Rose Velazquez | Jun 08, 2022

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, a 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.”

Top Questions to Ask a Mentor

  1. What do you still struggle with?
  2. How can I be a leader?
  3. How hard was it for you to grow your company and be successful?
  4. How and when should I reach out to you?

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.


Questions to Ask a Mentor

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? 

Soft skills such as learning how to communicate credibly, have productive conflict and hold yourself and others accountable need intentional work to improve.

Aponte pointed out they become more critical as a professional rises through the management ranks, while the importance of specific skills wanes

Most of his mentees focus on the skills they need to have a successful business

“That’s only part of professional success,” Aponte said. “People would be much better served focusing on the behaviors and attitudes they need to demonstrate in order to be successful.”  

One reason 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, Aponte noted. 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.

Soft skills 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.

No One is Talking to the Mentees | Victoria Black | TEDx Talks


Have You Ever Failed?

Failure in life and business is a given. Focusing only on success can skew reality.

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. 

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.


Who Else Can I Talk to and Learn From? 

Mentoring has a new model: The more, the merrier. 

Kirsten Newbold-Knipp, CMO at FullStory, a digital experience intelligence company, advises mentees to create their own personal boards of directors — a community of mentors who can help think through a variety of problems.

“The idea of the mentor of old, the person who says ‘I’m going to take you under my wing and I’m going to bring you along with me in my career and you’re going to learn all of the 27 things that you need to know to be successful’ is outdated and limiting,” Newbold-Knipp said. 

Still, it’s tough for a protege to ask a mentor for more mentoring sources because the implication is that the mentor isn’t helping adequately. “It’s getting both more important and easier as corporate America really starts to understand the value of a diversity of opinions and viewpoints,” Newbold-Knipp said.

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


What Do You Still Struggle With?

Asking about struggles invites a constructive conversation and helps mentees grow by realizing they’re not alone in mistakes, said John Matlosz, CEO and founder of Epic Software Development.

“We work in a complicated business, with a lot of pressure,” he said, adding that he mentors every employee at Epic.

So why don’t people ask about struggles? “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?

Julie Novack 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.

When she meets with a mentee, 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.

“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.”

She loves 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. “I’ve met with every Silicon Valley investor... I have so much knowledge about business, about what they’re 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?

Questions around leadership help mentees in their personal growth and encourage them to look for opportunities to take initiative, advised Ari Kryzek, co-founder and chief creative officer of Chykalophia, a Chicago-area agency that helps women-led business boost their brands.

“I really wish more mentees would ask me how to become a leader,” she said. 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.

“I really wish more mentees would ask me how to become a leader.”

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?”


How Do You Make Money?

Mentees need to understand the numbers around their businesses, but Kryzek understands why they avoid the topic.

“We aren’t really comfortable talking about money,” she said. “Talking about it could appear rude.”

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.


What Should I Not Do?

Mentees should be making thoughtful decisions about what not to do, said Andy Crestodina, mentor at startup lab 1871 and founder of web design and development agency Orbit Media Studios.

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. 

“Conversations with mentees typically focus on their desire to do the right things,” he said. That’s good, he noted, 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.” 

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 Hard Was It for You to Grow Your Company and Be Successful?

Mentees should ask and be aware of how hard success in the tech business is so they are ready for the journey and prepared to put in the work, said Yoni Mazor, chief growth officer and co-founder at Getida, a data-driven tax refund site.

Tech success looks shiny, clean and effortless. “That is very misleading,” Mazor said.

When mentees ask this question, mentors can share stories of overcoming challenges and hardships that tech entrepreneurs face, said Mazor, a mentor in sales, marketing, development, logistics and other fields for a decade.

“Such a learning experience can be very useful to get people on the correct mindset and stamina for long term success.”


How Do I Create a Sustainable Company?

With rapid growth, culture can erode unless leaders plan intentional steps to preserve the elements that drove success, explained Sasha Siddartha.

Siddhartha is co-founder and CTO of Thrive Market, an online shopping platform. 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.

Further ReadingHack the Career Ladder by Finding a Mentor


How and When Should I Reach Out to You?

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. 

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.”

“Meeting with a mentee is often a much needed mental break for the mentor.”

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. 

“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.”


How Can I Stand Out As a Remote/Hybrid Employee?

This question is key because sustaining innovation, collaboration and culture becomes increasingly difficult as companies shift toward remote and hybrid workplace policies, said Frank Weishaupt, CEO of Owl Labs, a Boston-based maker of hybrid collaboration tools.

It might not get asked because remote and hybrid work is, for many people, unexplored territory, Weishaupt said. Weishaupt mentors former employees and colleagues and also mentors through peer groups. He adds related questions to the main one: How to make the right impression and navigate a company as a remote-only hire, and how to encourage innovative ideas among teams that interact virtually. 

Weishaupt suggests reaching out to colleagues for virtual or in-person coffee, asking for time from managers to build connections, asking for a buddy to help you wind your way through the first month or two on the job, and regularly checking in with your manager to make sure you and your work are on track and being recognized. Onboarding teams should also develop a process for connecting new remote-only hires with more tenured employees.

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