18 Surprising Hurdles to Business Velocity: Lessons from Entrepreneurs

One of the toughest challenges to scaling quickly was finding out that hiring more employees would slow us down initially. In response to the growing client demand over a period of just two months, I hired three additional SEO specialists with the assumption that having more employees would allow for faster project completion. Instead of faster completion, however, we experienced a communication breakdown in regards to how to strategically develop links between accounts. The three new employees developed their own interpretation of our link development standards, resulting in inconsistent content briefs from one employee to another. Ultimately, our clients noticed the decline in quality, and the turnaround time became longer as opposed to shorter.

By putting hiring on hold for 90 days and developing our own internal systems first, I was able to address these issues. All of our processes were documented in detail. A centralized knowledge base was also developed that contained all of the information we had gathered. Four months later, we saw an increase in our delivery speed of 40%. The lesson I learned here is to avoid the temptation of growing your team before your systems are built. Develop your systems with great attention to detail, document everything and ensure that each member of your team has the ability to perform tasks in the exact same manner as their teammates.

One unexpected challenge was discovering that speed exposed ambiguity faster than it exposed technical limits. As we tried to move faster, delivery did not stall because people lacked skill or effort. It stalled because decisions were unclear. Teams moved quickly in different directions, solved the wrong problems efficiently, or waited for confirmation that should have existed upfront.

Velocity amplifies whatever already exists in the system. If priorities are fuzzy, speed turns that fuzziness into churn. If ownership is unclear, speed creates conflict. We learned that adding tools, process, or pressure did not fix this. It made it worse.

We overcame it by slowing one layer down on purpose. Not execution, but decision making. We forced clarity before work started. What problem are we solving? What does success look like? Who decides when tradeoffs appear? We wrote these things down in plain language and revisited them often. That removed hesitation later. Once teams knew the direction and boundaries, execution accelerated naturally.

Another adjustment was limiting parallel work. Trying to do everything at once feels fast, but it fragments attention. We reduced active initiatives and focused on finishing fewer things completely. That created momentum and restored trust in delivery.

The advice I give others is simple. Do not confuse motion with progress. If velocity feels hard, look for hidden ambiguity before you look for better tools or tighter timelines. Speed comes from alignment more than urgency. Clear goals and clear ownership do more for speed than any deadline ever will. Velocity is earned through clarity.

An unexpected challenge we faced when we were trying to speed up our growth was software compatibility. We aimed for high velocity in our onboarding processes for small businesses, but we hit a wall: clients were using all kinds of platforms to run their stores, Shopify, ShipStation, Easy Ship, to name a few.

Our growth was stalling since we were spending weeks trying to manually get our shipping rates to talk to each client’s specific software. It was as if we were becoming an IT Partner rather than a Strategic Shipping Partner.

To overcome this, we built our “Self-Setup Library” where we have simple, easy-to-follow guides for the top 5 platforms our clients use, allowing clients to connect their own system in minutes without our help, giving us the time to save them money.

My advice to others who are stalling in business growth would be: don’t just look at your own product, but also look at what your clients are already using. If your product can’t plug into your client’s existing tools easily, that integration step is your actual bottleneck. Standardize it early, or it will strangle your growth.

When I confess to people that the biggest obstacle that I faced in increasing my own business velocity was myself, they tend to laugh, but it’s the honest truth. As I moved from QuickMail to building and growing out MonsterOps, I realized that I was trying to oversee every single bit of detail or at least as much as I could.

And that meant that the whole company was waiting on my “158 open tabs” to get cleared. I ended up overcoming this by implementing a “Scorecard” system where the team has clear numeric goals they are accountable for. And that essentially gave them the permission to move forward without me having to approve every little decision.

The result was a massive spike in velocity because we stopped having bottlenecks at critical junctures. If you really want to move fast, you should be willing to be the person who doesn’t make all of the decisions.

Initially, a major obstacle for us in achieving a greater business velocity was that the marketing department had scaled faster than the sales team could handle. Marketing was generating more leads than sales could properly process. Instead of growth, we ended up with overworked sales reps, inconsistent follow-up, and lost opportunities.

To fix this imbalance, we needed to align both teams to the same weekly priorities and adjust our capacity for each department accordingly. To begin with, we slowed down the volume of leads being sent from marketing to sales, while the sales team began ramping up their employee headcount and improving their internal processes. As both teams synchronized and began operating at the same rate, we noticed a natural increase in velocity and an increase in conversion rates.

