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Me and my business partners–Chuck, Kurt, and Mike–at Clockwork's 10th anniversary party.
2022 is Clockwork’s 20th anniversary. Many statistics suggest we should not be celebrating this milestone: we’re small, independent, (partially) woman-owned, women-led (did you know that less than 1% of creative agencies in the US are women-led?), and we were a start-up creative tech company that opened its doors four months after 9/11. Yet here we are, arguably stronger than ever, if only because we’re older and wiser.
This company milestone also means I’ve been a founder and CEO for twenty years. As you can imagine, I learned a lot during that time by experimenting, messing up (a ton), and evolving.Here are twenty lessons, in no particular order, that I want to share from the last twenty years, which, I’m sorry to say, literally flew by:
1. Pick your partners well.
Liking someone isn't enough reason to go into business with them. Being pals isn't enough. The decisions you have to make and the strategies you have to define need more common ground to be done successfully. You and your partner(s) should share values, establish ground rules before difficulties arise, and have meaningful conversations about goals and vision to really understand where each other is coming from. Anticipating and processing how you’ll respond to the big bumps is critical. Similar definitions of success, boundaries, and business approaches are more important foundations than simply liking each other.
2. Be willing to work hard.
Starting a company is hard but keeping it going is really hard. As the company grows, your work might change, and your job might (ahem, will) look different day-to-day. Some years you might have more people at the company, some years fewer, but the one thing you can count on is that you will have to work hard to succeed.
3. Don’t take an 'us too' approach to business.
You're not differentiating if you're looking at your competition in your industry and thinking, “We can do that, too! And we can do that other thing, too!” At that point, you’re mimicking. That’s not only limiting–it’s dangerous. Innovation is critical in every industry and at every company, and any time you say, “us, too,” you’re definitely not innovating. Consistently evolving and continually differentiating your product, service, attitude, culture, mission, or model is how to build a sustainable business that lasts for twenty years, or beyond.
4. Hire people who are better than you.
To start a company, you must have a healthy sense of ego—you have to believe in yourself and your idea so much that you can bring others along—but that ego can’t get in the way of surrounding yourself with people who are smarter than you. No matter who you are, there is someone (or many) who can lead better and someone more advanced and knowledgeable than you in some parts of the business. Find them, hire them, and get out of their way. Do not believe you are the best at everything. You are not. And you’ll tire yourself out if you go down that path.
5. The CEO serves no single person; they serve the mothership.
I have to spend my time considering what is best for the greatest number of people in the most ways to sustain the company for the longest time. I can’t worry about what Sylvia in marketing or Tyler in engineering wants. I always say that the CEO's job is global, and everyone else’s is local. Both are important, but they are very different. At times, people will get mad at you. At other times, you will make decisions that are not wholly popular. People will have feelings, good or bad, and you’ll never make everyone happy. But your job isn’t to make everyone happy (tough news for us people pleasers). Moving everything forward is what’s crucial.
6. Mental healthcare is healthcare.
Every leader should be thinking about ways to support wellness among the staff. The mental health of your people and you are probably the things you have to care for the most. You can work around physical limitations, but when people are burned out, exhausted, fried, or frustrated, there's almost no way of working around or through that. Get specific about what you and your company mean by wellness and self-care, and talk about it. Perhaps it's a walk around the block, a nap in the middle of the afternoon, an extra meal, or a run. Whatever self-care is to you, encourage it, support it, and make sure it exists.
7. Adaptability is the key to success.
Although most people have a rough time with change, it really is the only thing you can count on. When you embrace innovation (see #3), change immediately follows. Adapting, responding, being quick on your feet, and practicing resilience are important to discuss with everyone in the company at every turn. These are not just leadership skills—they are human skills that are necessary for work in the 21st century.
8. Listen as much as you talk.
A key component of a leader's job is inspiring people. You want them to believe in the mission, vision, and values and reflect them. You want to convince them to care and to show up with good energy. It may sound like you’d be talking a lot to achieve all of that, but listening is everything. Nothing you say will be impactful if you haven’t listened first and listened well.
