Set Up to Fail, Failed to Set Up

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Some years ago, we had a fresh out of college employee at Barrel who was sharp and smart. This was during a time when we had a very flat structure and whoever was available, regardless of experience, was staffed on projects as needed. We staffed this employee on a number of fairly important projects and told the employee to figure things out. That’s what smart people are supposed to do, right?

Some weeks later, we realized that projects were beginning to fall behind and clients were unhappy. We took this employee aside and asked what was going on and why things weren’t going right. As was our style especially back then, we defaulted to an accusatory and impatient tone, demanding to know how this employee had messed up.

This particular employee, while young and new to the job, wasn’t one to meekly take our reprimands. The employee lashed out at us and refused to accept the blame.

“I was set up to fail,” was the response.

We were a bit taken aback by this response and chalked it up to the employee’s immaturity. What a victim mentality, we thought, definitely not someone we should have on the team!

We ended up firing this employee. This employee would go on, from what I can tell, to thrive and do incredibly well elsewhere. This wasn’t a one-time occurrence. We cycled through many people over the years, often ending on bad terms. We told ourselves that we had hired wrong and that these people just weren’t cut out for an agency job. We just needed to find better people.

Even with a modicum of awareness, it’s possible to see patterns emerge if you witness enough instances. As we continued to see evidence that people who had “failed” at Barrel were doing just fine or excelling elsewhere, we began to question whether the problem was less about who we were hiring and more about what we were (or weren’t) doing to help these people succeed.

What we came to realize over time was literally what this employee told us to our faces: we were setting people up to fail.

As we reflected on this more and more in subsequent years, we developed a mantra that’s one of our most common refrains today whenever we face any challenging situation at Barrel: set up to fail, failed to set up.

This applies not only to employees but with clients, projects, and any other activities and people we interact with as an agency. Embracing this mantra, I believe, has helped us escape the rut of being stuck as a business and has opened the doors for continuous improvement.

Why This Mantra Works

Before I share some examples of some ways in which we’ve failed people and the business, it’s worth noting why this mantra of “set up to fail, failed to set up” is useful.

  1. Start by accepting responsibility: The more accurate way to read this mantra would be “I/We set [person/org/project] to fail, I/We failed to set up [person/org/project] with what they need to succeed”. The core behavior is acknowledging that whatever issue or challenging you’re facing is your own fault, or at the least, that you had a hand in it. This immediately shifts the focus from blaming to the more constructive activity of figuring out what can be learned from the experience.
  2. Identify the underlying issue: We repeat the phrase “set up” twice in this mantra because it forces us to dig deeper for answers. It’s not enough to talk about the end result and nitpick the most visible mistake. By inquiring about how things were initially set up, it’s possible to learn more about the conditions, miscommunication, missed details, and other factors that contributed to an undesired result. Dig deep enough and it’s possible to uncover structural setups that keep on causing the same problems.
  3. The impact on those who “failed”: Having accepted responsibility, it’s also possible to examine how our failure to set up impacted the party that ultimately “failed”. In the case of an employee struggling with their workload, this mantra makes us ask how things might be better or different if they had the proper resources, guidance, and training to do their job. The mantra demands empathy and ensures that the lessons we learn help to improve the experience of others.

Of course, a mantra is only as useful as the effort you put into having regular discussions and debriefs along with actionable next steps. At Barrel, our weekly 2-hour Partner meeting is a prime forum for this mantra to shine, and it’s a key driver for many of the follow-up actions and initiatives that get assigned.

Ten Ways We Set Up to Fail, Failed to Set Up

In no particular order, here are some of the classic “set up to fail, failed to set up” scenarios that we’ve experienced at Barrel over the years.