My recommendations: speed only works if all the departments are scaling at the same rate. If one team outgrows the other, you are going to lose momentum. To maintain tight alignment, conduct regular reviews of capacity and ensure that every department is capable of keeping up with the rate of business velocity that you want to achieve.

One of the most challenging realizations was that I had become the key bottleneck in our agility. In the early days, I was involved in every single aspect of the business, including product designs and email copy. I tried to keep the same involvement as we attempted to increase velocity, believing it to be the best way to keep quality high. In reality, projects got held up waiting for my approval, and my team became reluctant to move forward without my sign-off.

I needed to transition from the control model to the context model. I stopped signing off on every minor detail and instead concentrated on providing fit strategic objectives and enabling frameworks. We created a system where the leads of the teams were given complete control and responsibility over their budgets and KPIs.

Business leaders need to audit their level of involvement regularly. If your team is waiting on you to act, you are not leading. You are blocking progress. To be able to prioritize and allocate tasks efficiently, I have started a “Not to Do” list, which serves as a constant reminder of responsibilities I need to let go of so that others can take control. Actual velocity happens when leaders of the organization trust their employees enough to make decisions when they are not in the room.

When trying to increase my business velocity, I realised that our messaging across channels was inconsistent. Employees were writing emails, social posts, and conducting outreach in their own styles. While nothing was widely off, these slight differences added up, and the message wasn’t as clear as I would have wanted.

This was something I needed to fix, so I called a meeting to get everyone on the same page about the problems we solve, why they matter, and how we solve them. We created shared resources and set up automation that changed based on where the prospect was in the funnel.

My advice is to keep your approach simple and consistent so it’s immediately apparent when something is confusing, and you can then iterate on your process to fix it. The less friction there is between teams, the faster everything moves. While it might feel easier to say more, every message should help your prospect better understand you.

Unexpectedly, I realized that trying to increase the speed of my business was not just a matter of demand, but also because of internal delays we hadn’t even noticed. I noticed that an increase in lead volume sales activities, scheduling, and installations was not aligned, which caused delays, miscommunications, and led to a differential customer experience. From one perspective, it looked as though we needed to increase our marketing efforts; however, the real problem was operational delays.

By taking a step back and looking at the entire customer experience, one system at a time, we were able to shift our focus to the customer journey and the process from the time the customer made the first inquiry to the time the installation was completed. This made it possible to establish in which areas changes in the system were needed to ensure a smooth customer transition from one system to the next, and to make definitive decisions. Our focus was on process standardization, clarifying responsibilities, and implementation of a new adequate system that allowed faster movement of the teams from one activity to the next. They were able to coordinate their efforts and the system finally started to function as a smooth internal flow (and) steady activities, which led to an increase in the turnover/sales of the business without burning out the teams or compromising on the quality.

To make it possible for the system to operate at the desired speed, not just working at a business without purpose, my advice is to shift focus from trying to create new demand to looking at the system to identify and eliminate delays. There is internal demand. If the business is busy, but the sales are not increasing, it is necessary to streamline the work, focus the teams around a desired business target, and eliminate obstacles in order to create a platform that allows the business to operate at the desired speed. Good quality of work is a function of a good system.

One challenge I didn’t see coming was that moving faster actually slowed us down. Strange, right?

About five years ago, I was managing multiple client projects and thought the solution to our growing workload was simple, just work quicker, skip some documentation, and push code faster. We’d circle back and clean things up later.

Within a few months, we were drowning. Small bugs kept resurfacing because nobody remembered why certain decisions were made. One client’s tracking implementation broke, and we spent days debugging something that proper notes would have solved in a couple of hours. Even onboarding a new team member took twice as long because everything lived in someone’s head.

The turnaround came when I (and obviously my team) forced our process to slow down intentionally. We started spending the first 15 minutes of each project day on documentation, nothing fancy, just a shared doc where we logged what changed and why. It felt counterproductive at first, like we were losing momentum. But within a couple of months, our actual delivery speed improved significantly. Fewer bugs made it to production. Client handoffs became smoother. The team stopped interrupting each other with “how does this work again?” questions.

My advice: if you’re trying to increase velocity, resist the urge to cut corners on communication and documentation. The fastest teams I’ve worked with aren’t the ones typing code the quickest but the ones who rarely have to fix the same problem twice.