9 Common Questions to Ask a Mentor

Don’t shy away from potentially sensitive topics such as money, leadership and failures.
Lisa Bertagnoli
June 29, 2021
Updated: September 9, 2021
Lisa Bertagnoli
June 29, 2021
Updated: September 9, 2021

When Greg Aponte’s daughter was born, he read about a concept called Wonder Week. During these Wonder Weeks, infants are fussy and even distressed — because they’re making a developmental leap and acclimating to the change, explains Aponte, head of data science and investments at Orchard, an Austin, Texas-based real estate tech company.

“The biggest opportunities for growth will usually be the ones that entail the most discomfort,” Aponte said. “Rather than being discouraged by discomfort, view it as a sign that you’re doing it right.”

5 Delicate Yet Essential Mentoring Topics

  1. Hard-core finance and business matters
  2. Soft skills
  3. Leadership skills
  4. Failures and how to learn from them
  5. Creating a sustainable culture

And that, Aponte said, is why mentees need to ask difficult questions about finances, soft skills, failures, leadership and other tender topics. Yet they rarely do, and he thinks he knows why: It can feel disrespectful, embarrassing and even downright cringey to ask sensitive questions. 

Yet the information the answers to these questions deliver is essential to growth in the tech industry, and worth a few minutes of internal fuss and discomfort. 

Aponte and seven other mentors reveal the questions they’re eager to answer, and explain why these questions need to be asked.

 

What soft skills should I develop? 

Most of Aponte’s mentees focus on the skills they need to have a successful business. “That’s only part of professional success,” said Aponte. “People would be much better served focusing on the behaviors and attitudes they need to demonstrate in order to be successful,” said Aponte, whose mentees are all people with whom he’s previously worked. That personal connection benefits both mentee and mentor, he said. 

He offers two reasons for mentees not asking about soft skills: Early career tech professionals might not understand how to get to where they want to go, and what it takes to get there, and it can be uncomfortable to hear what behaviors might be standing in the way of success. “It’s far easier to talk about hard skills like programming languages and frameworks, or what machine learning skills you ought to learn,” he said.

He pointed out that while hard skills evolve over time, soft skills, such as learning how to communicate credibly, how to have productive conflict and how to hold yourself and others accountable, need intentional work to improve. Soft skills also become more critical as a professional rises through the management ranks, while the importance of specific skills wanes. 

Soft skills also do double duty as work and personal-life tools. “You realize that there is significant overlap between ‘work you’ and ‘personal you,’ and working on things like accountability, integrity, and problem solving are useful in all aspects of your life,” Aponte said.

 

Have you ever failed?

Eric Tang, co-founder of Livepeer, a decentralized video streaming network built on the Ethereum blockchain, has been mentoring other entrepreneurs and Livepeer employees for about six or seven years. He rarely, if ever, is asked about his failures. He understands why. Talk of failure can bring up unpleasant memories, make a mentor vulnerable, or even embarrass a mentor. 

“It might feel awkward, but learning from other people’s failures is sometimes more important than learning from success,” he said. Failure, in life and in business, is a given, “yet we focus on the successes, which can paint a skewed picture of reality.” 

If you’re curious about your mentor’s failures, first ask permission to ask about them, then ask. “Knowing how your mentor has navigated failures is valuable, for background and for mentees who will inevitably face challenges of their own,” Tang said. 

Further ReadingWhat’s the Difference Between a Coach and a Mentor — and When Do You Need Each?

 

What do you still struggle with?

“We work in a complicated business, with a lot of pressure,” said John Matlosz, CEO and founder of Epic Software Development. “Everyone goofs.” Asking about struggles invites a constructive conversation and helps mentees grow by realizing they’re not alone in mistakes, said Matlosz, adding that he mentors every employee at Epic.

So why doesn’t it get asked? “Most mentees are not comfortable with anything that can be perceived as a weakness or shortcoming on their part,” Matlosz said. He suggests developing a strong rapport with a mentor, which will make it easier to broach the tough questions, including the one about struggles.

“It’s important to admit mistakes and tackle them as a team,” he said. “I try to lead by example by offering up challenges I’ve had in the past and how I worked with my colleagues to overcome them.”


What would you need to see to invest in my company?

