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Rookie Mistakes 101: Not Delegating

I shared my thoughts on people’s bandwidth the other day. Today, I want to elaborate on this a bit. I neglected to mention another tactic that helps founders get more done: delegating. It’s something I struggled with early on. Lots of other first-time founders do too.

Early founders often think they’re the only ones who can do something right. It’s the “if I don’t do it, it won’t get done right” mentality. The opposite is often true. Early founders are generalists: to get the company off the ground, they have to know how to do everything. They’re usually just okay at most things—meaning someone else can do them better. Most don’t recognize this, though, and are reluctant to give something up. They won’t let go until they’re forced to.

As I encountered new challenges, I rose to the occasion. I grew. And I learned to delegate. I thought through the best uses of my time and what others could handle. If a task wasn’t a good use of my time and someone else could do it, I’d train them and turn it over to them. This usually meant accepting that they were going to make mistakes at first and that they probably wouldn’t do it exactly the way I did it. This was hard at first, but I got over it. In the long run, it empowered our team and allowed me to focus on the things that mattered most. It increased my bandwidth—and the company’s, too.

If you want to be an entrepreneur (not a solopreneur), delegation is important. The quicker you embrace it, the quicker you allow yourself, your team, and your company to grow!


Making Better Decisions by Removing Emotion

One of the things I had trouble with for a long time was making a personnel change when someone wasn’t a good fit for their role. Once I hired someone, I’d invest time getting them up to speed and getting to know them as a person. When goals weren’t being met or performance wasn’t up to par, I struggled with what to do. The data and other facts were telling me one thing and my personal connection with the person was telling me something else. In most instances, the personal connection prevailed—often to the detriment of the team member.

Looking back, I was prolonging the inevitable. Most of these team members were great, smart people; they just weren’t good fits for the roles they were in. The more we tried to pound a square peg into a round hole, the more frustration swelled on both sides. When I recognized this and made a change, things started to go better for them and the business. Sure, there was short-term discomfort, but they transitioned to a position they were better suited to (with CCAW or another company).

I see now that my emotions have sometimes hindered me from making tough decisions. Subtracting feelings from the process is difficult. It requires taking a situation at face value, deliberately ignoring what you’re feeling, and reaching the appropriate decision. That’s no easy task, especially when the decision affects others and isn’t popular.

This is something I’ll probably never master, but I can aim to get better at it. I do a better job now of identifying when it’s happening—the first step. When I think it is, I get input from credible people (sometimes writing down my decision-making process and sharing it) before making a decision.


Michael Jordan Wasn’t Good Enough

As I was talking with a friend about mental toughness, he mentioned “The Last Dance” documentary about Michael Jordan a few times. I hadn’t watched it, and my interest was piqued even though I usually read in my downtime. (Side note: I share a birthday with MJ, so I’ve been a fan since childhood.) Today I watched some of the documentary. I was impressed. As can be expected when someone is striving for greatness, he had many behind-the-scenes struggles that most people never saw.

Jordan was the best player in the NBA in the late ’80s and early ’90s. NBA Scoring Champion, Defensive Player of the Year, All-Star . . . he won pretty much every individual accolade. Yet his team had yet to make it to the NBA finals. The strategy was to get MJ the ball and he’d make something happen. It worked, but it wasn’t enough to win a title.

The Bulls changed coaches and the strategy started to change. The legendary Phil Jackson wanted to play a triangle offense, but Jordan wasn’t a fan of it. He was used to having the ball, and Jackson’s offense would take it away from him. The triangle offense involved moving the ball around to everyone in a strategic manner, giving everyone a variety of scoring opportunities. Jordan reluctantly embraced it and they made it to the NBA Finals the next year, 1991. In game five, instead of forcing shots, MJ repeatedly passed to his wide-open teammate, John Paxson. Paxson rose to the occasion each time and lifted the Bulls to a victory and their first NBA championship. This game was pivotal in many ways. Most importantly, Jordan finally learned to appreciate team ball.

After the title win, Jordan focused on becoming a better leader. He was determined to win another title. He realized the Bulls could be great with team ball—and they could be elite if they all consistently played at a high level and with a high level of confidence. Jordan focused on making his teammates better. He led by example, giving 100% in every practice and demanding the same from his team.

The Bulls went on to win six NBA championships in three-peats in ’91–’93 and ’96–’98. Many still consider Jordan the best player of all time.

Jordan was an incredible player for many years. But in my opinion, when he started focusing on leading by example and making his teammates better, that’s when he began to achieve greatness.

Teamwork is dream work!


Preparation = Effective Meetings

Lately I’ve been looking for ways to have more efficient meetings. Especially with new entrepreneurs. I’m spending half our time trying to understand what problem they’re solving and how their product or service solves it.

At CCAW, I held weekly one-on-one meetings with direct reports. My days were full, so I kept them to a strict 30 minutes. I spent most of that time peeling back layers and asking questions that would get the other person to reflect on what they wanted to talk about. That meant that the meeting was almost over before I understood what we should be talking about. In the end, the meetings were of little value.

