Note: Greg Gunn, entrepreneur in residence at City Light Capital and co-founder of Wireless Generation, is guest-posting this week.

I’ve been privileged in my career to both be a teacher and to co-found a successful educational software company, Wireless Generation. During my decade of work there, I worked with thousands of schools around the country on using data for early literacy instruction. This included the entire range of public schools, including those in poor neighborhoods as well as middle-class and wealthy ones. An important part of our work in these places was figuring out how to use data to communicate academic goals and progress to parents so as to engage them in the child’s learning process.

As we did this work, I routinely saw schools who were only getting a third of their kids reading by third grade, while at the same time seeing others, working with similar populations, who were getting almost all of their kids reading in the same period of time. Like so many of my fellow African-American educators, I found these patterns especially troubling as they were affecting so many children in our communities. But in looking at the starkness of these comparisons, the questions that kept coming to my mind were these: Why aren’t more parents using this data to question the school’s placement choices and instructional decisions? Why aren’t more parents using this data to demand more from their schools? Wouldn’t the work of educational improvement be so much easier if they did?

At the same time, I saw middle-class friends whose kids were struggling in both public and private schools telling me about their difficulties asking the hard questions. They would tell me about how they felt like they waited too long to ask the hard questions, for which they now felt guilty, and that it took them a long time to get real answers and real solutions, for which they now felt angry.

I finally connected the dots when my own son started to hit some bumps in elementary school reading. As an expert in literacy assessment, I expected that I would find it easy to ask the right questions and hold my son’s teacher and school accountable for his reading development. But as it turns out, it wasn’t easy at all, even for me. Perhaps there was something more universal that parents are struggling with, that we all need.

This realization reframed the advocacy opportunity for me: How do we help all kinds of parents overcome their fear, ask the right questions of their educators, and get the information they need in order to demand the right things for their kids?

From my conversations with hundreds of parents from all walks of life coping with academic concerns around their kids, I’ve seen a few factors emerge repeatedly as to why we are afraid or resistant to ask the tough questions.

• We don’t know what we should be asking.
• We don’t know how to evaluate the answers that the schools and educators give to us.
• We’re worried that if we push too hard, there will be some sort of backlash against our child.
• We know some things seem to be working for our child (respect, happiness, or some achievement) and we are worried about jeopardizing those things.
• We’re worried that the problem may be our kid, or something we did wrong, and we’re not ready for that news.
• We don’t know what we would do anyway if the answers were unsatisfactory to us.

Note that many of these worries have little to do with whether the school seems approachable or not (though that obviously affects how we feel as well). But because of these fears, parents rich and poor feel too intimidated to ask their schools how they are doing by their kids. And with this core set of worries, imagine how much more difficult it is if you don’t speak the language? Or if you yourself don’t feel educated? Or if you fear your child has some kind of learning disability that you don’t understand?

Again, let me be clear that I do not underestimate the great differences in educational options that parents of different economic classes may face. What I am saying is that there are common needs that most parents have in learning how to advocate effectively for their children.

Now while more and more data is becoming available to parents about every school’s performance and environment, the questions around what one’s own child needs, and is getting, remain highly personal and emotionally charged. Even the best data available today only presents part of the picture.

So what are the questions that we should all feel empowered to ask of our schools and educators? Some of the obvious ones include:

• What do you know about my kid, both academically and otherwise? How do you know it? How do you update this knowledge?
• You’ve identified some issues where my child needs work. What are you doing within the school day to work on these individual issues?
• Is my child with the teacher best suited to support his/her needs?
• What is the school doing to support my child’s nutrition and physical health and growth?
• How can I help my child’s academic and personal growth? And how can my efforts stay in sync with yours?

I would love to see a service or tool (and fellow education entrepreneurs, I’m looking directly to you here) that helps every parent ask these questions, understand the answers and their importance, and act on this information for the benefit of the child. Such a service would tackle, clearly and directly, the following questions:

• What questions should I be asking of the school and the educators working with my child?
• What answers should make me comfortable, which should give me pause, and which should raise red flags? What kind of evidence is convincing?
• If there are issues, how can I find other parents sharing the same issues and how can we work together to get the change we need in the school?
• If I ultimately conclude that this school is not the right one for my child, how do I find better alternatives?

A service like this could be the basis for more effective parent engagement, more useful community advocacy, and more high-quality education reform. Most organizations evolve in response to their most demanding customers.

But helping parents ask the right questions is only half the battle--the other half is schools being able to offer good, real answers. And for this, a school has to understand how it has engineered itself to serve individual student needs. I’ll talk in my next post about what it takes for schools to develop this understanding of their own instructional operations.

--Greg Gunn