  1. Creating a fresh new role with big plans but not taking the time to detail out the responsibilities and outcomes, hoping the new hire will help figure this out. Even worse, failing to communicate to the team how this new role will be interacting and contributing to projects and workflow, prompting people to ask, “What does this person do exactly?” Frustrations mount for both the person in the new role and the team. The person quits or the role is phased out.
  2. Signing a new client to a project in a hurry, skipping out on various details and not fully aligning on exact scope. By the time the project kicks off, the client and the team are out of sync and it’s apparent that a) the agency will have to eat a ton of cost to get things done, b) client will be unhappy to revisit scope, c) team is confused on what needs to get done and spinning their wheels trying to figure out.
  3. Lacking an org chart and providing zero communication to employees on their potential growth path at the agency, leading them to make assumptions about their uncertain future. By doing nothing, setting up an easy way to encourage employee attrition.
  4. Related to #3, desperate to keep someone who is hinting at leaving the agency, hastily offering them a promotion and a raise without thinking about the actual fit and readiness for that position. There are no real discussions about what’s expected in the new role but the employee is held to a new, higher standard and inevitably disappoints, leading to downward pressure to “do better” and ultimately ending up burnt out and ready to quit.
  5. Having incredibly high expectations for a new hire coming in with “tons of experience” and throwing them into all kinds of new assignments right away hoping they’ll figure things out along the way. When the new hire struggles to catch on quickly to the agency’s processes and workflows, becoming quickly disappointed and questioning the effectiveness of the new hire.
  6. Promising a client that we will deliver on an incredibly tight timeline and budget while knowing the team is already pretty booked on work and hoping that we will “figure something out”. When we inevitability have difficulty hitting deadlines or deliver a lower quality product, questioning the team’s commitment to quality and their ability to do the work competently in a timely manner.
  7. Bringing in a department lead, telling them about all the problems they’re expected to fix, and then becoming impatient when progress doesn’t seem to be happening fast enough. This is without having any discussions and alignment on the lead’s game plan and time table.
  8. Setting up team-wide KPIs and telling employees it’s important to hit certain numbers without having a deeper discussion on why the KPIs are important and how they’re influencing decisions. When employees fail to hit KPIs, using that to point out their performance shortcoming and to justify smaller raises or delay in promotion. In the worst of cases, these KPIs are not accurately measured and have moving targets. Employees become frustrated and confused about what it means to perform well in their role.
  9. Having little to no upfront discussions about measurable results and outcomes tied to the employee’s role and as a result unable to provide any feedback on performance other than commentary on most recent observations along with some hearsay from other team members. Employee is uncertain of standing at company and unsure if they’re doing the right thing. Overcompensates by keeping busy and working long hours, hoping that will secure job standing. Unfortunately, they’re seen as working hard but not smart.
  10. Employees are provided with books and links to articles about important concepts, frameworks, and ideas that have been helpful to leadership with the expectation that they’ll absorb the same value. When nobody seems to have caught on or nobody has seem to have read the material, they are seen as unmotivated and faulty hires.

In writing these out, the recurring themes are so palpably apparent. So much of the mistakes made in running a team and working with people comes from incomplete and careless communication, where we fail to provide full context or go the extra step and outline the expectations with clarity and details.

The expectations themselves are also an issue–too often they are either unrealistic or not really thought out. A surefire way to set someone up to fail is to have expectations that they’re unlikely to meet.

Impossible to Eliminate, Work to Contain

Even when reflecting on the past few weeks, I can recall a handful of moments where I’ve set up to fail, failed to set up. I don’t think it’s possible to ever escape or completely eliminate such situations. There will always be instances where I could’ve communicated more clearly, supplied better information, had more realistic expectations, and been more empathetic.

The key then, is to contain as best as possible. Keep debriefing and raising awareness whenever I do fall short and take a bit more time whenever I interact with or involve others in some sort of initiative to fully communicate what I’m thinking, why I’m thinking in such a way, and doing my best to align on expectations that work for everyone involved.

Set up to succeed, succeed in setting up.


  1. Peter, I really enjoyed this. Thanks for sharing. As a small, newer agency, I, as the founder, have been primarily focused on scaling. I find that after reading all of your key points here, I am guilty of many. At least now I know what I must work on.

    By the way, if you have any advice you would offer younger leaders of new agencies, I would appreciate it so much, you have no idea!

  2. Ran Jaden Cao says

    I second what Dillon said above. Truly appreciate your points here as a founder of my own little practice!

  3. N. Dunn says

    Great article! I wish I could share on LinkedIn, much-needed wisdom here. I found your blog while looking for helpful additions to the notes I am taking while reading The Fifth Discipline.

  4. Daniel Frumhoff says

    Excellent article and super insightful! Can relate to a lot of these and totally agree! Set up is the foundation. Thanks for sharing.

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