Addressing the Pain Points

Why asking tough questions will benefit your community

Katelyn Gillum
Wise Words
4 min readSep 2, 2016

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This week my classmates and I officially got back into the grind after having a nice (almost) two week break between our summer and fall semesters.

Sweet, sweet freedom.

While many of us are taking electives, interning, or just being incredibly awesome and hardworking human beings (I’m talking about you, Sabrina S. Gordon), we were all able to come together in our required Entrepreneurial Journalism course this past Wednesday (bit of a caveat: I am SUPER good at spelling the word “entrepreneurial” after this week).

In this startup sprint course with Jeremy Caplan, and the first of three courses with an entrepreneurial slant, we spent much of our time thinking through the importance of building a specific community and then designing a product or service that meets those needs. After a few ice breakers and discussion in teams, we spent a large portion of our class time thinking through the specific groups we are each a part of and ultimately narrowing down the list to one group and to think more critically about what they care about, what they are worried about, etc. For us #SocialJ folks, this process has been ingrained in every single thing we do, so it felt nice to be very much aligned with the course content that day.

One of the main takeaways that I had when leaving our first startup sprint class was that it is important to think about addressing pain points when thinking about how to create a service or product for your community. As Caplan discussed in class, oftentimes we immediately think about all of the ways our service or product might positively impact a community. However, it is vital to the success of that service or product to first ask those hard hitting questions such as, “What worries you the most?” or “What’s the hardest part of your day?” in an effort to really understand the true problem that needs to be addressed.

As part of our assignment, we were asked to interview five individuals in our community in an effort to learn more about their needs. Although I have spoken to and interviewed several individuals in my community already, it was interesting to think about this interview process from the idea of addressing those pain points mentioned in class.

As a result of this, here are the ten questions I asked our Wise (seniors citizens):

1. Walk me through a typical day for you. What does that look like? What do you do on an almost daily basis?

2. Who did you last speak to on the phone?

3. Name an “a-ha” moment you’ve had when using technology? What’s something that went right?

4. Name a frustrating moment you’ve had when using technology? What’s something that went wrong?

5. What’s the hardest part of your day?

6. What’s the easiest part of your day?

7. What worries you the most?

8. How do you find information?

9. How do you prefer to communicate with others?

10. What would make your life easier?

My questions were pretty similar for our Wired (young professionals), with a few modifications:

1. Walk me through a typical day. What does that look like for you? What do you do on an almost daily basis?

2. Who did you last text/speak to on the phone?

3. What worries you the most?

4. What’s the easiest part of your day. Why?

5. What’s the hardest part of your day. Why?

6. What app do you use daily?

7. How do you find or access information?

8. How do you prefer to communicate with others?

9. Which social media platform would you refuse to give up? Why?

10. What would make your life easier?

By addressing those pain points, I hope to gain new insight into the needs of my community as I move forward with my courses and practicum projects.

Speaking of my practicum projects (that is, after all, what I am writing these Medium posts about!), I have spent a lot of my time this week really organizing myself in an effort to start executing (see photo below):

Grad school taking over my apartment walls

After thinking through the different steps that I need to take in order to get these projects really rolling, here’s what I have on deck for the week ahead:

  • Create a list of technology terms that the Wise really struggle with, and start to define those terms in an effort to build a glossary
  • Think through the logistics of the Legacy Project — location, theme, pre-interview, length, etc.
  • Planning and prep for our upcoming Wire the Wise event at DOROT on the Upper West Side on Sunday, September 11th! (*This is a new location space for us, which is very exciting)

I look forward to gaining further insight on my community after completing my interviews over the weekend as well as knocking off the above items on my practicum to do list!

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