Two modes of strategic thinking

Earlier this year, a colleague came to me asking for some advice about strategic thinking.

It gets mentioned in planning meetings, career frameworks, job descriptions – but is rarely pinned down. It’s not that often I’ve been asked directly about it head-on. 

I didn’t have a prepared or practiced answer. I could ask some questions – ‘what are you trying to achieve?’, ‘why is this on your mind right now?’, ‘can you put your finger on what it feels like you’re missing currently?’. That might help coach them towards a self-informed answer… but this was a direct request for practical advice. Could I kick things off with something relevant and useful, even if it was imperfectly informed or formulated?

I paused for a moment and reflected on my own recent experiences in this area.

After some thought, I shared a distinction that’s stuck with me – a way of looking at strategic thinking not as one singular process, but as (at least) two very different modes of thought: undirected and goal-oriented. Both are valuable, but they operate on very different principles and produce different kinds of value. Both demand structure and practice.

1. Undirected Strategic Thinking

This kind of thinking isn’t about solving a particular problem. It’s more likely to be the moment when you recognise new problems, challenges or opportunities you hadn’t even registered were there!

It’s about wandering through ideas, noticing things, and bumping into questions you didn’t realise you had. It’s loose, reflective, or even at times introspective. It’s also, vitally, unproductive, at least in the short term.

You must risk achieving nothing

That’s the point. There’s a risk that you’ll sit in your favourite café with a notebook and end up with... nothing. No new plan. No sharp insight. No realisation about your colleague, team, or company. Just an hour that looked a bit like daydreaming (or even skiving off!). That possibility can be incredibly off-putting.

As an engineer who naturally tends towards achieving and building things, working in redundancy, maximising certainty, and limiting risk, it felt unconscionable to hazard walking out after an hour with a latte in my stomach and nothing in my hands or head. Until I reframed – the priority here was exploration of an entirely different space. The achievement was giving time and space for my unconscious mind and my intuitive thinking to surface. Not to be actively ‘summoned’, but to passively rise.

This is often the space in which some of the best or most remarkable thinking happens. Not right away or on-demand, and not in the 60 seconds while you’re running between meetings or tasks, but after giving your brain time to notice what’s been quietly brewing under the surface unrevealed.

To remind myself of this counterintuitive principle, I set up a little Slack prompt that messages me each week with two questions:

1. Have you risked accomplishing nothing for at least one hour this month, to allow an unexpected strategic realisation?

2. If not, which day this week are you most likely to have the energy to do that?

I configured it for Tuesday lunchtime, after the rush of Monday meetings had subsided. The reminder is subtle but persistent. That small nudge toward depth in a world that rewards urgency prompts me to set aside the to-do list for a moment, resist the urge to fill every gap with more ‘doing’, and plan for some ‘being’.

Some Practical Pointers

Practically speaking, here’s how I look to craft a setting for this oddly idle activity:

• Scheduled (thoughtfully): If I don’t actually block out time in my calendar, it’ll just get eaten up by other things. So putting in a ‘meeting’ with myself is a must, to signal to myself and others that this timeslot is taken.

• Solitary: This kind of thinking is usually best done alone. A notebook or, if you must, a notes app on your phone (no laptop, no Slack!). A walk or sit-down somewhere pleasant. A hot drink and an hour where no one expects anything of you, even if that’s just a friendly chat. Strategic clarity often arrives in the quiet place. It’s about making space as well as time.

• Energy, Not Time: It’s easy to book time into your calendar, but if you don’t have the energy or headspace for it, it likely won’t be fruitful. I’ve found this mode of thinking is less about time management and more about spotting the opportune moment: the hour where your mind is open and clear and you’re not just recovering from the last meeting. So my reminder prompts for 'energy' not 'time'.

• No Agenda: This undirected time is where the “unknown unknowns” often live. You’re not looking for them – that’s the point. If you walk in distracted by a specific topic, or hunting in a narrow area, you might stifle that process. So try to pick a time when you can close the book on the rest of your thoughts and agenda. The end of the day works well for me. Leave your day behind, and let something else (who knows what!) emerge, quietly: A flaw in a plan; a half-formed idea; a reframing that changes everything.

• About an Hour: I’ve mentioned ‘an hour’ several times. You will likely need some time to push through distraction, and then boredom. It’s not dissimilar to the experiences people report with mindfulness and meditation techniques in this respect. An hour seems to be long enough to persist through, and short enough that if today is a ‘no result’ day you’ll still feel okay about that afterwards.

