Hold the Roof High When Challenging Work Falls Short

In elite sport, a training session in which everything works perfectly may not be as reassuring as it appears. The passes connect. The planned moves succeed. Players remain organised. The coach finishes the session with few mistakes to correct.

But that smoothness may reveal something uncomfortable. The training may not have pushed the team close enough to the uncertainty and pressure of the real contest. One experienced rugby coach described looking for an approximate balance in which most of the training succeeds, while enough goes wrong to create meaningful learning. The precise percentage was not a formula. It was a coaching judgement about whether the players were working near the edge of their present capability.

If every attempt succeeds, the challenge may be too limited. If too much fails, confidence and motivation may begin to disappear. The coach is looking for enough success to sustain belief and enough failure to expose what the team still needs to learn.

Business is different from sport. Managers should not aim for a percentage of projects to fail, particularly when the consequences affect customers, employees or significant resources. But the underlying tension still matters.

When managers give teams genuinely challenging work, the path cannot be completely certain, and success cannot always be guaranteed. There will be times that considerable effort still does not produce the hoped-for result. The quality of the development then depends not only on the difficulty of the work, but on what the manager helps the team do next.

Challenging work contains the possibility of falling short

Consider a team competing to win an important client project. The opportunity matters. Winning it would generate meaningful revenue, strengthen the organisation’s reputation and create future possibilities. Several competitors are pursuing the same work.

The team is capable, but the opportunity requires more than it has done before. It needs to understand an unfamiliar client problem, bring together commercial and technical perspectives, develop a distinctive proposition and present it convincingly to senior decision-makers. This is the kind of work that can help a team grow.

People need to collaborate across boundaries. Less experienced members take on greater responsibility. The team must make judgements without complete information. It cannot rely entirely on a familiar process because the client and competitive context are different. The manager may reasonably believe that the team can win. But the manager cannot know that it will.

After several weeks of work, the pitch is delivered. The team presents a thoughtful proposal and responds to difficult questions. Some parts go particularly well. Other parts feel less certain. A few days later, the client awards the project to a competitor. The team has fallen short.

The result may be explained in many ways. Perhaps the competitor offered a stronger package. Perhaps the proposal did not address one concern deeply enough. Perhaps the client valued a capability the team underestimated. Perhaps the outcome was influenced by an existing relationship the team could not see.

Whatever the cause, the disappointment is real. The team invested effort, carried pressure and believed the opportunity was achievable. This is the moment when the manager’s work changes.

Success still needs to be recognised

When a consequential project is lost, it is easy for the final outcome to become the only measure of everything that happened before it. The team did not win, so the work is described as unsuccessful. That conclusion may be commercially accurate. But it is not necessarily a complete assessment of the team’s performance or development.

The work may have produced genuine successes. The team may have developed a clearer understanding of the client. Different functions may have worked together more effectively than before. A developing manager may have led an important part of the proposal. The team may have strengthened its ability to explain complex work in practical terms. It may have responded well when challenged during the pitch.

Recognising these things does not turn a loss into a victory. It identifies what the team should retain. This matters because confidence is not built through reassurance alone. It is built through credible evidence that the team possesses capabilities it can use again.

If the manager treats the entire project as worthless because the final answer was no, people may learn the wrong lesson. They may conclude that the effort revealed nothing, that the new responsibilities were beyond them or that challenging work is dangerous because only the final outcome will be remembered.

The manager needs to help the team separate two questions:

Did we achieve the result?

What did we demonstrate that remains valuable?

The first answer may be no. The second should still be examined honestly.

Setbacks reveal the edge of current capability

Recognising what worked should not prevent the team from examining why it fell short. The loss may have exposed weaknesses that successful work would have kept hidden.

Perhaps the team understood the client’s stated need but not the concern underneath it. Perhaps technical expertise dominated the proposal while the commercial value remained unclear. Perhaps several people contributed good ideas but no one delivered the central argument in a coherent manner. Perhaps the team relied too heavily on the manager when questions moved beyond the prepared material.

These are not reasons to celebrate losing the pitch. They are information. Challenging work reveals the point at which the team’s existing habits, knowledge or coordination are no longer sufficient. That is part of its developmental value.

But failure does not automatically create learning. People may respond by protecting themselves. They may explain why another function was responsible, why the client misunderstood or why the result was decided before the pitch began. Others may become excessively self-critical and interpret the loss as proof that they were not ready.