When she meets with a mentee, Julie Novack cheerfully answers what she calls “check the box” questions, such as how she found her co-founder, John Haro, and how she raised $11 million for Partyslate, an online platform that helps people find event-planning professionals, vendors and advice for all types of parties. 

What Novack really wants to do is take a good, hard look at the mentee’s business plan. She wants mentees to ask her what she thinks of their business model, or key metrics used to run a business, or how to tell if a business is working. “If you don’t know the answers to those questions, you will not be able to raise funding,” said Novack, who began mentoring in 2017 and mentors through groups such as Women Tech Founders and Women’s Wisdom.

Novack would love to look critically at the business and pressure-test it, just as a potential investor would. It’s the best use of her time and expertise. “Ive met with every Silicon Valley investor... I have so much knowledge about business, about what theyre looking for,” she said. 

She’d ask mentees if their addressable market is big enough, who the competition is, what the moat is, what the network effect is, and other topics likely to surface in a pitch meeting. “Those meaty business questions are the best questions to have,” Novack said. “And you don’t have to worry about looking bad in front of me because I’m not a potential investor.”

If mentees don’t ask those questions, Novack will get them there — and then she’ll answer questions about her funding rounds and co-founder. “After 25 years in sales I am good at peeling the onion,” she said. 

 

How can I be a leader?

“I really wish more mentees would ask me how to become a leader,” said Ari Kryzek, co-founder and chief creative officer of Chykalophia, a Chicago-area agency that helps women-led businesses boost their brands. Over five years, Krzyzek has mentored almost 50 people, many of them women aged 30 to 45 in the midst of a career change. Not once has she been asked about leadership. 

She understands the hesitancy. “When I got my first mentor I wasn’t even thinking about leading,” she said. Her mentor encouraged her to get involved in groups and establish herself as a leader, but the prospect “almost felt like a burden,” said Kryzek, who like Novack is a member of Women Tech Founders. 

Krzyzek listened in on a Clubhouse discussion during which people wondered why they don’t see more women leaders. “That got me thinking,” she said. “Is it because women are too shy to ask about how they can become a leader? Or are they not confident to ask because they don’t want to be perceived as too ambitious?” Mentees should definitely pursue questions around leadership, she advised. “It would help their personal growth and encourage them to look for leadership opportunities."

 

How do you make money?

Kryzek’s mentees avoid “money talk in general,” she said. She’s not asked about her hourly rate, revenue goals, how she structures projects or determines a minimal level of engagement. “‘How much do you get paid?’ They never ask that,” she said. Mentees need to understand the numbers around their businesses, but again, Kryzek understands why they avoid the topic. “We aren’t really comfortable talking about money,” she said. “Talking about it could appear rude.” 

 

What should I not do?

“Conversations with mentees typically focus on their desire to do the right things,” said Andy Crestodina, mentor at Chicago-based startup lab 1871 and founder of web design and development agency Orbit Media Studios. That’s good, he said, but it’s equally important for young tech professionals to know what not to do. The question seems counterintuitive, he said, “because once you have an eye on the prize, you look for ways to get there.” 

Successful people have the time to do what they need to do because they’ve abandoned low-value activity. They are focused because they’ve removed distractions. They capture opportunities because they choose their battles, Crestodina said. “It’s important to make thoughtful decisions about what not to do.”

If they’d ask this question, Crestodina would tell them that they should be honest about what they’ll never be great at, then design a life that does not include that task and lets them focus on the things they are great at. For instance, when Crestodina started Orbit Media Studios in 2001, he was involved in design, project management, account management, sales and marketing. He slowly took off hats until in 2010, he was left with only one — marketing. “Most of my success came from this kind of delegation,” he said.

 

How do I create a sustainable company?

Sasha Siddhartha is co-founder and CTO of Thrive Market, an online shopping platform based in Los Angeles, California. Siddhartha has mentored engineers for about 18 years, and for the last six to eight years has focused on early stage founders and chief experience officers. Questions overwhelmingly focus on tactical execution and milestones — understandable “given the existential threat that nascent companies face,” Siddhartha said. 

Seldom, if ever, do entrepreneurs ask about creating a healthy, sustainable company and technology culture. “As leaders, especially in technology, we need to think ahead to handle scale and success,” he said. “As companies and teams rapidly grow, it is easy for culture to erode unless we plan ahead and take intentional steps to preserve the very elements that drove that success in the first place.”