Over time, I started using software to help. The day before each meeting, the software prompted my direct reports to answer these questions:

  1. What have you accomplished since the last time we met?
  2. What roadblocks have you encountered since we last met?
  3. What do you plan to accomplish before our next meeting?
  4. What are you most worried about today?

If they didn’t answer them, we wouldn’t meet.

This was powerful. Their preparation made our meetings more effective. They could see their previous responses, including what they’d committed to being responsible for. Formulating their answers required reflection and planning and instilled accountability. All of this made our meetings richer.

My own preparation was equally as helpful. I reviewed the answers beforehand. I compared actual accomplishments to planned accomplishments and made a point of discussing gaps. I set expectations and helped my people prioritize. I learned about challenges early and was usually able to address them before they turned into bigger issues. I went into each meeting ready to discuss the things that mattered most to that person and to CCAW’s objectives. The tone of my meetings changed, and people looked forward to them.

Consider preparing for your meetings more effectively and asking or requiring (depending on the context) the other person to do so too. Your meetings will be more productive and helpful.


Don’t Assume. Verify.

I once listened to a founding executive of a publicly traded Atlanta company speak. Bob helped scale the company from a five-man team to an IPO with thousands of employees. He was sharp and reminded me of a startup founder. He always believed the impossible was possible. When asked what the secret to his company’s success was, Bob said his team didn’t blindly trust anybody or anything. Their motto: “prove it.”

As it scaled to an enterprise-size organization, his company was pitched tons of products and services. Often, when he asked why ABC product or XYZ service was the best, the answer was, “All the big companies are using it.” This never made any sense to him. His team learned to give that rationale zero weight. They tested everything to find out for themselves if it was the best. Often, they found that big companies were not using the best—far from it. They’d find competitors with superior offerings. And knowing the shortcomings of other companies gave them insights on how to differentiate themselves to customers.

This approach ultimately produced their competitive edge. Bob and his team did the tedious grunt work of vetting everything that underpinned their technology. Their competitors had chosen the lazy way, piggybacking on big companies’ decisions. Over time, using the best of the best made Bob’s company’s platform lightning fast. Once customers discovered how fast it was, the company developed a cult following.

My big takeaway from his story was to trust but verify. You can’t lean on someone else all the time. You have to dig in and put in the time yourself.


Contrarians Make Groups Better

I tend to be a fact-driven independent thinker. I enjoy hearing different perspectives, though, and I’m happy to be persuaded by sound logic. Today I had two great conversations about group decisions that got me thinking. How do you get the best decisions from a group?

Groups of credible people are powerful. They can make great decisions. Each person brings a perspective shaped by their unique experiences. When they share it, everyone else glimpses the world through their lens. Incorporating the views of disparate people produces a better, more comprehensive decision. Will it be a perfect decision? No. Will it be stronger and more cohesive? Absolutely!

I’ve often found that it’s difficult to get every member of a group to speak up. A confident, perhaps dominant, person who shares their opinion early on can sway others too easily and discourage them from sharing their thoughts. Groupthink is the result, and it’s not a good thing. If everyone rallies behind a single perspective instead of discussing different ways of looking at the problem, the result is a consensus decision that is weak.

I’ve read lots about this and I believe consensus decisions can be dangerous. One of the conversations I had today affirmed this. The lack of a contrarian perspective in a group is a warning sign. If everyone sees the issue the same way, the group may be overlooking something material. If they are, the decision they settle on will be flawed and probably wrong.

The next time you’re working in a group and you have a different opinion than others do, let it be heard (respectfully and collaboratively). Even if the group doesn’t agree with you, you’re adding value. You never know—your contrarian view could be the difference between a disastrous decision rooted in groupthink and an amazing one!


The Cycle of Growth, then Efficiency

This past week I talked with two founders. Both of them have wildly successful companies that are still growing. But they told me they’re reducing head count. For most companies, the customer landscape has changed—but for these companies, not so much. They’re still growing at a healthy clip (just not as fast as they were). Even so, I wasn’t surprised. Their need to get leaner is rooted in decisions made during a period of rapid expansion.

Both founders have hired aggressively over the last few years as they’ve grown rapidly. In that scenario, roles can be created without anyone knowing whether they’re needed. I’ve seen companies hire someone to do manual tasks that custom software could handle. The person responsible for the department doesn’t have time to delve into what each person is doing or how they’re doing it. They just know their team is maxed out because of the company’s growth, so they go to HR and ask to add more people. And even if they knew that software could help them, it probably wouldn’t get built. Engineering teams are focused on customer-facing work to increase revenue—new product features, bug-fixing, etc. They don’t have time to consider projects that would make internal teams’ lives easier.

Quality can slip, too. Instead of hiring an A player in a two-month recruiting process, you add a B player because you have just thirty days to fill the role. Over time, the quality of your team falls, which has all kinds of ramifications down the road.

