When Do I Let A Team Member Fail?

This week, we continue our series Ask Mission Central, where we tackle real questions on spiritual life from emerging Christian leaders. Subscribe to get the next post in your inbox!

Ask Mission Central: Question Fourteen

“How can a Christian leader discern when to let a team member fail and learn from that failure versus when to step in (potentially self-sacrificially) to prevent the team member from failing?”

Verona, WI


Surgeon and author Atul Gawande’s first book, Complications, covers his experiences as a surgical resident, when he was still learning the craftwork of scalpels, sutures, and stents. He grapples with the moral dilemma that a medical residency is: How can we let new doctors learn skills that only come with practice when “it is people [they] practice upon” (p. 18)? Gawande muses:

“This is the uncomfortable truth about teaching. By traditional ethics and public insistence (not to mention court rulings), a patient’s right to the best care possible must trump the objective of training novices. We want perfection without practice. Yet everyone is harmed if no one is trained for the future” (p. 24).

Medicine is marked by a tension between providing the best care for today’s patients and training doctors who can serve tomorrow’s. A similar tension marks any endeavor where new team members must learn the ropes. How do we weigh the costs of the mistakes novices inevitably make against the benefits of the lessons they will learn from those mistakes?

The example of surgery is instructive, because the costs of failure are so stark. The “July effect,” so-called for the month when U.S. medical residents begin their work, has an even bleaker nickname in the United Kingdom: the killing season. That irreverent moniker reminds us that there is no “failure free” option for teaching human beings new skills, even in life-and-death disciplines. Every summer, the experts grimace and hand over the knife to those who have never held it before. Whatever our line of work, we can learn to do the same for those who need the chance to learn.

Ready, Set, Fail

The best way to define failure is to define success first. What objective are you and your team trying to fulfill? How will you be able to tell if you have succeeded? Although many meaningful outcomes resist measurement, you can do your best to count what you can. Frameworks like Andy Grove’s Objectives and Key Results (OKRs) can provide a way to communicate clearly within a team about what success looks like. A failure which amounts to less than flawless performance may not be a failure in terms of overall objectives. In fact, leaders who expect flawless performance from their team members at all times will foster an environment in which people feel afraid to take the risks necessary to learning. Bearing this in mind, you might want to use a framework like OKRs to define learning goals for different team members—and to keep yourself from failing to encourage healthy risks!

Your gut may also give you a less formal, but no less important, assessment of your team’s situation. The way your question is phrased makes me think you’ve experienced that moment when a team member has been given a responsibility and you can tell from the way they’re going about it that things will be bumpy. When that’s the case, how do you respond? Obviously, you may be concerned about how the team member will feel about any intervention—and how they will feel if their project flops. For simplicity’s sake, I’m going to assume that this team member would be open to appropriate offers of help and support. I’ll also assume you’re in a supervisory or team leader role. If that’s the case, then it’s just a question of making the right call about whether and how to intervene. Asking yourself a few clarifying questions can help you make that call. Let’s start with these two:

  • In this situation, how catastrophic are the results of failure?
  • If I “let them fail,” how bad will it be for our overall endeavor?

This first set of questions addresses your responsibility to ensure fulfillment of the task at hand for the sake of the organization’s overall mission. The lower the cost of failure to an organization, the more easily it can be used as a learning device. For example, suppose that you are on a software development team, rolling out a new version of an outdated, internal tool. Rather than putting your best coder on the job, you could have a newcomer take a stab at writing the code. It will be tested before being put into production, so the risk is low. Even if their design for the code lacks the elegance of what the more experienced coder would have accomplished in half the time, it could be the right moment to let the newbie cut their teeth.

Contrast this situation with the discovery of a bug in a live client-facing tool which could compromise sensitive user data. With such high stakes and a time crunch, putting your most experienced and effective coders on the job is probably the right call. Or, to get closer to the spirit of your question, you may have to pull a less experienced coder off of the main development work (even if it was “their project” to start with) in order to ensure that a solution can be developed, tested, and deployed quickly. At the same time, even in this situation you could include the newer team member in discussions about how you are fixing the problem, so that they can at least benefit from seeing the process and imagine how they might play a role in a similar scenario in the future.

On to our second set of questions:

  • What will help my teammate learn the relevant skills better: Someone stepping in to help, or their own experience of trying and failing?
  • Is there a way to step in that still lets them do as much as possible?

These questions help you think through what your teammate most needs as a learner. Thankfully, you don’t have to take an all-or-nothing approach to the question of whether to get involved when someone else is floundering. There are things you can do to set your teammates up for success that will also help them make the most of experiences of failure. Actively supporting someone else’s learning means providing at least the following:

  • A defined objective
  • Clear expectations
  • Timely feedback
  • Opportunities to ask for help
  • Encouragement to reflect on their work and what they are learning as they do it

If a hard-working and conscientious team member receives all these ingredients for success, and still fails, it’s likely not because anyone did anything wrong. It’s simply because they are a novice, and they need more practice. That’s “smart failure,” the inevitable run of mistakes that are simply part of learning anything.

