The Satisfactions of a Small Business Owner

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I’ve been running a small business for the past 16+ years, and in that time, my relationship with the business has evolved quite a bit. One way to reflect on this evolution is to share the things about the business that please me and bring me joy. I’ve compiled a list of five “satisfactions” that have energized me and kept me going with the business.

Satisfaction #1: An Impactful Hire

I don’t think I can ever tire of the feeling you get when you realize you’ve brought on an impactful hire. But the satisfaction isn’t something that comes right away. I’ve learned to be cautious about gauging the impact of a new hire. Some people make great impressions at the start but can have performance and/or cultural fit issues as they start getting deeper into the work and collaboration with team members. Others may struggle at the beginning and even cast some doubt on their hiring but with the right conversations and even adjustments to their role, can turn into superstars who lift up their team members.

Whether it takes a quarter, half a year, or even a year-plus, there comes a time when I can reflect on a person’s hiring and confidently make the call that they were high-impact and someone whose contributions to the team are unmistakable. Make enough impactful hires in a consistent manner over a few years and it’s inevitable that you’ll have a high-performing team that achieves great results. On the flip side, go a long time without making impactful hires and it’s possible that the team’s performance and overall culture may suffer.

While I believe that an organization should do everything it can to provide support and clear feedback for people to improve, I also believe an organization should move as quickly as possible to part ways with underperformers / poor culture fits in order to make room for a potential impactful hire. It’s hard work and requires tough decisions, but failing to move quickly will drain the org of talent and momentum.

Satisfaction #2: Client Account Growth

Being in the professional services space, we pride ourselves in delivering exceptional client service and impactful work that help our clients grow their businesses. One of the hallmark satisfactions is seeing our clients’ businesses take off, and with it, seeing our relationship with them grow in meaningful ways.

One of our longest-tenured and largest clients first started as a low-budget redesign project. We lost money working on the initial engagement, but we poured our heart and soul into the design and build of the website. The client kept us for ongoing work, and gradually, over time, they began to grow. Eventually, they were acquired by a public company and scaled up further. We were retained and became an even more integral part of their business, essentially their product team. Reflecting on this relationship gives me great satisfaction. My only regret is that we failed to develop more such relationships during the same time, but that’s where the opportunity lies as we continue to nurture and grow more client accounts.

Satisfaction #3: Improving from Mistakes & Lessons Learned

One of our oft-repeated maxims at Barrel is “turn setbacks into opportunities.” We’ve had our fair share of setbacks and continue to experience challenges on projects and in the course of collaboration with team members and clients. I get immense satisfaction when, as a team, we learn from our mistakes and implement new processes and procedures to avoid making them in the future. To see the team in action faced with a similar challenge and expertly dealing with it is very rewarding, and also a sign that we’re expanding our knowledge and level of skill.

There are times when we end up making the same mistake even after having identified and discussed it as a team. It’s hard not to feel disappointed or upset when this happens, and it’s the reason why we’ve invested a great deal of time and effort to having project debriefs, the writing of standard operating procedures (SOPs), and frequent account check-ins with executive sponsors.

Related: Check out the Seven Learning Disabilities from The Fifth Discipline – I wrote about this several years ago and still reference the learning disabilities periodically to remind myself that it’s easy to keep ourselves from being a learning organization.

Satisfaction #4: Learning from New Approaches & Experiments

The opportunity to try new things with the business is something I truly cherish. Whether it’s testing out a new services offering, pricing our services in a different way, or tweaking the way we handle performance management, there are countless new processes, policies, techniques, and other experiments that we can run and learn from on a regular basis.

For me, a big learning over the years has been to find the balance of pushing for new approaches and experiments while giving things time to take hold and give us actionable insights. For example, experimenting with and rolling out new software tools to improve collaboration has opened my eyes to the challenges of replacing existing behaviors and getting buy-in to new processes. It’s often a slow and gradual process that requires patience.

I’ve also come to accept that new approaches and experiments can be failures and that it’s okay to cut losses and admit that something wasn’t a good idea. A couple of years ago, I championed a pod structure for our agency that was met with skepticism, especially by our project management team. I had been inspired by a much larger, successful agency that touted the beauty of their pod structure for resourcing, so I thought we ought to give it a try. With little buy in and immediate challenges the moment we rolled it out, it wasn’t long before I saw the writing on the wall – after a few months, we scuttled the pods and went back to discipline-based resourcing. It wasn’t a great feeling, but I learned from the experience.

