Developing Questions for Your Next Informational Interview

One essential method to grow your skills, knowledge, and experience as an urban planner is to speak and learn from other leaders in your field or specialty. This is why I have dedicated to interview urban planning leaders and share it with you on this site.

I often struggled in reaching out to leaders because of my limiting belief that I wouldn’t be able to effectively engage in a conversation worth their time. To help me overcome this barrier, I developed strong, engaging questions that I felt confident would create a deep, engaging conversation. To become an urban planning leader, asking deep, engaging questions is a key skill to learn.

“The wise man doesn’t give the right answers, he poses the right questions.”

-Claude Levi-Strauss

In the interviews I have held myself, I developed my own questions that were unique to what I wanted to learn. Here’s how I did it:

Ask: What do I want to learn from this urban planning leader? I start by asking myself this question to determine my goal for the informational interview and how the person can help me grow. The answer is a guide to what questions you must ask for you to learn. For example, my answer may be, “I want to some advice on how to shift my career”, or “I want to learn more about Transit-Oriented Development”. Knowing this, helps me determine the focus of my questions such as, “in your experience, what is the biggest hurdle in changing your career path?” or “What case study should I research that you believe is a great example of TOD?”

Use example questions online and make them authentic to you. There are plenty of blogs that provide good example questions for informational interviews. Pick the ones that interest you the most, and put your own twist on them that align with what you want to learn.

Do your homework. Look up the person and the organization they work for to better understand what they do on a daily basis. This leads to more informative questions and better answers. Also, these leaders will respect your preparation and be more open to engaging with you. This will also avoid answers such as, “check my website, there’s information there.”

Start with simple questions. I like to ask very simple questions first to get the juices going in the conversation. Such as, “what are you working on currently?”, rather than leading with, “what’s the biggest mistake you made and wish you could go back and change it”. As the dialogue and energy picks up, ask more in depth questions to receive a better result. 

Provide context. If I ask someone, “why has transit mode share declined?” One, they may ask, has it? or why do you think so? Instead, use context as to where you derived the information and then ask the question: “After reviewing your Quality of Life study I noticed the percentage of transit mode share has decreased the last two years, why do you think that is occurring?” This gives the leader a better idea what you are asking and can provide a more informed answer.

Ask follow-up questions during the conversation. When the leader answers your question, ask follow up questions for three reasons. First, it shows you are listening and increases engagement. Second, it gives the opportunity to dive deeper into what the leader is saying. Third, it lets the conversation flow naturally. A prepared list of questions is your starting point and you may not get through all your questions within the time you have with the leader. That’s okay, the goal is not to get all your questions answered, the goal is to learn and grow.


Jim Chappell: An Urban Planning Leader Continuing to Stretch the Boundaries of Knowledge through Listening and Humility

I had the honor to connect with Jim Chappell and learn about his leadership qualities and how he has been successful. Jim is an urban development expert, strategic thinker, community opinion leader, and the previous President and Executive Director of SPUR.

Jim built SPUR to become one of the nation’s leading community development organizations and led the opening of the Urban Center in May 2009. During his time at SPUR he provided community leadership and government relations on projects such as reorganizing Muni management structure; development of the Presidio Trust; development of a comprehensive strategic city parks plan; design and financing of Doyle Drive; conception of the Transbay redevelopment area; the community strategy for the de Young Museum and the California Academy of Sciences.

He continues his work today by providing strategic assistance to the development community, public agencies, and community organizations, including the Fort Mason Center.

What do you believe are the characteristics and actions that you used to get to where you are today?

1. Diligence. Do my best. If you don’t do your best all the time there is no point in doing it at all because someone else will be doing their best and they will succeed and you won’t.

2. Rigorous honesty. Tell everyone the same thing.

3. Never attribute blame to anyone; do not characterize or name people by their beliefs (e.g., NIMBY, greedy developer, etc.)

4. Do not attribute motives to others’ actions. You can never know another person’s motivations, nor is it helpful.

Ask, probe, guide, lead by example, but don’t dictate.

What are you doing to ensure you grow and develop as a leader?

I try to stretch the boundaries of my knowledge… especially talking with youth …who bring a whole experience and knowledge base that I don’t have. I am having a ball talking with young people in India…they are anxious to talk with Americans and it is absolutely fascinating how they see the world…Indian politics, American politics, marriage and the all-important family, education and careers, etc. How do I know that it isn’t better to have your more experienced family pick your life partner? How can I possibly tell people in the chain of a 7000 year culture that I am right and they are wrong?

