Making strategy with a progressive person: think big, choose deliberately

The goal of the strategy session seems straightforward: fewer customers should drop out during their first month. The team discusses clearer instructions, shorter onboarding, and an extra check-in. Then your progressive colleague asks, “What if customers did not have to go through our onboarding, but the product adapted to what they are trying to achieve?”

The question opens up something valuable. Suddenly, the discussion is no longer just about three small improvements, but about a different relationship between customer and product. Fifteen minutes later, the board is covered with adaptive paths, new services, and a completely different revenue model.

The original assumption has been broken. It is just not yet clear what choice the team will make today.

That is the strength and risk of progressiveness in a single session. A progressive person readily thinks beyond existing frames, connects ideas from different worlds, and keeps seeing possibilities even when the picture is incomplete. Without boundaries, a sharp reframing can turn into a strategy that grows every time someone asks for specifics.

Good strategy does not ask this colleague to think smaller. It deliberately separates opening possibilities, choosing a direction, and proving the most important assumption.

Progressive does not mean the newest idea is the best one

In a personal user guide, a progressive person sits on the side of new experiences, abstract ideas, and complexity. This colleague does not need to know how every part will be executed before they can explore the value of a new direction.

That can add a great deal to strategic work. A progressive person is quicker to see when a familiar solution only makes sense within an old assumption. They can connect developments from other fields, describe a future state, and give language to a possibility the team cannot yet draw in full.

The downside belongs to the same preference. A new concept can feel more interesting than a small improvement that is likely to work. Complexity can look like richness even when it mostly adds dependencies. And a question about execution can sound like a premature restriction while the team is trying to discover what the proposal actually requires.

That is why “we need to stay realistic” is not a useful response. It protects the existing frame without saying which boundary matters. The better question is: which new possibility changes our choice, and which assumption must we prove first?

ConservativeCuriousProgressive

Open the frame first, then close the choice

A progressive person needs room to make a strategic question bigger. A team then needs an explicit moment when expansive thinking turns into choosing.

Start with the intent, not the current solution. “How do we improve onboarding?” already keeps the existing process in place. “How do we help a new customer experience value independently within one day?” creates room for routes that do not yet fit the process. At the same time, state what is fixed, such as the target group, a legal boundary, or the result this period requires.

Next, show no more than three genuinely different directions. A long list of features is not a strategy. A direction describes whose value you choose, which assumption is different, and what you deliberately say no to. Include the existing model as a comparison route.

Finally, choose one assumption that can make or break the preferred direction. Design the smallest piece of evidence that makes it visible. The future state does not have to fit into a complete delivery plan immediately, but it does have to make contact with reality.

1. 1
   FrameOpen the strategic question

   Describe the desired effect without fixing the current solution, and state what does remain fixed.

2. 2
   DirectionChoose from three real alternatives

   Compare different value choices and show what each route deliberately says no to.

3. 3
   EvidenceTest the decisive assumption

   Identify which uncertainty could reverse the direction and collect small, useful evidence for it first.

Give the same message more context and meaning

A progressive colleague does not necessarily disengage from a concrete task. They may find it harder to judge why a narrow assignment matters when only the action is visible. “Update these three screens” can sound like local work inside a frame that may itself deserve scrutiny.

The content does not need to become more abstract. Connect the task to its purpose, the wider principle, and the space that remains open. This lets the colleague see which parts are fixed and where a better idea is welcome.

That is why we offer transformations inside personal guides. Open the guide of the person you want to write to. When your preferences differ, the guide suggests a fitting transformation. Paste in your message and the tool returns a version that lands better with the recipient. Its content and intent remain the same. Only tone, wording, structure, and framing change.

For a progressive colleague, “Add context and meaning for Noor” is one fitting option. The three screens, Friday deadline, and agreed user group remain the same. The wording simply shows earlier which customer problem the task is exploring and which question is still open.

Original

By Friday, update the three introduction screens for new administrators. Use the agreed copy and leave the rest of onboarding unchanged. We will then measure how many people invite their first team.

Transformed

We want to learn whether new administrators experience value sooner when the first steps match their goal. By Friday, update the three introduction screens with the agreed copy. Keep the rest of onboarding unchanged so we can see how this different explanation affects the first team invitation.

Three perspectives on the same strategy

What you need to watch when working with a progressive colleague also depends on your own preference. Two progressive people can build a powerful future state together and test each other’s leaps too little. A curious person can translate between imagination and application but keep too many routes under serious investigation. A conservative person can make necessary boundaries visible while reducing a new frame to current practice too early.

If you are progressiveValue difference more than novelty

Choose the direction that genuinely changes the strategic assumption and park variants that mainly add more possibilities.