A team that appeared collaborative while the opportunity was progressing well may become fragmented once disappointment arrives. Its behaviour was supported by momentum, but it was not strong enough to survive the loss of momentum. The manager now needs to help the team face what happened without allowing the result to become larger and more final than it is.

The manager needs to hold the roof high

Pressure can make a setback feel as though the room is becoming smaller. Questions arrive from senior leaders. People speculate about what went wrong. Competitors celebrate their success. Team members replay particular moments and wonder whether they caused the loss. The noise begins to press down.

The manager may feel it as strongly as everyone else. They sponsored the work, committed resources and perhaps assured others that the opportunity was worth pursuing. They may be disappointed, embarrassed or concerned about how the result reflects on their leadership.

If the manager reacts from that pressure, the roof can fall further. They may demand an immediate explanation before the team has enough information. They may search for someone to hold responsible. They may dismiss the work as a waste of time or step in and personally control the next opportunity.

Each response may create a temporary sense of action. But it can also reduce the team’s capacity to think clearly, speak honestly and recover. Holding the roof high means doing something different.

It means acknowledging the consequence without treating the situation as total collapse. It means recognising the surrounding noise while deciding what information is actually useful. It means preserving enough perspective for the team to distinguish what has been lost from what remains possible.

The manager might begin by helping the team establish what is known.

What feedback has the client actually provided?

Which conclusions are evidence-based, and which are assumptions being made in disappointment?

What part of the proposition remained strong?

Where did the team become less clear or coordinated?

What should change before the next opportunity?

These questions create space without avoiding accountability. The manager is not telling the team that the result does not matter. They are preventing the result from becoming so psychologically overwhelming that the team can no longer learn from it.

Holding the roof high is not rescuing the team

A manager can create space for recovery and still take too much ownership. They may analyse the loss themselves, redesign the approach and personally lead the next pitch. The intention is to protect the team and improve the chance of success.

But the team may then lose the very development the challenging project was meant to create. Recovery requires participation.

The team needs to examine where its judgement was sound and where it was weak. It needs to hear the client feedback, test its assumptions and decide how it would approach a similar opportunity differently. The manager can guide the process without supplying every answer.

They may need to challenge an easy explanation. They may need to prevent one person from carrying blame for a collective weakness. They may need to bring the discussion back when it becomes defensive or overly negative. But the team should still do the thinking.

Holding the roof high creates room for people to recover. It does not complete the recovery for them. This distinction matters because resilience cannot be handed to a team as reassurance. It grows when people experience a setback, remain engaged with it and discover that they can take a useful next step.

Recovery creates a different kind of confidence

A team that has succeeded only when circumstances were favourable may appear confident. But that confidence has not yet been tested.

A team that has experienced disappointment, examined it honestly and returned to difficult work develops something more durable. It knows that a setback does not need to become paralysis. It has practised separating useful information from emotional noise. It has learnt that one lost opportunity does not invalidate every capability involved in pursuing it.

This does not guarantee that the next sales pitch will be won. Recovery is not a promise of immediate success. It is the restoration of the team’s capacity to think, coordinate and act.

The next opportunity may still be difficult. But the team approaches it with more than optimism. It carries experience of what happens when confidence is disturbed—and evidence that it can find its way back.

The real work

Managers develop teams by giving them work that asks more of them. But challenging work will not always produce the result everyone hopes for.

When it does not, the manager’s role is neither to minimise the disappointment nor allow it to define the team. It is to keep reality visible and possibility open.

Enough success helps people believe they can do difficult work. Setbacks reveal where their current capability ends. Holding the roof high gives them enough room to learn, regain perspective and begin again without the manager taking the work back from them.

The real work is not protecting a team from every failure. It is helping people discover that when difficult work falls short, they can remain capable of responding.

One question for reflection

When your team experiences a significant setback, do your actions create enough room for people to recover—or make the roof feel lower?

Continue Exploring

Growth rarely comes from challenging work alone. It comes from how managers help people respond when difficult work does not produce the result they hoped for. If this article was useful, you may also enjoy:

• The Right Stretch Helps People Grow — why meaningful development requires the right balance of challenge, support and responsibility.

• Momentum Begins with the Reality in Front of You — how managers and teams rebuild momentum by taking thoughtful action and learning from reality.

• What Can You Rely On When You Do Not Know the Answer? — how confidence is rebuilt through judgement, process and responsible leadership after setbacks.

• Challenge Is Not the Same as More Work — why purposeful stretch develops capability more effectively than simply increasing workload.

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