Sometimes leadership is listening. Ask, probe, guide, lead by example, but don’t dictate. At any rate, this is how I am trying to continue to develop.

What drives you to be successful?

I subscribe to the campground rule: leave the world a better place than you found it.

What questions do you often ask yourself?

What am I missing?

Why don’t I see it the way x person does?

How do you ensure Fort Mason’s and its activities are aligned with your “core values”?

Provide gentle guidance. At the beginning of every year, talk to the staff and board about our values, what we are going to accomplish, how we are going to get there, what are the rules of the road. Big picture overview; enunciate higher principles; assure everyone explicitly thinks at least once a year about them.

Banish excuses. And then stand back. 

What is the biggest challenge leaders in urban planning face today?

Distrust of government. Few people trust government like we once did. “Everything thing is a conspiracy. Every politician and bureaucrat is a crook.”

Lack of common knowledge base and source of information. We have limitless sources of information online but no one is editing it. Anyone can say anything and who with knowledge and authority is to contradict? We often empower the least informed among us. And these two factors reinforce each other in negative ways.

What are the most important traits of successful leaders in urban planning today?

Ability to listen and HEAR – take in all viewpoints. 

Understand that your role is to make a considered recommendation to the elected decision maker. You must be able to enunciate all sides of the issue to that decision maker, let go and let the decision maker do as she sees fit, and resist any thought of ever embarrassing him/her. If you can’t do this, go sell shoes, or get yourself elected to public office.

What sacrifices do you make as a leader?

You have to meet the public when and where they are. This means night meetings on their turf. It also means putting yourself out in public for whatever comes down. 

Home life suffers.

This is the first of a series of interviews I am committed to conduct of today’s leaders in urban planning and gain insight in their leadership qualities and how they have been successful.

For more information about Jim, check out his LinkedIn page.

Jedi Mind Tricks for Urban Planning Leaders

This post is not about how to deceive others in getting your new transit line, road widening, or bike lane. This post is how to change YOUR OWN mindset to be more effective in accomplishing your goals and contributing to your community.

You have power over your mind – not outside events. Realize this, and you will find strength.

-Marcus Aurelius

Be curious, not furious. When you meet opposition from the public, elected officials, or engineers, be aware of the emotions that come up and switch your mindset from being upset, to genuinely curious about why that person is opposing your initiative, project, or idea. Sometimes you may just be misinterpreting what the other person is saying and clarification can help. You may even find out you both are saying the same thing, just using different language! Other times they may actually be opposing it and it’s critical you understanding why because it is an opportunity for your initiative, project, or plan to evolve and improve. This takes powerful listening skills and thoughtful questions in order to really understand the person’s perception and understanding.

They’re calling your baby ugly. It can be extremely challenging to take critical feedback of our own project, plan, idea, or initiative. As Urban planning leaders, we put a lot of blood, sweat, and tears into our projects and see it as our baby. We may have created it, put in hours to develop it, refined it, and started all over again to make it “perfect”. We get emotionally tied to its success (or failure) because we know that emotion creates motivation and progress. So when someone gives us critical, yet honest feedback, we may perceive it as a threat to our own ability, lack of understanding, or just downright cruel. Since this project is like our baby, we must protect it at all costs, and defend. However, if you can’t receive feedback in a constructive manner, learn from it, and respond constructively, then you don’t grow and your idea, project, or plan doesn’t improve.

Focus on the message, not the delivery. One strategy to better receive feedback is to focus on the message of the provider rather than the technique they provide it. For example, I was completing a slide deck for a bridge rehabilitation project to be presented to elected officials and I asked my boss for tips on effectively delivering material to elected officials. Instead of giving me general tips (what I was looking for) he dove into the details of the presentation and began providing specific feedback on specific words and content. At first, I was frustrated because he didn’t answer my question in a delivery I wanted, such as “here are the 5 general tips when presenting to elected officials”. However, I remembered to focus on the message he was sending, rather than focus on how he was delivering it, and realized he did gave me a general tip. Remove technical jargon from the presentation! When someone may seem to be upset when providing you feedback, try to really listen to what they are saying, rather than how they are saying it.

