From Doer to Strategic Thinker: What the Shift Really Takes

From Operational to Strategic Leadership: A COO Perspective | The Strategic Leader Podcast

There is a very particular kind of discomfort that arrives when you reach the top table and realise nobody is going to fill your in-tray anymore.

For most of us who have built careers on getting things done, ticking things off, delivering projects, being the reliable pair of hands, this is a quietly confronting moment. You have been promoted for your doing. And now you are expected to lead with your thinking.

For COOs, this tension is especially sharp.

Defined by doing

In the latest episode of The Strategic Leader, Gemma and I are joined by Divinia Knowles, a former COO and CFO who went on to become CEO, and who now coaches COOs in technology-led businesses across the UK. She also runs the COO Roundtable, a peer community of around 250 COOs who learn, challenge and support each other.

Divinia is candid about her own experience. Growing up through the ranks at Moshi Monsters, moving from junior roles into Head of Operations, then CFO and COO, the doing was, in her words, "in her blood." Learning to show up differently, to develop and share a genuine view on the business, to challenge the visionary founder sitting next to her, was a shift that took real effort and, at times, real courage.

"I always felt a bit of a fraud," she says. "He would come up with ideas and I would think, where did that even come from? And then to critically evaluate some of those ideas... it took me a long time to validate that I actually did have something to bring."

It is a feeling that will resonate with a lot of leaders. And it is much more common than people tend to admit.

The problem with "be more strategic"

One of the most useful moments in the episode comes when Divinia and I compare notes on a piece of feedback that keeps cropping up across our collective years of coaching and being coached: you're not being strategic enough.

It is, as Divinia puts it, feedback that should probably be banned.

Not because the underlying concern is not real, but because it is so poorly defined. Nobody hands you a playbook when you join the top table. The expectation that you will somehow intuit what strategic leadership looks like, particularly if your whole career has rewarded you for execution, is, to put it plainly, a bit unfair.

I have had that exact feedback myself, at a critical point in my career, and I did not push back on it. I did not ask what it actually meant. I just wrote it down and went away thinking, well, how on earth do I do that? My advice now: go straight back in. Ask for specific examples. Ask who is doing it well and why. Do not accept vague as an answer.

Because somewhere underneath "you're not being strategic enough" is usually a misalignment of expectations, and that is something you can actually work with.

Where your value really lives at the top table

A thread that runs through the whole conversation is the shift in where value is located as you get more senior.

Early in a career, value lives in what you produce. Then it moves into how well you navigate. And eventually, if you are sitting at or near the top table, it lives largely in how you think.

I find it useful to think about it in terms of where you sit in a car. For much of our careers, we are passengers. Someone else is driving, someone else is choosing the route, someone else is deciding the destination. We show up, we contribute, we get out at the other end. Getting more senior means moving from the back seat to the navigation seat to the driver's seat. Each shift requires a fundamentally different way of paying attention. And plenty of people, if they are honest, have never really had to navigate before. They have just trusted that someone else knew the way.

Divinia builds on this with her Three Rs model, which she uses when coaching COOs who are trying to articulate their own role more clearly. Role is the functional expertise you bring. Remit is the cross-functional influence you hold across and on the business. And Relationships is the web of connections, both through reporting lines and through pure influence, that make a COO uniquely positioned. Thinking about all three, she argues, is what moves a COO from operator to strategic asset.

The permission question

Something Divinia raises that does not always get talked about openly is the question of permission.

At the top table, many senior leaders, and not just COOs, struggle with whether they are allowed to challenge. Whether their perspective is welcome. Whether it is okay to push back on a founder or a CEO whose vision you admire, or whose experience dwarfs your own.

The answer, of course, is yes. That is part of why you are there. But arriving at that confidence takes time, and often requires someone to name it first.

This is something I think about a lot in the Belbin team role work I do with senior leadership teams. Every single one of those behaviours and perspectives has value. The evaluator, the challenger, the implementer: they are all needed. The fact that some feel more legitimate than others is often a function of culture, not reality. If you are the person who instinctively wants to sense-check an idea, slow it down, look at what could go wrong, that is not obstructionism. That is an essential role. And learning to own it, and to offer it constructively, is part of what strategic leadership actually looks like in practice.

Make time to think

Divinia's most practical piece of advice comes near the end of the episode, and it is deceptively simple.

If you are a COO, or frankly any senior leader who has been promoted for getting things done, you need to ring-fence time to think. Not to respond. Not to action. To think.

She references a principle from resilience coaching: roughly 65% of your time should be spent working on things, and around 35% should be protected for thinking. She knows that for a COO who equates busyness with value, that figure will feel shocking. But even 10%, even 15%, she says, starts to move the dial. It creates the mental space to form opinions, to develop a perspective on the business, to notice what the strategy is missing or where it might be stronger.

Somebody has to do some thinking. And the higher you get, the more of that thinking falls to you. I believe that. It is something Gemma and I come back to again and again in this series, and it is so much easier to say than to actually carve out the diary space for. But it matters. A lot.

Worth a listen if...

You are in or approaching a senior leadership role and wondering why it feels harder than the rungs below it. You have ever received the feedback "be more strategic" and were not sure what to do with it. You work with COOs, or are one, and want some honest, experienced perspective on what the transition actually involves.

You can find The Strategic Leader wherever you listen to podcasts. And if you have a strategic dilemma you would like Gemma and me to explore in a future episode, we would love to hear from you.

Fi Craig is the founder of GoodThinking, a Bristol-based team and executive coaching practice working with senior leaders and their teams across the UK and internationally. The Strategic Leader podcast is co-presented with Gemma Bullivant.