<img height="1" width="1" src="https://www.facebook.com/tr?id=260954267578739&amp;ev=PageView &amp;noscript=1">

Strategic Planning and Management Insights

What is the Role of a Strategy Leader? Interview with Jonathan Rewers

[fa icon="calendar"] August 16 / by Anthony Taylor

In this issue of our Strategy and Leadership Podcast, we talked with Jonathan Rewers, the Manager of Design Strategy and Delivery at the City and County of San Francisco Municipal Transportation Agency.  While Jonathan works with a wide variety of projects within his role, his main purpose is to lead teams through the strategy process to provide innovative ideas and solutions for city transportation. In essence, Jonathan is a problem solver. 

During our chat, Jonathan shared information about some of the recent projects he's been working on, and also delved into the following topics: 

  • Tips and ideas for becoming a good strategist, and understanding the role of a strategy leader
  • Why you should view strategy as a product 
  • Understanding the role of technology and up to date facilities when innovating change within a growing city
  • Limiting information silos by encouraging different departments to communicate and work together on deliverables
  • Looking at strategy as a framework, something fluid that isn't a document on a bookshelf. 
  • Learning from other people: while critical and strategic thinking is important, it's also good to look at what methods others have used in similar situations (perhaps even in a different industry) to achieve success 



Anthony Taylor (AT): Anthony Taylor here with the Strategy and Leadership Podcast. Thank you so much for joining us, and welcome back.

Today I am joined by Jonathan Rewers, who is the manager of Design, Strategy and Delivery at the City and County of San Francisco Municipal Transportation Agency. It’s a long title, and we’ve got lots to talk about. Jonathan, how are you today?

Jonathan Rewers (JR): I’m great. It’s been a great day so far.

AT: Amazing. I’m so happy to hear it. Thank you so much for taking the time to share with us today. Can you tell our listeners a little bit more about you and what your job entails?

JR: I’ve been in the city for about 20 years, building buildings, coming up with new policies, and that has all evolved into a job in which I have, where I pretty much figure out how we optimize cities to prepare for the massive growth we know we’re going to be seeing over the next 50 years.

We have mass migrations going on across the world. People are moving to cities, and cities tend to be a little bit of a bureaucratic structure, if you hadn’t noticed, and so we need our cities to have the ability to change, and evolve, and meet the needs of the people we know are coming. That’s pretty much what my day looks like.

I work with a non-profit. We’re doing a big partner plan for San Francisco right now. Here at the MTA, I’m working currently on our advanced transportation program. I’m going to be working a little bit with some design firms on how to innovate cities. I love what I do.

AT: Fantastic. Thanks, Jonathan. One of the reasons I really wanted to chat with you is after looking at your profile and learning a little bit more about you, you have to solve some of the biggest problems that no one else knows how to solve, on a scale that nobody’s seen before, and what I gather from our earlier conversation, you take big visions and figure out how to make them happen. Is that correct?

 JR: That is exactly, that is a part of my job that’s exciting. We have big visions and big ideas on what we want to do, and most corporations and businesses have that. Where strategy comes into it is asking the question of: how do we actually achieve it, both within the business environment that we work in, but also with the skills, the talents, the tools that we have internally? 

It’s sort of the role of a good strategist to take that big idea and that vision, and come up with the how that vision can be achieved. It’s not exactly project management, because that’s when you get to the execution of things, but it’s essentially coming up with the plan on how to achieve the plan. That’s the stuff I get to do. A lot of the time it’s really about problem solving. It’s really about we know we want to get there, and let’s figure out ways to get around barriers or come up with ways of doing things that we can achieve the vision that we set for ourselves.

AT: I have a few questions, but let’s take a step back and talk about that vision. How did the Municipal Transportation Agency, which as far as I know, is the only agency of its nature in North America … How did you get to your vision in the first place, and maybe some practical approaches for the people that are out there looking to create a vision with their team. What does that look like?

JR: I’ll give you a very specific example. Recently, we have a strategic plan for this organization where we have a goal, for example: Vision Zero, to get to zero traffic deaths by 2024. We also are purchasing a brand new bus and light rail fleet. Here’s an example of a problem. We have spent close to two billion dollars to purchase a whole new light rail and bus, and we want to provide reliable transportation service to the people of San Francisco, especially transit service.