Check out my post 5 Tips to Brief Elected Officials on your Project for more info!

Focus on what you can control. I was recently introduced to Stoicism, a philosophy dating back to the 3rd century BC that focuses on self-control and to accept the world around, even if its painful. As a planner, it is difficult to know what will come next, and therefore uncertainty provides a challenging environment to know where to put your resources and time. Therefore, focus on improving and growing yourself, since this is the one thing you can control.

Successfully Planning for Uncertainty

Envisioning the future for cities and making decisions to help your city thrive in the face of uncertainty is challenging and painful for some. Planners may wonder, at what rate will sea levels rise? Will there be a recession this year? Will Transportation Network Carriers (TNCs) be a dominant force in transportation? Will millenials stay in cities as they grow up and have families, or move to suburbs like their parents? These uncertainties make it challenging for planning organizations to know where to invest their resources, and for planners to know what skills and knowledge they should gain to grow their careers. Uncertainty can cause fear, anxiety, and doubt, which may lead to organizations and people trying to control as much as possible or give up and say, we will wait until the future happens. However, both strategies are barely handling uncertainty and can cause immense costs financially and socially.

The problem isn’t uncertainty itself. The problem is our rejection of it.

From: 5 Tools for Thriving in Uncertainty

There are two types of uncertainty, internal and external. Internal uncertainty is within yourself, or within an organization. Am I doing the right things and making the right decisions? Am I on the right career path? Does the organization have the right skills and resources to help their cities thrive? Can I reach my goal? Basically, it can be doubt about who you are and what you are doing. External uncertainty is how the world is changing and all the possibilities that exist. For example, whether a Republican or Democrat will be elected, or will a devastating earthquake erupt? Will walkability be a norm, or will we continue our autocentric ways?

So how can urban planning leaders successfully plan cities in uncertainty?

Change your mindset. This is the most important. Change what you think about uncertainty. “The problem isn’t uncertainty itself. The problem is our rejection of it.” Certainty may actually deprives us of developing sustainable and livable communities because it oversimplifies the complexity of the world. A sexy light rail system will not be successful everywhere in every situation. Uncertainty brings challenge and pain in our lives, yet it brings the most growth, fulfillment, and joy. Rather than running from the challenge, embrace it. Know that in those uncertain moments, especially the ones that are the most painful, you are growing the most and great opportunities are forthcoming.

Uncertainty brings challenge and pain in our lives, yet it brings the most growth, fulfillment, and joy.

Focus on Internal Uncertainty. There are many things in this world that are out of our control. That’s why I am a big believer in focusing within myself in situations of uncertainty and challenge. Focusing on what we can control (ourselves), rather than what we cannot (the world), brings better decision-making to better our cities and peace within ourselves. This doesn’t mean to not be aware of the outside world, just don’t dwell on what’s wrong with it or try to control it. Prepare for uncertainties by being adaptive, developing skills, and being emotionally intelligent. Focusing on yourself can be very difficult, especially when everything around you feels like chaos. Kyle Eschenroeder, describes the Triad of Control as a tool to help. Where “you simply distinguish, in any given situation, whether you have total control, no control, or some control. Then, focus on what is in your control with your whole being.”

Experiment. Reflect. LEARN. Repeat. Successful businesses and communities are running more low-cost experiments to gain results for learning, rather than develop elaborate plans that may not work and cost a lot of money. For example, Tactical Urbanism has become an international movement that uses flexible, low-cost, and short-term projects to advance long-term goals related to street safety, public space, and multi-modalism. It’s something you can control directly and see if it functions well with the community. Learning is a key ingredient here to understand what works, what doesn’t, and to adapt to situations efficiently and effectively.

Temporary Bus Platform on Telegraph Ave. in Oakland, CA

Learn Emotional Intelligence. This strategy may not seem relevant, however it has really changed my life in being able to handle uncertainties. I have learned how to pinpoint the anger, fear, and/or vulnerability when uncertainty is present. Learning how to deal with emotions helps the brain focus on solutions, rather than focusing on the uncertainty itself. You can actually use those negative emotions as power to find solutions. Our emotions drive our behavior, and sometimes we don’t even realize it!