Further ReadingHack the Career Ladder by Finding a Mentor

 

How and when should I reach out to you?

Desa Burton has mentored throughout her career, as a senior officer in the U.S. Navy, a law professor, and now executive director of nonprofit coding school Zip Code Wilmington. “Mentees do not take the initiative to own the schedule and agenda for meetings and contact with mentors,” Burton said. “They wait for the mentor to take the lead rather than managing the relationship.” 

Mentees, she said, sometimes think that they are imposing on their mentor. Not true, as the whole act of mentoring entails the giving of time. That said, mentors should not be responsible for making the relationship work, Burton said. If mentees don’t set the tone for consistent communication, “the relationship begins to fall apart because the mentor gets the impression that the mentee is not invested in the relationship or does not appreciate the connection,” she said. 

Mentors are more than happy to hear this question because it signals interest from the mentee and because it gives mentors something to look forward to. “Meeting with a mentee is often a much needed mental break for the mentor,” Burton said. “Also, mentors get as much out of the relationship as mentees – it provides new perspectives and exposes mentors to new technologies and solutions.”

Jobs from companies in this blog61 open jobs
All Jobs
Finance
Data + Analytics
Design + UX
Dev + Engineer
HR + Recruiting
Marketing
Operations
Product
Project Mgmt
Sales
Sales
new
Orchard
Austin, TX
Operations
new
Orchard
Austin, TX
Marketing
new
Orchard
Austin, TX
Marketing
new
Orchard
Austin, TX
Data + Analytics
new
Thrive Market
Remote
Design + UX
new
Thrive Market
Remote
Design + UX
new
Thrive Market
Remote
Developer
new
Thrive Market
Remote
Operations
new
Orchard
Austin, TX
Data + Analytics
new
Orchard
Austin, TX
new
Orchard
Austin, TX
new
Orchard
Austin, TX
Developer
new
Orchard
Austin, TX
HR + Recruiting
new
Orchard
Austin, TX
HR + Recruiting
new
Orchard
Austin, TX
Developer
new
Orchard
Austin, TX
Operations
new
Orchard
Austin, TX
Finance
new
Orchard
Austin, TX
Finance
new
Thrive Market
Los Angeles, CA
Product
new
Thrive Market
Remote
Developer
new
Orchard
Austin, TX
HR + Recruiting
new
Orchard
Austin, TX
Operations
new
Thrive Market
Reno, NV
Operations
new
Thrive Market
Reno, NV
Project Mgmt
new
Orchard
Remote
Marketing
new
Orchard
Remote
Marketing
new
Orchard
Remote
Operations
new
Orchard
New York City, NY
Operations
new
Orchard
Remote
Operations
new
Thrive Market
Reno, NV
Operations
new
Orchard
Austin, TX
Operations
new
Orchard
Austin, TX
Product
new
Thrive Market
Los Angeles, CA
new
Thrive Market
Remote
new
Orchard
Austin, TX
new
Orchard
Austin, TX
Sales
new
Orchard
Austin, TX
new
Orchard
Austin, TX
Finance
new
Orchard
Austin, TX
HR + Recruiting
new
Orchard
Austin, TX
Operations
new
Orchard
Austin, TX
Operations
new
Orchard
Austin, TX
Product
new
Orchard
Austin, TX
Operations
new
Orchard
Austin, TX
Data + Analytics
new
Orchard
Austin, TX
Developer
new
Orchard
Austin, TX
Operations
new
Orchard
Austin, TX
Finance
new
Orchard
Austin, TX
new
Orchard
Austin, TX
HR + Recruiting
new
Thrive Market
Remote
Marketing
new
Thrive Market
Remote
HR + Recruiting
new
Thrive Market
Los Angeles, CA
Operations
new
Orchard
Austin, TX
Marketing
new
Thrive Market
Remote
Operations
new
Thrive Market
Remote
Operations
new
Orchard
Austin, TX
Data + Analytics
new
Thrive Market
Remote
Sales
new
Thrive Market
Reno, NV
Project Mgmt
new
Thrive Market
Reno, NV
Developer
new
Thrive Market
Remote
Developer
new
Thrive Market
Remote

Great Companies Need Great People. That's Where We Come In.

Recruit With Us