If you are curiousTranslate and recommend

Make the new direction testable, but also state which route best fits the agreed intent.

If you are conservativeMake boundaries informative

State which quality or restriction is fixed, then let the colleague redesign within that reality.

If you are progressive too

Two progressive people can understand each other quickly. You do not have to simplify a half-formed idea immediately, you see connections before every intermediate step is visible, and together you can describe an ambition that helps the team leave a worn-out frame behind.

The blind spot is that every new connection feels like a deepening of the work. You build on each other’s thoughts, giving the conversation energy while the direction keeps shifting. Criticism mainly takes the form of even more interesting ideas, not evidence that weakens a choice.

Separate the roles of opening and closing. Let one of you collect new possibilities during exploration. The other records which strategic choice each possibility changes, which assumption belongs to it, and what disappears from the previous proposal.

Before the end, ask a colleague who was not part of the ideation to repeat the chosen direction. If they hear three different strategies, you have a shared world of thought but not yet a shared choice.

If you are curious

As a curious colleague, you can usually move comfortably with a new frame while also asking how it works in practice. That makes you a natural translator between a progressive future state and colleagues who first want to see what changes on Monday.

The pitfall is wanting to give every possibility a fair experiment. What started as three directions then becomes a portfolio of trials. The team gathers plenty of information but still does not have to say which future it values more.

Distinguish between a useful learning question and a strategic choice. Not every uncertainty deserves a test. First ask which direction best serves the intent. Then test only the assumption for which sufficiently strong evidence could reverse that preference.

Give your recommendation too. “We can investigate both” may sound careful, but it leaves the hardest trade-off untouched. State which route you choose, which criterion supports it, and what new evidence would change your mind.

If you are conservative

As a conservative colleague, you often know the value of the current method, the exceptions a plan must survive, and the resources that are actually available. You can prevent a future state from depending on conditions nobody has named.

Tension arises when you immediately assess every new direction through the current implementation. A strategic idea that is not yet fully developed will always lose against a process that has had years to accumulate detail. Your progressive colleague then does not hear which boundary matters, only that a different reality is unwelcome.

Turn your objection into design information. Do not stop at “our system cannot do that.” Say, “The legal check must remain, and we can change one integration this quarter. Which version of your idea works within those two boundaries?”

Also contribute one proven quality the new direction must preserve. That lets you represent continuity without making the current form the only possible form.

Five agreements you can copy directly

Making strategy with a progressive person does not require a brake on imagination. It requires reciprocal agreements that turn a new frame into a shared choice and useful evidence.

1. We begin with the desired effect. We state the strategic question without fixing the current solution and identify who must receive value from the result.
2. We make fixed boundaries explicit. Regulation, available resources, and proven qualities are design information, not objections that appear only after the choice.
3. We compare no more than three genuine directions. Each direction makes a different value choice and visibly says no to something attractive.
4. We choose before testing extensively. We use intent and criteria to set a preferred direction, then test only the assumption that could reverse it.
5. A new idea replaces or parks something. Every addition shows which part disappears, comes later, or remains outside this strategy.

These agreements also help when nobody calls themselves progressive. In our analysis of 2,705 personality profiles, 11% were conservative, 43% curious, and 46% progressive. Nearly half therefore identify most strongly with the anchor that actively seeks new ideas, complexity, and change. A strategy process that only refines existing options leaves considerable thinking power unused. A process without a decision point sends that same power in every direction at once.

What usually backfires

“Let’s not make it too big” is not a useful boundary. State what is fixed, which decision is needed now, and which part of the bigger idea may become a separate question later.

Do not ask for a complete project plan immediately either. That judges a new direction on delivery details before the team has established whether the underlying choice is valuable. Ask for the assumption and the smallest evidence first.

Unlimited brainstorming is no better. For a progressive person, every connection can open another possibility. Agree in advance when the board closes and which criteria the group will use to choose.

And do not treat enthusiasm as evidence. An idea can create energy and still solve the wrong problem. Ask its owner to state which result would count against the direction and what the team would then stop.

The smallest useful start

You do not need to introduce a strategy framework. At the start of the next session, complete these four lines together:

The effect we want to achieve is: …

These boundaries remain fixed: …

Our preferred direction is: …

That choice changes if we learn that: …

This short block gives a progressive person room to change the frame, a curious person a focused learning question, and a conservative person a place for boundaries that genuinely need protection.

An anchor point only becomes useful when it leads to an agreement like this. Read what conservative, curious, and progressive mean in practice and how to solve problems with a curious person. On Personal User Guide for work, you can then create your own guide and place your preferences next to a colleague’s. That way, you make strategy with the people who must understand, test, and carry it out, not for a label.