Leading in the trenches: The strategy that executives are missing

They called it the “launch that would change everything”. After 14 months of development, a major tech company rolled out a new platform aimed at small businesses. The rollout was pristine on paper: flawless decks, detailed forecasts, and a confident executive team. But just three weeks in, users began abandoning the tool. Why? It was designed by senior leaders who hadn’t spoken to a small business owner in over a year. While they managed from the tower, the frontline realities changed beneath them. One quiet intern later revealed in a post-mortem, “If anyone had spent one week shadowing our support team, they would have seen it coming.” That failed launch didn’t break the company, but it broke the illusion that distance can substitute for leadership insight. The moral? What you don’t stay close to, you eventually misread.

In an era obsessed with scaling, leaders are often taught to step back, delegate, automate, and abstract. But leadership is not just elevation; it is immersion. The higher you rise, the more intentional you must be about staying close to what matters: your people, your product, and your process. Influence does not thrive in distance; it flourishes in proximity.

“While surveys and dashboards looked fine, they hadn’t visited their stores or spoken with actual customers in years.”

A Harvard Business Review study from 2023 found that senior leaders who spent at least 20 percent of their time embedded in frontline functions had teams that outperformed peers by 31 percent in execution and 26 percent in retention. The implication is simple: leaders who stay connected lead more accurately.

Yet proximity isn’t just about physical presence. It is about emotional and intellectual closeness. Leaders must have their finger on the pulse of their people’s morale, the market’s mood, and the mission’s meaning. Detachment breeds delusion. Proximity builds credibility.

Consider Satya Nadella’s first year as CEO of Microsoft. Rather than launching a new product or restructuring teams, he quietly toured teams across divisions, asking questions, listening deeply, and absorbing pain points. One of his earliest decisions, redefining Microsoft’s mission around empathy and empowerment, came directly from those frontline observations. Today, Microsoft is not just profitable again; it’s culturally alive.

Compare that with a once-prominent retail chain that collapsed because executives failed to recognise how outdated their customer experience had become. While surveys and dashboards looked fine, they hadn’t visited their stores or spoken with actual customers in years. The data said, “All is well.” Reality screamed otherwise.

Research by McKinsey shows that organisations where executives maintain regular contact with operational teams are 3.5 times more likely to anticipate risks before they escalate. Leaders who stay close build foresight, and foresight is the twin sibling of agility.

So, what must leaders do? Staying close doesn’t mean micromanaging. It means mindfully embedding. It is about proximity with purpose. Here’s how leaders can practise it meaningfully:

Get in the field monthly. Whether that is joining a sales call, attending a product stand-up, or shadowing customer service reps, make frontline immersion a ritual, not a rarity. You will gain insights no report can offer.

Create feedback loops that actually loop. Don’t just collect feedback; respond to it visibly. When a team sees you acting on their insights, trust compounds, and so does innovation.

Invite discomfort weekly. Hold unfiltered town halls. Ask, “What are we missing?” from junior staff. Let people challenge your ideas without fear of reprimand. Proximity means proximity to truth, not just affirmation.

Embed curiosity daily. Leaders who ask better questions build stronger cultures. Try asking, “What am I not seeing?” or “What would you do differently if you had my seat?” These aren’t just queries; they are bridges.

Anchor strategy in story. Facts inform, but stories inspire. Stay close enough to the ground to gather the stories of your people, the customer you saved, and the frontline hero who improvised a solution. Strategy must breathe, and stories give it lungs.

Leadership at a distance may seem efficient, but it is rarely effective. Detachment erodes relevance. And in times of complexity, your edge isn’t just foresight; it is nearness. Nearness to your people. Nearness to purpose. Nearness to what you are building.

So here is the question: What have you grown distant from that you were once deeply connected to? What truth might be hiding in the voices you haven’t listened to lately?

Your organisation doesn’t just need a visionary. It needs a witness. A leader who walks the floor. Who hears with the heart? Who doesn’t confuse oversight with insight?

Because leadership is not a perch; it is a practice. And proximity is not a burden; it is a responsibility.

In the grand scheme, greatness isn’t found vanishingly far away; it is forged in closeness. The leaders who win tomorrow will be those who stay near enough to understand today.

Leadership isn’t about rising above; it is about staying rooted within.

About the author:

Dr Toye Sobande is a strategic leadership expert, lawyer, public speaker, and trainer. He is the CEO of Stephens Leadership Consultancy LLC, a strategy and management consulting firm offering creative insight and solutions to businesses and leaders. Email: [email protected]