Working from rather than working toward

While we work toward goals as locations, we work from directions as lenses. We don't presume that what we even honestly declare as goals can live up to all the assumptions that we use to legitimize them.

Working from directions, we use them to reveal new questions and options. Directions are completely realistic because we see them as lenses. We know from experience that they amplify our perspective in ways goals and our reactions to goals do not.

The Art of RoadMapping questions

There are many possible forms when we translate directions and actions into questions.

  • What would it look like if…?

  • Could we…?

  • What if…?

  • What would it mean to…?

Each leads to new kinds of research, actions, options, decisions, experiments. They spark and sustain momentum in the directions we work from.

Pathways and perspectives

In RoadMapping, we work from pathways. A pathway is a direction that matters to us. Each pathway is a unique perspective, a lens revealing new possibilities in the present. Multiple pathways reveal multiple vistas of possibilities. Altering pathways creates new perspectives.

Pathway length matters. The longer a pathway, the more possibilities it reveals. A 10 or 20 year pathway will illuminate far more possibilities than a 1 or 2 year pathway. Short pathways have more power when they feed into longer pathways. They can reveal new ways to move along longer pathways.

The relationship between pathways and goals

Goals imply commitment to assumptions. We assume some end state is the best we can do and is achievable with the schedule, activities and costs we assume will work. Our commitment to these assumptions shuts down our openness to other possibilities. Openness would constitute failure to reach the goal.

Pathways are future directions we are attracted to as good. We are open to multiple and agile pathways. Our commitment is to our questions empowered by our continously unfolding unknowns. They are not assumption based in any way. We move forward on the power of our questions.

The Art of identifying assumptions

One of the most accessible and effective ways to identify assumptions we can turn into questions is to consider the whole spectrum of possible assumptions.

This includes: What we don't know, aren't clear about, aren't certain of, aren't convinced about, aren't confident in, what we're perplexed about, puzzled about, frustrated with, confused by, surprised about, frustrated by, what we don't have quick or easy explanations for, what seems unexpected, irrational, unreasonable.

Working pathways from questions

In RoadMapping, we work and adapt our pathways from questions.

Questions keep the work realistic, engaging, responsive and inclusive. They are the opposite of assumptions. Unlike goals and plans, pathways and questions never pretend to work from assumptions.

Each pathway suggests all manner of unknowns and actions. Unknowns are anything unclear, undecided, unconfirmed, unresearched, unresolved. Actions are anything we can research, draft, design, decide, build, test and launch.

Questions commonly come in the forms of: who, what, when, where, why, which, what if, should we, could we.

We translate each unknown and action into one or more questions. We work each path from our questions, in an order that makes sense.

Beyond goals and plans

Goals are future states whose value and validity are equal to the accuracy of assumptions they are based on. Assumption accuracy is equal to future predictability.

Specifically, it's having predictable:

  • Knowns, unknowns and learning

  • Capacities, resources, degrees of freedom

  • Stakeholder expectations and requirements

  • Relationships, collaborations and contributions

To the extent that these are not fully predictable, leading to unreliable assumptions, goals can actually lead to more costs than gains.

Plans are assumption-based linear methods to achieving goals. Because they are as assumption based as goals, they compound the risks and opportunity losses. Psychologically, people are more stressed than energized and engaged by plans because goals and plans evoke more doubt than confidence, which is what assumptions essentially do.

One alternative is the mindfully question-based process of RoadMapping. This keeps everything continuously realistic and rewarding. People feel inspired, energized, engaged and confident. This is the power of adaptive pathways and smart questions.

The wisdom of multiple pathways

In RoadMapping we pursue multiple pathways. This approach is based on two realities: there are always different right ways to make possible the future we would love to see and the ultimate constant on any pathway is change.

It is the ultimate planning assumption/delusion that a single pathway we call our “plan” could be the only right way or a way that will resist life's constant of change. When we have an honest relationship with the future, we are clear that realistic means moving along at least two pathways.

We want to start a new product or service. We describe two ways it could go forward, in design, production, funding, marketing. Because we're working from questions, we pursue the continuous emergence of new questions as we go. Ultimately, one becomes more promising, both work, we discover a much better third way, or we move forward with useful elements of each.

We're guided the whole way by the North Star of our highest good which is doing good, making money and having fun.

RoadMapping FAQs

Why don't we just plan? Isn't planning more reliable?

