The Quality of Your Questions

The best mentor-mentee relationships thrive on curiosity and powerful questions. Mentors should resist the urge to “fix” problems and avoid prescribing specific actions. Mentees should focus less on being who they think their mentor wants and more on approaching interactions with a willingness to learn, grow, and discover how to think.

I am always seeking great questions to facilitate these interactions. Recently, I discovered three excellent questions while listening to the audiobook Clear Thinking* by Shane Parrish. Parrish suggests that when seeking advice, your goal should be to understand how the other person thinks, not just what they think. Although his book is not specifically about mentoring, the questions he proposes can be highly beneficial for both mentees and mentors.

Questions Mentees can ask their Mentors
Mentees might ask….

1. What variables would you consider if you were in my shoes?
How do these variables relate to one another?

2. What do you know about this problem that I don’t?
What can you see based on your experience that someone without it cannot?
What do you know that most people don’t?

3. What would your process be for making this decision if you were in my shoes?

Questions Mentors can ask their Mentees
These questions are also valuable for mentors. Instead of offering solutions or suggestions, mentors can prompt their mentees to reflect by asking:

1. What variables in this decision are important to you?
Who else or what else does this decision impact?

2. What are you most worried about in making this decision?
What possibility excites you the most?

3. What have you tried so far?
What do you think is the best process for this decision?

These questions encourage reflection and empower mentees to solve both the current problem they are facing and future problems. They also enable mentees to develop authentic solutions that fit their unique needs, values, and learning styles.

What questions have you used to encourage clear thinking in your mentoring relationships?

*Clear Thinking by Shane Parrish: (Farnam Street, 2023, ISBN: 0593086112)

The quality of your questions

Mentoring the Mentors: Advice and inspiration for working with startups

Posted by: Rick Turoczy (Originally published at siliconflorist.com on July 3, 2012)

Around the time PIE was starting the accelerator phase of this ongoing experiment, David Cohen, cofounder of TechStars, shared the TechStars Mentor Manifesto. And it served as an inspiration for me. A post by Micah Baldwin, a former TechStars mentor, provided a similar nudge for me.

I’m often reminded to go back and reread both of these posts and am inspired, again and again. So I thought I’d take the opportunity to augment the PIE mentor guidance a bit with some things that we’ve learned from observing PIE startups and mentors over the years.

We shared these tips with the PIE mentors and a few of them suggested we turn it into a blog post for the broader mentor community.

So we took that mentoring to heart.

If you’re thinking about becoming a mentor for startups — either in a formal accelerator program or independently — here are some tips for thinking about how to work with entrepreneurs.

Read on here for 10 tips for mentoring startups.

Your Mentoring Year Tip #9: Maintaining Accountability

Your Mentoring Year Tip #9: Maintaining Accountability

Maintaining accountability in a mentoring relationship is critical for success. But it’s not one-sided. Accountability must be mutual. “Wait, what?” you might be thinking. “Accountability is hard enough, but mutual accountability?”

Yes! Making sure both mentors and mentees are accountable keeps mentoring relationships moving and on track thanks to regular care and attention. Regular monitoring of your relationship guarantees that even when the relationship seems to be going well, you can still promote mutual accountability and, therefore, a healthy relationship.

How do you get started? Use the following conversation tips to provide a framework that drives mutual accountability — and helps maintain it.

  1. Check in at the beginning of your meeting. Regularly ask, “How is it going?” Probe your mentee’s response, and take it to a deeper level.

  2. Share your observations about how things are going and what concerns you have about the learning process. For example, “I’ve noticed that our discussions are very general and theoretical. Are you finding them helpful?”

  3. Take a step back before you go forward. For example, “Let’s take a look at how we’re doing. What’s particularly helpful to you in your learning? What has been least helpful? What do you think is going well? What do we need to improve? What kind of additional assistance do you need?”

  4. Use your mentee’s goals as benchmarks for measuring the progress and achievement of learning goals. Refer to them frequently. Evaluating progress regularly maintains momentum, keeps learning goals at the forefront of the relationship and holds partners mutually accountable for achieving them.

Your Mentoring Year Tip #6: Setting SMART Goals

Your Mentoring Year Tip #6: Setting SMART Goals

Last month, we offered some tips about how to set starter goals. As we noted then, the key to exploring starter goals is to get to the heart of the learning need and create specificity around your desired outcome. This month, let’s discuss how to turn starter goals into the kind of goals that help mentees achieve their mentoring objectives — we call these goals “SMART goals.”

SMART goals are goals that are: Specific, Measurable, Action-Oriented, Realistic and Time-bound.

How to create a SMART goal:

  1. Ask questions to really understand your mentee’s desired outcome. The best way to create SMART mentoring goals is through conversation. Together with your mentee, take a look at the starter goal you created. Make sure you are clear on what success looks like. Be as specific as possible, and drill down until you come up with a way to measure success. Ask: “How will we know if you achieved it?” “What will success look like?” “What will be different when you achieve this goal?”
  2. Encourage action rather than contemplation. Mentors help mentees create action-focused goals by reminding them that clarity comes from engagement, not thought. Too often we see mentees set goals that start with “I will think about” or “I will explore” or “I will learn.” SMART goals have action words and should answer the question: “What will you DO?”
  3. Provide a reality check. SMART goals are realistic. Help your mentees set realistic milestones that link to a larger goal. That will keep them motivated and create enthusiasm for further progress. Ask “What are the obstacles to your success?” and “On a scale of 1 to 10, how confident are you that you can overcome those obstacles?” For anything less than an 8, work with your mentee to identify and anticipate obstacles. If obstacles can be overcome, create learning around that. If they cannot, create a more realistic goal.
  4. Set a deadline. Too often, development goals languish because they feel important but not urgent. Having time-bound goals helps measure progress, create a sense of urgency, generate momentum and provide natural check-in points along the way. Set a date by which the goal should be achieved, and continually track progress towards that date. It’s perfectly appropriate — even, at times, encouraged — for a mentee to choose a lofty goal that will really propel them forward. But unless that goal is broken down into smaller steps, your mentee may get fatigued or burned out. Set timelines for milestones along the way.

How have you used SMART goals in your mentoring relationship?