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IMAGE: ANDY DUNN

Running a mid-sized business or managing a team of employees requires unbelievable patience, understanding, forethought and vision — and some of the most successful leaders will tell you that acquiring these traits does not come easily. Problems are bound to arise.

It’s inevitable for business leaders to be faced with questions: “How should our business adapt through expansion?”, “How can I be a better manager?” and “How do I move on from mistakes that I’ve made?” Mashable spoke with five business leaders who have, through little and large tumbles alike, learned how to approach roadblocks with poise, steady minds and healthy expectations.

1. Andy Dunn, CEO of Bonobos

Bonobos, an online retailer that built its reputation on better-fitting pants for men, sells clothing through an online shop, several “guideshops” across the country and at select Nordstrom stores.

When managing your company … There is a balance between being too involved and not involved enough. If you are too involved, you will micromanage talented people and they’ll be annoyed. If you are not involved, it seems like the company’s most important leader — the CEO — doesn’t care. Walking that line requires giving feedback in a structured way; I learned that from Ben Horowitz, and from having talented employees teach me how great CEOs — like Mickey Drexler and Reed Hastings — do their work.

Listen to your customers … One thing I’ve learned is to let your customer settle your debates. Your brand isn’t only what you want it to be, it’s what your customer decides it is. When we surveyed 1,000 customers on what they loved about Bonobos, they said this: Fit, service and fun. With that roadmap, I bet we’d have made it to dress shirts sooner, given the opportunity to build an amazing experience in that category between tailored fits, our tremendous service policies and the energy we bring via color and print to our clothing.

Having to adjust over time … When we started the company, we assumed that we’d be online-only given our commitment to delivering incredible service. What we’ve learned with partnering with great companies like Nordstrom and Trunk Club is that great service can have a physical presence. With that in mind, we invented the Guideshop, which is pure, fantastic one-on-one customer service. Try everything on, get styled and we’ll ship it to you. We think it’s the reinvention of the retail store, and with the 10 that we have, we’re just getting started.

Three business commandments … I’ve learned three things that I believe matter a lot: You catch more flies with honey, a.k.a. there are no diminishing returns to specific positive feedback (I learned this from our founding angel Joel Peterson); adequate performance gets generous severance, which is Netflix’s policy for being dignified but decisive with employees who are not a fit (which I learned from our former CTO and now founder/CEO of Attune, Mike Hart); and if you aim to please everyone, you will please no one — that’s one that I’m learning right now.

2. Nathan Hamblen, VP of engineering at Meetup

Meetup helps people with similar interests connect online to plan fun, interesting and engaging events and meetings offline.

No engineer left behind … Engineers spend most of their time interacting with each other and with their software as they solve problems, while companies on the whole tend to function more socially. As engineering managers, we have a responsibility to ensure that no one’s being left behind for being too focused on the software, and that instead they’re being recognized and rewarded with more responsibility. It’s a problem we’ll never fully solve, but it’s the crux of our day-to-day management work. I have to remind myself that as engineers we aren’t weird, we’re just differently informed. The better we can inform everyone in a software company, the better it will function.

Communication across disciplines … I think of management errors as worse than programming errors, usually more destructive. They have a long-term effect on a small group of people rather than an immediate, short-term effect on a many people. Unlike bugs, they can never really be fixed and for the same reason they’re private.

Engineers often want the same thing, but it can be difficult when we don’t. Communication is not always easy, especially across different disciplines and software platforms. My goal in these situations is to be the most understanding person in the room, to help people understand each other’s views. Over time, understanding each other becomes a habit of a team and you don’t need to be in the room anymore.

Working smarter and harder … It’s always been hard to find the right engineers for a team. In my years as a manager, we’ve gotten better at it, but the hiring marketplace keeps getting tighter. We have to work smarter and harder just to maintain staff across an ever-increasing number of software platforms. One way we’ve done much better this past year is with a fleshed-out college recruiting operation. Once we were past 100 employees, we were able to focus on and hire graduates in a way that just wasn’t possible before. It’s an eight month process, from interviews to on-boarding.

3. Lisa Falzone, CEO & co-founder of Revel Systems

Revel Systems is an iPad point-of-sale system that helps businesses boost security, manage payroll and track inventory.

On hiring the right people … One particular mistake I made early on is not interviewing thoroughly enough. We would get new hires on board, only to find out later that they weren’t a right fit for our culture and their work ethic didn’t measure up to the company as a whole. Developing a more careful interview process and getting the right hires to start with is the number one thing [I’d recommend]. I learned to do more data-driven interviews. I find this approach gives candidates an opportunity to back up what they’re saying.

