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My biggest career failure.

Being thankful for the biggest career failure of my life

🤔 I have never viewed myself as a great leader (I wish so much that I was one).

I’d like to share one of my largest failures of my career.

I know my weaknesses well (too many sleepless nights internalizing and beating myself up over them).

– I have a lot to learn.

– I have learned a lot, but not enough.


I saw a post today on LinkedIn about leadership and it inspired me to share this leadership moment.


This story is real and it was a massive failure on paper, BUT it’s something I’m VERY proud of and I learned more than any other single moment in my career.


I was hired by an agency to come in and as one of the owners put it, “save the agency.” And to this ownership group’s credit, they saw the writing on the wall years before the agency was to go bankrupt.

The agency was a good size, but needed to re-invent itself.

It was built on services that were no longer were valid at the time.

I was replacing someone that the owners felt was a failed leader (but I would later find out was deeply loved by the entire team).


So right off the bat, the majority of employees had a negative view toward me before I even stepped in the door.

I was replacing a loved manager, that had fallen out of love with ownership.

On top of that (what should have been a red flag), ownership did not speak well of this individual, and moved him into another department upon my arrival (a demotion).

So not only does my new team highly dislike me, this individual (not disgruntled), is still around speaking negatively every. single. day.


However, I gained favor quickly with the ownership group by suggesting some administrative changes and process re-organization (bringing money in the door sooner from clients).

And over time I began to try and build rapport with team members.

In hindsight, I felt good about it, but it was never enough.


My approach will always be to take care of the people, and the people will take care of the business.

However, roughly 3 months in – as I’m setting my plan in motion to re-build the team’s confidence and put them into a place where every, single individual felt empowered – I begin to learn that the ownership group had a completely different view.


You see, this ownership group believed the exact opposite.

In their eyes, we needed people that put the business first. The business was the most important thing and if an employee’s views didn’t align with this simple, yet complex view, this WAS the problem that needed to be solved.


The next 5 months were then the hardest of my career.

I began to try and solve for all situations.

I wanted to create a new, positive culture (empower employees, create a great work/life balance, put client view top of mind first and foremost, and more) at the same time the ownership group was pushing me to put the business first (replace employees that don’t walk the line, deploy strict employee policies, and push their agenda).


The two didn’t mesh well.

I failed at almost everything I was doing. I was spread too thin and failing both the employees and the ownership group.

And around month 6, the ownership group began to talk with employees directly. The were asking about my effectiveness and if I was being successful in their eyes.

They were also talking to the individual I replaced who continued to discredit and poison my efforts.


The environment of cynicism, closed door whispers, and gossip was winning vs. my efforts to employ a positive, empowering, and employee-first culture.

I had failed.

  • I failed to communicate the benefits of a new culture
  • I failed to show how an employee-first approach helps the business
  • I failed to build trust with my team members
  • I failed, I failed, and failed more in so many ways (that this list was actually 20 different items I paired down)


Over the next 2 months the ownership group continued to sow dissent, the individual I replaced continued to sow dissent, and it was over. 

I had a last ditch effort to try and create a new agile program/project management workflow (the agency needed it), but I was fighting so many fires with so many individuals all round me that this workflow (that should have been in place 2 weeks from inception), wasn’t ready 2 months later. That was the failure needed to break my contract and fire me.


So why is this massive failure something I’m deeply grateful for?

  1. People-first is the right approach: When I was let go, the very first reason stated was “I didn’t put the business first, I was too busy worrying about the employees… I didn’t care about the business enough.”
    • They were right; and I’m ok with this. I failed to drive my approach and management philosophy home with everyone. I didn’t get everyone on-board with this approach before I walked in the door. I believe in empowering my teams and letting them run things. I believe in frameworks and workflows that support this approach. And I haven’t been the best at managing to this in the past – that’s something I’m working to get better at. And I value the experience of going through this.
  2. I was so excited and prideful about being the savior of something that it clouded my judgement.
    • What a huge lesson learned on so many levels, eh? What a lack of humility I held. To think I could just come in, ignore (and be naïve) to company history, ownership disposition(s), and the plight of the individual I was replacing. To think the team would just love a new culture and not considering the environment of incredulity that was so intoxicating! I was too prideful and appreciate the experience/realization as it has helped me grow as a leader.
  3. I am not alone: When things were going well at the beginning, everyone was in sync. The principal owner said to me, “You’re doing great things here! You’re going to make this company great” at a team gathering; this was 3 months in. He was the lead speaker at my firing. 
    • As things turned sour, I felt the walls closing. I think a great leader might have pivoted, re-won hearts and minds, or do a plethora of things differently to not fail. I didn’t do those things. I thought my actions would win the day, and alone I could show the way. I wasn’t working in a box by myself, I did select key individuals on my leadership team to try and push my new agenda… but over time my actions were more solo vs. team-based. I’m thankful to learn that being a leader is more than I can do alone and is a team-based sport. 
  4. So, so, so many more lessons. Again, I had a list of ten things or so, but I think I’ll just say this: 
    • I don’t blame anyone but myself (nor should I). I wasn’t good enough. At times I didn’t communicate well. I did too much to satisfy everyone and got lost. I was prideful. And more…  And I’m grateful for this experience.


So what happened to this company? 

They struggled for many years thereafter.

At one point I learned that the individual hired to replace me had formed his own coup with another VP hired (against the ownership group). The two of them tried to purchase the company out right.

I don’t think that worked, as later the original ownership group was fishing for a suitor to purchase it.

I’m not sure the company exists anymore (as of 2024). Nor am I happy that it might not exist… I think we had 50-ish people employed at the time I was there. Those are real people with real needs that an employer provides.


Even though my hair went from dark brown to silver during these 9 months – I harbor no ill-will toward the employees, the individual I replaced, nor the ownership group. 

I failed them.

I’m sorry that I failed them.

I’m thankful for the lessons learned and experience gained.

But I’m sorry I wasn’t able to turn the company around…


It still haunts me till this day.



– Jeremy Riley

Follow Jeremy on LinkedIn »



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