There’s a particular silence that fills a room when a strategy isn’t working and everyone knows it. It’s not the silence of confusion — people understand what’s happening. It’s the silence of waiting. Waiting for someone with enough authority to say what everyone is thinking: this isn’t going to work, and we need to change direction.
I’ve been on both sides of that silence. As a team member, earlier in my career, watching a leader double down on a failing approach because the sunk cost felt too large to abandon. And as a founder, sitting in the chair where the pivot has to originate, knowing that changing course means admitting I was wrong.
The second experience is harder than it sounds. Not because leaders are uniquely proud — though some are — but because changing strategy mid-execution has real costs that go beyond ego. It disrupts workflow. It creates uncertainty. It raises the question: if this strategy was wrong, how do we know the next one is right?
Getting this moment right — the pivot itself, and the way it’s communicated — is one of the most important things a leader does. And most leaders handle it badly.
Why We Hold On Too Long
The psychology of sunk cost is well-documented, but I think there’s something more specific happening when leaders persist with a failing strategy. It’s not just that they’ve invested resources they don’t want to waste. It’s that changing direction feels like an indictment of their judgment.
A founder who chose a strategy — who argued for it, resourced it, aligned the team around it — has their identity wrapped up in it in a way that a team member executing the strategy does not. When the strategy fails, the team member loses time. The founder loses something closer to credibility.
This is why the pivot often comes too late. The leader waits for incontrovertible evidence of failure before acting, when the team could see it failing weeks or months earlier. By the time the change happens, the team has lost not just time but faith — faith that leadership is reading the same signals they are.
I’ve done this myself. About a year into PipelineRoad, we committed to a content distribution strategy for a client that I was personally convinced would work. We’d invest heavily in LinkedIn organic content — four to five posts per week from the founder’s account — and use that to drive demo requests. The logic was sound. The execution was solid. The results were negligible.
By week six, the team knew it wasn’t working. The engagement was fine, but the conversion to pipeline was essentially zero. The audience was wrong — lots of peers and marketers engaging, very few actual buyers. I could see the data, but I kept finding reasons to wait. “It needs more time.” “The content mix isn’t right yet.” “Let’s adjust the call-to-action.”
It took ten weeks before I called it. The team was gracious about it, but I could tell they’d been waiting for me to see what they already saw. Those four extra weeks weren’t spent learning — they were spent avoiding an uncomfortable conversation with myself.
How to Make the Call
I’ve developed a simple decision framework since then. When I suspect a strategy isn’t working, I ask three questions.
What would change my mind? Before I look at the data, I write down the specific conditions under which I would abandon the strategy. This prevents me from moving the goalposts after I see the numbers. If I said “we need to see a three percent conversion rate by week eight” and it’s week eight and we’re at half a percent, the answer is clear — regardless of what narrative I can construct to explain the gap.
What is the team seeing that I’m not? The people executing the strategy always have information the leader doesn’t. They’re closer to the work, closer to the responses, closer to the friction. If I ask the team whether the strategy is working and I get hesitation, that’s a signal. If I get enthusiasm, that’s a different signal. Both matter more than my analysis from a distance.
What’s the cost of waiting another month? This reframes the decision from “should we change?” to “what happens if we don’t?” Usually, the cost of waiting is not just the direct expense of the failing strategy — it’s the opportunity cost of not doing something better, plus the morale cost of a team executing work they don’t believe in.
The Communication Problem
Deciding to change direction is hard. Communicating the change is harder.
The temptation is to minimize the pivot — frame it as an “optimization” or an “evolution” rather than an admission that the original strategy was flawed. This is a mistake. Your team already knows the strategy failed. Dressing it up in euphemistic language doesn’t save face — it signals that you’re not being honest with them, which is worse than being wrong.
The communication I’ve found works best has three parts.
Acknowledge what happened, plainly. “The strategy we committed to three months ago hasn’t produced the results we expected. The data shows X, and that’s below the threshold we set. This is on me — I pushed for this approach and I should have pulled the plug sooner.”
Explain the new direction and why. “Here’s what we’re going to do instead, and here’s why I think it will work. The key difference is…” This needs to be specific enough that the team can evaluate it, not just trust it. After a failed strategy, asking the team to take another leap of faith is asking too much. Show your work.
Create space for the reaction. Some people will be relieved. Some will be frustrated — they may have been raising concerns for weeks. Some will be anxious about another potential pivot. All of those reactions are valid, and suppressing them in the name of momentum is a mistake. Let people say what they need to say.
The Trust Paradox
Here’s the counterintuitive thing: changing direction, when done well, builds more trust than staying the course. A leader who can say “I was wrong, here’s what I’ve learned, here’s what we’re doing instead” demonstrates exactly the kind of judgment and intellectual honesty that teams need to see.
The leaders who lose trust are not the ones who change strategies. They’re the ones who change strategies without acknowledging the change, who pretend the pivot was the plan all along, or who blame the team for a failure that was fundamentally a strategic misjudgment.
I’ve noticed that the most resilient teams I work with — both our own and our clients’ — are the ones where strategic changes are discussed openly. Where “this isn’t working” is a statement of fact, not an accusation. Where the culture allows for experimentation, which necessarily includes experiments that fail.
Building that culture requires the leader to model it first. You can’t expect your team to raise concerns about a strategy if the last time someone did, it was dismissed. You can’t expect honest assessment if the last strategic review was a performance — everyone saying things were going well because that’s what the founder wanted to hear.
The Speed of Recovery
The final lesson I’ve taken from our own mid-course corrections is that the speed of recovery is almost always faster than you fear. The anxiety before a pivot — the weeks of deliberation, the dread of the conversation — is disproportionate to the reality of the change.
In practice, when you tell a team “we’re changing direction,” most people exhale. They were waiting for it. The uncertainty of executing a failing strategy is more stressful than the uncertainty of a new one. At least the new one carries the possibility of working.
Within a week of our LinkedIn-to-pipeline pivot, the team had already started executing the replacement strategy with more energy and conviction than they’d brought to the original approach in its final weeks. Not because the new strategy was obviously better — it was unproven — but because there was something clarifying about a fresh start that had been earned through honest reckoning.
The courage to change direction is not about being decisive. It’s about being honest — with yourself, with your team, with the data. The strategy was wrong. Everyone knew it. And the moment you said it out loud, you freed everyone to move forward.