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The Rise of the Retreat

With more companies working remotely, I’ve been hearing more founders searching for ways to keep their teams connected on a deeper level. Some of them are putting more thought into their retreat planning. Retreats are usually meetings outside the office where everyone gets together to bond and discuss the business. Some last one day; others are multiday. Many include team-building activities to allow team members to overcome a challenge together.

I’m a big fan of retreats and attended two a year before the pandemic. Most were for two to four days and attended by other entrepreneurs. Without a doubt, these have been some of the most transformative and enlightening experiences I’ve ever had. I’ve always left more focused and excited about what lies ahead.

Retreats were helpful before the pandemic, but I think they will be a critical tool for leaders going forward. Can’t wait to see all the creative ways people find to get teams to bond.

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A Picture—or a Clear Summary—Is Worth a Thousand Words

A friend does real estate projects, which I love hearing about. As we walk his sites, he tries to describe the end product. It’s hard to grasp what it will look like as I listen and look at the incomplete construction. He recently began getting renders, and he showed me one of the final version of his current project. I got it right away. The rendering brought his words to life and filled in all the gaps in two seconds. We discussed how helpful that rendering was for someone like me, and he shared an insight: it’s also been helpful for his workers and vendors. They understand what he’s aiming for now, and they make better decisions on their own that align with that vision rather than constantly ask him questions.

This past week I had a conversation with an early founder who’s building a software company. We’ve been working on his one-page strategic plan for the last few weeks. It includes his vision, mission, values, target market, three-year-goal, annual goals, quarterly goals, and quarterly projects. It’s essentially a roadmap that measures progress. It details where the founder wants to go, how he’ll get there, and what he needs to be working on this quarter and this year. The founder rolled out the plan to his team and got an interesting response from a team member: “I don’t feel like an employee anymore. I feel like an owner now, and I know exactly where we’re going and what I need to be doing.”

The founder was surprised that a simple one-page document was so illuminating. Having been a founder, I knew exactly what he meant. I also knew what he was missing. I reminded him that founders have more background knowledge about their market and where the company is heading than anyone else on the team. It’s all in the founder’s head. He’s been thinking about it nonstop. It’s clear to him. It makes sense to him. Other team members’ knowledge is full of gaps. Laying it all out in a simple way fills the gaps, making clear to everyone what’s so clear to the founder. It can be a rendering, a one-page strategic plan, or something else. If it connects the dots for other people, the outcome should be the same.

These two conversations were independent and about different industries, but the founders’ conclusions were the same. It’s important for founders to empower teams by painting a clear picture of where they’re going and how they plan to get there!

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Teams Will Have Their Ups and Downs

Yesterday I watched an MLS game and noticed something interesting. The game was overshadowed by an unfortunate dynamic on the home team. The star player and the coach weren’t seeing eye to eye, so the player sat out the game. His team lost. There’s no guarantee the home team would’ve won if their star had been on the field, but naturally the fans, including me, wondered.

As in most relationships in life, teams go through their ups and downs. There will be wins and losses. Good days and bad. It’s normal—part of the journey. The teams that achieve greatness find a way to ride it out when things go wrong and stay united in their goal. They continue to operate as a team.

Building a big company requires a team. Founders should be mindful that keeping their team united and motivated to move toward the goal is one of their main responsibilities as the leader. Compromise will be required. People will have to put their egos aside at some point. At the end of the day, it’ll be worth it if the team wins together!

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Owning Your Shortcomings: A Superpower

Today I had independent conversations with two entrepreneurs at different stages of their journeys. One just exited his second company and is beginning to think about what problem he wants to solve next. The other is still building his first company. Both of them mentioned that they’d spent considerable time identifying what they need in an early core team and recruiting people who fit those criteria.

I went a bit deeper, and both revealed gaps in their abilities or experiences that could prevent them from being successful. They’re both smart, super talented, and successful—and very self-aware and upfront about their limitations.

No one is good at everything. We all have shortcomings. But not everyone will admit to them. That’s too bad because being transparent about shortcomings can actually help founders. Sounds counterintuitive, I know. Many founders think they have to be great at everything—superhuman, practically—but that’s not realistic or sustainable. Acknowledging their shortcomings can help them understand what gaps they need to fill to round out their team. Recruiting efforts can be more focused and attract candidates who know what they’re good at. And it supports a culture of teamwork—people pay attention to what the leader does and follow suit.

Founders who want to build great businesses should consider being transparent about their shortcomings. It’s a great way to turn something that could be perceived as a negative into a superpower that can propel you to new heights.

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Office Politics Will Undermine Company Culture

I listened to a founder discuss the dynamics of his company recently. He raised capital and the business is growing aggressively. He’s adding to the team and giving more responsibility to legacy team members. There’s more hierarchy (a good thing) but also more politics, which the founder hates. Decision-making has slowed, and receiving individual credit is prioritized over teamwork. They’re playing the Game of Thrones.

I haven’t worked in a large organization in many years, but I remember that when I did, the politics were apparent. I didn’t like navigating that environment. It felt like a popularity contest. I ended up leaving for a variety of reasons (not just that), but the experience stuck with me. When I started my company, I wanted to avoid politics. I think we accomplished that.

