "Smart Women Love Money," a guide to investing. (Some of the questions here are from her book.)

Fee-only advisors might charge a percentage of the assets they manage for you (1% is common), a flat fee for services or an hourly fee. If cost is a concern, you may want to go with a low-fee robo-advisor or an online planning service like those mentioned above.

3. What are my all-in costs?

In addition to paying the advisor, you’ll face other fees — and you'll want to know what they are. Fees can decimate your savings over time. "You can lose half your net worth without even knowing it," Finn says. "You want to be vigilant."

4. What are your qualifications?

Financial professionals can have a confusing list of initials behind their names. And whether a finance professional goes by "investment advisor" or has a certified financial planner designation, it's your job to vet them. The Financial Industry Regulatory Authority's professional designations database will tell you what they mean; if there are any education requirements; if anyone accredits the designation; whether there's a published list of disciplinary actions; and if you can check professional status.

You can also use a Form ADV to check an advisor's record.

5. How will our relationship work?

Put another way: How much access will you have to the advisor? You want to know how often you’ll meet and whether they're available for phone calls or emails outside of scheduled appointments. (Learn more about what financial advisors do and what you can expect from the relationship.)

6. What's your investment philosophy?

It’s important to ensure you have the same investment management philosophy. Here’s why: “You have to believe in what they’re doing to stick with it,” Finn says. “When financial advisors really do their job is when the market is down and they can convince you to stick to the same page,” she says, so you don’t sell at the bottom of a market cycle.

It's also important to make sure you and your advisor align on investment style. For example, if impact investing is important to you, you may want to ask whether or not your advisor will be able to help you create a portfolio that aligns with your values.

Also ask: Who are your typical clients? Find an advisor who is used to a situation like yours and able to help you meet your goals.

7. What asset allocation will you use?

You’ve heard how important it is to be diversified, right? Your asset allocation is how you create a diversified portfolio. “It drives most of your returns,” Finn says.

“You don’t want someone who is just going to pick U.S. large-company stocks,” Finn says. Your portfolio should include domestic and international stocks, and small-, mid- and large-cap companies.

8. What investment benchmarks do you use?

Advisors should use benchmarks that directly relate to what they’re invested in, or be able to explain why they don’t.

Some managers will use a “straw-man benchmark,” Finn says. For example, the advisor says: “My goal is to beat the Standard & Poor's 500.” But if that advisor is investing in a diversified portfolio beyond simply large-cap U.S. companies, that benchmark is a mismatch. “Over time they should beat the S&P 500 because they’re taking on more risk,” Finn says.

9. Who is your custodian?

Ideally, your financial advisor has hired an independent custodian, such as a brokerage, to hold your investments, rather than act as his or her own custodian — à la Bernie Madoff, the notorious financial advisor who defrauded clients through a multibillion-dollar Ponzi scheme.

That provides an important safety check. “If I send my clients performance information … and it tells them how much I say is in their account, they can go online any minute and double-check,” Finn says.

10. What tax hit do I face if I invest with you?

This helps ensure the advisor has your tax bill in mind when making financial decisions. And asking about taxes and fees is a way to explore what your estimated net return might be. “What you want to know is: What do you get to keep after fees and after taxes?” Finn says.

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