10 29 18

ExO Sprint, ExO Workshop, ExO Orgs

Successful Failure Within Sprints

Written By

Emilie Sydney-Smith

5 min read

How do you find the balance between assisting a team as they learn and embrace the tools and mindsets needed to succeed while giving them the autonomy and the freedom to make mistakes?


Fail fast, fail often, fail well.

It's the mantra of many recent business methodologies, including ExO and Lean Startup, but how can productive failure best be fostered within an ExO Sprint?

Where is the sweet spot between assisting teams to learn so many new tools and meeting the high expectations for their initiatives in a short timeframe—all while giving them autonomy to fail along the way and learn from those mistakes?

Every Coach will have their own approach. Here is what seems to be working best for my style of Head Coaching. 

An Approach for Fostering Successful Failure in ExO Sprints

The in-person Align Workshop kicking off the Sprints is a great time for teams to fail a bit since we are there to help them learn from the experience. I want teams to be helped just enough to find inspiration in their successes and while presenting their work to everyone. This should be balanced with opportunities to fail publicly, even just a little, and recognize that they won't be vilified because of it.

Being somewhat hands-off and observing team members during our first interactions provides some great insights into personalities, skill-sets, and team dynamics.

"Bad" Ideas Can Pave The Way For Great Ones

We will, honestly and constructively, point out flaws in their thinking, but always suggest tweaks and pivots that can turn that failure into success.

Being somewhat hands-off and observing team members during our first interactions provides some great insights into personalities, skill-sets, and team dynamics. These early intuitions generally prove useful for the duration of the Sprint.

For example, if I see more dominant or senior team members tell their teams why their ideas are bad too often, I might speak privately with the senior or dominant person—and remind them that the brainstorming of new ExO-scale business initiatives is completely new to most people.

As a result, their peers need space to come up with some really awful ideas, sit with them for a while, explore them, have a lightbulb moment, and recognize that the idea truly sucked.

Sharing that perspective usually creates much more collaborative behavior, but generally needs reinforcing a few times during the Sprint (when old habits creep in).

I’m often reminded of my brother-in-law, Barney Saltzberg’s, blockbuster children’s book, The Beautiful Oops, during Sprints.

Accidentally spill something?

Pull out some craft supplies and turn the splotch into a work of art. We adults could do with a bit more playfulness too as we find creative solutions ASAP to increasingly prevalent disruptions.

I’m working with the core ExO team to think up ways to incorporate more creative and impactful fun into the Align Workshop.

Recognize What's On The Line

I’m cognizant throughout the Sprint of how much the Sprint participants have on the line. Many have had no previous exposure to any of their executives and have never even given a formal presentation—yet after the challenge of distilling many weeks of their hard, complex work into a presentation, they will stand not once, but twice, in front of their executive team during the Disrupt and Final Presentations. After that, they will have to answer tough questions and ask for funding.

I’m prepared to administer some tough medicine along the way if I feel a team is lagging behind the others.

Their futuristic brainchildren initiatives will be really “out there” for some of the executives, adding a fear of looking foolish. I make it clear throughout the Sprint that they can trust me to help them really shine in front of their executives and that the Coaches and I will be there to help them get through tough spots.

As a result, I’m prepared to administer some tough medicine along the way if I feel a team is lagging behind the others. It is better that they hear constructive feedback from me during the “sausage making” part of the Sprint. That requires a lot of trust with the wonderful Coaches, as we collaborate on when to allow a bit of creative failure versus when and how to intervene.

Coaches Aren't Exempt

Perhaps, most importantly, we as Coaches also need to try, succeed or fail—and continually learn and improve.

I often remind teams that my advice may be wrong. So long as they look into it and can give me a well-reasoned answer as to why I may be wrong, I’ll likely agree with them.

I used to take the coaching versus consulting mantra more literally—well, I never managed to be a pure coach and felt guilty.

I’ve learned through trial and error that ExO Coaches have a lot of contacts and relevant information that would be a huge shame to withhold. It would be just as much of a shame to force the team to use up one of their scarce advice "tickets" in order to gain that same knowledge from a different ExO Ecosystem member.

I now share away, provided that the teams have come up with their own ideas and I’m just working to turbocharge them.

Some Things Need to Be Repeated

I’ve also learned that I often need to give a team a particular piece of advice or lead a few times before it gels with them. I’m around these high-tech ideas and entrepreneurial methods all the time and they are not. They come to it when they are ready, with some continued encouragement.

I’ve learned that it is great to mention at the start of a Sprint any technologies or trends that teams might not naturally come across in their mad dash to research all things disruptive, but which might be very relevant to theirs and adjacent industries.

The most popular initiative in a Sprint I just finished Head Coaching derived from one of those tips on stealthy technologies, but the team came up with a mind-blowingly innovative spin on it.

Recognize the Ideas Worth Fighting For

The team flunked their initial presentation of the idea in a weekly Results Call, so I back-channeled with the client Sprint Champions, who also provide feedback to teams during Results Calls, to make sure they were given a second chance. I then sent the Champions some primers on the complex technology, which got them very enthusiastic to hear more.

That is, don’t let a team fail when it is really important, but let them learn the lessons nonetheless. I’ve also learned the hard way that successful initiatives usually have initial growth stages that leverage the client’s existing talents and unfair advantages, then become more futuristic as they scale. Funding is highly unlikely for initiatives that lack the company relevance at the start.

We meet our MTP goals of global business transformation and the company’s goals of exponential profitability and diversification with the later growth stages of the same initiatives. Note that the ExO Attributes should be integral to the initiative throughout their growth stages – this is never an excuse to just tack on the ExO pieces later.

Nurture your Champions

Lastly, we also have a role in training the Champions to think like a VC and provide useful guidance. Champions should feel free to use some trial and error in creating their personal style of feedback and seeing what resonates.

I tend to give my feedback first to provide an example until they feel confident, then mix up the order each week. I usually ask the team Coach to speak last, so as to reinforce the ExO-specific guidance and as a lead-in to his or her debrief with the team.

What are your thoughts? 

I’d love to hear your thoughts on allowing the optimal amount of productive failure within a Sprint.

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