In contrast, if a team member is given a new responsibility without these key ingredients of support, they are often doomed to what I call “stupid failure,” if you’ll forgive the abrasive adjective. The team member isn’t stupid, but they are condemned to fail because of a lack of intentional leadership. If they do manage to pull off a success without these ingredients of support, they will do so in spite of their leadership environment, not because of it. Failure due to inexperience is necessary; failure due to poor management isn’t.

Stupid failure also diminishes the value of failure as a learning experience. The team member might wonder, “Would I have done better if I had been given clearer expectations, or if my supervisor had been available to answer questions?” Getting a measure of their own skill is difficult, because they can’t determine whether the poor results were a function of their mistakes or of the unnecessary constraints placed upon them. Consider the bogey of vague expectations: it’s hard to tell if you’re aiming well if the target is hazy or keeps jumping around. 

If you’re reading this and you realize you’ve caused a team member to land in stupid failure, you need to do some repair work—not just on the work objective, but also on the work relationship. Own your part. Communicate to your teammate that the failure was your fault. Listen to any critical feedback they may have, and their assessment of what they need. Work together to identify specific ways that you can provide better support in the future. Showing genuine humility and the Christian virtue of contrition in interactions like this, besides being simply good for your soul, will also help rebuild trust.

When Smart Feels Stupid

My taxonomy of “smart failure” and “stupid failure” doesn’t take the sting out of messy learning experiences. Often, we delegate a task to someone because we believe that they are ready to succeed, not because we have judged that we can afford for them to fail. Failure catches us by surprise. Even if we know our team members well and have worked to prepare them for the challenges we pose for them, we can feel embarrassed, anxious, or disappointed when things don’t go as we’d planned.

It’s important, especially for our team members’ sake, that we be aware of such emotions and pay attention to how failure affects us. If we suppress or ignore our feelings, they will end up charging our interactions with the people involved (and often with others, too). Our emotions will also influence our attempts to reach a solution. It can be tempting to step in more often than we should to prevent failure as an attempt to manage our own anxiety, rather than as the result of a measured judgment about what’s best for the team. At the same time, if we feel afraid to “step on someone else’s toes,” we might hesitate to intervene in situations when it’s actually best to forego the learning experience and simply prevent failure. Know your tendency. Before deciding whether to intervene, ground your decision in a fair evaluation of the situation.

After a failure, it’s also wise to reflect on what happened and run a post-mortem. Running this kind of meeting with emotional intelligence will also be a gift to your team: encourage people to think about the how and why of what went down—without casting blame or avoiding responsibility. A key question for you to take away from that meeting (not necessarily to share with the whole team) is, “How soon is this team member ready to try this challenge again?”


There are exceptions to the rules of thumb I’ve articulated here. Two common cases deserve to be noted:

Learning Plateaus

I’m a firm believer in lifelong learning, partly because of the long path of sanctification. We are never done becoming more like Jesus! The opportunity to keep growing is always there in spiritual life, and I believe it’s helpful to aspire to in professional life as well. That being said, there are some people who will “peak” and then plateau in their work performance. They have found their niche, and they want to keep doing what they’re doing. Although my personality is such that I’ll see if I can inspire or invite my teammates to tackle a new challenge, there’s also something to be said for accepting someone’s decision to “stay put” if they’re doing well where they are. For someone like this, assigning them new responsibilities where they have not proved themselves may actually cut against their job satisfaction, and taking the risk of letting them fail may not result in them learning new skills.

Getting Overruled

At times, your best judgment of the tradeoff between the immediate pain of failure and the long-term benefit of a team member’s learning may differ from your supervisor’s judgment. You know the nuances of how freely your superiors’ have delegated responsibility to you, and you’ll need to operate within the freedom that they’ve granted. If they are dissatisfied with the outcome, it’s your role to take their feedback, while taking full responsibility for what happened. Even if the failure is largely the result of someone else’s mistakes, you’re the one who delegated the responsibility to them and gave them permission to try. You can protect and build trust with your teammates by protecting them from undue skepticism from their boss’s bosses in situations like this. A helpful way to frame things is to say, “This is on me; I’m the one who thought so-and-so was ready for this challenge, and they’ve been doing what I’ve asked them to. They’re still learning.”

You asked a question that’s tough to answer, but I hope this response provides a framework for navigating your options when a team member is facing failure. The good news is that handling situations like this with clarity, grace, and an encouraging attitude will reinforce trust throughout your whole team. And if you botch it, remember: You can learn from failure, too. Like doctors, leaders also have to practice with human beings. Let’s be quick to own our own failures, ask forgiveness, and try again. With time, we’ll learn to be skillful leaders who serve our teams well.

Illustration from 愚木混株cdd20 on Pixabay

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