Guided Insights

A friend’s daughter just announced her family’s sudden decision to pack up and move several states away, with no jobs, no residence, three school-age kids, one dog and two cats. My friend is agonizing over whether to try to talk her daughter out of it (“How will you live?  Where will you live? What about health insurance? How are you moving your stuff? What will this do to the kids?”), or to simply wish them well and wave goodbye.
I have faced similar quandaries, though on a much smaller scale, when my own kids have made questionable decisions that I suspected would haunt them sooner or later, like reneging on a commitment with a good friend in favor of an invitation that sounded way more fun, or spending hundreds of dollars for a “new” iPhone from someone online who demanded gift cards as payment.
My friend’s recent quandary led me to wonder: Is it better to allow someone we care about to “fail fast,” even when we’re convinced that the results will not be very pretty? Or should we stand back and let them go so they can learn whatever lesson might be coming their way, even faster?
In the agile software world, the notion of “failing fast” gives developers the ability to quickly flush out design flaws early enough in the process so they can be corrected and retested before going live, when problems become more costly to fix. More broadly, the concept of failing fast has gained currency across many organizations looking for ways to survive and thrive amidst a fast-changing environment and near-constant ambiguity

In this edition I explore how leaders of virtual teams might embrace the concept of “failing fast” to help team members work more self-sufficiently, with greater confidence, more quickly–without feeling like they’ve been thrown into the deep end without a lifejacket. Many of these same tips can be applied, with modifications, in other environments as well.


  • Establish concrete goals. Work with each team member to set unambiguous goals that are reasonable, specific and trackable, using agreed-upon metrics. For example, instead of a vague goal that no single person can realistically be held accountable for, like “improving customer satisfaction,” try something like “minimizing the number of handoffs required for customers checking on the status of their requests.” Work together to create a series of goals that are valuable, achievable, measurable and reasonably challenging.
  • Make “failure” a viable option. Let people on your team know that you encourage them to venture outside of their comfort zone, try “crazy” ideas, and be ready, willing and able to fail as a necessary condition of learning and growth. Make yourself vulnerable by sharing real-life examples of risks you have taken in your professional or personal life that didn’t pan out as planned, and share what you learned as a result. Make a “lessons learned” conversation a routine part of your team meetings, where team members can safely discuss mistakes or miscalculations and examine what they and others can learn as a result.
  • Set clear parameters. Be specific about situations where you want to see your team members take initiative or make autonomous decisions, and where you want (or need) to be consulted or to approve their proposals. Without such clarity, team members are likely to feel a need to seek validation or approval more often than either of you would like, depriving them of the opportunity to establish greater self-sufficiency. For example, there may be monetary thresholds that require your approval, or proposals that require buy-in at senior levels that you’ll need to review and endorse. For decisions you prefer that team members make independently, let them know that they can bounce ideas off you, within reason, so they can learn from your thought process. Make sure team members know that if their plans go awry, you’ll back them up, especially if they can explain their reasoning or, as my kids’ teachers say, “show their work.”
  • Encourage critical thinking. Helping team members to ask the right questions can be the best way to help them gain the confidence and competence they need to work without the need for constant guidance. Simply giving them the solutions, while often the most efficient path, will do little to help them operate independently. For example, if a team member comes to you for help in removing a roadblock that’s thwarting their progress, you might ask questions like: “Who/where have you tried to find the answers? What incentives might appeal to them to cooperate? What other approaches can you take? What can you accomplish while you’re waiting for a response? Who else might be able to give you what you need? Which team members may have encountered similar issues?” By posing questions to help them find the answers they’re looking for, you’re modeling critical thinking skills they can use next time they encounter a roadblock.
  • Have safety nets in place, just in case. None of us want to see someone we care about do irreparable damage if they fall flat on their face after taking a leap. Safety nets can take different forms and be available at different times. For example, before your team member takes action, you can help them identify risks and find ways to mitigate in advance. If you clear the way for your team member to go all-in, despite your doubts about the outcome, be there to help pick them up, dust them off, and talk through what lessons they can apply for the next time.

Whether you’re a team leader, a parent or a teacher, it can be agonizing to let someone you care about take what you consider to be a questionable risk or make an ill-informed decision. But if we want them to learn and grow, we have to let them fail fast, if that’s what it takes, as long we’re ready, willing and able to support them when they’re ready to try again.



Evaluating Your Decision After the Fact – downloadable PDF checklist from Guided Insights
How to Listen Deeply When Working Virtually – downloadable PDF checklist from Guided Insights
Forget About Failing Fast – If You Must, Fail Forward Instead – by Howard Tullman, in Inc. Magazine
“What Is a Fail Fast Organizational Culture?” by Janet Sernack, appearing in Innovation Excellence

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