Sidenote: One useful short-hand summary of our engineering career framework I sometimes use, when explaining the distinction between Senior Software Engineers and Senior Staff Engineers, is this: Senior engineers are adept at solving big, difficult problems independently. Staff engineers are adept at seeing/intuiting far enough into the future that big problems never arise in the first place. This kind of thinking is part of what develops that sort of foresight.

2. Goal-Oriented Strategic Thinking

Okay, but what about when I do have something specific in mind? That’s fine too! It’s just different.

This thinking mode is more deliberate. You have a specific problem to solve, or a direction, opportunity or challenge to assess. You’re trying to figure out something you already know about, rather than leave room for something unexpected to emerge.

In many ways, this is the more familiar activity for most people. The kind of strategic thinking we often picture: someone breaking down a big challenge, exploring different paths forward, or identifying leverage points to make a break-through.

Interrogating what we do

Goal-oriented thinking has a clearer output than undirected thinking – but it still begins with reflection, not just reaction.

Strategic thinking often involves organisational self-awareness – a willingness to interrogate what we already do, how we do it, and why. It’s easy to get locked into default ways of working, especially when they’ve brought some success, or have been ‘the way we do it’ for years. But strategy often lives in the margins: in careful consideration of deeper motivations that ripple outwards into adjustments to process, positioning, or priorities.

Allowing some time to regularly step back and ask whether the way we work still serves us, and being willing to entertain change, can be revitalising and transformative.

Question-oriented, not task-oriented

It can still be difficult to zoom out and look at the wider picture, especially when you might already have candidate solutions to evaluate or failed attempts to assess. You can be drawn immediately into the weeds of options and next steps, especially if your strengths lean towards execution.

I find the trick here is staying with the questions. Strategic thinking isn’t about listing out tasks. It’s about holding the ambiguity long enough to ask: What are we actually trying to solve? What does success really look like? Would that be enough? What might unlock something bigger?

In this sense, goal-oriented strategic thinking is about resisting the urge to act prematurely. It means refusing to confuse activity with progress.

If you’ve arrived on the scene with a list of strategic things that you want to achieve, try converting these into things you really want to know instead, for instance:

• Task: Look at success rates in each of our three focus markets →

  • Question: Are all three of our focus markets still right for us?

• Task: Work out how to make the admin feature-set more accessible →

  • Question: What are our admin users most/least happy about, and what do they need from us that they’re not already getting?

  • Question: Is this subset of users actually even the most important focus right now?

Now any actions or next steps you decide on will be geared towards answering your most deeply felt questions and uncertainties, and not just crossing tasks off your list.

Build in a review from the outset

It’s helpful to recognise and accept from the outset that you likely won’t answer your question or solve your challenge in this moment. Hopefully though, you’ll identify an approach or next step which might do so in time.

So build in a check-point a month from now, to give yourself both some self-accountability and a fallback position.

If you’re walking out with a good question, ask yourself that question again a month from now. Do you know the answer yet? Has it yielded a new direction or action that you can now pursue, or perhaps another question to keep digging deeper?

You may get a different answer when replaying the same question after taking action or time passing, or you may not, but you'll likely learn something either way.

If you’re leaving with an established process to tweak or a task to complete, ensure you make the time to check-in with yourself on whether your action has done the trick. Is the issue now closed, or is there more to do?

A note on tooling

Both modes of strategic thinking benefit from good tooling, but the tools don’t do the thinking for you. A strategic mind doesn’t emerge from the right journal, app, whiteboard, or canvas. Don’t fall into the trap of thinking that if you can just find the perfect tool, this will all become automatic.

That said, it does help to have somewhere to catch the fragments: fleeting thoughts, partial questions, half-formed ideas. If only so you can set them down for a moment to make space for more to surface.

For undirected thinking, I tend to favour more analogue tools: a physical notebook, a voice memo, or sometimes a notes app on my phone (if I disable notifications that might steal my attention at the wrong moment).

For goal-oriented thinking, I’ll go with whatever allows for structured exploration of the topic at hand. That could be a shared doc, a Miro board, a mind-map, or just a bullet point list of hypotheses or questions.

Above all, you should feel free to use whatever medium suits you and feels natural. There’s no single right setup. The important part is that it’s not getting in the way by distracting you or forcing you to work harder, giving you the maximum time, space and energy for your thinking to happen.

Closing thoughts

Strategic thinking isn’t a fixed skill or a task that you check off a list once you’ve completed it. It’s an ongoing practice that depends on silence, risk, and knowing yourself. It asks us to think beyond the next task or challenge, and sometimes, beyond what we even know to look for.

So next time someone says, “We need to think more strategically,” you might like to ask: which kind of strategic thinking do you have in mind?