9. Relationships are still everything.
Sales, hiring, recruiting, retention, and culture are all rooted in and flourish with relationships. In fact, every aspect of business is based on relationships. I am a tech entrepreneur and introvert who will pick Zoom or a call over just about anything else, so it might seem counterintuitive for me to say this, but here I go. Relationships cannot all be fully fostered on the internet. You have to connect, share energy, have awkward pauses, laugh at bad puns, or just spend face-to-face time together sometimes. We haven’t moved past our basic human need to connect and to want to work with people who we connect with.
10. Ideas are a dime a dozen. Delivery is rare.
Everybody has great ideas. Many people even have million-dollar ideas, and a few have billion-dollar ideas. The difference between all the people with big ideas and those who can actually call themselves entrepreneurs is doing. Entrepreneurs make their ideas happen. Interestingly, the word entrepreneur is from the French word entreprendre, which means to undertake. Having an idea won’t necessarily get you to your finish line. You also have to take on the work to see that idea through.
11. Failure is part of it all.
You might fail with your staff. You might fail at a particular moment. You could fail at a potential sale or miss a big opportunity. You might head in a direction and find out it is not the right thing. Your ego will be bruised or embarrassed, but it’s all part of the ride. When you recognize failure is part of every journey, you can wrap your arms around the lessons, take some comfort in knowing that failures can make you a better leader and a better human, and not only heal the bruises, but build enduring strength.
12. Know your numbers.
You don't have to be a mathematician or a chief financial officer to have a solid handle on your finances. But you do have to know the basics about what numbers are meaningful for your business. When I started Clockwork, I took a basic accounting class and made sure I paid attention (and as some of you know, I have ADD, so that’s harder than it sounds). As a result, I can recognize patterns and trends in our month-to-month numbers that tell me what I need to know about company finances. Of course, I work with financial folks who are much better than me (see #4), but I have never handed off the finances entirely. You have to know when you can take risks, and when you can’t, which is all tied to your financial health.
13. Ethics and attitudes can make all the difference in the world.
We have been made to believe that the only way to succeed in business is to destroy the competition, to be cutthroat, and to sabotage everybody else in your path. I don't think that's true. I believe there's enough work for everybody, and honesty is everything. Our values should speak to who we are and how we show up in the world, and living your values could be the thing that helps people decide to work with you. Work is work, but how work feels is the difference between a fine place to work and a great place to work.
14. Emotional intelligence is everything.
Skills can be taught, but understanding people, showing up with empathy, and legitimately caring for other people cannot. Business is relationships, and in successful relationships, you care. You have to be able to understand people, shape-shift your approach to have effective conversations, and be able to interact with many types of people. Reading the room and sensing what people need will take you and the people around you further than being an Excel pro or a marketing genius.
15. Go for contribution over fit.
Hiring for fit means you’re hiring for comfort. Hiring for contribution means you’re inviting people who will challenge you, who are willing to look at things differently than everyone else in the room, and who bring something to the table that you don’t have. Surround yourself with people who push you out of whatever point of view or zone you gravitate toward. It takes bravery to contribute, to throw ideas into the ring, and that’s exactly what great people will do.
16. Build to last.
We spend a lot of time celebrating ‘new’ companies: new companies create jobs, launch new products, and contribute to the economy. We don’t often revisit those companies five and ten years down the road. Once a company has been around for a while, the press disappears, the romance dies, and it can feel like a total slog. But it matters that you’re still here. It matters that you continue to care about your teams, the quality of your output, and the communities in which you live. Nothing says you have to be Tesla or Uber to matter, even if the press seems to suggest as much. Collectively, small businesses are the largest employers in this country. We may not be romantic or sexy, we may not be shiny and new, but we are steady and dependable and we have staying power. That is worth celebrating every day of the week.
17. Customer experience starts with the internal customer.
How your external customers experience everything from your phone calls to your emails, your processes to pricing, your strategies to interactions, and your enthusiasm to your energy all starts with the people on your teams. If they are not equipped, accurately trained, and engaged, your end customer’s experience will suffer. Pay as much attention to your team’s experience as you do the external customers, and you’ll find higher rates of satisfaction among all your customers.