Develop Scenarios. Organizations are now using scenarios of the future to drive decision-making and be prepared for what could be ahead. MTC, the transportation planning, financing and coordinating agency for the nine-county San Francisco Bay Area, created three scenarios of what the Bay Area future could be. They created regional forecasts in areas of jobs, housing, population, travel needs, and funding for transportation improvements to help drive decision-making for uncertainties.

SPUR, also created a comprehensive future scenarios report that lays out potential futures in the economy, housing, transportation, and physical form. The looked at uncertainties the region does not have control of, and outcomes that will be shaped by choices. “It is a way of understanding choices, chains of events, alternatives and possible outcomes to support better decision-making in the face of a future with great uncertainty.” Check out my links page for more info.

So embrace uncertainty, and see the opportunity it can bring for your city. Prepare for uncertainty by focusing on yourself, experimenting and then learning, gaining emotional intelligence, and using strategic planning scenarios.

Happiness and Mobility

Amsterdam is arguably the biking capital of the world.Spend even just a day there and you’ll see firsthand the massive volume of Dutch bicyclists that constantly cover Amsterdam’s streets. Stay there long enough, and you might notice how happy the Dutch seem to be. (A quick google search of the World Happiness Report puts the Netherlands at the 6th happiest country and the U.S. at 18th). I think a key to their happiness is that the Dutch are presented with abundant mobility options. Yes,they can drive, but there is public transit, the cities are walkable, and the emphasis on bicycling and bike infrastructure is unparalleled. The Dutch don’t spend over an hour each commute night sitting in frustrating traffic, because they have other feasible transportation options. The urban planners in the Netherlands successfully connected networks of bike paths and public transit, created narrow streets to slower drivers, and wide, attractive sidewalks to encourage pedestrians.

In the U.S., public transit use and bicycle networks are far from the high Dutch standard. Instead, the average American relies on personal vehicles and sits in ridiculous amounts of traffic. When Americans arrive home after their daily commute, they tend not to decrease the time that they spend watching TV. Time at the gym, with family, and sleep all decrease, and so does happiness. Having better options besides cars- transit that allows for reading time, or walking and biking which provide exercise, are factors that contributes to happiness. Aside from needing urban planners to help make other transportation options a reality, the U.S. needs urban planning leaders. There is no right answer or way to improve multimodal choices and contribute to American happiness. The best leaders understand that, so they lead with curiosity and passion. Leaders also focus on professional growth, which includes networking. This combination can put urban planning leaders in touch with others that have experience with reducing car-centric transportation and assist with creativity and new ideas. Collaboration between leaders is an important step that will manifest as urban planning leaders make their way in the field. Urban planners must work together to improve cities by providing multimodal transportation options to everyone, and simultaneously increasing our happiness.

-Written by Marissa Brown 

5 Reasons Urban Planners Must Use Facilitative Leadership

Urban Planners must make decisions and complete analysis with more diverse groups of people and tremendous amounts of data. With more diverse teams and stakeholders involved in transportation and development projects, conflict arises out of differences in priorities, values, communication styles, and personalities. The tremendous amount of data available for decision-making and analysis increases the complexity of connecting all the pieces to see the whole. In order to make progress in making sound, sustainable decisions and analysis in this landscape, urban planners must use facilitative leadership.

Facilitative leadership is a people-centered approach to achieving complex goals within a team setting through learning and systems thinking.  They in turn create synergy within groups to produce something that no individual can do alone. Here are 5 reasons urban planners must be facilitative leaders do to create a comprehensive process in achieving the most difficult goals:

1. Continuously Learn

Most working planning professionals aren’t providing the time or incentive for reflection and real-time learning. Once a project is completed, it’s onto the next one. This can cause planners to make snap judgement, rather than seeing the underlying issues and patterns. Facilitative leaders create an environment for teams to reflect on lessons learned and achievements to either repeat or adjust in the future. This type of learning is not taking in information, but a shift in mind how people and teams influence the world.

2. Enhance Creativity

Many past solutions to cities’ problems have found to be not working, such as our huge highways that are congested and falling apart. Facilitative leaders stimulate creativity within teams by using conflict and using different approaches to change desired outcomes.