We’ve increased that service in our operating budget, which is over a billion dollars, by 10%. We have actually increased the frequency of service for the people, for the million people plus, that come and visit San Francisco every day, and work here, and live here, but we have a facility and infrastructure. We have a set of buildings and grounds that are close to a century old. We have old technology, an old way of doing things, supporting a brand new fleet. That’s a huge problem.

We have five different divisions that manage this particular service, so I’ve spent the past 18 months looking at all the services, consolidating the organization, looking at new ways of doing business, coming up with a construction program where … This is a transportation agency, so we don’t really know how to build buildings, so part of it is let’s not figure out how to build buildings ourselves, but let’s find somebody else who knows how to build buildings to do it right.

How do you do outreach? How does the Transportation Agency become a developer, because there’s an expectation that we do joint development. These all, as I said, a good strategist comes up with the tools, the processes, the methods by which we will deal with this problem. To provide great transportation, just a great service, have your subway car show up to have it be cleaned, have it be well maintained, not fail, requires somebody in the back shop to have a modern facility, modern tools, and maintain it in a brand new way. 

That’s resulted in a whole new divisional unit of 100 people, a 1.3 billion dollar capital program, and just completely re-looking at the way business is done overall. That’s one problem that I’m dealing with.

Another one is the voters in San Francisco passed a 500 million dollar bond two years ago, and this is a very complicated organization I work in, and many big corporations are complicated. You’ve got many different divisions, you have different skillsets. To the people out on the street, the people who are experiencing the sidewalks, streets, driving in their car, they don’t see you’re the painter who paints the lanes, or they don’t see that you’re the person replacing the sewer, or you’re the engineer that’s drawing the curb.

We were not good at looking at a project from curb to curb. We were good at each discipline doing their work well by themselves, and that creates delay. It creates redundancy. It creates confusion. The question was, from just the design strategy perspective: how are we just better at delivering projects? I took a team of 50 - We sat in a room for two hours every week, and we just went step by step, so people were using the same language when we were talking about the steps, so people understood who was responsible for what, and when handoff would happen between divisional units, or experts, or designers and engineers.

We agreed on what certain deliverables were along the way, and when those deliverables weren’t required before, we talked about why they were required now and why they were needed. We came up with a project delivery framework. I just talked about the facilities framework; this is the project delivery framework, where we’ve created a new project management office, so a new organization to support project managers, and train them, and give them tools, or develop a new technological tool to help them get what they need. 

It’s almost like they’re speaking their own language in their own country, and now you’ve got to get everybody to speak the same language and understand one another. Project delivery for a four billion dollar program – pretty rough, but I feel like we made a lot of progress.

Typically, to your question is, I get question and I am a designer by practice. How might we deliver projects in a more effective, efficient way? How do we have the support facilities we need to provide better and excellent transportation services to the people of San Francisco? Those are the visions that are handed to me, and then my job is to figure out they how by which we will do that. That’s the strategy part, design strategy.

The other part was, and I think it’s kind of unique to my job, is that you need somebody to deliver on the strategy. You have project managers and product managers that execute, but you need somebody who takes that strategy who is a coach, and follows through, and provides oversight towards execution. I think that’s kind of unique about my job. We turn the strategies into programs. People still run their day to day operations, but I’m the one who’s always pushing and driving the strategy to make sure that we get to that completion.

We don’t just create visions or strategies that end up being books, or decks, or websites that go nowhere. We’re constantly following through until we get things done. When I described the frameworks, that’s essentially how we do that. We create a framework. There’s a series of projects or initiatives, and then we follow through and achieve on that within a certain period of time. I always like to say, when it comes to strategy, you need to think of strategy as a product. Once the strategy develops, you need to have somebody who works to deliver on it.

AT: Somebody’s giving you the why, and you have to figure out the how, like how to get it together. Another part of that was getting all your people together to look at the process and speak the same language, and not just on a one to one basis, but really from beginning to end, the entire flow of how those things work. It sounds like you do it really well, in getting a lot of stakeholders involved to get their feedback, so you really get the whole perspective of it. The coach and oversight piece was really cool to hear. There was one more piece that I can’t remember exactly at this moment, because there was a lot of stuff in there that was super cool, but I’ll get to it later

JR: The bottom line is strategy is meant to come in and help you figure out how to emanate, or be more efficient, or deliver on something. That’s why it exists. It’s the how we intend on achieving an objective, or a vision, or a goal we have.