Emphasis on teamwork … Empowering my employees to work better together was a bit of a struggle — especially during the transition from 30 to 100 employees. To combat this struggle, I placed a heavy emphasis on the importance of teamwork. We developed core company values, of which teamwork is a main tenet, and work to show employees that teamwork is really important. These values play a major factor in our quarterly review process.

Cross-department communication … We’ve helped emphasize teamwork by putting structural meetings in place. For example, our support team and sales team meet on a weekly basis, and customer service has regular check-ins with engineering. These meetings enable sales escalation and foster communication between departments. They also resolve any communication issues that individual departments are experiencing and encourage cross-department communication.

Mistakes won’t break you … It’s important to identify the issue and recover quickly, and to not make that mistake again. There’s no need to beat yourself up for mistakes you’ve made — every company, and every manager, experiences the same problems at some point. How you’re able to learn from your mistakes and how quickly you overcome them determines the success of your company.

4. Oisin Hanrahan, CEO of Handy

Handy (formerly Handybook) is an online platform that allows users to book pre-approved cleaners and handy workers instantly, making house chores easier.

Managing as you grow … As a startup, every day brings new challenges. Especially as we enter into new markets, we’re met with new obstacles that motivate us and provide opportunities for innovation. In the past year alone we’ve added more than 125 employees, opened offices in six additional cities and grown our team of service professionals to more than 3,000 across the globe. Managing such a large number of employees across multiple time zones is a certainly a challenge, but my goal is to ensure that we’re all working toward the same vision.

System failure … Early on, we had a system failure and accepted 50% more bookings than we actually had staff for. So we rallied the whole team — the engineers, the designers, my co-founder Umang [Dua] and myself, anyone who could help — and we went out and completed the jobs ourselves to make sure we didn’t let our customers down.

A culture of collaboration … At Handy, we strive to always foster a culture of collaboration. No matter how big we grow to be, whether we’re 25 employees in New York or 3,000 across the globe — I want to make sure Handy is run like a small business. This begins with the office design itself. The Handy headquarters is an open floor plan that encourages colleagues across all teams and positions to sit, meet and build connections. My co-founder and I make a point to sit in the center of the office where we are accessible to everyone.

Building success … One of our key mottos is “recruit smarter than you.” We want the best minds working with us so Handy can realize its full potential. We admit what we don’t know, and that helps us make a stronger product and work environment. By staying dedicated to the idea of giving the customer a simple and easy experience from beginning to end, we can always keep ourselves on track.

5. Brad Hunstable, CEO of Ustream

Ustream, which Variety recently labeled the next billion-dollar takeover target, is a live video platform that offers high-quality streaming, social networking integrations and scalability to reach millions.

Re-organizing based on the industry … When we started Ustream, the goal was to get consumers around the world broadcasting themselves through live video. As we accomplished that, we realized that the real business growth opportunity lay in the enterprise space, and our challenge became rebuilding our team to ensure we had the skills and experience specific to enterprise. We built out entirely new teams, required new philosophies from product and UX development and even developed a new brand identity.

Vision for the whole team … Aligning hundreds of people with a new direction has required a number of qualities: The flexibility to see if our existing team was able to evolve into new roles; the honesty to be clear where they were not; the humility to figure out what we didn’t know; and knowing the right questions and people to ask for problem-solving. Ustream’s interests must come first, with a meaningful, powerful vision. Your employees’ interests comes second, and your personal interests as a leader must be a distant third.

Right people, right skills … Over the years, I realized that business is not just about having great people, it’s about having great people with the right skills and experience to deliver on your vision. If you have Michael Jordan playing for your hockey team, he probably won’t be as effective as he would be playing basketball (though, with him you never know). I learned that it is okay to change what you ask of people, as long as you are transparent about the change, over-communicate and have the company’s best interests at heart.

Keeping employees on the same page … With roughly half of our employees split between our San Francisco and Budapest offices, we are always looking for ways to keep everyone better aligned and moving faster in the same direction. Fortunately, our platform helps! We can stream town-halls between locations and allow everyone to hear directly from the team leaders, make comments or simply share videos with each other to keep the information flowing.

One lesson learned … is you cannot re-state the goals, direction and vision too many times. It is tempting for executives to think that after you’ve explained it once, people will keep the direction at the forefront of everything they do. But of course, everyone has had the experience of falling into old patterns of behavior without even realizing it. So keep up the relentless drum-beat and remind everyone what lies on the other side of all the hard work.

Nothing worth building is too trivial to accomplish; life is too short to spend your time on anything less.