18. Nothing is easy.
I often worry that the GoFundMe approach to starting businesses might make running a company feel easier than it will ever be. In my day (I had to say it), we didn’t have crowdfunding, and coming up with cash to start a business was PAINFUL. But the process was necessary. We must stop looking for the easy way around obstacles, fast fixes, and quick wins. Easy doesn't exist. Spend that energy building your capacity for resilience and patience. That will prove to be a much better investment in the long run.
19. Make it matter.
Never just sell something. Never just work to build wealth. All your effort can't just be about money or recognition, there has to be more on the hook. There is enough capitalism, enough ultra-wealthy humans, enough busyness, and enough people exploiting other people in our world right now. What's the difference between them and you? Figure out what matters to you and focus on that.
20. Selling the company doesn't have to be the ultimate reward.
In the start-up world, selling always seems to be the carrot, the surest sign of success. What about how people feel? Whether they are proud to say they work at your company? Or whether they grew as professionals and as people while working with you? I’m super proud of Clockwork. We’re more than what we do. Media and other organizations look to us for our opinions. People say they admire us for our social presence, our social impact, and how we contribute to our community. A big-money buyout can’t be the only way to know we’ve succeeded at what we’ve done over the past twenty years. The people we've worked with, the careers that have started here, the friendships and families that have flourished, and the clients whose businesses we've changed can be the ultimate rewards. And for me, they are. The lives we’ve changed and the way we’ve cared are the things that matter most.
Tech has changed dramatically in the twenty years I’ve been doing this—mailing CD-ROMs through USPS was an actual marketing strategy back then. And amidst all the change, I’ve learned that some things never change: people come first, focusing on humanity will help you make good decisions, and candy drawers are really popular.
I am not Mark Zuckerberg. I am not the lady who made Spanks or the CEO of some glamorous tech start-up in Silicon Valley. Fast Company might never care about me. But I will tell you: I am mostly happy. I feel good about how we’ve treated clients and teams. I feel good about how we’ve shown up as citizens in our home state of Minnesota. I feel solid about the truths we’ve told and the products we’ve delivered. I appreciate the causes we’ve been able to show up for. I feel good about our reputation, our work, and our story. I am proud of Clockwork. I am proud of the business partnership at the heart of Clockwork. I am proud of these last 20 years. There have certainly been some dark days. But, honestly, I wouldn’t change a thing.
Happy Birthday, Clockwork. I sure do love you. I’m looking forward to the next 20 years.
The last two years have been weird and wild and like nothing we’ve lived through before. For Clockwork, it was hard as hell. But it was an opportunity to step back and take a look at all aspects of our business and prepare for our 20th anniversary by sharpening our focus and story. All of that effort has culminated in what you can see and what, maybe, you can’t. So, because you are my favorite subscribers, I’m going to share them with you.
We’ve refined our positioning and focused on shining a light on the industries in which we have significant expertise: healthcare, financial services, insurance, and manufacturing. We’ve spent so much time in these spaces over the last 20 years and believe our experience in regulated industries is unparalleled. And we’re going to emphasize that every chance we get.
We’ve got new leadership! Continuous improvement sometimes requires a fresh perspective and new ideas. And so I’m partnering with Jenny Holman in her new role as Clockwork’s President and Vince Cabansag as our COO.
We aren’t like any other small shop, you know. The last few years have allowed us to double down on building our consulting business. Clockwork doesn’t just build software solutions, we also have the expertise to ensure it succeeds. Kasey Ross, our Director of Change Strategy, and her team bring an enlightened perspective on change enablement as well as product adoption, governance, and workflow.
We’re more agile, strategic, and client-centered than ever. And the entire story is encapsulated in our brand new website at clockwork.com. We haven't even announced it yet, you get a sneak peek! We’ve long suffered from being the cobbler’s children: we seldom had time for our own website. But we made time to share our evolution and our expertise with this new iteration, and we’re really proud of it. I’d welcome your feedback if you have a minute to visit.