But, change is hard. People and groups in organizations want to do work … These are common quotes, like “This is the way we’ve always done it. This is how I understand it. This is the first I’ve heard of this type of thing.” You need somebody on the backend, on the delivery side, who’s … Change management is a term that’s used in IT, but you need to have somebody who’s delivering on the strategy, who’s delivering on the strategy of the product, not just recommending that other people change things, and then stepping away.

AT:  I just realized the other piece, and we’ll talk about change shortly, was that when you were looking at your buildings and the infrastructure, there’s where we’re at right now, and where we actually want to get to, and not letting the status quo stop you from, or using it as a barrier to getting you to that next place. That’s just what it is, and if we want to get to where we want to go, there are some things that are going to need to change in order to get there. That’s where you can be creative in your plan.

Personally, you definitely shared a lot about what you actually do on the court, but best practices for leading strategy – You’ve got a manager or a CEO and they’re really working to get their own strategy off the ground with their people. What would you tell them?

JR: I talk about this all the time, funny enough. The first thing I always tell people, and I have a great example of this, is see what others did, like how they achieved on things. Don’t look at the specific outcome and deliverable, but look at how other people did things, and let’s see if we can replicate or take the method and apply them to something different.

I’ll give you a specific example. It’s going to be something I’m working here, in San Francisco, on. Many major park organizations, almost everywhere, but I’m going to use the City of New York as an example, they want to know who their user of the park system is. A park system, typically when they want to know how many people have used a park, how are they using a park, they use their reservation system. The reservation system pretty much tells you the people who are already interested in a park, because they’re willing to go to the website, figure out what you need to do, fill out the paperwork, go online, do all that stuff. You already have that core group of super users who you’re essentially counting and applying to the public at large.

New York wanted to know: well, how many people are coming to our parks? How many people are coming in and out, and what are they doing? When I talked to their commissioner for innovation when I was in New York, the first thing they did was ask other park districts, and other park industries “How do you do that?” I kind of advised him a good designer, and even a good strategist, look to other industries, look at how other people went about to solve this problem. It doesn’t need to be the exact same problem. It just needs to be the same outcome. What method did they use to solve that?

My example was transportation figured that out 15 years ago. We have a perfect method to determine who’s getting on and off busses, who’s getting on and off trains, counting them, figuring out times of the day. The method by which to do that sort of thing exists, but it exists in another industry, in another way. That’s why I always tell people the first thing you should do when you’re developing a strategy is just start doing general research on what were the means and methods to solve that type of problem, not to get to the exact outcome, but to a similar type outcome.

Then the second thing, which is something we talked about, you need to see strategy as a product. It needs to be something that is implementable. Good strategists are kind of a good balance between constraint and innovation. It’s a thing that I always like to talk about. I tend to think planners, because I happen to be an urban planner too, they’re very good at the vision and coming up with what is right, what should we do, but not necessarily figuring out the how, which is why so many great plans end up on shelves, and we just start planning again.

Good strategists want to look at the how, and they do want to be creative, and they do want to innovate. A good strategist should always start at the new, I always think. Let’s not look at how we’ve done things. Let’s pretend we’re just completely redesigning how we do this. Let’s start at the new, and also looking at other industries and how they might not achieve it. Let’s not be stuck in the industrial bubble of how others do this. Let’s just look at we’re starting new, and how we do that.

A good strategist also creates constraint. The constraint, unlike project management or product management, is more things like tools and technology. What really exists to solve this type of problem? What kind of people or human resources do you have to realistically achieve this, and then the skillset. 

AT: You look at what’s possible, and then what’s actually going to hold you back in your strategy, and then to be realistic enough to realize that there are going to be some things that are going to happen that are going to hold you back, or just be waiting around the corner to stop you from getting to success. Life isn’t always easy like that, right?

JR:  That is very true. We shouldn’t come to a complete halt because we find a barrier, so that’s what we’re always trying to solve.

AT: Perfect.

JR: In my industry, people love to do that, but we don’t have the people. We can’t do that because no one knows how. We can’t do that because we don’t have the gizmo that would help us do it.