One day you look up and see people who aren’t fully utilized . . . employees without a clearly defined role . . . team members who aren’t carrying their weight.

Both of these entrepreneurs see staff reductions as a way to address these issues. In my opinion, they’re able to consider layoffs because their focus has changed. They know it’s easier to keep a customer than find a new one (especially in this environment). They want to better serve their current customers in order to reduce churn. At this moment, efficiency, not growth, is the goal.

Business is cyclical, and I suspect that despite the pandemic, what’s happening with these companies is part of the normal business cycle.


Helping Others Fill Their Gaps Will Light Their Path

Achieving entrepreneurial success can take many years. Many things make the journey difficult, but I believe gaps play an outsize role. Big relationship, knowledge, or capital gaps can break an entrepreneur. Maybe you don’t know anyone to introduce you to a decision maker in your industry. Or you’re unsure how to recruit the right team members. Or you don’t have the money to fund your growth plans—and don’t know how to go about acquiring it. I want to be clear: all entrepreneurs have gaps—extra-large ones are what I’m referring to.

To succeed, you have to figure things out as you go along. You must find the ideal path to your destination. If your gaps are yawning abysses, you’re looking for a path that’s in pitch-black darkness. But if they’re minimal, the path is lined with bricks and LED lights. You still have to find it and walk down it, and there will be obstacles along the way, but it will be far less difficult and time consuming to traverse.

My gaps were huge when I founded CCAW. I didn’t realize they were, though, until I surrounded myself with others through organizations like EO. I was able to start filling those gaps with their help. It’s still a work in progress, but plugging my gaps gave me a much better chance to succeed.

I’m a strong believer that Atlanta’s entrepreneurial ecosystem can reach the next level. The city has a lot going for it. Let’s help rising entrepreneurs who have big gaps gain the knowledge, build the relationships, and acquire the capital they need. Together, we can help Atlanta reach its full potential!


What Drives My Why?

Last week I taught Intro to Entrepreneurship at Atlanta Tech Village’s Startup Summer School. My session touched on the need to know your why. Since then, I’ve been in touch with a few of the people who attended, helping however I can. This morning I received a Slack message from one of them. He asked a great question: “So what was your why with CCAW, and is it changing as you start your next chapter?”

This entrepreneur’s business is in its early stages but making great progress. He built a working MVP and then signed twenty or so paying customers within a few months of launching. All during a pandemic. He’s on to something, in my opinion.

When I started CCAW, I was a few years removed from being an undergrad. I had some corporate experience and no real responsibilities. A car enthusiast for years, I had automotive parts relationships. As a parts consumer, I knew how difficult acquiring the right part at a fair price could be. In high school and college, I had a company that developed and executed plans to customize customers’ vehicles (think Pimp My Ride). Having worked with parts manufacturers and distributors, I knew their struggles well. My why was simple: I wanted to help consumers easily connect with parts companies. This would help two groups I was familiar with. There was also a financial motivation, but it was secondary.

Now to part two of his question. What’s my why for my next chapter? I’ve thought a lot about this and it’s simple, too: I want to make life easier for entrepreneurs and small and medium-sized business. Especially those with big gaps in knowledge, relationships, or capital. (In other words, people like me in CCAW’s early years.) I know their struggles. I’m one of them, and I’m passionate about helping them. If I’m successful, I’ll accelerate their success. I’m hopeful they’ll give back to someone else when they’re able to.

My whys were born of my personal experiences. That makes me credible and able to relate well with the folks I seek to help. And it drives the passion behind my why.

What’s your why?


We Don’t Like It, But We Need It

This week, I shared some lessons I’ve learned with Startup Summer School attendees. One of the biggest was how important a cofounder is. I started CCAW as a solo founder. Even though it worked out—CCAW was a success—it was painful. Our progress was slower than it could have been and I was stretched super thin. I’ve thought more about why a cofounder is so beneficial. One word sums it up: accountability.

I often hear “not having to report to anyone” and “being my own boss” as top reasons for being an entrepreneur. But the most successful entrepreneurs are accountable to someone: a board of directors, cofounders, investors. Accountability leads to success. No accountability can prevent or slow your success. Why is that?

Accountability means that you’re expected to deliver on commitments by taking action. Others are relying on you. If you don’t deliver, there are clear repercussions for yourself and others. Translation: you can’t do whatever you want, whenever you want.

When you’re accountable to no one, you don’t have to commit. No commitment means no clear repercussions. Translation: you think you can do whatever you want, whenever you want. Entrepreneurship is all about taking action to meet a goal. But when you’re not accountable to anyone, you tend to take action when you want to, not when you need to. Over time, no action or slow action hinders you. And you shortchange yourself and everyone who works for you but doesn’t have the power to hold you accountable.

If you’re starting a company, try not to go it alone. And whatever you’re doing, find a way to make yourself accountable to someone.


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