In 2022, I decided to take the leap and build a team.
And so I did… but I failed.
Why I Thought It Was Time to Build a Team
Over my 10+ years in business, building a team was the last thing I wanted to do. Managing and being responsible for people’s livelihood was not something I was interested in. No thank you.
But then in 2022 something changed.
Suddenly, I wanted to step away from tech work. Don’t get me wrong, I really enjoy programming and building useful tools for companies. This change of heart had to do with movement (as in physical movement) more than anything.
My body finally grew tired of sitting and standing in front of a screen all day. It reached a point of inquietude.
Quitting my business wasn’t an option. It was my principal source of income and I still had active clients and projects.
So, after a lot of thought and prayer, I decided building a team was my way out.
If I spent the next few years building a brand that reflected a solid team, then I could eventually replace myself little by little. This would turn my business into a real asset.
So, the decision was clear. It was time to build a team. Little did I know that this leap would come with challenges I hadn’t anticipated.
There are 3 snowballing mistakes that caused my venture’s demise over a span of 2 years. It’s time to vent and share these lessons with you.
Mistake #1: Underestimating Personal Effectiveness Skills
As soon as I made the decision, more work came my way — I took this as a confirmation and went ahead and made my first hire: a junior developer.
Honestly, I didn’t have much of a plan regarding onboarding and training. My plan was to figure it out along the way — this was the beginning of my first mistake!
I underestimated how skills like time management, learning speed, and work integrity (meeting deadlines) wouldn’t be guaranteed in a new hire.
These things became challenges very quickly. I had to develop a lot of processes to smooth these things out.
For example, at the previous company my junior dev worked for, it was normal to miss client deadlines. It’s like that in many companies — they overpromise, underdeliver, and constantly deliver work late — but that’s not the way I roll. So, it baffled me every time he was so relaxed and chill about missing target dates for a timeline he set himself with a client. Not good for business!
It’s no wonder why so many teams use daily stand-ups, time tracking, and sometimes annoying project management tool features. It’s really about accountability.
All of this comes with the territory of building a team. This is the kind of stuff I avoided for years. It’s the hard work of every team builder.
Just to be clear, I don’t think I was being unreasonable about expecting deadlines to be met along with some healthy level of resourcefulness in learning things quickly — this is what being a developer means!
Things eventually became clearer to me (more on that later).
This first mistake was two-fold, made before I even started hiring:
- Not having a game plan with clear measurable expectations.
- Not knowing how to discern personal effectiveness skills prior to hiring.
While I was grappling with onboarding challenges, I realized another issue.
Mistake #2: Hiring in the Wrong Order
At some point, I read a book named ”Buy Back Your Time” by Dan Martell. It was eye-opening.
Dan has a philosophy on what he calls the “Hiring Ladder”. He teaches that you should replace yourself in administrative work before anything else.
He stresses that every business leader’s first hire should be an Executive/Administrative Assistant. That way, the leader can use their time and energy in tasks that require more specialized skills and knowledge. For me, that was sales and programming.
This made a lot of sense to me, since the administrative part of my business was suffering. I couldn’t keep up with my workload while managing/teaching my junior dev and cleaning up some of his code every so often.
So, I pulled the trigger and hired an assistant.
Now, I was managing two workers. More of my time went to ramping up my assistant. My junior dev struggled to keep up with the workload and pace.
Eventually, too many deadlines were being missed and I couldn’t keep up with the level of attention my junior dev needed. I let him go and kept the assistant.
Side note: My ex-junior dev fully expected me to let him go and was surprised it took me so long. He knew he wasn’t performing well for months and may have been too green in some ways. He’s a good guy and found himself a more compatible job in which he’s thriving. I’ve continued to mentor him whenever he needs advice.
Once my assistant and I developed daily, weekly, and monthly rituals for her admin tasks, she blossomed and made my life easier. The return-on-investment was solid and she was way more affordable. What a win.
This confirmed the fact that I hired in the wrong order. I’m not saying this is the case for every business owner, but it for sure was for me — a freelancer/consultant who wore all the hats and beanies in his business.
Mistake #3: Prioritizing Cost Over Experience
There’s another team member I haven’t talked about. He’s been with me for over 5 years now and works part-time. He’s almost a decade older than me, highly skilled and has loads of experience. I pay him a lot too. His expertise happens to be in the kind of work I don’t like to do.
And guess what? He’s extremely low-maintenance. We can go months without checking in with each other — yes, as in zero meetings.
This was night and day compared to working with the junior hire. When we parted ways, his feedback was that he felt he needed more of a team environment with frequent huddles and team coding sessions. In retrospect, this makes total sense. It was his first time really developing more complex solutions.
I had expected him to have all the essential skills of self-management, but then again, those skills come with experience and years of practice, challenges, and completing projects.
And so this tied everything together for me. It was evident that when hiring for a technical position like this, it would have been better for me to invest more money in someone more experienced like my part-timer.
My mistake was underfunding that position. Couple this with the other two mistakes and it quickly became a snowball effect I couldn’t manage for more than a year and a half.
Back to Basics: The New Game Plan
I’ve gone back to what I know: freelance software development. These days, I’m laser-focused on building custom solutions for growing e-commerce brands and retailers — simplifying complex workflows is what I do best.
Note: If you own or work for a growing e-commerce brand, let’s talk! Feel free to check out my LinkedIn.
The learning experience of taking steps to build a team cost me a lot of time, money, and energy. I’m sure the venture earned some greys in my beard.
Going forward, I’m taking more of a hybrid approach. I’ll scale a team whenever it makes sense to.
I’m keeping an assistant but when the time comes to hire for a highly technical position, I’ll make sure to save up more money and hire someone with more experience — that is the main takeaway (from many) for me.
If I want to manage less, then I need to hire people with more experience. And to do that, I need to have more funds, work, and cashflow.
Whether you’re running a business or working solo, the lessons are universal: plan before you leap, invest in quality, and know when it’s time to pivot.
Is It Wisdom or a Cop-Out?
A part of me feels like saying “managing people isn’t for me” is an excuse to not do the hard work. Another part of me feels like there’s wisdom in knowing when to quit versus when to stick (shoutout to The Dip by Seth Godin).
Quitting for the right reasons requires a healthy level of humility — it can end up being the bigger win in the long run.
What do you think?
Would you have kept pushing through? Or would you have quit while you were ahead?
Looking forward to hearing/reading your thoughts.
Luis
PS – This newsletter is longer than usual — a lot has happened! We’ll return to our standard Coffee Talk format length after the new year.