AT: In the face of all of that. I think that happens all the time. For example, I run into a lot of people who say “Oh, our people are not willing” or they just don’t have the time. They just don’t have the time is the one that drives me crazy.

Let’s look at all that, and then if there were some risks to avoid in the planning process … Let’s say you’re getting together with your people, and obviously you have a larger team, but some people might have a team of 15 or 20. How do they overcome those, not necessarily objections, but how do they deal with those risks and uncertainties that come up?

JR: We talked about the innovative part, the balance that a strategist plays, so let’s talk about the constraints: the tools, the people and the skills to be able to get that done. That’s where a good … The risks to avoid, again, are to not be too innovative. You absolutely need to have that balance between constraint, and the constraints that I just gave, and innovation, and what is actually achievable and possible.

An important part to avoid, an important thing you need to do when you’re developing your strategy to avoid that, is you do need to create a business case, which is why I said strategy is a product. It’s something to be delivered. As a strategy develops, and as you’re doing that - your planning, you want to make sure to make the analytical case that what you’re proposing is achievable based on those constraints. That’s why it’s important to identify them.

What are the constraints in the tools and technology? What are the constraints in people, meaning do you have the people who can do some of this work? Is there a skillset you need to bring in, and how achievable is it to actually hire a person to do that? If you start hitting those constraints, which you should identify up front, then you need to come up with another strategy. You have to do that.

That’s where we’re not fully designers and we’re not fully planners, because they get to work in the dreamy world of no constraint. We need to work in the constraint of how, and those general things: tools, people and skills are things. Now, they’re always tied to money. They’re always going to be tied to money, budget, but if you hit one of those walls, and it can’t be overcome, then again, a good strategist is going to probably come up with another way.

I have an example now where we don’t have a budget to hire a person, but we have a whole division of this organization that can use a tool that we have in place. Okay, we can’t hire a person, but can we get a consultant, for a shorter period of time, that could get these people caught up, and then that makes the work burden on them reduced. That’s again, to my point, an analytical exercise where I can make the business case. If you make the strategy, we’ll achieve the outcome we want, but here’s a different way to do it.

AT: The key to that is actually knowing what you want to accomplish full out, because if you just start acting on things, you don’t actually know if the actions are going to be sufficient to get you the results you want, or even can foresee the full depth and breadth of risks that might come your way on there, including money.

JR: Exactly, yeah. You should take those two steps up front, to directly answer your question. If a good strategist is a balance between constraint and innovation, the first thing you should do is: what question are you answering, what industries are you going to look at, and it’s okay to start it new. I always tell people that. A lot of people just want to tweak around the edges – well, let’s start it new, and then let’s constrain that against the tools, the people and the skills. Then we end up with our list of strategies that we can work with.

AT: If you don’t know how to do that, then you can hire an outside consultant, like us. I had to throw in that shameless plug there.

JR: Don’t always think that you need to in-house everything, and also, a perfect example I’m going through: we had no way here to manage how we allocate resources around here, so we spent a year coming up with a model on how that should be achieved, so people could answer “How am I resourcing a certain effort?” Nobody could tell. One of the findings, once again, where you get into the analytical part of implementing the strategy, is people were turning tasks to jobs.

People were overwhelmed with work. They couldn’t get to a certain thing, and the result was: if I hire this person, this task can be completed. What we found was the person was hired, and they only had a workload of 20%. That’s just kind of a way where, well again, was there a different strategy we could have taken to get to that outcome? Look at different methods rather than the standard method you would typically use resulting in we need to add another human being.

AT: Right, so it’s really underutilization of resources by finding what seems like the simplest way to solve the problem, but …

JR: Well, you know – Could we train somebody to be more efficient? Could we hire an outside resource? Then you start asking those questions

AT: I know you’re limited on time here, so I’ll ask you one more question. When it comes to the people side of things, how do you develop that culture? For you to foster the vision that you see, and one of things that I saw is: My job is to communicate a clear and compelling vision and strategy to help organizations be more innovative and successful. How do you get that juice into the entire being of your team? Within that, I would tie that to culture.

