Thinking Strategically

When the feedback makes you want to scream

As middle managers, when we get that feedback from above, “I need you to think more strategically”, we often want to scream.

I have spent many hours in coaching conversations with managers who have just received this feedback, asking some version of the same question. “What does this actually mean?”

Because the language around thinking strategically can feel quite removed from the reality of the role. It tends to be very senior leader focused, without really acknowledging what it looks like when you are trying to think big picture and, at the same time, make sure reports get written, services get delivered, and everyone’s leave requests and timesheets are approved on time.

It can feel like you are being asked to step into something unclear, on top of a job that is already very full.

And there can also be something else going on here, which is worth paying attention to.

Sometimes middle managers are not struggling to think strategically because they are too busy. Often they are busy, and that part is real. And sometimes they are also staying quite deliberately in the operational side of the role, because that is where they feel most useful, most capable, and most on top of things.

Operational work gives you a very clear sense that you are doing your job well. You can see progress, finish things, and solve problems for people in real time. There’s a rhythm to it that feels productive and reassuring.

Strategic thinking feels different.

It asks you to spend time looking at things that are not resolved yet, to think about people and priorities that sit outside your immediate team, and to hold a level of uncertainty without immediately trying to tidy it up.

Which is why, rather than trying to “think more strategically”, I think it’s more helpful to shift the question slightly.

What if it’s less about better or smarter thinking, and more about widening the way we’re already looking at things?

Starting there tends to feel a bit more practical, and a bit more doable.

Looking at things through more than one lens

I think it’s more helpful for managers to think about thinking through multiple perspectives (which also happens to be a core skill set for leading through uncertainty and complexity). Instead of trying to “think more strategically”, we try looking at situations through multiple lens.  

Time - what does this situation look like 3 months / 12 months / 5 years from now?

Budget - what does this situation look like from the perspective of our local budget, as a relative spend compared to the rest of the division, or from the perspective of recurring total spend over time?

Senior leaders - what does this situation look like from the perspective of the CEO? The Minister? The Board? How is it connected to their priorities? Or to the things they need to make decisions about?

Stakeholders - what does this situation look like from the perspective of everyone else involved? Clients? Other teams? Other organisations?

This is not about agreeing with every perspective.

It is about understanding enough of the system so that you are not making decisions from inside a small part of it, and then feeling surprised when there is resistance or unintended consequences.

From a single pathway to something more realistic

Another shift that often needs to happen sits in how we think about getting things done.

Managers who are strong operationally are usually very good at working out the most direct path from where things are now to where they need to be. That is a strength, and it is a big part of what keeps things moving.

Where it becomes more challenging is when the outcome you are working towards depends on other people changing something. Changing priorities, shifting how they work, supporting something that is not immediately theirs.

At that point, the straight line tends to fall apart a bit.

Then, I want to think through multiple pathways. Often managers who have thrived in the operational, struggle to get more strategic, because they stay focused on the singular pathways from where we are to where we want to be. The higher we go, the less likely that is going to be the pathway through! Instead we want to 

Map the people who will need to change something in order for the thing we want to happen, to happen.

Get to know those people - what do they care about, what are they trying to achieve, how do they communicate

Steps in the process - we dive a little deeper into the potential pathways, the contingencies, the divergences, the convergences, the potential ways in which something unexpected could happen.

The small shifts that make bigger things possible

Then, eyes on the prize, being very clear on what the outcomes are we’re trying to achieve, and holding the How we get there very loosely, we start mapping the nudges.  

What are the seeds we need to plant to help someone see something differently?

What’s the repeated or evolving conversations we might need to have, to open up other ways of seeing things?

Who is really key here, how do we build relationships or communication pathways toward them?

What are the multiple nudge points we could be gently working on, the small changes along the way that will add up towards the bigger changes?

We’re watching out for the blocks, the blockers, anything that might get in the way. Rather than judging that or getting defensive, we get curious - how might we work around that? What might be or feel true from where they are sitting?

That question on its own can shift how you approach a situation.

Is there time to actually do this in the day to day of managers’ roles?

Rarely! But also, if we don’t, we get caught in the bubble of our own work, not fully understanding the interdependencies between our own team’s work and bigger organisational outcomes. We try to force things through against the tide and get shouted down, lose momentum or goodwill.
We miss the opportunity to bring people with us, to be seen to compromise and help others achieve their agendas. To look up, beyond our own bubble, and really expand our perspective, so that we can think, and then lead more strategically.  It can start to feel like you are working very hard, without things quite landing in the way you expected. Taking the time to widen your perspective does not remove the operational work. That part is still there. But it does change how that work connects to everything around it.

A more useful way to hear the feedback

So when you hear, “I need you to think more strategically”, it can help to translate that into something more practical.

Lift your head a little more often from what is directly in front of you.

Look at the same situation from more than one perspective.

Think not only about the outcome, but about the pathway and the people involved in getting there.

And at times, be willing to step outside the part of the role where you feel most comfortable and capable, and spend some time in the part that feels less certain.

Strategic thinking is not about stepping away from the operational. It is about staying connected to it, while also seeing how it fits into a much bigger picture.

Both are part of the role.