Lastly, prioritizing and identifying the highest leverage experiments is something that’s become top of mind for me. My filter has grown stronger in weeding out activities that are merely incremental and not worth the effort involved. I’ve also become better about keeping the number of concurrent experiments and new initiatives manageable–anytime the list becomes too long, it’s immediately clear that we’re not gonna get much done, so our time should be spent in culling and focusing our efforts.

Satisfaction #5: Hard Conversations That Pay Off

Having hard but necessary conversations is akin to eating your veggies or getting in a tough leg day workout – it may not be pleasant but it’ll most likely be good for you. The hard conversations that pop up again and again in my line of work is around performance. Anytime an employee is not meeting agreed-upon expectations or behaving in ways that detract from the success of the team, it’s imperative that someone, usually the direct manager, has a 1-on-1 to address the issues.

When it comes to these types of conversations, there are typically a few other things going on in the background before a 1-on-1 happens. The manager needs to feel certain about the performance issues, which requires a combination of direct observations and feedback from peers and other team leaders. This takes time and cooperation from others. The manager may also be someone who is hesitant to have conversations around performance. This means the manager’s manager has to be involved and provide coaching and support to ensure that the proper conversations happen. In certain instances, the manager and the manager’s manager may both need to be present for the conversation with the employee in question. And then there is the question of follow-ups, documentation, and any accountability measures that need to take place. Will the employee be put on a performance improvement plan? Will the employee be given some kind of warning? How will things be documented?

In a small business like ours, it’s possible that a lot of these activities happen without a dedicated human resources team and instead, it’s the executive leadership team that’s providing guidance. Either way, we prefer that hard conversations happen as quickly as possible so we can address issues before they fester. The satisfaction comes when the conversation happens and we have greater clarity on what happens next: the employee has a path to improving performance and shows changes or we decide, with ample data, that it’s time to part ways. The pay off is in knowing that we don’t have to deal with recurring complaints or uncertainties about someone’s performance.

The Things That Matter Less Now

I cared about different things in my earlier days of running a business. Here’s a small sampling:

  • Headcount growth: I loved adding more people to the team and being able to brag about how many people worked for the company. The greater the year-over-year growth, the more I could brag to others outside the company.
  • Cool projects: I was easily bored by doing similar things again and again, so I invented internal projects to keep myself engaged while paying less and less attention to the work that were “paying the bills”; my belief was that doing cool projects would also allow us to retain better talent, but many of these cool projects quickly lost steam when I personally lost interest or when the client work got too hectic.
  • Pedigreed employees: I was enamored with hiring folks who went to “good” schools and worked at “prestigious” companies even if there were clear flags during interviews. The thinking was “if they’re good enough for X, they’re good enough for Barrel.” Over time, I realized that what mattered more was the actual substance of the candidate’s experience, their attitude, and their overall fit with the role they were interviewing for.
  • Employee perks: I over-indexed on providing employee perks as a way to “keep people happy”. We provided free lunch daily, stocked up on booze, had tons of happy hours, and had all kinds of social activities in an attempt to “develop culture.” I’d learn over time that a truly effective way to keep people happy was to provide engaging assignments, ongoing coaching with career development, and the tools and effective team members to be productive.

Taking Pride in Small Business Satisfactions

There was a time when I used to feel very insecure and dissatisfied with where I was as a business owner. A big part of it came from feeling like we weren’t scaling up fast enough as a business and stuck at a small size. What impact could I possibly have with a team of a few dozen working on not-so-glamorous web projects? I was perpetually in glass-half-empty mode and envious of those who had grown to manage huge teams with large corporate clients.

But thankfully, over time, as I read more about business while also writing and reflecting on my role, I came to see that I had a lot to work with and a perfectly fine canvas to practice the craft of business. Regardless of company size, I realized that I had the same type of people challenges as any CEO and I also had my own set of customers to take care of and bring value to. There was no upside to feeling sorry for myself that I wasn’t playing on a bigger stage. I could still take pride in trying to be good at business and to be a good leader with the business I had.

The mindset switch has been very productive–it’s helped me to focus my energies on what I can control, and in turn, I’ve become more confident about my own abilities and potential. I’m completely okay if others are quick to dismiss me for being small-time or not getting to a certain size in all the years I’ve been in business. I’m immensely grateful that I still get to play the game every day and show up to work full of energy and ideas. That’s priceless stuff that I’d be hard-pressed to give up or trade with anyone else.

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