JR: Two things, we talked about this a little … One: change is hard. Right? We just have to realize it. People go to their comfort zone and we’ve just got to walk into it knowing that, but on the positive side, good ideas spread. These are things that if it’s a good idea and people see that it works, you kind of see that change in culture happen itself. There’s a great quote in one of my favorite movies, Life as a House. I highly recommend it. At the end, the main character talks about really successful change is change you never noticed happen.

Here are some things that I do, and I’ve probably been using these schemes for a good 15 years. I always set a standard first: This is what we want to achieve. This is what we want to do. Have the reinvent, and set it for myself, and my personal team. Then, set the example. When there’s a change or a strategy we want to implement, and somebody says that it can’t be done, or the resources, again those constraints, tools, people, skills, are there, I try to pilot it or implement it on a project or initiative going on in the organization, to prove that it will work.

Setting that standard, then setting the example, then step three is to tell the story. “Well, this is what we wanted to implement. This is the strategy we wanted to try. This is where we tried it. This is how it works. It proved to be extremely successful.” Another example is I recently took a 40 million dollar project, and we were going to have it fully designed and constructed in 24 months, which here is unheard of, like unheard of, like not done. We developed a bunch of tools, tricks, and methods to go about doing that, that we will implement and advance in our larger program.

Telling the story is an important thing. Then the last thing is to provide the support. When people want to dip their toe in the water, you need to be their lifeguard. You need to provide that tool or give them the little extra resource, and then once they’re comfortable, the good ideas spread, and they do it on their own. Those are kind of the steps that I’ve taken for a long time: setting the standard, setting the example, telling the story, and providing the support. I have, I don’t know, I think I’ve changed four or five different organizations doing that.

It’s better than having the executive give the dictatorial, because then you’re spending more time with the resistant than you are with the 40 people spreading the good idea. Even making the pitch, you need to start with … A good strategist, or somebody who comes in, is coming in for a good reason, and I often give this metaphor to myself. It’s like the principal is coming. You’re going to the principal’s office, like “You’re not quite doing this right, so we need to coach you on how to be better,” and no one likes to hear that. Right?

You just want to come up with this method that the change happens and they never notice it. It’s kind of the method I use. Everybody should watch that movie. Then you’ll understand.

AT: Alright. Life as a House.

JR: Yeah.

AT: Ok, got that. Awesome, Jonathan. Thank you so much. Is there anything else that you want to share with our managers and leaders listening to this? Definitely good ideas spread. Do some story telling. Pull them into the thing, and don’t push it on them. Don’t coach them hard, because you want them to take it on themselves.

Congrats on that project, because that sounds just amazing. That’s where innovation at work, in evidence right there. 

JR: Yeah. It’s been a great conversation. I think just the overall industry and practice needs to move just from providing a strategy and providing recommendations, to also providing the means, the methods and support to implement on those recommendations, which is why my title is design, strategy and delivery.

I use the methods that we’ve discussed to come up with the strategy and what should be done, but again, as we’ve brought up in this discussion, you immediately go into resistance mode. If you can be that support, and you can be the one telling the story, and you can be the one setting the example, and you can be the one setting the standard, I think you’ll find that the strategy, the frameworks you develop, will be a lot more successful and you’ll see a lot more change.

AT: Amazing. Thank you so much, Jonathan. This has been extremely valuable, and I really appreciate you taking the time with us today.

JR: Absolutely. Happy to.

AT: I’ve been chatting with Jonathan Rewers, who is the Manager of Design, Strategy and Delivery the City and County of San Francisco Municipal Transportation Agency. If you’re riding a bus in San Francisco, or any method of transportation for that matter, you can thank Jonathan for that. For more on the Strategy and Leadership Podcast, please be sure to subscribe and rate us on your favorite podcasting player, whether that’s iTunes, Soundcloud, or Stitcher.

Thank you so much. I look forward to sharing with you very soon.

Topics: Strategic planning, Leadership, podcast

Anthony Taylor

Written by Anthony Taylor

Anthony Taylor is thought leader on strategy and leadership. He's a published author on the subject of entrepreneurship and strategy, Anthony can be found doing keynotes in both French and English. You can connect with him on Twitter @anthonyctaylor and have him work with your team on your strategy and organizational development.

Strategic Plan

Lists by Topic

see all

strategic planning consultant podcast.jpg
Strategic planning consultant podcast stitcher.jpeg
Strategic planning podcast facilitator soundcloud.png