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?

Your Mentoring Year Tip #3: Establishing Ground Rules

Your Mentoring Year Tip #3: Establishing Ground Rules

Discussing ground rules is one of the most important conversations you will ever have with your mentoring partner. Ground rules not only manage expectations in your mentoring relationship, but they also lay the foundation for building and strengthening your relationship, allowing you to focus on learning. Rather than restrict the relationship, they encourage and support accountability. Without them, you may end up spending more time managing the relationship than actually learning from your mentor. Here are some strategies for setting ground rules in place:

  1. Focus on:
    • How you will go about allocating and managing your mentoring time
    • How you want to give and receive feedback
    • Your mutual role expectations
    • How and when you will connect and communicate with each other
    • How you will address stumbling blocks should they occur
    • What steps you will follow if you need to prematurely end the relationship for any reason
  2. As you discuss your ground rules, keep in mind that they should not restrict your relationship. Their purpose is to encourage and support accountability.
  3. Once you and your mentoring partner have decided on ground rules, be sure to schedule some checkpoints to determine whether the ground rules are working for you or simply providing unnecessary obstacles.