For many of us, planning feels like a necessary obligation. We're not fond of plans, especially when they're created without regard to our actual capacity and questions. Plans engender more doubt than confidence and enthusiasm. Plans based on assumptions rather than questions are unrealistic from beginning to end. They are not reliable. Even when we achieve them, they can be at the expense of causing other efforts to struggle, stall or fail.

On what scales does RoadMapping work?

It works on any scale, from efforts that span weeks to 20 year dreams and beyond. It can be used in place of project, operational and strategic planning. In larger, longer efforts, multiple teams can work in networks to make complex paths possible through multiple simpler paths.

How do we manage everyone's expectations?

By making everything we do, think and communicate transparent. This leads to minimal or no negative surprises. Alignment is easier when everyone is continuously realistic together. We rely on the management of momentum to the best possible good things happen with the least calendar and costs possible.

How do we spark and keep momentum?

We create a regular rhythm of huddles. In huddles, we review progress, identify new questions and commit to doing what we can with what we have to continue progress in our path directions. We refresh paths when it makes sense. This sustains optimal momentum. We always feel like we're always doing the right things, for the right reasons, at the right time. A very satisfying way to make good things happen.

Putting roadmapping to work

Roadmapping is a scalable process for organizing the way we shape the future we want to see. It is realistic, responsive and resourceful.

As realistic, it works from questions rather than assumptions. As responsive, it adapts our maps to changes in our knowns and unknowns. As resourceful, it is based on and grows our capacities.

The 4 Principles of RoadMapping

Begin anywhere

It can be a dream or wish, problem or opportunity. From here, we have everything we need to make something good happen.

Create multiple paths

A pathway is a direction that matters to us. They are pathways that make sense. We can create two or more.

Move forward, one question at a time

We work along our paths through questions representing what is available and curious to us. Questions lead to individual and shared learning and doing.

Refresh your paths

Moving along paths reveals new possibilities. As we move along our paths, we edit, delete and add them in ways that make sense.

RoadMapping in a nutshell:

  • Start with anything

  • Sketch out two or more pathways

  • Translate relevant unknowns and actions into questions

  • Work and adapt your pathways, one question at a time

RoadMapping

It's time to rethink planning.

Many of us have an ambivalent relationship to planning. It is often as unsatisfying as it seems necessary. The whole idea of "staying on plan" provokes eye rolls of doubt, knowing that change is life's constant.

Roadmapping is an alternative approach to creating and responding to our ever-shifting sense of the future. It's the practice of open-mindedness. It's being open to new questions, new opportunities and new ideas. It's based on the premise that there are multiple possible paths to any direction that calls us. It's making movement in the direction we seek in a dynamic rather than static way.

It's a realistic, responsive and resourceful approach to the future. It's the continuous process of roadmapping.

*Many thanks to old friend and entrepreneurial genius Doug Craver for the unique and powerful frame of “Roadmapping.”

Leader as teacher

Leaders have one metric: people are growing. Growing implies learning, discovering and getting better. They have one thing to do: teach. Teaching implies pairing with people, storytelling, guiidnvk giving feedback and participating in reflection.

Workflow

Thriving teams pay attention to their workflow: how information, ideas, questions, updates, work and resources flow. Accelerating flow is making changes in the character of work flows.

Entrepreneur tracks

Imagine every high school in the world where students in any grade of high school can spend an amount of time in an entrepreneur track where they develop abilities in entrepreneurial mindsets and skillsets. It could radically increase viable employment which is sorely missing for so many people schooled in traditional methods.

The insanity of "work life balance"

Because of the dynamic nature of work and life, we are always to some degree out of balance, on one side or the other. We can even feel out of balance in both. The struggle is more intense when work or life demands the impossibility of complete time commitment and accessibility. We restore a semblance of sanity when we work and life with others more by agreement than assumptions.

Task management

The problem with everyday tasks is their multiplicity of origins. They emerge in emails, meetings, calls, hallways, on the floor, texts, phone conferences and in our own random 24/7 reflections and musings.

The key is to have them live in a single space. It can be in analog or digital form. It just matters that they're co-located for optimal progress toward done.

Engaging work alumns

Every organization has valued people who have moved on. They still have exprience and perspectives helpful to our efforts. Why not invite them to being in our dynamic resource network for just in time engagement?