“Not Strategic Enough”: The Label That Hides the Real Problem

Executive Team Coaching

I read an article of someone who overheard it in a café recently. Two people over open laptops and half-eaten lunch. One leaning in, lowering their voice slightly: “She just needs to be more strategic.”

It resonanted directly as I have heard these type of qualifications before. So, I felt for the woman they were talking about. Not because the observation was necessarily wrong, but because it almost certainly wasn’t the real diagnosis.

“Not strategic enough” is one of the most common things said about people who are otherwise highly regarded but seem to have hit an invisible career ceiling. And it is almost never the full story.

What the Label Actually Means

Before we can address a development need, we need to understand what we’re actually observing. In my experience coaching executive teams, “not strategic enough” is a phrase that carries a surprisingly wide range of meanings:

• She challenges decisions in ways that make the leadership team uncomfortable, and they’ve decided that’s a “her” problem.
• She doesn’t socialise her thinking upwards before meetings, so her ideas land without context and feel less considered than they are.
• She was promoted into a role with no clarity about what “strategic” actually means here, given no support, and the organisation is now surprised she’s struggling.
• She is the one who says what others think but don’t say — which makes her uncomfortable for the system, not strategically weak.

Each of these situations calls for a completely different response. And yet they all receive the same label.

The Team Coach’s First Move: Treat the Label as Data

When a leadership team brings this kind of feedback about one of their members, the team coach’s first move is not to work on the individual. It is to get curious about the label itself.

Questions worth asking the team:

• Who decided this, and on what basis?
• What specific behaviours are you observing — and in which contexts?
• What does “strategic” actually mean here, in this organisation, at this level?
• Has she ever been told directly, clearly, and with concrete examples?

Often the team cannot answer these questions cleanly. That itself is information — and it shifts the focus where it usually belongs: onto the system, not just the individual.

The Systemic Function of the Label

In team dynamics, labels like “not strategic enough” frequently serve a function that has little to do with the person being labelled. They can:

• Deflect discomfort — she challenges the status quo, and this is the socially acceptable way to sideline that.
• Maintain hierarchy — her thinking threatens someone’s position or authority.
• Avoid accountability — the team promoted her, shaped her context, and now externalises the problem onto her.
• Signal group norms — “strategic” often means “plays the game the way we play it.”

A skilled team coach names these possibilities — carefully, but directly. Leaving them unnamed is itself a form of collusion.

Three Situations That Look the Same — But Aren’t

Before any intervention makes sense, the team coach needs to diagnose which of these three situations they are actually in:

Moving too quickly to individual coaching — without this diagnosis — risks colluding with the very dynamic that’s getting in the way.

The Psychological Safety Angle

If she genuinely challenges decisions and that makes the leadership team uncomfortable, that is a psychological safety issue in the team — not a strategic thinking issue in her.

Amy Edmondson’s research is instructive here: in teams with low psychological safety, dissenting voices tend to be managed out, relabelled, or marginalised over time. The team coach’s job is to make this dynamic visible — and to help the team see what they are losing by doing so.

The sharpest question for the leadership team: What does it cost you when the person who sees things differently gets labelled rather than heard?

When Individual Coaching Is Warranted: Do It Honestly

If, after proper diagnosis, there genuinely is a development need — then the coaching conversation needs to be honest about what is actually happening.

Not: “you need to be more strategic.” But: here is how your thinking is landing with this specific audience, here is what is getting in the way, and here is what you can do differently.

Not sanitised performance review language — “can sometimes come across as” and “might consider” — conversations that reach the point and then pull back at the last moment. That kind of feedback softens the edges but doesn’t help anyone.

The goal is not to fix her to fit the system. It is to help her navigate it with full awareness of what that system is. That is a crucial distinction.

The Harder Conversation: With the Team

The most important work in these situations often happens not with the individual, but with the leadership team itself. The questions that matter most:

• Are you modelling the strategic thinking you are asking of her?
• Are you giving her the room, the information, and the sponsorship she needs to operate at that level?
• Did you define what “strategic” actually looks like in this role, in this organisation, before you promoted her?
• Is this label protecting someone — or something — in this team from being examined?

That last question is the one most leadership teams resist. And it is usually the most important one.

A Final Thought

The leaders I have worked with who carried the “not strategic enough” label for years often turn out to be among the sharpest thinkers in their organisation. They did not need a new set of skills. They needed someone to help them see how they were landing their thinking — and an organisation willing to look honestly at the context it had created.

Strategic thinking can absolutely be developed. But you cannot develop it in someone if you have not first understood what is actually getting in their way.

Before we write someone off as not strategic enough, it is worth asking whether we are truly modelling strategic thinking ourselves.