3. Empower Everyone

Everyone has a unique skill, talent, or expertise in a subject. Facilitative leaders understand this and seek to extract it from each individual to contribute to the team.  They do this by asking powerful questions, actively listening, and creating psychological safety for open and honest dialogue. Facilitative leaders listen for and seek to help others make the connection of all the data and the differing points of views, comments, and values of others. They create psychological safety by helping the team develop guidelines on how the team treats each other in their interactions. One guideline could be to put away phones and actively listen to the person who is speaking. Urban planners must use a facilitative process to develop inclusive and comprehensive solutions to today’s most challenging planning issues.

4. Ensure Accountability

Accountability is one of the biggest needs in urban planning today. To build accountability with others, facilitative leaders encourage feedback, even when its uncomfortable. One technique facilitative leader use to stimulate feedback, is to share their “own observations or perceptions with the team and invite others to do the same without judgment or recourse”. Feedback then becomes routine in a teams daily interactions.

5. Use Systems Thinking

Facilitators are aware of underlying patterns and structures that influences human behavior and how individuals and teams can influence the systems with the right leverage. Urban planners must use this way of thinking to focus on influencing the future, rather than reacting to the present by seeing patterns and interrelationships, rather than cause-effect linear events.

So what are the strengths of facilitative leaders?

  • They are great listeners – they listen to understand, not to respond.
  • They have high emotional intelligence – they are aware of their emotional triggers and of others.
  • They are courageous
  • Powerful inter-personal skills, and
  • They love to learn and learn how to learn.

To better understand this leadership style, I may write more in depth about the following topics:

  1. Holding an effective stakeholder meeting for your project
  2. Facilitating public input to create value
  3. Listening Skills

If there is a specific question or topic you would like to hear more about please write it in the comments below. Check out my resources page here for more information about this topic.

3 Realms of Urban Planning Leadership

To accomplish your goals and aspirations as an urban planner, it’s critical to understand the type of leaders influencing places. Richard Hambleton distinguishes three realms of place-based leadership who are key drivers of creative, livable, and sustainable communities

1. Political Leadership

The public officials elected to office who have authority in decision-making such as Mayors, Supervisors, State Senators, etc.

2. Community and Business Leadership

Civic-minded individuals, organizations, and businesses contributing resources and energy into community activities and decision-making. The Bay Area have very strong community leaders such as: SPUR, Bike East Bay, Transport Oakland, Connect Oakland, Sports Basement, etc. Engagement with these locally embedded leaders contributes immensely to our communities.

3. Managerial and/or Professional Leaders (aka Urban Planners)

Public servants in government organizations, such as SFMTA and MTC, and consultants who help aid in planning and managing services for the public.

Figure by Richard Hambleton

Because the roles of these leaders overlap, conflict can arise from different values and perspectives, competing priorities, and methods of work. However, “if the leaders step out of their ‘realm’ of authority and engage with the perspectives and realities of others” it can create, what Hambleton describes as, “innovation zones” (see left). This requires listening, vulnerability, and active participation in personal conversations.

Urban planners can lead this process by being facilitative leaders. Facilitating conversation, inquiry, and interaction with these 3 realms of leadership to create livable and sustainable places.

Leadership in Urban Planning

Leadership in urban planning is critical to developing livable, equitable, and vibrant places for people, yet it’s overlooked in its significance. One of the misconceptions is that leadership is thought to be positions in power such as directors, city officials, and board members.

One of the misconceptions is that leadership is thought to be positions in power.

Yes, these positions have the authority to make decisions on whether housing is built, new transit lines are funded, or where to prioritize resources, but I argue urban planners also make powerful decisions. They decide on which stakeholders they interact with, how they communicate with these positions of power, and how they set their own priorities.

One of my greatest achievements of a entry-level planner was knowing I didn’t have to be in a management position to be a leader. I had as much, or even more, influence on the organizational culture, how decisions were made, and planning sustainable projects. Luckily my current boss saw this in me and promoted me to a senior planner.

The only studies about leadership in planning describe Place Leadership and Place-based leadership. These definitions still seem to be focused on positions of power.

A more comprehensive approach is to instill leadership in our urban planners by providing research on skills, behaviors, and habits of great leaders.

This is what I intend to do with this website: Make the connection of why leadership creates great cities, and how urban planners can integrate leadership skills, behaviors, thinking, and habits into their daily lives.

Here are some posts:

Strategies to Engage in Tough Conversations.

Advice from Jim Chappell

Jedi Mind Tricks for Urban Planning Leaders

For any suggestions, examples, or needs that will help urban planners become leaders please comment below!