Culture is a key ingredient in success. I think this founder is right to be concerned about office politics eroding the culture of his company. I hope he can get his team thinking with a “we” mindset again.

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Build a Company, Not Just a Product

I recently spoke with a founder who’s had some turnover on his team. He’s an early founder and doesn’t have a working MVP yet. He said that his highest priority is finishing the MVP, which he’s considering doing himself. He isn’t worried about trying to replace his team.

This founder has hit a rough patch on the people side of the business, and he’s understandably frustrated. I’ve been there as a founder, so I get it. But it’s part of the journey —most founders experience it at some point.

This founder wants to forgo replenishing his team and focus intently on building a great product by himself. He’s very smart and will likely build something impressive. The problem is that building a product isn’t the goal. The goal is to solve a problem extremely well and get customers to pay for the solution. To achieve it, product development isn’t enough—you also need to develop other functions, including marketing and sales. To put it another way, you need to build a company.

Early-stage founders should keep in mind that their goal is to build a company. And that requires a team.

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Never Be Above Getting into the Weeds

Founders usually start off doing everything. They’re the glue that holds the company together in the beginning. They’re in the weeds executing to move the company forward. As the company grows, that’s not scalable, and founders begin delegating (or they should). This usually means they’re managing the executors or managing the managers. If done correctly, this allows founders to look at things from 50,000 feet, metaphorically speaking, and think more strategically about the business.

Having to think only high-level about the business is a great thing. I remember when I was able to do this. It felt like I was lifting my head above the clouds and seeing the horizon clearly. Once you’re above the clouds, it can be hard to go back.

Today I spoke with a founder who has removed himself from the weeds of his business, but it isn’t going well. The business isn’t performing as it should, and he knows he needs to replace the people who are executing (or failing to execute). The problem is that he doesn’t want to go back to executing. He can’t wrap his mind around doing that type of work again.

I lived this situation myself in the early days of CCAW, so I can relate. I delayed making changes because I didn’t want to get back in the weeds of a specific area of the company. That delay proved costly and the business suffered. The business lost so much traction that I was ultimately forced to go deep into the weeds to identify the issue and reverse the damage. I had waited so long that we had a razor-thin margin of error. With the support of others team members, I dug in and figured things out. We reversed the trajectory, and I was ultimately able to get back out of the weeds. With the problem solved, the team thanked me for jumping in alongside them. They hadn’t expected it (neither had I!), and they appreciated it.

My lesson from this was that I should’ve always been ready to jump in and do what was needed. I was the founder and it was my company, but I wasn’t above getting into the weeds. Founders do what needs to be done, even when they don’t want to.

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Commit to Your Solution, Not Just the Startup Life

I was chatting with a founder friend about early-stage entrepreneurs. This person was a founder for over a decade and then sold his company. He’s lived it and achieved what many founders aspire to, a liquidity event. During our chat, he mentioned that early founders need to be committed to the problem they’re solving, not just fixated on being a founder or being part of a startup.

He’s right. He and I both spent over a decade building our respective companies. There were many tough periods and trying moments. Those are the times that test founders, and their commitment to the problem determines whether they pass the test. If a founder cares mostly about the title or the “glamour” of startup life, they probably won’t be motivated to stick it out during tough times.

Starting a company is hard, and building it is often a journey of a decade or more. If you’re considering being a founder, make sure that what you’re working on excites you enough to make you want to push through thick and thin.

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More Early Founders Have Coaches

Over the past few months, I’ve been hearing more early-stage founders say they have coaches. Some sought coaching on their own. Others did so because it was suggested.

I’m a fan of coaching and have experience with it myself. Quite a few of my founder friends have also been coached. It’s a great way to foster self-awareness and work toward becoming the kind of founder you aspire to be. It’s not always fun or easy. A good coach will tell you things you don’t want to hear and have you do exercises you’d rather not do. But the effort is usually worth it in the end.

It’s great to hear more early founders openly discussing coaching. I think this a big plus for them, and I hope the trend continues!

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Meaning Is Beginning to Matter

A friend and successful entrepreneur who recently sold his company shared an interesting prediction with me. Purpose is what motivates most people. The events of 2020 helped many people crystallize what matters most and what motivates them. My friend thinks that companies whose only purpose is profit showed their true colors during 2020, and their employees took note. He predicts an exodus of employees from these companies over the next year or so. Companies that have a clear purpose above profits have built significant trust with their employees and communities with their actions. They are likely to see an influx of people wanting to join them.

On various fronts, 2020 was extreme. I’d imagine almost every company was affected to a lesser or greater degree.

I agree with my friend’s observation. More people are professionally motivated by purpose rather than money. I think this was happening before 2020 but that last year accelerated the trend. I’m not sure if this will cause people to leave their jobs in the short term, but I believe it will be a bigger factor in recruiting going forward. More candidates will judge companies by their purpose.

So, what does this mean for early-stage founders? You can’t build a great company by yourself. You need great people to help you get there. If this trend continues, it could be a boost for companies led by missionary founders. Founders driven by success or financial gain may find themselves at a recruiting disadvantage.


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